Life in my early twenties was great. My entry level job bored me to tears, and the paycheck wasn’t anything to brag about. But I had my college degree, loads of free time, and just enough pocket money to get myself into all kinds of trouble. Plus I was young, and it seemed like the world had been made for me. There were bars where the drinks were cheap and the music was good, sweaty clubs where the girls showed off more shimmering, smooth skin than they covered, and shitty parties where the food was bad and the music too loud but the stories were always entertaining. Most important of all, I had one of my best friends from college as my roommate. He shared in all of my adventures, kept the trouble from getting too big, and helped keep the bills low.
That all changed when my roommate fell in love. He met this sweetheart of a shy and beautiful girl, and they became inseparable. The idiots got engaged at 24, and just like that my good times were over. But even when I realized how bad it was going to be for me when my roommate told me he was moving in with his fiancé, I had no way to anticipate the gut wrenching ride I was about to experience.
The serious trouble started a couple weeks before my roommate was due to move out. His fiancé told me she had heard I was trying to line up another roommate so I could keep my place, and she said she had a roommate who was now looking for a new apartment to share. I should have asked why I had never met her roommate, that would have been warning sign. But the question didn’t cross my mind at the time.
A few days later when I met the roommate at a happy hour, I knew I was in a tough spot. The girl was gorgeous. Her name was Cassidy, which also should have been a warning.
She was clearly the type of girl who worked out a lot, standing atop long, shapely legs that were toned with muscle. Her whole body was lean and toned. She was pretty tall at about 5’7″, and had fiery red hair that hung down in soft curls just below her shoulders. When she was introduced to me, her deep blue eyes twinkled, and her bright white smile lit up her entire face, all the way to her high cheek bones. She was wearing a low cut green top that clung to her large, C cup breasts. The way her creamy breasts were on full display was another warning.
Cassidy seemed very sweet. She knocked back her drinks faster than I would have expected from someone with her light frame, but other than that she seemed very nice and dangerously charming. That’s why I really wanted to say no to her moving into my apartment. Even at 25, I had learned it was dangerous to get too close to a really attractive girl. If you spend too much time with a girl, if you became friends or roommates, and she was even moderately attractive, you were going to end up falling for her one way or another. Even if you didn’t develop romantic feelings for her, you’d start to wonder what she was like in bed, how good she was at blowjobs or fucking. And the next thing you know, you’d be thinking about fucking her every time you were together. And you could never fuck her, because that would just mess up the friendship. So you were always royally screwed one way or the other in the end. It was best not to get too close to attractive women, unless you were trying to date them. And living with a hot girl was a recipe for disaster. Cassidy was definitely beautiful.
But as much as I wanted to say no, I was in a tough spot. Cassidy had learned that my apartment was slightly bigger than hers and in a better location. She really wanted to move into the place. And I didn’t want to start off on a bad note with my best friend’s soon-to-be wife. So I stalled for a couple of days before deciding I had to agree to the deal. It was better than interviewing replacement roommates, and how bad could it really be to live with a sweet, beautiful woman? Stupid decision
I knew Cassidy’s sexy body was going to be a huge distraction for me the second she moved in. She showed up with her first few boxes of stuff wearing booty shorts and a tank top over a sports bra. When she was walking away from me, I couldn’t stop looking at her impossibly shapely round ass. When she was walking towards me, I couldn’t stop stealing glances at her large, round breasts pressed firmly against the tightly constraining fabric of her sports bra.
I tried to tell myself not to be a pig about it. She was much cleaner than my old roommate, which I liked, and she didn’t constantly borrow my groceries. She also offered me leftovers from her dinners, and she was a pretty decent cook. We had separate bedrooms and separate bathrooms, so when I got a little too interested in her attractiveness, I would excuse myself and spend some time reading or watching tv in my room. She watched horrible reality tv shows that were all about drama between women, but other than that we got along okay. Still, it was easy to try to tell myself to calm the fuck down when Cassidy looked particularly sexy getting ready to go out at night, or even leaving for work in the morning. It was a different matter trying to hide my erection when she bounced her way onto the couch in short shorts and a virtually see through white t-shirt, flashed me her dazzling smile, and then changed the channel to something on the E network.
———-
The real trouble began very early one Saturday morning. I woke up to the sound of a woman’s loud moaning and pounding on the wall. I decided to peek out my bedroom door to make sure everything was okay, because my bedroom and Cassidy’s didn’t even share a wall. So the pounding was crazy loud for it to have woken me. The light was on in the living room and some shoes and sets of keys were strewn around the place. It was close to 4 in the morning as I tip toed down the hallway towards Cassidy’s door.
There was no mistake that Cassidy was moaning with arousal like she was losing her mind. The thing that really alarmed me is that it sounded like two distinctly different male voices were coming out of Cassidy’s bedroom. The banging on Cassidy’s wall was so loud that it almost sounded like someone was punching the wall with their closed fist. I considered for a brief moment that someone might be hurting my roommate.
Then Cassidy’s voice came loud and clear through the doorway, dripping with delight and sexual energy, “Oh yes!” she cried. “Fuck me! Fuck me harder! Give it all you got!”
The last syllable of her encouragement was cut off with a muffling sound. If I had to bet on the cause, I’d have wagered that one of the two guys in there had shoved his dick in her mouth. Both seemed amused, their laughter ringing loudly through the doorway.
“Oh yeah? You like that baby?” One of the men inquired. Cassidy moaned her approval in response.
“Whatever” I thought to myself. I padded silently back down the hallway to my room and closed the door. After a couple of minutes trying to muffle the moaning and screaming with a pillow stuffed over my ears, I drifted back off to sleep.
I’ve never been able to sleep late, and despite the disturbance in the middle of the night, I was awake by 8 the next morning. I walked quietly out of my room and through the living room dimly lit with the early light of morning. On the way to fix myself breakfast in the kitchen, I noticed the strange shoes and extra pairs of keys I had seen a few hours earlier were all gone. Curious, I tip toed back down the hallway towards Cassidy’s room to see if there was anything wrong.
Her door was half open, and through the doorway I could see that Cassidy was alone on her bed. She was passed out on her back, the sheets askew and the comforter half over her. There were small items lying around the floor of her room, like things had been tossed to the floor or knocked over during the night. But what quickly drew my attention was that Cassidy appeared to be naked and the comforter only covered her from her waist to her ankles. Her large, creamy breasts were on full display, little light pink nipples resting atop her round, pale mounds. Her breasts were magnificent, big and full with only a slight sag from gravity pressing them down onto her chest. I got hard just seeing her round breasts, and Cassidy’s peacefully sleeping face framed by bright red hair. Her skin seemed smooth and flawless, pale with a light rosy glow that made me think of strawberries and cream. And topping off the pink and white colors of her body were her small, light pink nipples sitting atop her breasts. I still get hard, years later, remembering how perfectly smooth and round and flawless those breasts were. An hour later, I was spraying my cum against the wall of my shower, imagining what it would be like to have those soft, full breasts wrapped around my cock.
I went out to run some errands before Cassidy woke up. When I returned that afternoon, Cassidy was awake and cooking herself some eggs over the stove.
“Hey,” she greeted me warmly. “I’m really sorry and I hope you don’t mind, but I was out of condoms last night and I needed a couple.” Well, I thought to myself, there goes any awkwardness about whether I should pretend to have not heard her sexual antics the night before. “I know you keep some in your bathroom, so I borrowed a couple. I went to the shop on the corner and bought you some replacements, and they’re already back in your stash. I hope that’s okay.”
“Sure, no problem,” I replied. I really didn’t mind her borrowing my condoms, I just wondered how she had known that I kept some in my bathroom. And although you could get to my bathroom from both the living room and my bedroom, the door from my bedroom to my bathroom had been open the night before. How had she gotten the condoms without waking me?
———
The following week, I met my old roommate for lunch. We spent most of the time talking about his wedding planning and how he was adjusting to life living with his girlfriend. But inevitably he asked how I was doing with Cassie. I related to him what had happened the previous weekend.
I knew something was wrong when he looked down at his plate, poked at his food with his fork, and then slowly looked back up at me. “Listen,” he began, “I really wanted to warn you, but Kate told me it was impolite gossip and you didn’t need to know.”
“Tell me what?” I asked warily.
“Well Cassidy,” he began uncertainly, continuing after a pause, “she’s a bit of a partier. And well… I’m just going to say it, that girl has a hell of a sex drive. She used to bring boys back to their apartment and get caught in all sorts of crazy situations with them. But Kate never minded because she insisted Cassidy was a good roommate, and her wild flings were kind of entertaining. And Kate didn’t think you would mind. You’re not upset about it are you?”
“No,” I responded quickly. Then after a moment, “But that’s good to know.”
A couple of weeks after that warning, I walked out of my room getting ready for work on a Wednesday morning to find Cassidy passed out on the couch. She was wearing a green string bikini that showed off the large, round swell of her breasts, and a string bikini bottom that hid very little of her shapely bottom and smooth legs. The green also nicely complimented her deeply red hair and fair skin. I couldn’t figure out where she had gone on an early September night that required her to wear a swimsuit, or how she had gotten drunk enough to pass out on the couch on a Tuesday night. But I knew I was treading deeper and deeper into troubling waters when I realized with a start that I had been staring at the cleft between Cassidy’s beautifully big breasts for several minutes. I was infatuated enough to spend minutes admiring Cassidy’s body while she slept. Worse, by the time I got to work my erection still hadn’t fully subsided after seeing Cassidy yet again with most of her hot young body on display.
———-
I knew there would be a breaking point one way or another, but I could never have anticipated how it would happen.
One Saturday maybe six weeks after Cassidy moved in with me, I got home around 1 am from a night out drinking with friends. I was making myself a little snack before bed when my cell phone rang. It was Cassidy.
“Are you home?” she asked. There was a lot of loud noise in the background and it sounded like she was slurring her words just a little.
“Yes, is everything okay?” I asked.
“Oh great! I have a HUGE favor to ask,” she responded. Now I was sure from her speech that she had been drinking.
“Okay, what is it?” I replied.
“I’m on a scavenger hunt, I’ll explain when I get there,” she told me hurriedly, “Please don’t go anywhere, I’ll be right there.” With that, she hung up.
Not sure what was going on, I went to use the bathroom, and by the time I walked out I heard Cassidy’s keys in the front door. She entered the room in a hurry, dressed in a tight little t-shirt and shorts that somehow still displayed the swell of her round bottom and the curve of her hip. She flashed me one of her dazzling smiles as she closed the door behind her, and bit her lower lip apprehensively as she walked into the living room.
“What’s up?” I asked.
She hesitated, looked through my open bedroom doorway for some reason, and then back at me. “This going to sound crazy…” she began, before trailing off.
I stood there silently, with no idea what she was about to say but allowing her silence to put together her thoughts. Finally, she surprised me by giggling, looking at me with a twinkle in her deep blue eyes. Then she continued.
“Okay, I’m just going to say it,” she began, rushing through her words. “Some friends and I are in this bar scavenger hunt league, it’s lots of fun and totally crazy.” I remembered her mentioning this scavenger hunt team before, it sounded fun and just like the type of activity she would love. “Tonight is the fall championship, and they make you find really crazy things but the point totals are HUGE. I mean, you could go from fifth place to first place if you got all the points tonight. Anyway, one of the big things we might actually get is if one of the girls shows up with cum in her hair and a judge verifies it.”
I laughed without thinking about it. It sounded like a ridiculous but intriguing challenge to me, but what came out of my mouth was, “That sounds a little gross.” Cassidy paused and looked into my eyes uncertainly. “Unfair to the girls, I mean,” I added.
“Yeah, true,” she plowed onward hurriedly, “But it’s worth a thousand points. That’s huge, I mean really huge. Some things in a scavenger hunt are worth ten, some things tonight even are only worth fifty. And this one is a thousand, and it’s totally doable, unlike some other things on the list where you either know how to find them or you’re screwed… anyway, some of the other teams have couples on them, which is totally unfair. Some of them saw the list and rushed right off to the bar bathroom.”
“That’s unsanitary,” I said with a laugh.
Cassidy ignored me and continued. “It’s not fair to my team, we only have one guy on our team and he would just love to cum in our hair, but there’s no way we’d let him, it’s a long story… anyway… I reminded my team that I live nearby with a guy for a roommate.”
It FINALLY dawned on me where this was going, and I was so surprised that it felt like the whole apartment spun for a second.
“And I told them you were cool and I totally trusted you…” she continued to explain.
“Wait,” I cut her off, my mind still reeling, “Why me?”
Her blue eyes studied mine, uncertainty flashing across her pretty face. “Like I said, I trust you. And of course if we really wanted it, I’m sure some stranger in the bar would agree to do it, but I don’t want to have to do that. That would probably be gross.”
And this isn’t?!! I thought to myself, but what I said was, “Are you serious?”
“Yeah listen, if you don’t want to do it, I totally understand. But like I said, it’s HUGE points. HUGE! And I thought, I’m not ugly. What guy wouldn’t want to cum in a pretty girl’s hair, especially if she was asking for him to, you know? And I don’t mean to rush your decision, but we have two hours for this hunt. It’s already been 30 minutes since it started, and I need to get back to the bar because there’s other stuff we can do for points. So like… I just need to know if you’d be willing to do it.”
I had no idea what to say. Looking at Cassidy, her blue eyes blazed now with something I couldn’t quite place. Determination? Desire? If I hadn’t been drinking earlier, if I hadn’t been so turned on by seeing her naked before, if I hadn’t found myself admiring her body so many times, I might have said no. But of course, if I had said no, I wouldn’t be telling you this story.
“Am I hideous?” she asked, prodding me teasingly. “A cute girl is asking you to cum in her hair.”
“Okay,” I replied weakly. “How are we going to do this?”
“Yes!” she shouted triumphantly, a bright smile immediately lighting up her pretty face. She actually began bouncing on her toes in excitement. “I mean, I knew you would do it, and this is a lot of points… we can do this however you want, I just need you to make sure to cum in my hair. We talked about it before I left the bar, my team, and you could cum in a condom and just put it in my hair. But the scavenger hunt list says the guy has to cum IN your hair, so just to be safe it would be better if you could actually, you know, do it in my hair”
“It feels weird just sort of… whipping it out in front of you,” I said.
“I could close my eyes if that helps,” Cassidy offered.
“It might,” I said, “It just… I don’t know.”
“Listen,” Cassidy told me, trying to be reassuring but speaking with a rush of words that underlined her urgency. “You don’t have to do the whole thing right here in the living room. You could, you know, get yourself going in your bedroom if you want and then I could come in and you’d just have to… finish in my hair. I don’t mean to pressure you,” she continued, “I know men don’t do as well with this sort of thing under pressure, but time is important and it would be really helpful to me if we could do this quickly.”
“I understand,” I responded, and quickly decided to take her up on her offer. “Let me… go to my room an I’ll call you when I’m ready.”
Cassidy’s pretty face looked up at mine, her eyes surprisingly full of gratitude. “Thanks, I really appreciate this.”
My mind just had time to register how strange it felt to have a girl be so grateful that I was willing to jack off in her hair. The next thing I knew, I was sitting in front of my laptop watching some of my favorite porn, rubbing away furiously at my cock. I’d like to claim that my pecker was a solid, throbbing rock of manhood, but I couldn’t get the thing fully erect. My eyes were watching some young porn star get nailed on the screen in front of me, but my mind was all over the place. Wasn’t this crossing a dangerous line? What kind of girl asks her recently new roommate to jizz in her hair? Why did she even think of asking ME in the first place?
Beating half limp meat is not a lot of fun, but I couldn’t get myself to concentrate. And then I focused on what was really happening here. Beautiful Cassidy was asking me, even convincing me to cum in her hair. Cassidy, with the big, beautiful breasts and the tight little ass, NEEDED me to cum on her. Cassidy, with the pretty face, and full, soft lips, wanted ME to cum on her.
My cock swelled with desire, and I realized how great it was going to feel to cum on Cassidy. The naked chick with the bouncing boobs in my video was arousing, but the thought of Cassidy waiting in the next room for my cum was electrifying. What I wanted was Cassidy’s wet lips wrapped tightly around my cock. What I wanted was to feel Cassidy’s smooth breasts in my hands, and to wrap them around my manhood. What I wanted was to deliver my steaming load straight up Cassidy’s wet, tight pussy.
Those thoughts were all I needed, I felt the tingling sparks and knew I was close. “Cassidy!” I yelled, “I’m almost ready.”
“I’m in your bathroom,” Cassidy’s voice replied, surprising me from just a few feet away. “I thought it would be easier to clean in here in case there was a mess.”
“I’m coming,” I said, rising to my feet while continuing to stroke my eager cock.
“I hope so,” Cassidy responded with a giggle. It was good to hear her still making light and joking about all of this.
As I turned the corner into my bathroom, I found her kneeling in my bathtub, still fully dressed, eyes closed. Her pretty face and cute little nose, which I had been fantasizing about covering with my cum mere seconds before, was tantalizing. But the rest of it was.. awkward. The glaring bright lights of my bathroom and the cheap white porcelain of the tub made me feel uncomfortable. Even the sight of Cassidy submissively waiting for me was both arousing and confusing.
“I’m ready when you are,” she said. “Please try to get it all in my hair, just to be safe.” Even those words should have driven my libido crazy, but instead they reminded me that this was a task that I was no obligated to complete.
As I walked awkwardly towards her, stroking my cock furiously, the pleasurable tingles started to fade away. My erection was losing some of its rigidness. But I continued towards Cassidy’s waiting body, and her long, smooth, red hair, steadily stroking my dick.
“Tell me when you’re going to do it, if you can,” she asked.
“Okay,” I grunted in reply. Stroke, stroke, stroke. Stroke, stroke, stroke. I stood over her waiting face, admiring her flawless skin and the way her proud breasts pushed out against the fabric of her shirt. But the tingle of impending orgasm was fading.
“Is everything okay?” she asked, eyes still closed. I didn’t know what to say in response, so I kept looking at her sexy little body kneeling before me, her big breasts pushing proudly out against the fabric of her shirt, and I kept beating my meat. Stroke, stroke, stroke.
“Do you need some help?” she asked. Again, I didn’t know how to respond. “It’s okay,” she continued, “I’ll help. You’re doing me a favor after all.”
Without opening her eyes, she grasped the bottom of her t-shirt and pulled the fabric up over her breasts. The sight of the creamy tops of her breasts, bulging out of the top of the purple bra which tightly encased them, sent a little tingle through me. But I had seen more of her firm, young tit flesh when she was passed out in her green bikini. Then she quickly reached behind herself, and her bra was falling away. As I continued to jack my returning erection, her big, round breasts were exposed all the way to her little, pink nipples. I could feel the tingling return.
“Does that help? I can show you my ass if that’s better,” Cassidy offered.
“No,” I grunted, “That’s great.”
Still with her eyes closed, Cassidy reached up towards me with one hand. “Give me your hand,” she ordered. “If you want, you can touch them.”
I reached across my erection with my free left hand, and met Cassidy’s soft fingers. Quickly, she guided my palm down to the top of her right breast. Her tit flesh was warm, and smooth. I squeezed just a little, and felt unbelievably firm fullness in her tit. I moaned softly, the tingles now building in my loins as I palmed Cassidy’s little nipple.
“Mmm, you like that,” she encouraged. “What else can I do to get you to pop?”
“Tell me to do it,” I ordered.
“Tell you to cum in my hair?” she asked, and I moaned my response.
“Cum in my hair, Kevin,” she pleaded.. “I know you would just love to empty your balls right into my hair, and I’m asking you to do it. Cum for me.”
The rivers of pleasure were exploding inside me, flowing through my cock and getting close to overwhelming me. I reached down and gently took a handful of Cassidy’s soft, straight, red hair. She did not flinch or move as I wrapped her silky strands around the tip of my member.
“That’s it, cum for me,” Cassidy whispered.
“Here it cums,” I warned.
And then I was cumming, squeezing the tip of my dick through Cassidy’s red hair, the orgasm bursting out of me in a sharp, pleasurable wave. Cassidy’s eyes opened and she looked up at me as I came, electricity flowing between us as our eyes met while she watched me orgasm. Spurt after spurt of my hot jizz was pumped right into Cassidy’s silky hair, and the visual was seared into my memory. Cassidy smiled, her blue eyes taking in the scene of me cumming on her, her big, creamy breasts on display for me as she knelt before me. My legs shook and I almost lost my balance as I came in her hair, finally having to sit back on the cold edge of the tub.
Cassidy quickly bundled up her hair with one hand to hold in the cum, pulling her shirt back down with the other hand.
“Thank you, I really mean it,” Cassidy said as the afterglow of orgasm wrapped warmly around me. “That was really hot getting to watch your face as you came. And I hope you don’t mind me saying it, but you have a nice, big dick. It’s impressive.” She was already getting to her feet. “Sorry if this was weird, but I have to run back to the bar for the hunt. I’ll see you later, thanks again!”
And with one last smile over her shoulder, she was running out of the apartment. It took me a couple of minutes to clean myself up and process what had just happened. I couldn’t fall asleep for a while, but I had dozed off in my bed before Cassidy returned.
————
The next day, Cassidy didn’t come out of her bedroom until almost two in the afternoon. I grew more and more nervous over the course of the day, wondering what she was going to say and if things were going to be really awkward between us. When she finally emerged, yawning and sleepy eyed, she barely acknowledged me as she headed straight for the kitchen and some food.
Then, as if the thought had just occurred to her, Cassidy yelled to me, “Hey, I really hope last night wasn’t weird. I super appreciate it! My team won the hunt!” And that was all she said about what had happened. She went on for several minutes about how her team had never placed higher than third, and she really loved the fun of the scavenger hunts, and she met a lot of fun people at the party after the hunt.
That was it. Nothing about her asking me to cum in her hair, how she had encouraged me to feel up her bare breast, or how she had egged me on while I ejaculated right into a ball of her red hair. Nothing.
For the first couple of days, I wondered if Cassidy was avoiding the topic. Maybe she was embarrassed. Then one day I came back from a workout and Cassidy was in the kitchen.
“I don’t know how a never noticed before that you have such a big cock,” she told me casually. “It’s not like you hide it.”
To my incredible embarrassment, I could feel my face flushing bright red AND my cock growing a little from the attention.
Cassidy could see the reaction in my face. “Oh come on, there’s no need to be shy about it. You saw my tits and I saw your cock. It’s nothing to be ashamed about, especially in your case.”
I laughed, trying to be light. Before I could think of an appropriate response, Cassidy was walking away towards her room.
And that’s when I finally got it. Cassidy just didn’t care. It wasn’t a big deal at all to her that we had done something sexual, or that she had showed me her breasts, or asked me to jizz in her hair. She didn’t really care.
And that’s also when I finally understood that I was totally and completely screwed. Cassidy didn’t think it was dangerous at all for us to have crossed some personal lines, or that we had ever crossed any lines. It was inevitable that something was going to happen again.
———-
Much like her surprise request for assistance with her scavenger hunt, the event that pushed me and Cassidy into the wild rollercoaster that would wreck us both came as a unexpected, chance encounter.
I was jerking off quietly in my room one afternoon. I don’t remember much else about the day or why I was beating my meat, but I remember almost everything else vividly. I was watching some porn on my computer, and I was getting really close to cumming. I could feel the orgasm building, looking forward to the explosion of pleasure from a sweet, orgasmic release, when I thought I heard my bathroom door open.
“Hey, I was wondering if you have any…” I could hear Cassidy saying.
My mind raced with a thousand thoughts at once. My bedroom door had been locked, but my bathroom door leading to the hallway had been left unlocked. And the door between bedroom and bathroom was open. And I was sitting at my desk with only a t-shirt on and my fully erect dick in my hand. And Cassidy was walking into my bathroom. Why the hell didn’t she at least knock?!!
Without thinking I jumped out of my chair and tried to slam shut the door between the bedroom and the bathroom. For half a second, Cassidy was looking through the doorway, her eyes going wide at the sight of me naked from the waist down with my dick in my hand, and then the door slammed shut in her face.
“What the hell?!” she yelled through the doorway. Without hesitation, she was turning the handle and reopening the door.
“What the hell yourself?” I demanded as the door opened. “Don’t you knock?!”
I thought I would look less guilty if I at least let go of my cock, but as the door opened and Cassidy looked into the room, it still looked pretty bad to be standing with only a t-shirt on and a full erection pointing towards the ceiling. Oh yeah, and the porn was still playing on my computer behind me.
“You were jerking off,” Cassidy said matter-of-factly.
“You can’t just barge into my room, Cassidy,” I replied, trying to deflect the topic but failing to inject the proper sound of irritation in my voice because I was so surprised and uncomfortable.
“Oh, don’t worry about it, it’s totally natural,” Cassidy responded with a reassuring tone, continuing to walk slowly towards me. She was wearing a simple t-shirt herself and a tight pair of jeans. I finally noticed that her blue eyes seemed fixed on my cock, just before she said to me, “That might be the biggest dick I’ve ever seen in person. You mind if I touch it?”
“Cassidy, I don’t…” I began to say, but before I could finish I felt her soft fingers slowly closing over my thick cock.
“Yeah, it’s big,” Cassidy said with some appreciation. “I maybe saw some bigger, but I’ve never touched one like this.”
“Cassidy, you shouldn’t be doing this,” I tried, making no move to actually stop her.
“Why, you’re clean aren’t you?” she asked.
“Of course!” I responded somewhat offended.
“Then it’s totally natural,” She tried again. “Are you forgetting that you already wrapped my hair around this thing and came on me? I’ve kind of wanted to see what it felt like since I saw it.” Her soft fingers were now closed around the head of my cock and began sliding gently up and down over the tip of my shaft.
“Cassidy…” I started, totally distracted by the warm feeling of her light hand job.
“What?!” she interrupted, playfully exasperated. She finally looked up at my face and her dazzling blue eyes met mine. “You jerk off, I use a vibrator. Sex is a totally normal thing, there’s no reason to hide it.” Her fingers were now gripping me more deliberately, my cock still lubricated from the lotion I had been using and the previous tingling from my near orgasm quickly returning.
I just could not believe what was happening. “Cassidy, what are you doing?” I asked.
“I thought it was obvious, I’m jerking you off,” she responded with a bright smile. Her fingers were sliding around my cock head, jacking me more quickly and tightly. “What’s wrong, don’t you like it?”
“Ohhh,” I moaned, “I don’t know…”
“You don’t know if you like it?” she teased, rubbing insistently at the little spot under the head of the very tip of my dick. Her big breasts were beginning to move up and down under her shirt as her arm rose and fell more deliberately with her effort. “That’s too bad because I want you to cum for me.”
“Oh Cassidy,” I couldn’t help myself. She was smiling at me, her blue eyes searching mine while her clever fingers teased and rubbed at my excited manhood. “I’m close.”
“You’re close already,” she asked with a giggle, her blue eyes dancing with amusement. I didn’t know if her girlish playfulness was an act, but it was working.
“I’m going to cum,” I warned.
“Oh, you were serious,” she responded, standing there in my bedroom, fully dressed, while her fingers softly milked my manhood.
“I’m serious, I’m going to cum,” I replied, the familiar fire bubbling up inside my pleasure centers.
A thoughtful look crossed Cassidy’s pretty face as she said, “Where are we going to put this?”
It was too late, the bubbling was boiling over, and the burst of pleasure was on it’s way. “Oh shit!” I blurted uncontrollably.
With a sweet laugh, Cassidy simply closed her other hand over the tip of my dick while somehow still rubbing at that one sensitive spot under my cock head with her thumb. The orgasm seemed to fly up from my feet, shake my legs, and then burn its way through my loins and out of my pulsing member. I arched my back as I came hard, and I could actually hear my cock shooting spurt after spurt of hot cum into Cassidy’s cupped hands.
This time, I didn’t try to catch myself. I fell backwards awkwardly into a sitting position on the floor, with my eyes closed, while the after effects of my orgasm radiated through me. When I opened my eyes a short time later, Cassidy was standing over me with a big smile, her cupped hands full of my dripping cum.
“Didn’t that feel good?” she asked.
“Yeah,” I had to admit, “it really did.”
“Good,” she said. Then she walked away into my bathroom while I stared up at my ceiling trying to figure out what the hell had just happened. I heard the water in my bathroom sink turn on, and what sounded like Cassidy washing her hands carefully in my sink. And then as I lay there with my deflating cock out in the open, I was surprised to hear the water turn off, the bathroom door open, and the door close again as Cassidy left.
———-
It took me a few minutes to get cleaned up and get some pants back on. As I walked out into the living room, I wasn’t sure what to expect. With the way Cassidy had mostly ignored our last sexual encounter, I sort of expected she would just blow right past this one too.
Instead, she greeted me with a smile as I entered the room, looking up from the food she was preparing in the kitchen. “Feel better?” she asked.
“Yeah… I do,” I responded honestly.
“Good,” she said with a smile.
I sat down on the couch, not really doing anything except letting the quiet stretch to see where Cassidy would take the conversation.
She seemed to notice. “I have an idea, and if you think it’s crazy, we can totally forget that I ever mentioned it.” She licked her fingers delicately, to clean off the remnants of the meal she was making, before giving me a slyly inquisitive look.
“Okay, what is it?” I asked.
“Just hear me out for a second,” she began, leaving her food and walking into the living room, “and like I said, no pressure if you think it’s crazy.”
“Okay.”
“I just think,” she started slowly, with lots of pauses, “sex to me is like this totally natural and enjoyable thing. Everyone our age loves sex, so it’s crazy that we’re not supposed to talk about it. I mean, you’re my roommate. I don’t know if you want to know that I masturbate with my vibrator at least once a day, twice a day most days. But I don’t care if you know, I think it’s totally normal for me to want to orgasm at least once a day if I have the time and energy to do it. Who wouldn’t, you know?”
“Makes sense,” I admitted hesitantly.
“So instead of hiding it from each other like it’s this dirty, mysterious thing, I think we should just embrace our desires and our physical needs and be open about them,” she continued. “It wasn’t SHOCKING to me or anything to find you masturbating in your room, of course you jerk off sometimes, every guy does.”
That made me want to ask why she didn’t knock if she knew that I jerked off, but I held my tongue.
“So what I’m getting at,” she continued, “Is that we both know we do it. And you’re a cute guy. I’m not a bad looking girl, and you seem to like cumming with… my help. So why don’t we just, like, embrace it and help each other out, from time to time.”
Despite where the conversation had been going, that was a total surprise to me. “What do you mean?” I ask.
She actually laughed a little at the discomfort in my response, her mischievous blue eyes and bright smile teasing me. “I’m not talking about us just having sex all the time, whenever we feel like it. I mean, I like you, but that would be a little weird with us being roommates and everything.”
More than a little, I thought.
“And I don’t really like you like that, and I don’t think you like me like that. So, like, what I’m saying is, why don’t we just help each other out sometimes. Here’s what I suggest. No sex. No kissing. But basically, anytime you’re feeling really horny and you want some help, if I’m around and not busy you can just ask me for help and I’d be happy to help get you off. Sort of like what I just did for you. I can give you a handjob, I’ll give you a blowjob if you want. We can also do other stuff that you might like, just no sex. And if we’re doing a blowjob or something like that, you have to wear a condom. I mean, I’m clean and you told me that you were clean, but it’s always safer with condoms. If I’m feeling really horny, same thing. I can ask you to help me out. You can use your fingers, or your mouth if you’re comfortable, and help me get off.”
While my mind was still trying to digest what Cassidy was nonchalantly saying, she continued. “But I’m just a girl, and I know how boys are. So if we agree to this, I’m going to need you to help me two times for every one time I help you. I mean, it’s not like I’m going to be, like, super strict and carefully counting or keeping records. But I, like, know how boys can be, and… I just want it to be fair for me too. So it’s got to be about two times for me every one time for you.”
My mind was spinning, overloading trying to process Cassidy’s offer. Looking back, I wonder if my eyes were displaying that spinning hourglass icon from when computers are taking a while to process something. This was the OPPOSITE of what I had wanted when I had agreed to let Cassidy move in. That was my overriding thought. Fooling around with your roommate was even more dangerous than fooling around with a close female friend. Something was bound to go wrong.
But another part of me wondered whether Cassidy had been so logical about her scavenger hunt and helping me get off just moments before, that she could handle some sort of “friends with benefits” arrangement. And that other part of me that was doing some thinking was my penis. I mean, she had laid out the ground rules of this arrangement so precisely, maybe this would provide the dispassionate structure that would protect us. It also didn’t help that she was sitting in front of me, studying my face intently with her pretty blue eyes, her curvy, young body awaiting my answer with obvious eagerness.
Then a question occurred to me: the precise arrangement. “How did you come up with all these rules? Have you done this before?”
Her face dropped so abruptly that I almost regretted asking the question. Her eyes shied away from mine, and she wrapped her arms around herself. Eventually she admitted, “Yes, once. I tried this once before, that’s where the rules came from.”
I couldn’t tell if it was shame or hurt that was dragging down her pretty smile. But my regret at causing the emotion, plus the way she had sold her offer, won out over my better judgment. I should just be honest and say that my penis won the argument.
“Okay, I’m in,” I said, “Let’s do it.”
Her smile returned slowly, but was soon back at full glow. “You sure?” she asked, looking into my eyes. “You can think about it if you want. It is kind of crazy.”
“No, if I think about it, I’ll never make a decision,” I admitted to her. “Let’s agree to your offer now. I’m in. But what’s in it for you?”
“Are you kidding?” she asked with a laugh, her smile now back to full glow. “It’s SOOO much better with a partner. I get off so much quicker, I cum harder. Isn’t it the same for you? Did you cum better with my hand just now, or did you prefer what you were doing before with your own hand?”
“It was better with you,” I admitted.
“See, that’s why this is going to be great.” Without warning, while continuing to talk to me, Cassidy began unbuttoning and unzipping her jeans. “Even just doing it with another person is so much hotter. I rather you, like, even just be in the room and talk dirty to me than try to get off alone.”
“What are you doing?” I asked as Cassidy pulled her jeans and underwear together over the swell of her hips and down her smooth thighs.
“I’m asking you now,” she said with a smile. “If this is going to work, you have to be willing to hold up your end of the agreement. You have to be willing to do it when I want, not just when you want.” She playfully kicked her jeans off over her feet and was suddenly naked from the waist down. “Besides, I got a little turned on feeling your cock pulse between my fingers and shoot all that hot cum into my hand. Now I want to see what you can do for me.”
With that, she spread her legs, showing me her pussy for the first time. I’m not exaggerating, it was possibly the prettiest pussy I’ve ever seen. Her pale skin turned to a deep, healthy shade of pink at her pussy lips. Her sex was smooth and plain and totally bare of any hair. Her lips were small and neatly symmetrical. And she was spreading her legs for me.
I dove in head first at the invitation, leaping out of my seat. “Oh shit!” she exclaimed as my warm mouth closed over her soft pussy lips. My tongue slid up and down over her outer folds and I was greeted with a taste that was definitely feminine but much slighter than I was used to. My tongue bore into her hole, investigating the uniqueness of her pussy, and Cassidy’s hands went to the back of my head, pulling me in as she moaned.
It wasn’t just her outer lips, I confirmed with the tip of my wet, probing tongue. Her pussy didn’t have the musky taste I was used to. I quickly found her clit in my explorations, and I circled it and rubbed over it with my firm tongue.
“Oh fuck!” she hissed from somewhere above me.
I was focused on that little nub, teasing it and rolling over it with my saliva. When I began to lick up and down insistently, Cassidy’s body shuddered in response. My hands were now on the back of her bare thighs, pulling her pussy against my face as I eagerly explored her sex. My soft lips and warm mouth suckled on her womanhood as my tongue danced over her clit.
I sucked her little clit up between my lips and rubbed at it with both my tongue and my lips. Cassidy’s back arched deeply, almost bucking my mouth off of her pussy as she moaned. She seemed to love it as I rubbed at her trapped little pleasure bud, so I did it again… and again… and again….
“Oh shit, I’m….” she moaned loudly. “I’m… cumming! I’m cumming! Don’t stop!!”
I hummed as I held onto Cassidy’s clit with my lips, rubbing gently and insistently, coaxing the orgasm out of her while her pale, smooth thighs shook around my head and brushed against my ear.
When her panting had returned to more normal breathing, I sat back down on the floor and looked up at Cassidy. Her face was flushed, and a big smile crossed her pretty face, framed by her red hair. Her eyes were closed, but as she felt me looking at her, she eventually opened them and her satisfied blue eyes looked back at me.
“That was quick,” I teased.
“I thought you were going to use your fingers or something, most guys… don’t like doing that,” she responded.
“Well I do,” I replied.
“Obviously!” she laughed again, her light, sweet laugh. “You’re amazing at it. If I had known you were that good, I would have wanted us to do this a long time ago. Fuck, I came hard.”
“Good,” I said. “What do we do now.”
She took in a deep breath and then retrieved her discarded jeans and panties from the floor. “Now we just keep doing what we normally do until one of us needs a little helping hand again.”
———-
The new “arrangement” did not start off easily for me. Cassidy behaved as if nothing had changed between us. We hung out in the apartment as much as we did before, and it wasn’t like we suddenly talked about sex all the time, or even more than before. So I went back and forth between being somewhat wary that we had this new deal between us, and sometimes forgetting that we had even made a deal.
Worse, I felt embarrassed asking for “help” from Cassidy. There were a couple of times when she was around and I got horny, a couple of times even when she made me horny. One Saturday night I remember her getting all dolled up, wearing a shiny little dress and heading out to a club. She spent a few minutes chatting with me in the living room, waiting for her friends, and I remember thinking how sexy she looked. It was a classy but low cut top that highlighted her big, round breasts and left the creamy tops of her cleavage exposed. And her red hair was all smooth and silky straight, her pale, toned thighs fully on display. It really turned me on. But Cassidy was just casually chatting with me as if she was clueless to the effect she was having on me. I didn’t know what to say. “Hey, can you give me a quick handjob before you go out, your outfit has me really turned on?” seemed inappropriate. How did I initiate my end of the deal?
So I just sat there, waited until Cassidy left, and then went into my room and jerked off to porn. The whole time I was thinking about how firm Cassidy’s breast had felt in my hand, and how soft her fingers had felt as she rubbed the orgasm out of me. Just before climax, I was kicking myself for not having spoken up and asked for her to do something. And when I came, I pictured myself buried deep in her pussy, her curvy, young body spread out beneath me.
Cassidy, on the other hand, seemed to have no problems asking for my assistance. The first time was a weeknight, where I was predictably hanging out on the couch watching tv.
Cassidy walked into the living room and said, “Hey, can I ask you for a favor?”
“Sure,” I said.
“Well, you remember our deal? If now’s a good time, I could really use your help getting off?” she said. She was very polite about it, but also very much to-the-point in her typical way.
“Oh yeah? Sure,” I responded, getting up off the couch. “Where do you want to do it?”
Moments later, with little more spoken, we were on her bed with my head between her legs. Cassidy still had her t-shirt but was naked from the waist down, and my fingers were spreading apart her pussy lips as my wet tongue lightly circled her clit.
It was almost a pleasure to eat her pussy. Cassidy had such a light, almost indistinguishable taste that I had to seek it out with the length of my exploring tongue. And after several licks and flicks of my tongue over her sex, by the time I had identified her essence, she was moaning near a scream. I looked up at her from between her smooth thighs, bore in with my tongue on her clit, and concentrated on rubbing and flicking her sensitive little nub.
In very little time, Cassidy’s back was arched deeply, her round breasts proudly thrust outward, and her eyes tightly shut as she rode the electricity of pleasure flowing through her body.
“Oh, there…” was all she managed, and then she was nearly screaming. I slathered all over her pussy lips and clit as she came, her soft, young body trembling around me, her moans flowing like one continuous noise out of the back of her throat while she orgasmed.
Afterwards, Cassidy quickly changed and left to meet friends. I masturbated that night remembering the look of overwhelming ecstasy on her pretty face… and my cum spurting between her gentle hands.
The next day, Cassidy didn’t emerge from her room until 1 in the afternoon. I hadn’t heard her come in the night before, so assumed she was sleeping off a long night of partying. When I did finally see her, she shuffled out of her room in sweat pants and a baggy t-shirt and headed straight for our kitchen.
I was sitting on the couch watching tv, and a little surprised when she plopped down into the seat next to me with a cup of coffee.
“Rough night last night?” I asked somewhat jokingly.
“It was fun, but too much tequila,” she responded with a half smile. “Hey… I know I just asked you last night but… well to cut to the chase, you ate me out so good that all I could think about last night was how hard I came. Any chance you’d be willing to do that again to help wake me up this morning?”
We exchanged a quick look, my eyes searching her blue sparklers, and within seconds her pants were gone and I was back between her legs. I admired how toned her legs felt, taut muscle just below the skin as I wrapped my arms around them. Cassidy seemed to love me going straight for her clit, no messing around with nibbling or sucking on her pussy lips. She was writhing, her back arched as my soft lips closed over her hard little button and I sucked her nub up into my warm, wet mouth. Her red hair was a mess, framing her pink face and falling over her shoulders as she twisted her head back and forth while I attacked her clit with my wet tongue. She tasted a little more musty this morning, but as I bore down onto her pussy with my tongue, I marveled that I could still barely taste her.
I was so focused on thinking about Cassidy’s lack of any taste that I had failed to notice her breathing growing ragged, her back arching deeply. I just flicked my tongue over her sensitive clit over and over and over, trying to taste her, until screams finally made me realize that I had brought her to the brink of orgasm.
“Oh SHIT!” she yelled, and then a deep, low grunt of “Unnnnnngggggghhhh” as she came. Cassidy’s hips bucked against my tongue, her chest heaving, large breasts bouncing under her shirt, as she came. I kept steady, slippery pressure on her wet clit while she orgasmed, drawing out her moans as her orgasm subsided.
“You have a talent,” Cassidy told me afterwards, and she quickly pulled back on her sweat pants and headed for her room. “I’m so glad we made this deal.”
And she proved during the week that she wasn’t just trying to tell me what I wanted to hear. Two days later, on Tuesday night, I went out for drinks with coworkers and returned home a little after 8. I found Cassidy sitting on the couch in just a t-shirt and bikini briefs.
She turned and smiled at me with her perfect white teeth and mischievous blue eyes and said, “Can I ask you to go down on me again?” Less than five minutes later, Cassidy was pulling my face into her pussy as she came hard while riding my tongue. Afterwards, I looked up at her, a sleepy smile on her slightly sweaty face, her chest red with arousal, and thought she could not have looked prettier.
Friday morning, I was about to walk out the door for work and Cassidy hopped up on the kitchen counter in front of me. She was wearing a short but conservative grey skirt, and a white button up top that clung to her big, round breasts. As she spread her legs, I realized she wasn’t wearing any underwear.
“Can I get another wake-me-up?” she asked with a coy smile.
It took a little longer with Cassidy wearing her work clothes, forcing us to pause half way through so we could hike up her skirt a little higher. But it was kind of hot eating her out while she was basically fully clothed, suckling on her hard little clit while most of the rest of her was covered. I held her firm ass cheeks in my warm hands, pulling her pussy against my face, as she came on my suckling lips and wiggling, wet tongue.
Her face was glowing as I washed mine in the kitchen sink. “I love going through the day knowing that I already came in these clothes,” she said to me as she pulled on some underwear and smoothed out her skirt. She gave me a quick kiss on the cheek as she walked out the front door.
Cassidy’s sex drive was insatiable. I wanted to ask her to take a turn helping me get off, but couldn’t quite muster the courage. I was so turned on from watching Cassidy’s huge breasts shake while tightly encased by her button down shirt that I was on the verge of asking her to give me a hand job that Friday morning. But she was out the door before I got the chance.
Friday night I went out for drinks with my former roommate and we ended up going dancing with his new fiancée and some of her friends to celebrate their recent engagement. Some of the girls out with us were fairly attractive, and it got my libido going to watch them dance and shake their asses against me. I didn’t get back to the apartment until almost 2 am.
Feeling tipsy and more than a little horny when I got back to my apartment, I decided to do what I had done a hundred times before. I fired up my computer, surfed the internet for some porn, and started jacking off. The apartment had been quiet and empty when I walked in, so I assumed Cassidy had been long asleep. I had my fully engorged cock in my hand, stroking my meat, watching a busty porn star deep throating a big dick on my computer screen, when I was surprised by a soft knock at my door.
I was still wearing my clothes from clubbing, very aware of the bulge in the front of my pants, as I cracked open my bedroom door. Cassidy was standing in the hallway, her eyes looking a little sleepy, wearing a large, loose t-shirt as pajamas.
“Hey Cassidy, what’s up?” I asked softly.
“You just get home?” Cassidy asked, stifling a yawn with her fist over her mouth.
“Yup, you need something?” I asked, careful to keep my pants-filled erection behind the door.
“The power went out here earlier tonight. I had to reset my clocks, and my internet wasn’t working,” she explained. “I can help you get the wifi working again with your computer if you want.”
“No, thanks though. My internet is working fine,” I replied with a smile, hoping that would settle it and I could get back to finishing what I had started.
Cassidy looked at me questioningly, her big, blue eyes suspicious. “You’re already online?” she asked. “You just came in a minute ago. What are you doing in there?”
“Just needed to check some e-mails,” I responded, the smile never leaving my face.
Before I could react to what was happening, Cassidy had thrown a shoulder into my door and was slipping into my room. “You can’t check e-mail on your phone? What are you up to?” she demanded as she confidently bulled her way into my room.
“Cassidy!” I scolded her. “Personal space!” I was genuinely shocked by her intrusion.
“Personal space my ass,” she responded, “I came with your tongue in my pussy this morning, remember?”
She had already walked around to my desk and was looking at my computer screen. Her blue eyes quickly flashed back to mine, and then lowered to the noticeable bulge poking up into the front of my pants.
“Oh honey,” Cassidy scolded.
Prepare to defend myself against to usual accusations that watching porn was a dirty a deviant behavior, I responded, “Hey, it’s a totally natural thing.”
“Of course it’s a totally natural thing!” Cassidy responded, her hands going accusingly to her hips. “That’s why we made a deal, remember?! You help me and I help you. Why didn’t you just tell me, as soon as I knocked, that you were trying to get off in here.”
I was speechless. My brain was scrambling trying to catch up to the many unexpected turns in events.
“The deal means I help you too, when you need it. Especially a talented, big tongue like yours,” she continued.
Overwhelmed by trying to think through to an answer, my brain just defaulted to the truth. “I didn’t know how to ask,” I replied dumbly. “I didn’t know when it’s okay… like it’s pretty late tonight.”
Cassidy flashed me her sparkling, white smile. Slowly, she reached out and closed her small, soft hand over my fingers. She guided me to my chair and asked, “Were you doing it right here?”
She patted the seat, looking up at me coyly with her blue eyes from beneath her red hair, and I sat down. Then she dropped to her knees in front of me, her small fingers fumbling with my zipper and pulling it down. I could feel her soft touch as her finger closed around my still stiff pole, and she carefully pulled it free of my pants.
“Cassidy,” I said, unsure of what to say next.
“It’s okay, sugar, you just keep watching your video and I’ll just show you how much better I am than your hand, and why you should learn to ask.”
She turned around briefly, pressed a few buttons until the porn started playing again, and then turned back to me with a smile. Her bright blue eyes were looking up at mine, her big smile full of sparkling white teeth on her face, and her small fingers wrapped around the base of my cock.
“You have a really big dick, I don’t know if I’ve told you that already,” she said, still smiling. And then she leaned down and my aching cock head disappeared between her soft lips.
Cassidy’s soft, warm, slippery mouth closed over the head of my member, her tongue circling teasingly around the head of my cock. Then she plunged down, swallowing more of my long pole than any woman had even attempted before, slid her tongue back up over the underside of my shaft as her head rose, and then plunged back down again, tightly enclosing my meat in her warm, wet cheeks. For the first minute or so, I actually watched the porno blowjob on my computer screen behind Cassidy, my brain tantalized by watching a blowjob while also receiving a blowjob. And Cassidy was very good at sucking my dick. Her tongue swirled my tip and her soft lips sucked over my sensitive skin, and her hot, wet mouth enveloped me.
I eventually realized I was being an idiot. I had fantasized about Cassidy blowing me, dreamed about it, wished for it. And now it was happening right in front of me! Her long, fiery red hair hung over her face, hiding most of what was happening, but it was still a dream to watch her locks tumbled back and forth while her wet mouth suckled on my cock. She suckled noisily and hummed as her wet cheeks slid up and down my throbbing pole. Cassidy looked up and me from beneath her hair, her tongue swirling again around my cock head and she held just the tip of my cock between her full lips. She smiled when her blue eyes met mine.
Her soft fingers began sliding up and down my meat along with her mouth, exciting so much of my erection that I knew I wouldn’t be able to hold off for long. As her warm mouth sucked me and her slippery, soft fingers slid tightly over my erection, I felt the familiar tingles starting again in my body.
“Cassidy,” I tried to warn as her warm mouth continued to slide up and down my pole, “I’m going to cum.”
She never stopped sucking, never stopped jacking me with her small hand. Her mouth and her fingers slid up and down my sensitive meat, and when her blue eyes looked up into mine again, I exploded.
The orgasm was so powerful, I squeezed my eyes shut. But I could feel that Cassidy’ mouth never stopped sucking me, her tongue coaxing the cream out of me by lapping at the underside of my shaft as I sent burst after burst of cum flowing into Cassidy’s mouth. My toes curled and my legs strained with the pleasure of orgasm as I blew my load between Cassidy’s soft lips.
By the time I came back to my senses and opened my eyes, Cassidy was looking up at me with a beaming smile and a twinkle in her bright blue eyes. She had clearly swallowed all of my load.
“See,” she said coyly, “Wasn’t that much better than just doing it with your hand.”
“Oh my God, you have no idea,” I responded with a satisfied sigh, and a smile of my own.
Cassidy laughed her light, sweet laugh in response. She rose slowly, kissed me softly on the forehead, and began to walk casually out of my room. “Good,” she said over her shoulder, just before closing my door behind her. “Maybe next time you’ll ask.”
———-
The next morning I started my day with a shower. As I was washing away the sweat from the night before, I was completely distracted by thoughts of the amazing blowjob I had received. The blowjob was so good, I was still not completely sure that it hadn’t been a dream. Any lingering doubts were washed away with the sweat when I was startled by the shower door opening.
Cassidy just stepped in, completely naked. I was frozen, paralyzed by shock. This stuff happened in pornos, it didn’t happen in real life. Cassidy’s deep, loud laughter, and the way her big, round breasts shook as she laughed, knocked me out of my paralysis.
“What the hell are you doing in here?” I asked.
“Oh relax,” Cassidy replied, with a teasing slap of my shoulder. “Didn’t you enjoy last night?”
“Yes, you were great,” I admitted. “You can’t just hop in the shower with me. We need some boundaries.”
“Boundaries are bullshit,” she replied. “Or didn’t you enjoy how I got you off?” Cassidy’s hand reached out through the warm shower water cascading between us, and she grasped my cock gently with her soft fingers as if to emphasize her point. She rubbed softly at my cock head, and my meat instantly began swelling. “Ahhh, even if you don’t agree, your dick still remembers last night. You had so much cum, and you were such a dummy about just asking me to help, that I thought I would check on you.”
Cassidy’s fingers were running over the underside of my shaft, while her thumb circled my cock head. I quickly had a full erection, between her soft rubbing and the sight of her incredible, naked body.
“You do want this, don’t you?” she asked quietly, her fingers never stopping their gentle rubbing on my slippery manhood. “We made a deal, and I still owe you one from what you did for me this week.” Her blue eyes searched mine as her finger closed around my shaft and started jacking me in earnest. Her eyes were so beautiful, and her small, pink nipples were such a turn on for me to see.
“If you want me to stop, just say so,” Cassidy said softly over the noise of the falling water.
“No,” I replied quietly. “Don’t stop.”
“Then ask me for this,” Cassidy instructed, her fingers tightening slightly as her closed hand slid up and down my pole. “Ask me.”
“Jerk me off,” I responded.
“Ask me to do it,” Cassidy replied, color filling her cheeks. She was getting turned on by this.
“Cassidy, give me a handjob,” I replied firmly as her fingers milked my shaft.
“Tell me to do it,” she responded huskily, “Tell me so I know that you’ll be able to ask me again.”
“Cassidy,” I responded, my confidence growing. My hands reached up and grabbed her soft shoulders. “Use your hands to get me off. Play with my cock until I cum.”
“Ohhh,” she moaned, a dreamy look now in her eyes. Her moan and her facial expression turned me on more than her fingers slipping up and down over my wet cock.
I slid one wet hand down off her shoulder, over her chest, and rubbed softly at one of her pink nipples with my thumb. The warm water cascading over her smooth breasts, flowing into a river between her perky cleavage, was so arousing to see. My cock swelled between Cassidy’s fingers, and she grasped my pole with both of her hands. Her soft, closed fingers began gently squeezing me while turning in opposite directions, an amazing sensation of stimulation and arousal that is difficult for me to describe.
“You like my breasts?” Cassidy asked as my fingers slipped over the tip of one of her big, firm mounds. I was drinking in the sight of her pale, smooth tit flesh being washed by the water.
“Yes, they’re amazing,” I replied honestly.
“Tell me,” Cassidy asked breathlessly. Her red hair was beginning to get wet from the spray and sticking to her neck and back. Both of her hands were softly and gently milking my long dick. “Tell me what you like.”
“I love your breasts, they’re so sexy,” I responded as Cassidy’s hands tugged upwards over my excited pole. “Your face is so beautiful… your eyes and your lips… You’re so sexy!” I was losing control, both over my words and my body.
“Tell me what you want. Tell me what to do,” Cassidy instructed, almost begging. “Tell me what you like.”
“I love your breasts, I want to fuck them,” I responded.
Abruptly, Cassidy released her grip on my cock and squatted down under the continuing spray of the shower. The warm water washed over her red hair, flowed down her neck, and between the valley of her cleavage. She put her hands at the sides of her big, round breasts, moved forward a bit until my raging erection was between her tits, and then closed her interlocking fingers over her nipples and my cock.
“You want to fuck my breasts,” Cassidy replied. “Go ahead.”
I thrust my cock up between Cassidy’s soft melons. I LOVE tit fucking. It felt so soft and so firm at the same time, Cassidy’s smooth, young tit flesh tightly enclosing my shaft as it slid up and down between her wet melons. As I thrust back and forth into her tunnel of tit flesh, I was also amazed that Cassidy would let me do this. She had to squat in the shower, with spray from the shower water running over her face, but she smiled up at me with her big, blue eyes as I pushed my cock in and out from between the tight tunnel of her breasts.
After only a few thrusts, the experience and the unbelievable sight before me began to overwhelm me. I felt the familiar pleasure of an impending orgasm.
“Oh Cassidy,” I moaned, “I’m going to cum.”
“Where do you want to cum?” she asked, her bright smile never wavering. “Tell me.”
“Ohhh,” I moaned as the pleasurable flows began to build beyond the point of no return. “On your face. I want to cum, on your face.”
Cassidy paused, the smile faltering for just a second, before she replied. “Well go ahead then, cum on my face. Cum for me.”
One more thrust between Cassidy’s slippery and soft tit flesh, and I pushed my cock so the tip was sticking up above Cassidy’s cleavage. I came hard, fighting to keep my eyes open as the orgasm burned like lighting bolts through me. A fat stream of white cum shot out of my tip and splattered from just beneath Cassidy’s nose, down over her full, smiling lips, and puddling on her chin. My cock spurted again and again as I came, but the rest of my spunk struck Cassidy under her chin and dribbled down wetly over her neck and the tops of her breasts. By the time the tingling stopped, I was greeted by the sight of Cassidy’s red hair plastered wetly to her back, a line of white cum over her smiling lips, the length of my shaft tightly encased between her big, beautiful, round breasts, and my cock head popping out of the tops of her breasts in a puddle of cum.
Cassidy slowly stood and carefully began to wipe the cum off of her face and chest with the aid of some soap and shower water. I tried to help her wash some of the cum off of her chest, then realized that my hands were also pawing at her round, firm tits
“Is this okay? I asked.
“You are a sweet one,” Cassidy responded, and then gave me a little peck on the cheek.
As we were both drying off with towels a few moments later, Cassidy said, “Now I hope you know you better ask the next time you need a little help.” Her accompanying smile was honest and warm, empty of any teasing or irony.
“I do,” I replied.
———-
I’m sure a lot of people will be exasperated by my timidity at this point in my story. All I can offer in my defense is that I really did not want to screw up my living situation, and I thought a good outcome was very unlikely. I was not the type of person who this kind of stuff happened to, and I knew all this fooling around between me and Cassidy could be dangerous if it didn’t go well. It turned out that I was mostly right.
I’d like to say that, after the blowjob and the shower, I dove right into exploiting my deal with Cassidy. That’s not totally true. We did fool around A LOT. I haven’t met any women who could match her sex drive, so she was always asking me to pleasure her. She especially loved me going down on her, and that became almost all we did. She asked me almost every other day, mostly at night though sometimes in the morning before work. I began to catch on to when she was having her period, because she would be less interested in sex just before and during her period. But immediately after she was done, she would almost attack me as soon as I got home, and would ride my mouth and my tongue to screaming orgasm. I got very good at figuring out how she especially enjoyed me just tickling lightly over her clit with my tongue while she came, and she got so loud that I’m sure the neighbors heard us at least once or twice.
I also got better about asking for her “help,” which was a blowjob most of the time. Cassidy was VERY good at blowing me, and she loved hearing that she could take more of my dick in her mouth than any girl I had met before. She tried deep throating a couple more times, but she would quickly start gagging if my cock was in her throat too long. Still, her soft lips and slippery cheeks made me cum quickly every time. But I didn’t ask to fuck her tits again, and I didn’t ask to cum on her face. I could tell that she hadn’t been thrilled when I asked to cum on her face the first time. Sometimes a hand job was good enough, and I really enjoyed watching her big, full tits sway back and forth as her hand pumped up and down my dick. But her blowjobs were so good, I mostly just asked for that.
Cassidy also began learning what I liked. She knew I loved her breasts, and would be sure to take her top and bra off at the start, whenever she was going to give me a tug job or blowjob. And she encouraged me to touch and play with her big, soft breasts while she was pleasuring me. I learned that her smooth, creamy inner thighs were very sensitive, almost to the point of being ticklish. To get her going, I would run my fingers lightly over her soft inner thighs before I went down on her.
Still, that was all we did. Three or four times a week, I would eat her out and make her cum. Once or twice a week Cassidy would blow me. She started getting comfortable wearing just a loose shirt and bottoms around the apartment, or sometimes just the shirt. And she was so sexy she still turned me on like crazy every day. But after four or five weeks of helping each other cum, it almost got routine.
We may have eventually gotten bored of deal… maybe… if not for a couple of events that escalated our situation. Both were Cassidy’s fault, of course. The first erupted over a scandal at the University of North Carolina, of all places. Cassidy had graduated from UNC, as had most of her family. She had grown up cheering for the school. So when news of a scandal broke, and the university was charged with allowing hundreds of athletes to take a fake class in order to inflate their grades, Cassidy insisted it couldn’t be true.
One evening I was watching the news and a story came on about the UNC scandal. Cassidy blurted out, “You’ll see! It can’t possibly be true.” She was normally so free spirited and laid back that it was the closest I had ever seen to her becoming angry.
“I don’t know,” I replied honestly and skeptically. “It seems like they have a lot of evidence. They’re talking about firing people over this.”
“There’s no way it’s true,” Cassidy insisted loudly. “It’s a respected institution! There’s no way the university would let bad people cheapen the value of a degree from UNC just to help out some athletes. You’ll see!”
“I don’t know…” I responded carefully again. “I’m not trying to get you worked up, I’m just saying that it seems like they have a solid case. I don’t want you to be stunned or disappointed when it turns out that they really did have this fake class for athletes.”
“Well, you’re wrong!” Cassidy snapped back. “You’ll see, in a couple of weeks it’ll turn out that this was some kind of hoax started by someone with a grudge against the athletic program. I don’t know why you’re even arguing against me anyway, you know how I love UNC.”
“I do know,” I tried to soothe her. “But I’m just trying to tell you that this thing looks real. Don’t be surprised if it turns out to be true.”
“You’ll be eating those words and feeling like a jerk when this all gets disproved,” Cassidy replied confidently.
“It doesn’t look like it’s going to get disproved,” I responded, now getting a little irritated that Cassidy was so obstinate about this news story.
“Fine,” she replied icily, “If you’re so sure of yourself, then agree that you will wear UNC t-shirts and gear every Saturday and Sunday for a month after they admit that this whole thing was made up.”
“No fucking way,” I responded with a laugh.
“Because you know you’re wrong!” Cassidy roared, her blue eyes burning with her own irritation.
“Calm down,” I said. “I don’t own any UNC clothes, and I’m not wearing that crap for a month.”
“I have some jerseys and an old sweatshirt that would be big enough for you,” Cassidy parried. “You just know you’re going to be wrong.”
“What do I get when it turns out this whole story is true?” I demanded.
“Whatever you want, because you know I’m right,” Cassidy offered, her lower lip stuck out like an indignant child.
Irritated by her insistence on arguing, I thought over what I wanted for a moment. Looking at her pretty but angry face, the thought hit me. “You didn’t like me cumming on your face that one time, did you?” I asked.
Cassidy paused cautiously before replying. “Not really. I don’t hate it, but I don’t really like it either, so I normally don’t let guys do that.”
“Fine,” I said triumphantly. “That’s what I want. If you’re right and this story turns out to be wrong, I will wear your UNC gear every weekend, all weekend, for a month. But if I’m right, you have to let me cum on your face.”
To my surprise, Cassidy didn’t hesitate. “Fine, it’s a deal.” She extended her hand, and we shook on it, after which she said, “You’re going to hate being wrong.”
The days passed and the evidence began to build that the stories about UNC were true. One person resigned and others were fired. University officials apologized. The days turned into a week, and there appeared to be no doubt that UNC had permitted student athletes to attend a fake class.
Cassidy and I did not stop our deal during this time period. One night as soon as I got home from work, she jumped me and I ended up eating her out on the living room couch. She crushed my ears with her thighs as she came on my flicking, wet tongue. That Friday night, she came home from the bar a little drunk and horny, and I went down on her on her bed. She moaned loudly and deeply several times as she came, and fell asleep with a smile on her face shortly afterwards. On Saturday morning, shortly after I woke up, she rewarded me with a sloppy, wet blowjob while I lay in my bed.
But we never talked about the UNC scandal. I felt a little bad at even making the bet, knowing that the evidence on the news seemed so strong and Cassidy was blinded by her loyalty to her school. I decided not to mention our bet or try to redeem the prize we had agreed upon.
But Tuesday afternoon, when Cassidy got home from work, it was the first thing she mentioned when she walked in the door. Normally she got home before me, but that day I had changed out of work clothes and was drinking a beer while watching tv on the couch. The door had barely closed when she said, “Alright, you win. The stupid story about UNC allowing athletes to cheat was true.”
I looked over my shoulder at Cassidy. She was wearing one of her tight little black skirts with matching black jacket over a white top. It always impressed me that she looked sexy and deliciously curvy no matter what type of clothes she was wearing.
“I’m really sorry about your school,” I replied. “It really sucks, but it sounds like they’re now trying to do the right thing by firing people.” I felt genuinely bad for her.
“I know, thanks for saying that,” she said dejectedly as she tossed her keys and her purse onto the kitchen counter. “But a deal is a deal. You can cum on my face.”
“I don’t have to, don’t worry about it,” I offered.
“No, no, no,” Cassidy responded, shaking her head emphatically to emphasize her point, her smooth red hair waiving back and forth. “I was raised that a deal is a deal. You make an agreement, or you have an obligation, you live up to it and fulfill your part. I said you could cum on my face and you were right, so I’ll let you cum on my face.”
“You sure?” I asked. “I don’t want to make this news story any worse for you.”
“It can’t get much worse,” Cassidy said with a sigh, before putting her hands on her hips and fixing me with a smile. “But if it’s all the same to you, I’d rather get this over with sooner rather than later. You think you could do it tonight?”
“Cum on your face?” I asked.
“Yeah, I rather just get it done with so I can know I lived up to my end of the bet. You can do it however you want,” Cassidy offered, her bright blue eyes never leaving mine. “I can help you out, or I can come in your room, or you can go watch porn and just let me know when you’re ready. I can get naked or whatever, I just don’t want to mess up my clothes or any of our furniture.”
“Well that all sounds reasonable to me,” I responded with a laugh at how much thought she had put into this. I considered my options for a moment and then said, “Why don’t I try to make this as easy for you as possible, to show there are no hard feelings over the bet. I’ll go in my room and jerk off, and when I’m ready I’ll yell for you and just finish on your face. Just go in my bathroom and we can do it in the shower so we don’t make a mess.”
“If that works for you, it works for me,” Cassidy responded. “You want me to be naked when I come in your room?”
“Honestly, I’d prefer you look just like that,” I said, “You look so sexy in those work clothes. But you said you didn’t want to mess up your clothes, so come in wearing whatever is comfortable. You know I love your body, so naked works fine for me.”
“Okay,” Cassie responded with a smile. “That works for me. Just yell when you’re ready.”
Seconds later I was naked myself, sitting my desk chair, jerking off to an orgy scene from a hot, high end porn. I hadn’t had to use porn much to get off, with Cassidy so willing to help when I needed, so there was something really hot about seeing those sexy bodies fucking. It was like my mind had forgotten some of the hotness of porn. My cock was rock solid in no time, and I felt the excited pleasure flowing through me like I could cum. The thought of cumming on Cassidy’s beautiful face, her smooth skin and sparkling smile covered with my spunk, also got me turned on and ready to burst. But I remembered how I’d had a little trouble cumming in her hair the first time I came with her, so I took my time and made sure my balls were churning and I was really close to popping before I called her into my room.
“Cassidy!” I finally yelled, “I’m ready!”
Just a second later, my bathroom door opened and I heard Cassidy walking into my room. I was very distracted, so close to cumming. I was trying to walk from my desk to my bathroom with my aching cock in my hand, trying not to hold it so tight that I rubbed it and came prematurely. I was aware in the periphery of my vision that Cassidy was kneeling in my bathtub, but I was in for another surprise when I finally got to the edge of the tub.
“You’re still wearing your work clothes,” I said. She looked so smart and sexy in that outfit, her red hair loosely falling over the shoulder of her black jacket. Her white shirt fell loosely over her chest, but with the dr*pe of her jacket and the way her large breasts poked out through her front, it almost accentuated her round, firm chest.
“You said I looked sexy in these clothes,” Cassidy replied with a slight smile.
“But you said you didn’t want to mess up your clothes,” I stated, confused.
“The point is to cum on my face, remember,” Cassidy responded. Her eyes moved to my still engorged cock wrapped tightly in my hand. “Go ahead, honey, cum on my pretty face.”
“You sure?” I asked, “I don’t want to mess up your clothes.” My hand began to slide up and down my cock, the pleasurable tingling returning as I looked down at Cassidy’s beautiful, waiting face.
“Then cum on my face,” Cassidy replied, her blue eyes moving up to meet mine. “Isn’t that the point? Don’t I look sexy for you dressed up like this? I’m on my knees for you, just waiting for your hot cum on my face.”
“Oh God,” was all I managed, as my hand slid up and down my cock and I looked at Cassidy’s smooth, smiling cheeks. Seeing Cassidy’s sparkling blue eyes looking up at me, the smile on her full, pink lips, I lost total control. The orgasm burned up suddenly through my loins and burst out in a surge of pleasure through my cock. I managed to keep my eyes open, transfixed by Cassidy’s dazzling white smile as she closed her eyes, and my first thick, hot rope of cum splattered squarely over her smiling, pink lips. My cock pulsed again, and another rope of cum landed on Cassidy’s smooth right cheek. Then another on her chin, and another drawing a while line on her soft, pink lips. Finally my cock sent a weak glob onto the tub between my feet, but the orgasm continued to light up and tantalize my body for several seconds afterwards, as I soaked in the view of Cassidy’s sexy, pale face covered by my hot, white cum.
Finally, with her eyes still closed, Cassidy asked, “Did you get any on my jacket?”
“No,” I said, trying to inspect her clothing, “But it’s starting to run down onto your shirt.” I reached for some toilet paper and tried to wipe away the little bit of my spunk that had splattered around her closed eyes.
“That’s fine,” she said with a smile, carefully removing her jacket while she kept her eyes closed. When I was done wiping, she opened her eyes and stood. “You enjoy that?” she asked me.
“Hell yeah,” I responded with a beaming smile.
“Good, I’m glad,” she said as she stepped out of the tub. “A deal is a deal. But now I have to go clean myself up. Thanks for not getting cum on my jacket.”
“Thanks for letting me cum on your face,” I replied.
“Anytime,” she said with a smile, as she walked out of my room. Anytime?
————
The following weekend, just a few days after spraying my jizz all over Cassidy’s face, I was asleep in bed around 4 am on Saturday. I started to wake just as I realized that Cassidy was in the bed with me.
“What the hell?” I asked groggily. I was sleeping under a sheet in just my boxers, and I could feel Cassidy’s firm young body pressed against me beneath the covers. I could also feel her hand on the waist band of my boxers, and it felt like she was trying to pull them off.
“I want you to fuck me” she whispered. I could easily smell the strong scent of alcohol on her breath.
As I rolled onto my back, Cassidy’s hand closed around the base of my cock and pulled my manhood out through the front of my boxers. “You said no sex,” I reminded her, still trying to wake my muddled mind. I felt one of her full breasts resting against my chest and asked, “Are you naked?!”
“I know what I said,” she hissed, the smell of vodka almost overwhelming me. “But I need to get fucked tonight and I dream of feeling this cock inside of me.”
Cassidy’s soft hand was gently pumping up and down my mostly flaccid member. My mind was still confused but my cock was beginning to react and inflate on its own. “I don’t know..” I began to say.
“Don’t you want to fuck me?” Cassidy asked insistently. She threw a leg over my body and began straddling me, her hips now on my thighs and her hand still rubbing at my cock head. “What do I have to do to you? You make it seem like you don’t want me. Do I have to throw myself at you? Why don’t you want my body like other guys do?”
“Cassidy, you’re hot,” I tried, still rubbing my eyes and not sure if I should stop this or encourage it. “But you said no sex.
My cock was now mostly hard, between Cassidy’s insistent rubbing and feeling her big, firm, bare breasts against my chest. “Then let me feel this big cock inside of me.”
Cassidy lifted her hips and placed my cock head at the entrance to her wet pussy. I could feel the softness of her pussy lips and the slight moisture of her opening. She was turned on. Cassidy put her hands on my chest, sunk her hips down, and my cock head popped through the tight opening of her sex and slid a few inches into her hole.
“Ohhh yes,” Cassidy moaned. She lifted her body up, letting my cock slide most of the way out of her tight, wet tunnel, and then settled back down on my erection. My dick was now fully erect, and she didn’t quite make it to the bottom of my rod before she began sliding back up my pole again.
“So fucking big,” she moaned, my big cock plunging back into the soft, wet embrace of her sex as she slid back down me. I couldn’t resist anymore and shoved my hips upwards, plunging the last few inches of my cock into the warm, wet tightness of her pussy walls.
Cassidy’s mouth formed an O as she sucked in air atop me and froze. “So full,” she squeaked. She had asked for this and I was going to give it to her.
My hands reached up, cupping her breasts, and I began to rapidly thrust my hips up and down, shoving my hard cock in and out of her. “Oh yes… oh God,” Cassidy moaned atop me. She tried to match my rhythm, but I was pumping up and down so fast that she began to just hold onto my chest as I rocketed my cock in and out of her tight hole. My palms were filled with her firm tit flesh as she held on while I rocked my cock rapidly back and forth inside of her.
“You want to cum?” I teased through gritted teeth as I fucked Cassidy hard.
“Yes!” she moaned.
“Then cum!” I demanded, never slowing as my long, thick cock plunged in and out of her pussy.
“OHHHHH FUCKKK!!” Cassidy screamed, and then her hips squeezed hard against the sides of my body. I never stopped plowing my hard meat in and out of her hole, my pelvis slamming against hers as I buried myself to the root, while the juices of her orgasm began dripping out of her sex and running down my pole. Her body shook and she closed her eyes as she came hard atop me, riding my stabbing cock into a deep orgasm.
“Fuck!” Cassidy finally exclaimed, throwing her leg back over me and falling off my cock like she was awkwardly dismounting a Rocky(H). “You fuck so hard,” she complained.
“You said that’s what you wanted,” I responded.
Cassidy laughed, a soft, sweet laugh, the smell of booze still floating on her breath. “If I had known you could fuck like that, I would have jumped you sooner.”
She placed a hand softly on my shoulder and nestled her head against my arm. Her red hair tickled the side of my body, but after a few, short, deep breaths she seemed to be fast asleep.
I couldn’t believe it. She had woken me, gotten me hard, and used me to get herself off. Then she had gone right to sleep, leaving me with a rock hard cock still wet with the moisture from her pussy. This girl was incredible. I was very aware of her large, soft breasts pressed into the side of my body, and that I was still turned on. For a moment, I considered what I could do to bring myself to orgasm. But I had never fully woken up, and that time considering what to do was enough for my eager cock to start deflating. I decided to try to go back to sleep, and before I knew it, I was dreaming again.
———-
When I woke up with a start several hours later, the sun was coming in my window. I looked over my should to find Cassidy awake, her red hair a mess around her head, and her blue eyes looking back at mine.
“Sorry about last night,” she said.
“You better be,” I replied with a laugh.
“You mad?” she asked.
“No, but you’re the one who said no sex,” I responded. I threw aside the sheet that was covering me and began to get out of bed.
“I know, I’m sorry,” she responded. “Where you going.”
“I have to piss,” I replied. Cassidy got out of bed, her curvy, young body still naked, and followed me. “You going to help me piss?” I asked.
“No, I just want to make sure you’re not mad,” she replied.
I left the bathroom door open, expecting that she would talk to me through the doorway, but she followed me all the way into the bathroom. With a sigh of resignation, I lifted the toilet seat and began to relieve myself in front of her.
“You don’t respect any boundaries, do you?” I asked.
“Boundaries?” she responded. “You’ve cum in my hair, on my face twice, and now we’ve had sex. You’ve seen me naked and gone down on me more times than I can count. I think we passed through most of the boundaries a long time ago.”
I thought about that as I concentrated on my aim for a minute, and as I finished up, I said, “Well I don’t like you suddenly changing the rules. And I don’t appreciate you attacking me in the middle of the night just because you need to get off.”
“I know,” Cassidy said quietly. “I told you, I’m sorry about that.”
I wiped my cock head with some toilet paper, flushed, and turned to find that she had been watching me the whole time. “I think there should be repercussions when you do something like that,” I told her.
“I agree.”
“So what did you have in mind?” I asked.
“Anything you want,” Cassidy responded coyly.
“What’s that mean?” I asked.
She paused for a moment, and then her big, blue eyes stared straight into mine. “I couldn’t resist, last night,” she began. “For weeks I’ve been thinking about how that big dick of yours would feel inside of me. I’ve never sucked one so big, and I couldn’t get it out of my head how it would feel stretching my pussy like it stretched my mouth.
“Anyway,” she continued, “I still shouldn’t have jumped you like that. So you tell me how I can make it up to you and I’ll do it.”
In truth, I had been contemplating this thought since Cassidy fell asleep next to me the night before. “First, the ‘no sex’ rule is done. If we’re both up for having sex, then let’s just do that instead of blowjobs and hand jobs.”
Cassidy hesitated just a second before saying, “Okay.”
“Second, you owe me sex twice, whenever I want it, within reason, since you just jumped into my bed last night,” I finished.
“Okay,” she replied. “That’s fair. I owe you sex twice, whenever you want it.” She looked at my cock, now standing stiffly straight with morning wood. “You want it now?”
“No,” I said, with a smile. “You also owe me a blowjob.”
Cassidy looked at me, her eyes questioning, and then dropped to her knees on the bathroom floor. I walked forward confidently, my cock pointed at her face, and stopped with my cock head just an inch from her soft lips. Looking up at me with her bright, blue eyes, Cassidy’s soft, pink lips parted and she sucked the head of my dick into her warm, wet mouth.
I didn’t last very long, especially with the activity from the night before. Cassidy’s tongue swirled my cock head, and both her hands and her soft, sucking lips slid up and down over my sensitive cock skin. She milked me with her firm fingers and her wet, slippery lips. When I felt the tingling of my approaching orgasm, I quickly withdrew my cock from between her soft lips.
Cassidy’s blue eyes looked up at me in surprise, as my hand grasped my dick and pumped up and down my swollen member just inches from her face. She didn’t have time to close her eyes before I blasted the first spurt of my load all over her pretty, little mouth. Cassidy recoiled in surprise, but I was careful to aim my cock lower so it sprayed it’s hot spunk all over the tops of her big breasts while I closed my eyes to enjoy the sensation of the orgasm flowing through my body.
When I was done cumming, Cassidy whispered, “Jerk.”
“You deserved that,” I said with a laugh, once again using toilet paper to help her clean her face. None of my cum had gotten in her eyes this time, though the tops of her full, round breasts were completely covered in my jizz. I was growing to love the look of Cassidy’s pale but pinkish skin coated in my white juices. “No more attacking me in the middle of the night, at least without my permission.
“We’ll see,” she said as she stood to leave my bathroom.
———-
That week, Cassidy asked me to go down on her a couple of times. I got a blowjob on Thursday night in return. At first she seemed surprised that I didn’t ask for sex immediately, but she quickly caught on that I was saving those opportunities.
Seeing her hot, naked body all the time, it was hard to resist asking. At one point she was watching tv in the living room wearing only just a pair of panties. Looking at her big, firm breasts on full display, I almost asked her then. I couldn’t stop staring at how upright and round her big breasts sat on her chest. But I held off, at least for a little while.
That Saturday night, Cassidy once again did something I had not expected, and I surprised myself. We went out to drinks with several friends to celebrate our former roommates’ upcoming wedding. Cassidy was wearing this short, tight, powder blue dress that showed off all of her fantastic curves. Her smooth, toned legs were on full display, with the hem of her dress ending well above her knees. The dress hugged her round, toned ass, and also clung to the swell of her big, round boobs. The front of the dress scooped low to show off the full tops of her smooth, perky breasts. And I was far from the only one to notice how amazing she looked that night.
When Cassidy went for drinks at one point late in the evening, two guys at the bar sidled up to either side of her and started chatting her up. Whatever they said worked like a charm, and Cassidy was soon laughing and patting the taller of the two guys on the arm. The twinkle was back in her blue eyes, and she looked like she was soaking up the attention.
To my surprise, I felt undeniably jealous. I hadn’t ever thought of Cassidy as “mine.” She was just my crazy roommate who made this awesome deal with me where we helped each other orgasm. I had no claim to her and she had no claim to me, even though we messed around several times a week. I was surprised that Cassidy was so comfortable flirting with these guys in front of me, but I was way more surprised that I wanted desperately to march up to the bar and haul Cassidy away with me. Had I developed feelings for her? What did I feel towards her? Or was I just being protective of Cassidy?
It was hard to name the emotions churning through me, but it definitely felt like jealousy. I was uncomfortable examining how I felt, particularly as I watched Cassidy laugh and smile brightly at these two strangers. But it quickly dawned on me that I had a solution.
I walked up to the bar with an empty glass, making it look clear that I wanted another drink. I stood at the bar just a little apart from Cassidy and her two admirers, and waited for the bartender to notice me.
Cassidy looked over and smiled. “You good?” she asked.
“Yup, you want anything?” I asked. The two strangers kept the smiles on their faces, but I could tell from their eyes that they were weary about my presence.
“No thanks, I’m good,” Cassidy responded. She began to turn back to her two new friends.
“Hey,” I said, as if the thought had just occurred to me. “You still owe me a couple.”
Cassidy smiled back at me, clearly not comprehending. Then, after a couple of moments, her smile faltered just a little. “I owe you?” she asked with a sort of puzzled look on her face.
“Yeah,” I said lightly, with the big smile still on my face. “You know, you owe me two.”
Cassidy looked down for a moment in thought, then looked up at the two guys with a bright smile and said, “Can you guys excuse me for one second while I help my friend here?”
“Sure, no problem,” one of the guys replied. The two moved off in whispered conversation, never looking back at me.
Cassidy came right up beside me so her shoulder was touching mine, looked back quickly over her shoulder to make sure the guys weren’t close enough to hear, and whispered, “I owe you two drinks, or the other thing?”
“The other thing,” I said with a mischievous smile.
“You want to collect right now?” Cassidy asked, her questioning blue eyes searching mine.
“Yup,” I replied casually, “If now is okay with you.”
Cassidy paused. “Why now? Why ask now?”
“Because you look amazing in that dress,” I responded immediately, without hesitation. “You’ve been turning me on all night, and I want to do it right here.”
“Right here?!” Cassidy replied skeptically. She thought for a moment, then her smile and the twinkle in her blue eyes returned. “You’re bad!”
We had been to this bar many times before, and I knew there was a second floor bathroom that not many people knew about or used because the second floor closed when the dinner service stopped at 10:00. “Wait one minute, then meet me upstairs in the men’s room. Okay?” I asked.
My heart skipped a beat for one desperate second, fearing that Cassidy would refuse me in order to stay with the two guys who were hitting on her. But after a quick second deciding, Cassidy replied with a big smile. “Okay.”
I tried to walk slowly up the stairs, but it was very difficult not to rush or to look back over my shoulder to make sure that Cassidy was going to follow me. Once in the stairwell, I was hidden from the bar.
I made it to the men’s room and was relieved to find the small space empty. Then I waited nervously in front of the sink for what felt like 20 minutes. I paced a little. Then I looked down at my watch. Only 45 seconds had gone by since I entered the stairwell. I paced a little more, for what felt like five minutes. I looked back at my watch. 65 seconds had passed. Cassidy wasn’t coming, I had told her to wait only one minute.
The door opened and Cassidy quietly slipped into the men’s room with me. I quickly bolted and locked the door behind her. When I turned back to face her, she was beaming, a nervous excitement in her eyes.
“I’ve never been in here before,” she said with a laugh, “It kind of smells.” She turned back to look at me. “So how do you want to do this?”
I opened my arms as if to hug her, and Cassidy walked into my embrace. She did look hot that night, the smooth fabric of the powder blue dress hugging her firm ass and big, round breasts. When she hugged me tentatively, I felt the firmness of her boobs as they pressed against my chest. I dropped my hands to Cassidy’s waist, quickly and forcefully spinning her so that she was facing the mirror over the bathroom sink with her back to me. I pressed my groin against the back of her toned ass, pleased to feel my erection quickly growing.
“How about like this?” I asked, looking at Cassidy’s bl
ue eyes in the mirror.
Her eye twinkled back at mine and a smile lit her face. “You ARE bad!” she said again. “I like this.” When I paused for a moment, trying to decide how to proceed, Cassidy placed her hands on either side of the sink and said, “Well go ahead, sugar. If you’re in charge of this whole set up, you should probably start by taking my panties off.”
My smile now stretched from ear to ear. It was disconcerting to see myself in that mirror, but I loved seeing the amused smile on Cassidy’s face. I slowly and deliberately ran my hand up the outside of Cassidy’s smooth outer thighs, slipping under the hem of her dress. I thoroughly enjoyed the way the tight cut of her dress pushed my hand against the smooth, firm swell of her ass. I hooked my fingers under the hem of Cassidy’s frilly panties and began to pull them down her leg. She offered no resistance, helpfully lifting her high heels off the floor so I could pull her bottoms free when I got to her feet.
I slipped Cassidy’s underwear into my pocket and lifted the hem of dress to expose her pale, bare ass cheeks. I ran my hand over that smooth firmness, then gave that ass a small slap, which made Cassidy yelp, “Hey!”
Standing directly behind her, Cassidy couldn’t see in the mirror that I was lowering my zipper. She could see me fumbling around, but couldn’t see when I pulled my long, hard cock free and pointed the engorged tip at the entrance to her exposed pussy. She wasn’t certain what I was doing until she felt me rub the hard head of my dick against her bare pussy lips.
“You ready?” I asked, looking at her eyes in the mirror.
“Oh yeah,” she responded with her bright smile.
The lead up had been so sexy and perfect, and I had been so confident and strong. I wish I could say the fucking started the same way, but it did not. After lubing the tip of my cock with my own saliva, I pressed my eager cock head against the tight opening to Cassidy’s pussy hole. She spread her legs a little to help me, but I could not quite get my fat cock head past the soft folds of her pussy lips. Cassidy was so much shorter than me, even in her high heels, that the angle was all wrong. I tried to squat a little lower, then thrust, but again could not get the right angle to allow my cock entrance to her tight, wet tunnel. Cassidy laughed a little, which did not help, but she also tried to raise her ass up higher by arching her back and standing on her toes. I loved the sight of her presenting her young, round backside for me, so I squatted lower and finally managed to push my cock past her tight opening and sink several inches into her warm, wet pussy.
Cassidy gasped when I shoved my cock deep inside of her. I had been so focused on making it inside that I hadn’t thought about how much of my thick dick I was thrusting inside of her tight pussy at once. I tried to ease up, focusing on making sure I had the right angle to work just a few inches of my cock in and out of her pussy at a time. I was so focused on squatting and getting the right angle, and enjoying the view of her firm ass as her pussy accepted my long pole, that I probably fucked her for a minute or two before I finally looked up at her face in the mirror.
Cassidy’s blue eyes were burning with lust, looking back at mine, and she was biting her soft lip. “You like it?” I asked.
“Uh huh,” was all she managed to moan with her lower lip held gently between her teeth.
I decided to tease her and began thrusting a little bit harder and a little bit deeper. Cassidy moaned her approval in response, her ass cheeks shaking invitingly for me as I began to bury my full, thick cock inside her wet little snatch. Cassidy hung her head down, her red hair hiding her face as I began to rock her curvy little body with my fucking. I grabbed her waist with both hands and began pulling her ass back onto my cock, impaling her on my pole as I fucked her. She threw her head back in response and moaned deeply, her eyes blazing with lust as she looked at me in the mirror.
“You like that?” I asked.
“Yeah,” she moaned, then added, “Baby, you fuck almost as good as you eat pussy.”
“Almost?!” I demanded teasingly, shoving my thick meat even harder with my upward thrusts into her tight, wet tunnel.
“Shit!” she exclaimed.
I reached around with one of my hands while I continued my hard, deep thrusts into her pussy, and searched with my fingers for her hard little clit. It was honestly difficult and awkward, with the way I was squatting and trying to reach around Cassidy’s legs. But when my fingers trailed downwards and found the little bump at the top of her sex, Cassidy reacted instantly with a loud, deep moan. I rubbed gently with my fingers while I continued to slide the full length of my meat in and out of her dripping wet pussy.
“Fuck, I’m going to cum,” Cassidy warned, her cheeks flushed and her intense, blue eyes focused on mine.
“Already?” I asked.
“Yeah, I’m… I’m close” Cassidy managed to say as I plowed my hard cock in and out of her.
“Well you better keep it down,” I teased, my finger still gently rubbing her clit, “People downstairs might hear us.”
“Oh God,” Cassidy moaned.
“You like that idea, don’t you?” I asked her, the full length of my pole driving in and out of her warm, wet hole. “You like thinking that people might be listening to you fucking?”
“Oh God!” Cassidy moaned.
“Go ahead and cum for them, Cassidy,” I teased, her pussy now dripping her wetness around my cock. “Why don’t you let them hear you cum!”
“Oh fuuuuuuuuuuuuuuuuuuccck!” Cassidy hissed between clenched teeth, stifling a scream as she came on my hard cock. I kept pushing my meat in and out of her, my fingers gentle on her clit, as she bucked and shook around me. I could feel her pussy tighten a little as she came, the wetness flooding around my cock in her pussy as she orgasmed.
Cassidy sucked in air deeply for a couple of minutes, her arms shaking as they supported her on the sink, and the whole time I kept working my cock in and out of her snatch. The extra lubrication from her orgasm felt good on my member, and combined with watching her face in the mirror as she orgasmed, I was getting close to my own release.
When Cassidy regained her senses, she looked deeply into my eyes in the mirror. “I’m close,” I told her.
“Go ahead, honey,” she encouraged, her face flushed and her eyes never leaving mine. “Cum in my pussy.”
“Is that where you want it?” I asked, my cock beginning to tingle as it rubbed back and forth against the soft walls of her wet tunnel.
“Yeah baby,” she replied.
Two more deep thrusts and then I felt the tingle grow to an explosion of pleasure. I held myself deep in her warm pussy as my cock sprayed spurt after spurt of cum into her. The orgasm was sharp and intense, but brief. Shortly after my balls had finished emptying their load into Cassidy, the tingling began to subside.
“That was awesome,” I told Cassidy as I slipped my semi-erect dick out of her pussy.
“I totally agree,” Cassidy responded with a smile.
She turned towards me, facing me for the first time, and I gave her a little peck on the cheek. Then I went to the sink and used some wet paper towels to help clean off my dick, before putting it back in my pants and making sure everything looked normal as I zipped myself back up.
“Now get out of here so I can clean myself up a little,” Cassidy ordered, pushing me gently towards the door.
I unlocked the bolt and began to walk out the door before I remembered something and stopped. “Hey, I forgot to give you these back,” I whispered, pulling Cassidy’s panties out of my pocket and offering them to her.
The mischievous twinkle returned to her blue eyes, and she responded, “Why don’t you keep them as a souvenir of tonight,” before she pushed the door shut behind me.
When I made it back downstairs, Cassidy’s two admirers were nowhere to be seen. After one more drink and about twenty minutes, Cassidy and I decided to call it a night and walked back home together.
———-
The next week was uneventful. Cassidy had her period late in the week, so we didn’t do any fooling around, which almost seemed nice in a way after how rapidly our activities had escalated the weeks before. When we were home together, we spent some time just hanging out, talking to each other while we made dinner or watched tv.
Early the following week, I knew what to expect: Cassidy the post-period raging sex fiend. Monday morning she practically begged me to go down on her before I left for work. She knew I had been ready to walk out the door, but her pleas worked. She ended up cumming hard on my tongue, screaming with her thighs clamped around my head and her toes curled as her tight, young body shook. I was very amused that she was completely naked, sitting on the couch as she came, with me fully dressed in my work clothes, on my knees, with my wet tongue rubbing at her clit.
That night, Cassidy was waiting for me as I walked in the apartment door, wearing sweatpants and a loose t-shirt. She had a rosy color in her cheeks and a heat burning in her blue eyes. As I began emptying my pockets of my keys and my wallet, Cassidy’s eyes never left me. She was looking at me like a hungry wolf admiring a piece of meat. I laughed as the thought crossed my mind.
That caught her off guard, throwing off her concentration. “What’s so funny?” she asked.
“I’m almost afraid that you’ll attack me and ravage me in the doorway, the way you’re looking at me,” I teased.
She laughed, a quiet and easy laugh. “Is it that obvious?” she asked. She thought a moment before continuing. “Don’t you ever get… just… CRAZY horny?” she asked. “Aren’t you a guy? I thought all guys get like that.”
“Of course I do,” I said, “You’ve seen me like that.”
Cassidy walked towards me. “I can’t stop thinking about that big dick of yours.” She approached me slowly, whispering, her hand a light pressure on my chest.
“Don’t we have a deal?” I teased, thoroughly enjoying where this was going. “No kissing, no sex… two for one?” I asked.
“Forget the deal,” Cassidy said, irritated and stalking back to the living room. “We already did it in a bathroom.”
“Fine, what do you want?” I asked, kicking aside my shoes and moving toward my bedroom.
I had started unbuttoning my shirt, mindlessly following the daily routine that guided me every time I came home. It took me a moment to realize that Cassidy hadn’t said anything, and when I did I turned. Cassidy was standing completely naked in the living room, her shirt and sweat pants in a discarded pile on the floor next to her feet. She knew just how to stand, one smooth, shapely leg in front of the other, the toes on her front foot pointed downward. Seeing her taut, athletic form completely bare still took my breath away. Her hips swelled so gently and gracefully up towards her flat stomach. Her pussy lips were completely bare, just the outline of her abs above them like a smudged line on a pencil drawing. Her big, proud, upright breasts sticking out from her chest as she drew back her shoulders, capped by her little pink nipples. Her red hair falling loosely around her oval face, making her blue eyes stand out like bright, shining gems. And her smile, her red lips contrasting with her sparkling white teeth, lighting up her whole face.
“You telling me you don’t want this?” she asked evenly, steadily. Her question was demanding and empty of desire.
I choked. I did, I honestly choked, the words catching in the back of my mouth as they all tried to come out in a jumble.
“Of course I do,” I finally managed, feeling my cock already beginning to stir in my pants.
Cassidy seemed to be shivering slightly, I assumed at the time that she was just cold from standing there in her birthday suit. Later on I came to recognize that Cassidy got so horny sometimes that she literally trembled with desire. “Good,” she responded quietly and evenly. “Then no more deals. If I want something and you’re up for it, we do it. If you want something and I’m up for it, we do it. How does that sound?”
Determined not to stumble this time, I replied, “Sounds good.” Looking back at it now, I realize that casual moment is where I completely lost myself.
“You feel like fucking right now?” Cassidy asked evenly. Her questioning blue eyes never left mine and they never blinked.
“Yes,” I said firmly.
“Then let’s stop joking around and fuck,” Cassidy responded.
She walked toward me confidently, her hips swaying seductively. Her hand went to the back of my head and drew me down into a kiss, her soft, sweet lips meeting mine and the tips of our tongues quickly flowing out in a gentle brush.
Cassidy’s small fingers began searching insistently for the zipper on the front of my pants, and my already swelling cock enjoyed feeling her fingertips brush me through the fabric. I think she thought she would take my cock out and we would fuck right there, but I had other ideas. If Cassidy was going to be more assertive, I was going to show her that I could be assertive too.
Before Cassidy could react, my hands were under her arm pits and I was lifting her off of her feet. She let out a cute little squeal of surprise that was half giggle, but offered no resistance as I set her down carefully on the kitchen counter. My hands went to her smooth, creamy inner thighs, and I spread her legs forcefully. Then my head and shoulders bent down between her knees and my tongue was gingerly licking the outer folds of her pussy. I could feel the heat coming off of her snatch, and sense the moisture that was building up just behind those folds. As my tongue snaked deeper into Cassidy’s womanhood, she let out a low moan and her fingers ran through my hair.
I traced her folds upwards, feeling her pussy start to leak its juices around my tongue, demonstrating her level of arousal. When the tip of my wet tongue brushed lightly against her clit, Cassidy shuddered.
“I’m not sure going down on me is going to be enough,” she said.
I looked up at her from between her legs, finding her blue eyes looking down at me pleadingly. “Every good meal comes with an appetizer,” I replied with a smirk.
With that, my hot mouth closed over her pussy lips. My tongue began to lash up and down over her clit, alternating with rubbing her little bud gently between my lips. Cassidy’s body shuddered around me and she moaned, her hands pulling my head into her aching pussy. Her slick juices dripped all around my slathering tongue and coated my face.
I bore down with my tongue, rubbing rapid circles around and around her wet, sensitive spot. I was about to slip a finger into her when Cassidy cried out, “I’m going to cum!”
I barely had time to register what she had said, thinking that it was much too soon, and then she screamed, “Shit!” and her strong thighs clamped around my head while she panted and her body shook around me.
When her thighs finally released their grip on my face, I stood up to find her chest pink with heat and her body covered in a barely visible sheen of sweat. Her eyes were closed and she was breathing heavily.
I had my pants and boxer shorts off in one quick motion, finally freeing my solid, throbbing cock. I lifted Cassidy’s smooth, shapely legs so that the heel of each of her feet rested on my shoulders and my excited cock head was rubbing at her pussy folds. Cassidy’s eyes opened and she smiled at me with her perfect, white teeth, her eager face framed by her silky red hair.
“Go ahead…” Cassidy began to say, but the feeling of the heat coming off of her pussy and her juices dripping around my hard knob were too much for me to wait. I slowly sank every inch of my thick meat deep into her hot, tight hole. Cassidy moaned in response, and her sparkling blue eyes grew wider as inch after inch of my hardness slipped between her swollen pussy lips and into her warm, wet channel.
I withdrew almost to the tip, feeling how tightly her slippery pussy walls clung to my thick meat, then plunged my full cock back into Cassidy, burying my manhood inside of her until my balls slapped against her bottom.
“Oh shit!” Cassidy exclaimed, one hand grasping the back of my neck to hold onto me as I withdrew most of my hard cock and then plowed it back into her. “Oh fuck!” Cassidy moaned, but her fiery blue eyes and smile were all encouragement.
I wrapped my arms around her legs and held her firmly in place as my long dick plowed in and out of her pussy. Cassidy dropped her hands to brace herself for my onslaught, and she was quickly gripping the edge of the counter top, trying to steady herself as I fucked her hard. My eyes broke contact with her sparkling, lust-filled blue eyes only to look down at Cassidy’s full tits as they flowed back and forth over her chest. I held her legs in place tightly as I rammed my meat into her over and over, my full balls slapping obscenely on her tight bottom.
“Fuck, that’s deep,” Cassidy moaned through gritted teeth.
“You want me to stop?” I asked, never slowing as my full, hard cock drilled into her over and over.
“Hell no,” Cassidy panted with a smile, her red hair swaying back and forth behind her with the motion of our fucking.
“Good,” I said, my grip on her toned legs tightening, “because there’s no place to go.”
Cassidy’s pussy felt so perfect, tightly milking my long cock but not so tight that it felt uncomfortable for my fat, swollen cock head as it flowed back and forth inside of her wet tunnel. I reveled in the feeling of the heat and the wetness as my hips rocked powerfully back and forth, sending my hard pole plunging in and out of her little hole. But what was really turning me on was watching Cassidy’s little pink nipples fly up and down over her chest as her big, firm melons were pushed up and down with the force of my fucking. I had never seen such smooth, round tits moving like that before, and it drove me crazy to know that the hard pounding I was giving Cassidy’s pussy was doing that.
“I’m going to cum,” I grunted, my eyes fixated on her big, bouncing boobs.
“Oh yeah,” Cassidy moaned, “Me too.”
I groaned a deep, guttural groan, and then I lost it. My orgasm peaked in a brilliant burst of pleasure that overtook me, and I could feel my legs shaking as my load squirted out of my cock and spewed my hot cum deep into Cassidy’s hot pussy. I felt my cock twitching deep inside her tight, wet pussy as it delivered its load.
“Oh God,” Cassidy moaned softly. I opened my eyes just in time to see her looking at me, and then she shut her eyelids tightly as her own body shook and vibrated through orgasm. She came hard, her muscular legs straining against my chest as she rode her blissful wave of pleasure.
When Cassidy finally opened her eyes, the sparkling blues had a dreamy quality about them. “That was so hot watching you cum and feeling you inside of me,” she whispered with a lazy smile. “It drove me over the edge.”
As my cock began to soften and I slipped it out of her wet pussy, I looked at Cassidy and felt something stirring in me. She looked so beautiful, with her sleepy blue eyes and pale face framed my her bright red hair, a contented smile on her lips. And at the same time she looked so sexy, all of her smooth skin completely uncovered and on display. A slight sheen of sweat covered her entire body, and her firm, round breasts were still a light shade of pink from her arousal.
Instinctively I leaned in and pressed my lips against hers. She kissed me back softly, and I felt an enormous damn break deep inside of me. It was like a pressure had been building and building, and I had built a wall inside stronger and stronger to deny it. And that soft, tender kiss was all that was needed to obliterate that wall.
As I pulled back and looked into Cassidy’s blue eyes, I knew it like I had never known it before. I was in love.
“What do you feel like doing now?” I asked Cassidy.
After a thoughtful moment, she replied, “I feel like I need a shower.”
“Ooohh, I can help with that,” I teased.
“That sounds like fun,” she responded with a bright smile.
Just a few minutes later, we were in the shower together, the hot water flowing over our naked bodies. At first it really was all about getting clean. I always loved a hot shower, and this one was helping to relax my muscles and calm my body. But there was also no resisting the appeal of Cassidy’s fantastic body next to mine, the water cascading over her large, round breasts and plastering her red hair to her neck and back.
I was quickly feeling playful, and soon my soapy hands were rubbing circles over Cassidy’s firm butt cheeks. “Let me help you clean back here,” I said with mocking seriousness.
“Oh, thank you sooooo much,” Cassidy replied mockingly with a laugh.
Cassidy’s smooth, lily white ass wasn’t big, but it had a toned firmness to it that I loved. I especially enjoyed feeling that firmness as my soapy hands slid over her wet ass cheeks.
“Here, let me help you clean this,” Cassidy said after a minute of letting me feel up her ass. She turned and brazenly grabbed my limp dick, her soapy fingers sliding over my cock skin. “This thing can be so dirty,” she teased.
“Oh it can,” I said, my hands sliding up her sides and over her breasts. As my palms slipped in circles over her wet nipples, the hot water flowing between our bodies, I said to her, “Isn’t it so much more fun getting clean with someone else’s help.”
“Totally,” Cassidy responded with a smile. Her hand was continuing to slide up and down my pole, gripped loosely in her soft fingers. While Cassidy’s attention felt good, my manhood wasn’t quite ready for a repeat performance.
I leaned my head down towards Cassidy and we kissed again, our lips meeting softly at first and then more insistently. Her tongue slipped out between her lips and soon our tongues were entwined, rubbing against each other as our mouths joined in passion.
I drew Cassidy towards me, and her free hand went around my back. Her soft but full breasts mashed against my chest, and I could feel the heat of her body against me as the warm water continued to flow over both of us. Cassidy’s hand was tugging on my slippery cock a little more insistently, but it still wasn’t ready to respond. So I slipped one of my hands down over Cassidy’s smooth, wet stomach, past her waist and between her legs. When I rubbed gingerly at Cassidy’s pussy lips, she moaned into my mouth, our lips still pressed together.
I quickly found the hard bump of Cassidy’s clit and rubbed gently against it. Then, with the hot water still flowing over us, I quickly slipped my finger past Cassidy’s pussy lips and deep into her hot, wet love tunnel. Cassidy gasped and broke our kiss to smile at me, and I took the opportunity to kiss my way slowly down her soft neck while my finger rubbed in and out of her tight, soft pussy. Eventually my lips found their way to Cassidy’s firm, perky breasts, and I sucked one of her pink nipples between my lips and slathered it with the full length of my wet tongue.
Cassidy moaned, lifting one foot onto the edge of the shower. With her legs more widely spread, I slipped two fingers into her tight vagina, pumping them in and out of her hole a little more gently than I had done with my cock. Cassidy moaned her approval, my lips still suckling on the tip of her big breast. Looking up at her blue eyes while I finger fucked her, with her nipple in my mouth, my cock finally started responding.
I began to pull my hand away, but Cassidy grabbed my wrist. “No,” she pleaded, “Don’t stop.”
I pulled my hand away, grabbed her by the shoulders and spun her firmly around until her hands were resting on the back wall of the shower. When I pressed my hand decisively into her back, between her shoulder blades, Cassidy compliantly leaned forward and stuck round her ass out.
I ran the palm of my hand down her smooth back, over her wet ass cheek with the shower water still running down the curve of her butt, and gave her a firm, wet slap on her bottom. Cassidy started and yelped, but did not try to turn around. With one hand still firmly on her round ass, I slipped two fingers into Cassidy’s open pussy from behind, jamming my fingers in and out of her and feeling her warm internal wetness.
I quickly replaced my fingers with my cock head, and had to crouch slightly like I had done in the bar to get the angle right. But with Cassidy encouraging me with a quiet, quick “Yes,” I slipped my fat cock head past her tight opening and shoved my thick, wet, man meat up into her pussy.
My hands gripped Cassidy’s hips firmly, pulling her back onto my pole as I thrust forward with my midsection. Soon her tight ass cheeks were jiggling as I rammed my hard dick into her hot tightness over and over and over again. I enjoyed watching the little sprays of water as the shower continued to flow over our bodies while her ass shook in waves from my pounding. With my insistent thrusts and hands firmly pulling her back onto my rod, there was little that Cassidy could do but hold onto the shower wall.
It may have been the finger fucking, but again Cassidy caught me off guard with how quickly she came. “Ohhhh… I’m close,” was all the warning I got before she screamed, “aaaaaAAAAAAAAHHHH!!” with rising pitch as she came. If not for her warning and a slight shaking of her legs, I would not have understood that her panting pleas were a signal that she was cumming on my cock.
I slowed my pace a little, but I was not done. Cassidy apparently was, as she reached behind herself to push back against my chest as she lifted her hips and my still hard pole slipped out from her wet pussy. Cassidy’s blue eyes dropped to my manhood, which was still rock solid and standing at attention, before looking up to mine.
“I need a break from fucking,” she explained weakly.
“I understand,” I said, still very aroused as I looked down at her curvy naked body sitting at the back of the shower. “You want to go dry off while I take care of this?”
“No, no,” Cassidy said determinedly, “If you’re going to keep going then let me help.”
Without another word, shifting to a kneeling position on her knees, Cassidy quickly took the tip of my penis in her mouth. She suckled on the tip, glancing up at me with her blue eyes as if to say that she wanted to make sure I was happy with what was happening, and then she plunged her soft, sucking lips down several inches of my cock. Her wet, red hair swung back and forth in the shower, kicking off spray as her mouth slid up and down over my sensitive cock skin. She suckled hard as she slid down, wrapping my pole tightly between her lips, and then swirled her tongue on the way up my meat.
An idea quickly sprang into my head, and I asked, “Since we’re in the shower, do you mind if I cum on your face.”
Cassidy released my cock head with a loud pop of suction and said, “Yeah, that’s okay.” She paused, looking up at me with those devilish blue eyes, and then said, “You ready now?”
“Yeah,” I said, my hand grasping my cock and beginning to stroke up and down my shaft.
When I began jacking myself, I realized that I wasn’t as close as I had thought to cumming. But Cassidy just closed her eyes and sat there, some of the shower spray sprinkling her pale face and running down over her chin. The submissiveness of her just sitting there, waiting for my cum, a slight smile on her full lips, her red hair stuck to the back of her neck, got me really turned on. Maybe thirty seconds of pumping my dick and I could feel the orgasm approaching.
“I’m going to cum,” I warned, “You ready?”
“Go right ahead,” Cassidy said with a smile, and I did.
I fought once again to keep my eyes open as I came, and I remember it being one of those delicious orgasm where the intensity of the pleasure builds and builds beyond the point where you think your cock should be spewing, but the ejaculation doesn’t happen. I was so turned on by waiting to see the ropes of cum cover Cassidy’s face that it made the orgasm even more intense, until finally something clicked and my white cumshot erupted out of my tip and splattered wetly onto Cassidy’s face. Rope after rope of cum painted her right down the middle, over the bridge of her little nose, and then over one closed eye and down over her chin, and then a thick string of white on one of her apple cheeks. For a brief moment she was covered, wearing my cum all over her face. Quickly the water from the shower began to cause some of the cum to wash away, and then with a few wipes of her hand it was all gone.
———-
I don’t recall a lot of details about what happened after the shower that night. I’m pretty sure we ate dinner, I don’t remember much else of what we did. I do remember being tired, both from the week and from all the fucking that afternoon and evening. I do recall that we never put any clothes on, spent the whole evening naked together. And I remember that we were talking in her bed and both ended up falling asleep next to each other in her bedroom.
When I woke up, there were many reasons why it took me a while to get my bearings. The first was realizing that I was not in my own bed and slowly having to remember that I had fallen asleep in Cassidy’s bed. The next was that the lights were on and I thought it might be morning but I had no idea what time it was. My first movement was to look down at the alarm clock by Cassidy’s bedside and seeing that it was 4 something in the morning. My next move was to look down my body to try to figure out what was going on.
Cassidy’s head was resting low on my chest, her red hair falling loosely all around her face and her blue eyes looking up at me. Her fingers were absently playing with my penis, alternately rubbing lightly over the shaft of my pole and twirling her fingers lightly around my cock head.
“Oh good, you’re awake,” she said in greeting, her blue eyes twinkling. And with that, she lowered her lips over the shaft of my cock and began licking on the sensitive underside of my soft rod.
As I came to my senses, I enjoyed the soft feeling of Cassidy’s big breasts pressed against my chest as she rested atop me. While her went tongue slid all over the sensitive skin of my shaft, I drank in the sight of her round, firm backside rising up off of the bed behind her. When she wetly sucked the head of my cock between her soft lips and began to run her tongue around my tip, she looked up at me with those beautiful blue eyes of hers. I could feel the warm blood rushing to fill my rapidly growing member.
As soon as Cassidy had gotten my cock to full mast with her soft, sucking mouth, I quickly slipped from beneath her and rolled myself atop her back before she had a chance to react. She was pinned lying on her stomach, beneath the weight of my warm body. My long, thick dick nestled in the crack between her firm, round ass cheeks.
“Careful back there,” she teased from beneath me.
I reached around her waist and Cassidy lifted her hips to accommodate me. My fingers soon found her soft feminine folds, and she wiggled her bottom as I rubbed gently around the top of her womanhood. By the time I found her clit with my probing fingertip, Cassidy had lifted up with her knees and was pressing her ass upwards against my excited cock.
A few gentle flicks of my finger against her hard little nub and I could feel the moisture beginning to coat Cassidy’s pussy lips. Our success at figuring out how I could fuck her from behind while she was standing had made me want to try something else. It was something I had tried before with another partner, but we could never figure out the right angle or maybe just weren’t well matched in our parts. But I wanted to try it with Cassidy.
I placed my feet on either side of Cassidy’s hips and stood over her in a very low crouch. It was a strain in my thighs to stand over her that way, but when I took my hard dick in my hands and bent over to position it at the entrance of Cassidy’s wet and eager opening, Cassidy lifted her ass even higher and our sexes joined. I shifted my weight forward with my legs and my full, hard cock slid slowly into Cassidy’s tight, wet hole.
In this position, I all I had to do was lift with my legs to quickly withdraw the full length of my cock, and then crouch and hunch forward to let my weight bury the full length of my rod deep into Cassidy’s soft, gripping pussy. The first time I shoved the whole length of my pole deep into Cassidy, she let out all of the air inside of her with an uncontrolled gasp. I was surprised, after my prior difficulty, that this position worked so easily for us.
I grabbed hold of the smooth curves in Cassidy’s hips and went to work plowing her hard and fast with my stiff pole. Using the power of my legs instead of thrusting with my hips, it was the hardest and fastest I had ever fucked a woman before. My rigid meat flew in and out of Cassidy’s tight pussy, her soft, wet pussy walls gripping my super sensitive tip as it rubbed up and down her channel.
“Oh fuck, oh fuck, oh fuck,” Cassidy began to pant with my fast and deep thrusts. “Ggnnnn,” she grunted between gritted teeth as I shoved my dick into her hard. Her voice was high and full of arousal. “Oh… I’ve never… I’ve never been fucked so fast. OH SHIT! And you’re hitting right against… oh… right against my G spot.”
I could feel her pussy getting tighter around my relentless, pounding cock. With the mention of her G spot, I stopped burying myself up to my balls in her snatch and focused on just the first two or three inches of my member. With the downward angle of lowering myself, my cock was pushing hard against the front wall of her pussy, and her reaction to my new focus was immediate.
“Ohhhh!” she cried out. “Oh God… yeah… just like that… just like that!” She was practically screaming, oblivious as her chest was pushed across the bed by the motion of my fucking.
“Oh shit!” she yelled, her voice raw with pleasure. And then suddenly she was cumming hard, her shapely legs kicking behind her and her head thrashing from side to side as I continued my insistent plowing, pushing my hard cock in and out of her warm, wet hole.
I didn’t stop with Cassidy’s orgasm, just slowed a bit. I was nowhere near ready to cum, though her screaming and shaking had turned me on. I kept shoving my hard cock into her tight, wet walls, my cock head flowing back and forth against her sensitive, slippery skin. My fingers gripped deep into her hips, pulling her back to be impaled hard onto my rod, and holding her in place as I rapidly withdrew.
“Oh shit,” Cassidy began to moan softly. “Oh shit… oh shit.” She raised herself up onto her elbows to stop her chest from sliding across the bed.
I fucked her hard and deep, pumping my legs and my hips to push my cock quickly in and out of her wet pussy. I was fucking her so hard that the feminine juices of her orgasm began to spray out of her pussy every time I buried my hard meat to the hilt in her tight hole.
Cassidy’s voice rose in pitch as she began to squeal, “Oh God! Oh my God!” She began shaking her head side to side, her red curls flowing back and forth across the pale skin of her shoulders.
I could tell she was close and again focused on pushing just the first few inches on my thick dick into her throbbing pussy. I drove my cock head hard against her rubbery G spot, swiftly rubbing her wet spot over and over and over and over.
“Holy shit!” Cassidy screamed, her whole body shaking as she came again. She tried to shove her face into the bed to muffle her loud moans as she came hard, her whole midsection trembling with the power of the pleasure that coursed through her body. I could feel her pussy walls tighten around my thick member and her juices flooding outward around my pole.
I was so turned on by how hard she came, I could feel the tingling pleasure of my own orgasm beginning to build. My cock kept driving rapidly in and out of Cassidy’s pussy, but when her legs stopped kicking she quickly pulled herself forward and my cock popped free of her pussy’s grip.
“No more,” she panted, “Holy shit, no more,” She was breathless, her fiery red hair matted to her head and face as she turned to face me. “I need a break.”
But I was too close. My hand went immediately to my cock, completely coated with Cassidy’s slippery, wet juices. As Cassidy turned her body over to face me, it took only a few well practiced strokes of my closed fist over the swollen head of my dick and I felt the orgasm burn through my loins and out the tip of my manhood.
The first blast of cum caught Cassidy squarely in the chest, running down over one of her full breasts and covering one of her small, pink nipples with the whiteness of my spunk. Cassidy reached out instinctively, her soft fingers brushing against the tip of my dick, and the next spray of cum coated her palm and ran in a line down to her elbow. Her finger tips closed around the head of my cock, and with my body still racked by my own orgasm, I pumped two more squirts of my cum over the tops of her big, round breasts. My white cum mixed with the glistening sweat on her chest and both began to run down the valley between her two, perky globes.
Cassidy smiled up at me with her bright, white smile, her blue eyes dancing with delight in her eyes. It was both beautiful and obscene, my cum covering her chest and her fingers still softly holding onto the tip of my pole.
“That was fun,” she said. “I’m sorry I couldn’t feel that cum inside of me, but you pounded my pussy raw… Maybe next time.”
———-
After eating breakfast together the following morning, I sat down on the couch and my semi-erect cock was sticking straight up from my lap. We hadn’t put any clothes back on since the night before, and watching Cassidy move about, even the way her big, firm breasts swayed back and forth while she beat the eggs, had got me a little turned on again.
“So what does this mean for us now?” I asked.
Cassidy came and sat in my lap, facing me with her knees on either side of my body and her smooth, warm thighs settling over me. “I told you what it means,” she said looking down at me as she ran a hand through my hair. “It means we can fuck whenever we want to fuck. It means we don’t have to hold back if we don’t want to, we… trust each other enough that we can just be happy and do what we want.”
Cassidy leaned down and pressed her lips softly against mine. My fingers reached up and ran through her red hair and then down her pale neck as our tongues brushed softly against each other. Continuing down her body, my hand found the swell of her big, firm breast, and my thumb brushed across her nipple. Cassidy rocked her hips back and forth, rubbing her soft, moistening pussy lips up and down the length of my shaft.
As soon as I was hard, Cassidy lifted her hips and positioned the entrance to her womanhood over the top of my pole. Then she sank down slowly, covering inch after inch of my stiff cock with her wet, tight pussy. Both of my hands were on her big, round breasts, sliding over her sensitive pink nipples as she slowly raised herself up and down on top of my cock.
We didn’t fuck this time, we made love. And for me it was love. I kissed her deeply, the full length of my tongue probing into her mouth as my hard pole probed deep into her warm, slippery snatch. She slowly rode me, grinding her clit down into my pelvis, and gasping when I broke our kiss to take her little nipple in my mouth and toy at it with my wet tongue.
When Cassidy came, several minutes later, her hands were on the back of my head, drawing my head hard against her big, round breast as I teased her nipple with my hot mouth. Her cries pushed my own arousal to the point of ecstasy, and this time I came deep inside of her, my hard cock pumping its load against the velvety soft walls of Cassidy’s pussy. Where my previous orgasms had been a sharp, quick explosion, this slow love making had produced a deep and pleasurable burn. My own cries were muffled by the press of her full, firm breasts against my face.
———-
Cassidy and I did not have sex again that weekend. I wish I could say we spent a whole 48 hours doing nothing but pleasuring each other, but we both had other things to do. We barely spent time in the apartment until Sunday night. But every time I saw her, I knew with a deep, unshakable certainty that I had fallen in love with her. I realized I had been trying to deny it to myself for some time, but there was no denying it now. And yet I could not bring myself to tell her. If she did not already love me, maybe our new arrangement would give her that opportunity, and I didn’t want to say anything that could compromise that chance. Or stop the fucking.
Sunday night I was getting ready for bed when Cassidy finally came home. I was trying to play it cool, not seem too eager, and so I continued to putter around my room after I heard her arrival. My plan seemed to work as she slipped quietly into my room sometime later, wearing just a long t-shirt which barely covered her firm, round ass.
We had barely kissed before I was lifting her shirt over her head, her big, round breasts sliding back into view. I didn’t realize how much I had missed those beautiful boobs in two days until I saw the perfect pink nipples at their tips once again. She was hurriedly pulling down my pants and I was shedding my own shirt, and then I was on the bed on my back, and she was riding me.
She was a vision as I lay there, watching her lift her hips up and down while my stiff pole slid in and out of her. Her small hands were pressed firmly to my chest, her heavy, hanging breasts swaying back and forth with her efforts, her red hair hanging loosely around her smiling face. She panted as she rode me, the wetness of her warm, slippery pussy dripping down the length of my shaft. My upwards thrust were soon meeting her downward plunge, our pelvises slapping together with an obscenely wet sound.
The pleasurable sensations quickly built inside me and then I was cumming, thrusting upwards and planting my thick cock firmly and deeply inside Cassidy as I came. My cum boiled out of me and shot upwards into her hot and waiting womanhood. Cassidy ground her hips down against me, rubbing her clit over my skin as she watched my face while I came. And then she was cumming too, crying out her pleasure while her hips gripped hard against my sides.
She collapsed in a heap atop me, her big, soft breasts settling on my chest while my cock remained inside of her tunnel. We slept in my bed together that night.
We had sex at least every other day over the next two weeks. We would have fucked more, but we both had to work and we had social outings with our respective friends. Most of the time it was in her bed or mine, but I really enjoyed the times we did it in the living room, or the kitchen, or the shower. I remember bending Cassidy over the living room couch one afternoon when she got home from work, her cumming on my cock still clothed from the waist up, and then moaning words of encouragement until I came deep inside her tight pussy.
And I fondly recall having sex while floating in warm water in the bathtub. I was lying on my back, with Cassidy lying on her back atop me. We slipped my cock into her pussy and fucked slowly in the hot water, my hands sliding over her toned body and her smooth, wet breasts. Her big boobs were like two pale, floating islands in the water. It felt like we fucked slowly for half an hour before I finally came inside her pussy, my fingers rubbing her wet clit under the water until she came too with my cock still inside her.
Every time we fucked, I fell a little more deeply in love with Cassidy. She was so fun and sweet, and so admirably forthright. She went for what she wanted. And yet I was bothered about what we were to each other. We didn’t go out to dinners together. We didn’t go to see movies. She spent time on her own with her own friends and I spent time with mine. I couldn’t figure out how to ask her, yet again, what we meant to each other. Or more precisely, I didn’t know how to ask what I meant to her.
I thought that a golden opportunity presented itself when two wedding invitations arrived in the mail. Our former roommates had decided to get married quickly, so they could hold the ceremony in the early fall before the weather became too cold. In any case, everyone had expected this since they had decided to move in together. But I had not considered what this could do for my interest in Cassidy.
I was going to be a groomsman. I might have been the best man if my former roommate hadn’t had two brothers. Cassidy and I were both at home the afternoon that the invitations arrived.
“Hey, you’re going to the wedding, right?” I asked, trying to sound casual.
“Of course,” Cassidy replied, taking her invitation from me.
“We’re both allowed a ‘plus one.’ Were you thinking of bringing someone?” I asked.
Cassidy thought for a moment before answering. “I guess not.” She paused again. “There’s no one I could think of taking.”
“Why don’t we just go as each other’s dates?” I offered. “That way our friends save a little money because we won’t be bringing dates, and you can sit at the table with the wedding party.”
Cassidy’s face lit up, her smile quickly spreading. “That’s a great idea,” she said. “I’d love to go as dates.” We both looked over our invitations for a moment before she added, “Besides, I’ve always wanted to fuck a groomsman at a wedding.”
From the mischief dancing behind her blue eyes, I could tell that Cassidy was joking. But it was the best response I could have hoped for.
———-
Just under two months later, I was wearing a tuxedo and escorting Cassidy to our friend’s wedding ceremony. Little had changed since the day we got our invitations. We were still having sex a lot. There were times when we went a few days, for various reasons, without fucking. Sometimes I didn’t see her for a day or two. But every opportunity where we had a little time together, we humped like rabbits.
We still weren’t spending much time outside of the apartment with each other. Sometimes we did go to dinner nearby. When one of us was running late with work or some happy hour, we got into the habit of the other offering to cook dinner or order food so the meal would be ready when we got home.
Other than that, we just hung out together around our place. We definitely weren’t dating and that made me sad. Cassidy showed no interest in developing our relationship beyond the physical. She was warm and affectionate with me when we were together, and we talked and shared things with each other that only close friends would share. But she never asked about my interest in other women or my long term intentions with her.
If Cassidy had asked, I might have mentioned Kristen to her. Kristen was a coworker, a couple of years younger than me. She was short at 5’2″ tall, with pale skin and jet black, shoulder length hair. Her breasts were probably a large B cup, and she had a nice round bottom, more prominent and round than Cassidy’s. Kristen’s short frame and prominent breasts and ass gave her a curvy figure that made her seem almost voluptuous due to her compact height, even though she did a lot of yoga and did not have much extra body fat on her. Kristen also had a very pretty face, with light brown eyes and a cute little bridge of a nose.
Kristen was very focused and serious at work, but in personal interactions she was very fun and flirty. Many of the younger, single men that I worked with were interested, if not infatuated, by Kristen, and I would be telling a lie if I said she hadn’t caught my attention. Young men our age often found several excuses each day to stop by Kristen’s desk. I thought it was probably my imagination, but at work and especially at happy hours after work, Kristen seemed to be particularly flirty with me. I did wonder if she had caught my attention because she was such an interesting contrast to Cassidy. Where Cassidy was firm and fit, Kristen was soft and toned. Where Cassidy’s hair and eyes were light, Kristen was dark.
But I was in love with Cassidy, and Kristen was far from my mind as we approached the church where our friends’ wedding ceremony was going to be held. Cassidy looked amazing in a sea foam green dress that she had chosen to wear. She had taken the time to get her red hair done up in careful curls, and she had spent time to expertly apply her make up that morning. Her face was beaming with happiness, her smile lighting up our apartment when we left that morning. But the dress was also fantastic.
The dress was tasteful for a church, but still pulled in on her hips and clung to her curves. The scoop neck showed off just the pale tops of her big, creamy breasts, and the back end hugged the firm curve of her ass. The compliment of the green dress and her red hair made Cassidy’s pale skin seemed to glow.
The wedding ceremony itself was sweet and blessedly short. I was glad I didn’t have to spend too much time standing at the front of the church. Afterwards, there was almost an hour of picture taking before the wedding party went to catch the shuttle to the reception. I was pleased to find that Cassidy had patiently waited with the other wedding party dates instead of going on to the reception.
As we sat in the shuttle next to each other, I smiled at her. “I know I’ve said this at least four times already today, but you look gorgeous in that dress.”
She smiled back at me and replied, “You look pretty damn hot in that tuxedo yourself. I just love a man in a sharp tuxedo.” Then she lowered her voice and whispered, “I might not be able to stop myself from jumping you during the reception.”
Cassidy’s tight body in her sexy dress had held me turned on all day, and now her words made my cock twitch. All the sex we had been having had spoiled me. As I looked down into Cassidy’s green eyes, the tops of her full, creamy breasts below her face, I wanted her right there and then.
My right hand landed softly on her leg just above her knee, and I purposefully slid my fingers up her smooth, pale thighs and slipped them under her dress. Cassidy first dropped her hand in surprise, her fingers resting atop mine. But when it was clear that I was not stopping, she spread her legs for me. My finger tips brushed softly against the fabric of her panties, and I could feel the heat of her womanhood burning through the covering.
“You’re already a little wet, aren’t you,” I whispered teasingly into her ear. I looked carefully around us, and none of the other people seemed to be paying any particular attention to us.
“I told you, you look pretty hot in that tuxedo… Oh!” Cassidy began in a whisper, until my finger tip began to trace a little more forcefully upwards over her pussy lips.
It wasn’t hard to find Cassidy’s hard little clit under the fabric of her panties, and I was soon pressing my insistent finger tip against the edges of her sensitive nub. Cassidy spread her legs a little wider for me as I used a second finger to trace over her pussy lips and then began flicking alternatively with my two fingers right on her sensitive spot.
“Anyone who stood up to look would see my arm almost to the elbow is up under your dress,” I whispered softly into her ear. “But that’s what you like, isn’t it? You like the idea that someone could catch you cumming.”
“Mmmmm,” Cassidy responded, stifling a moan of arousal by biting down hard on her own soft lips.
Deftly, I slipped her panties to the side and began rubbing my finger tips directly against the bare hardness of Cassidy’s clit. Her pussy was practically dripping juices, and I coated my finger tips with her wetness before rubbing her own lubricant all over her most sensitive spot. Cassidy’s big, round breasts were beginning to rise and fall more rapidly as her breathing quickened with her arousal.
I was so focused on teasing Cassidy’s wet pussy that I didn’t notice we were almost to the reception. As our shuttle turned into the parking lot, I threw my tuxedo jacket over Cassidy’s lap, hiding our activities while my fingers continued to rub insistently over her pleasure center.
When the shuttle stopped and people stood up to leave, Cassidy whispered, “We should stop,” her voice practically oozing with arousal. Her blue eyes seemed a little paniced as they scanned the people around us.
“But I thought this is what you like?” I teased, my wet fingers now slowly but forcefully circling around the edges of her excited clit. “You like the idea that someone could catch us. You like the idea that someone might realize that you’re about to have an orgasm right in front of everyone.”
“Oh God,” Cassidy whispered in a half moan, her pale cheeks flushed with pink and her breathing growing ragged.
The other wedding guests began to file past us out of the shuttle, most paying us barely any notice as they were wrapped up in their conversations. I pointed with my free arm and said loudly, “Look at how pretty the sunset looks from here,” as the fingers on my other hand began to diddle Cassidy’s clit more quickly. If any of the other guests suspected something was wrong, none said anything while they quickly filed out of the shuttle. Even the driver got out and began to stretch his legs.
I could tell from the familiar pace of Cassidy’s breathing that she was pretty close to orgasm. Then a voice called from the front of the shuttle, “Hey you guys getting out?”
Cassidy’s eyes went wide with terror, but my fingers never ceased their insistent rubbing over her aroused sex. I looked forward and saw that it was one of the groom’s cousins, a college sophomore if I remembered correctly. He was gathering his things and beginning to stand.
“Just enjoying the sunset for a minute,” I yelled back with a smile, my finger continuing to dance wetly over Cassidy’s clit. She was starting to close her thighs against my hand, maybe wanting me to stop while this relative stranger looked at us, maybe wanting at least for us to wait while we were being watched. But I wasn’t going to stop.
“You like this,” I whispered softly in Cassidy’s ear, my eyes taking in the terrified look on her face and then turning back to our fellow passenger, who was still looking over at us. “You love the idea of cumming right in front of this guy, don’t you?” I hissed into her ear.
“No,” Cassidy whispered weakly, but I could still hear the arousal in her voice as my fingers rubbed against her clit.
“You want him to catch you, don’t you?” I whispered. “You want him to see you cum. You want him to know that you are cumming right in front of him.”
“Oh God,” Cassidy moaned quietly again. The young man at the front of the shuttle was still looking at us, a smile on his face. My fingers began alternating their flicking against her wet little nub once more. Cassidy’s face was now flushed almost bright red, and her chest was heaving up and down as she sucked in air in quick gasps.
“Cum for him,” I teasingly whispered. “Let him see you cum.”
“Oh God!” Cassidy barely managed to stifle her moan. Her blue eyes were glued to the young man watching us, and then her body began to shake. Cassidy fought hard to control herself as she orgasmed on my fingers, but her hips shuddered rapidly and the tops of her breasts quivered as she rode her wave of pleasure. Her thighs clamped down tightly on my hand, but my fingers were still close enough to her pussy to continue brushing her clit with my finger tips. She shut her eyes tightly and bit the inside of her cheek to keep from screaming as she came.
Cassidy was still sucking in air, reveling in the tingles of her orgasmic after glow, when the young man quickly gathered up his jacket and abruptly left the bus. We never found out whether he knew what he had watched. After slapping my shoulder hard with her hand, I removed my arm from under Cassidy’s dress and we exited the shuttle with as much poise as we could muster.
———-
The wedding party and their dates were seated at a large, rectangular table at the front of the reception, with the joyful bride and groom seated at a small table just a few steps away. After washing Cassidy’s juices off of my hand in the bathroom, the start of the reception proceeded without much to note. There were introductions and the last of the appetizers were served. Everyone got seated and then dinner started. We made polite conversation with our entertaining table mates, and some touching speeches were made.
After the dinner plates were carried away, and while we were waiting for dessert, Cassidy’s hand landed on my upper thigh under the table. She gave me a squeeze and I thought at first that she was trying to get my attention. Then her mischievous little fingers ran lightly over the length of my soft penis. When Cassidy’s thumb and forefinger found the tip of my dick and squeezed gently, I knew for sure that it wasn’t just an accident that her fingers had found my member.
“What are you doing?” I whispered to her with a smile.
“Having my dessert,” Cassidy whispered back with a devious smile of her own.
My eyes darted around the table and the room. A couple of people returned my gaze, but no one seemed very interested in us. Those who were looking were doing so because we were sitting at the head table.
Cassidy’s fingers had found the outline of my cock within my pants, and hidden by the draping tablecloth, her fingers began to slide up and down the side of my pole. Cassidy barely seemed to be looking at me, the movement of her arm almost undetectable. But I could feel Cassidy’s hand rubbing up and down my member through the thin fabric of my dress pants, and regardless of my intentions, my cock was getting hard.
“You need to have this dessert right now?” I asked in another whisper.
“No,” Cassidy whispered, her bright white teeth lighting up her smile as she leaned forward to whisper in my ear, “But I want to. I think it’s only fair after what you did to me earlier.”
With Cassidy’s warm breath on my ear, her fingers sliding insistently over my inflating pole, and the tops of her full, round breasts in my line of sight as she leaned towards me, I was completely hard in no time.
Silverware clinked against a glass, and the best man was soon giving his speech. Cassidy’s fingers never stopped lightly rubbing and teasing under the table. The maid of honor went next, followed by some random conversation, and then the father of the bride was dancing with his daughter.
As we watched the father/daughter dance, I told Cassidy, “You’re going to have to cut that out. All the friction is starting to give me an Indian burn.”
“No problem,” she replied smartly, eyes fixed on the dance floor. In about three seconds she had my zipper down, had reached into my pants, and had pulled my cock out through the flap in the front.
“Cassidy,” I whispered harshly and angrily, but the waver in my voice betrayed my conflict. We would be in so much trouble if we got caught doing this, my cock was out in the open air under the table, with a hundred people in the room around us. But I had been aroused by Cassidy all day, and the last several minutes of her gentle fondling had me wanting to let her continue.
Cassidy didn’t even look at me, let alone respond. Instead, she reached into her little purse, poured an ample amount of hand lotion out into her palm, and was quickly lubricating the length of my hard shaft with the slippery fluid.
What both saved and cursed me was that the dancing started. Almost everyone else from our table, and a lot of other couples in the room, moved to join the bride and the groom on the dance floor. The lights in the room also went down significantly. One of the bridesmaids asked Cassidy if we were going to join in the dancing, and without even looking at me Cassidy responded that I needed a little time to digest. I gave in, surrendering myself to the delicious sensations of Cassidy’s slippery hand gliding up and down over the excited skin of my rigidly hard penis. My loins were aching for the sweet release of orgasm, and Cassidy’s tight grip with her soft fingers was milking me steadily towards that blissful eruption. I was glad that the music had gotten loud and most people were watching what was happening on the dance floor, because the wet squelching of Cassidy’s hand job was starting to make noticeable slurping noises under the table.
Other than my concern over people hearing us, I was largely ignorant of anything else going on around us. My brain was all too happy to focus on the pleasurable sensations Cassidy was rubbing into my cock. That’s probably why I didn’t notice the one person still sitting at our table until the tingles in my groin had started to approach orgasm. With my body turned slightly towards Cassidy in order to provide her soft hands with better access to my rigid pole, my back was turned slightly towards our other table mate. Her name was Mary, the bride’s first cousin, who was at her first wedding since she turned 21, so she was able to celebrate with the open bar for the first time. Mary was a blond wisp of a girl, thin with skinny arms and legs. She also had a very pretty face, with sharp, angular cheek bones and bright blue eyes framed by long, silky blond hair.
I wasn’t thinking about Mary. I was thinking about how Cassidy’s arm was starting to shake the table cloth as her hand pumped faster and faster up and down my pole. The resulting vibrations were causing the pale tops of her big breasts to jiggle, which was getting me even hornier. But combined with the soft squelching noises coming from under the table, alarms were starting to go off in my head that someone might notice. Those alarm bells were being drowned out by the roar of my approaching orgasm.
“I think she knows what we’re doing,” Cassidy whispered with a devious smile. Her hands pulled insistently at the crown of my cock, sending tingling bolts of pleasure through my groin every time she slipped her closed fist over the sensitive head.
“Who?!” I blurted out with alarm, scanning the dance floor and seeing no one who was paying any particular interest to us.
“Mary,” Cassidy whispered with a slight head nod in Mary’s direction.
I turned to look over my shoulder and sure enough, Mary appeared to be looking at me and Cassidy. Her head was definitely not turned in the direction of the people on the dance floor. I looked back at Cassidy, unsure of what to do.
“Yup, she’s definitely watching us,” Cassidy whispered, now returning Mary’s stare while her fingers continued to slide tightly over my excited rod. “Look at cute little blondy, she must know what we’re doing.”
“Maybe we should stop…” I responded weakly.
“Why?!” Cassidy returned with unexpected vehemence. “Didn’t you do the EXACT same thing to me earlier?”
“I guess,” I responded breathlessly, my mind having a difficult time focusing on anything other than the pleasurable feeling of Cassidy’s closed fist pulling up and down over my hard cock.
“You close to cumming?” Cassidy asked.
“Yes.”
“Then LOOK AT HER!” Cassidy whispered demandingly.
I turned over my shoulder again, Mary’s blue eyes meeting mine as I turned to look at her, a slightly puzzled expression on her pretty face. There was just something both dirty and exhilarating about pretty Mary’s innocent blue eyes locked on mine while another woman was pleasuring my manhood. I was right near the edge of orgasm when Cassidy whispered softly right against my ear, “Cum for her.”
That little encouragement sent my libido shooting skyward and the resulting orgasm set my whole body aflame. My orgasm was a white hot burst of pleasure up through my body, my eyes drinking in one last glimpse of Mary’s pretty face before squeezing shut tightly. Luckily Cassidy had prepared for this moment, and one of the table napkins was covering my cock as my semen shot forth in a white rope. I tried to control my body and not attract attention, but Cassidy’s fingers continue to gently play with the underside of my cock head, coaxing the orgasm and cum out of me and into the napkin in her other hand. With Cassidy stoking my orgasm as I came, my midsection and my legs shook, and it was all I could do not to groan or yell.
When I opened my eyes, Mary was still looking at me. In the darkness, it almost seemed like there was a slight flush to her pale face, and her pink lips were slightly parted. Our eyes met for a brief moment, and then she quickly turned away and stood to leave her seat.
Cassidy carefully scooped up the cum on my cock as she lifted away the napkin, wiped the back of her slippery hand on it, and then discarded it on the floor under the table. “We should both probably go clean up in the bathroom to make sure we didn’t get any mess on ourselves.”
After a quick check in the bathroom mirror and wiping away some lotion from my pants, I met Cassidy on the dance floor. We were both big smiles and goofy energy, and really enjoyed the party. I bumped into Mary a couple of times on the dance floor, and she gave me and Cassidy some friendly smiles. But it also seemed like Mary tried to keep her distance from us.
———-
Inevitably the alcohol took over, and I remember dancing wildly and getting very sweaty but little else about the reception. I don’t even remember how we got back to the hotel afterwards, though I assume it was the wedding shuttle. And I do clearly remember one flash of the dance floor lights illuminating the tops of Cassidy’s full breasts in her little green dress, but that’s about it.
My memory starts to clear back in the hotel pool. When I had looked in on the pool after checking into the hotel, I thought it was a sad little place. Floor to ceiling windows let in a lot of light from the outside, but the view faced the back of the hotel which was a bunch of thick hedges and then the solid concrete wall of a warehouse next door. You couldn’t see the pool from the entry door, you had to walk a short way and turn a corner. Even then, what greeted you was a small cement pond that could fit a maximum of 25 people and smelled strongly of chlorine.
But when my memory began to clear, the pool was a happening place. There were at least a dozen of young revelers, loudly laughing and some still drinking, as we splashed around drunkenly in the water. I was (thankfully) wearing swim trunks that I had packed for some reason. Many of the people with us were in their underwear, men in boxers and women in bras and panties. Cassidy was sitting on my lap on the steps in a mismatched bra and panty set, with one of my t-shirts over that which stretched almost down to her knees.
I vaguely recall the bride and groom being at the pool party at one point, which explains why I was told afterwards that they started the partying there. At the point my foggy memory starts to clear, the people with us were still being loud and splashing around the small pool, but the party was winding down and people were starting to leave.
As the other partiers began to filter out, I realized that blond, willowy Mary was sitting in a pool chair near the short entry hallway. She was wearing a long t-shirt, like Cassidy, and I guessed she was also down to hear underwear underneath. I wasn’t paying much attention to Mary, because she seemed to be quietly keeping to herself. Most of my attention was focused on sharing stories and laughing with the other guests. Cassidy sitting on my lap was the most affectionate thing she had ever done with me in public, but otherwise she was largely ignoring me, talking to other people.
Finally there was just me, Cassidy, and another young couple left at the small, indoor pool, along with the empty bottles and plastic cups that represented the remnants of the party. Mary was still sitting in her chair near the doorway, her blond hair wet and stuck to the back of her neck and her shirt clinging to her thin frame, so I assume she had gone into the pool at some point.
Cassidy, predictably, had started getting frisky. While still chatting with the other couple present, she began wiggling her smooth, slippery, wet butt cheeks across my lap under the water. One of my hands slipped casually down Cassidy’s slippery thigh and found the soft spot at the joining of her legs that I had grown to know so well. While Cassidy and I casually chatted with the other couple, she slid her slippery butt cheeks over my growing erection and I playfully ran my finger up and down over her pussy lips.
The other young couple got out of the water and spent a few minutes collecting their things. The girl couldn’t seem to find the shoes she remembered wearing down to the pool. While we laughed about their misplaced items, Cassidy began really pressing her firm ass against my crotch. Emboldened by the alcohol and irritated with her teasing, I opened the front flap of my swim shorts and drew my hard cock through the opening. Cassidy caught me off guard by quickly reaching down, grasping my cock between her soft, slippery fingers, and giving my meat two friendly tugs.
If the other couple noticed our friskiness in the water, they did a good job of hiding it. More likely, they were distracted by the search for their things and the water did an adequate job of covering our shenanigans. I slipped my fingers under the waistband of Cassidy’s bottoms and tugged downward. She helped by lifting herself off my lap and moving to the edge of the pool, enabling me to pull the bottoms over her tight, round ass and most of the way down her leg. She lifted her chest onto the deck of the pool, the top of her ass floating to the surface of the water, and I could see her bottoms dangling off of one ankle. It took me a second to realize that she was pointing. She had spotted the missing shoes under one of the chairs.
The other couple was so grateful to find the shoes, they barely noticed that I strode up behind Cassidy with my full, proud cock sticking out in front of me. I grabbed Cassidy’s hips, pointed my round cock head at the opening of her pussy, and was about to thrust myself home when Cassidy pushed me away. The other couple offered their thanks, awkwardly gathered up their things, and said goodnight.
“Not in this dirty pool water,” Cassidy whispered, turning back to face me with a serious look on her face. “There’s so much chlorine.
“What was he about to do?” came a soft voice. It was quiet Mary, who we had mostly forgotten during our time at the pool.
I froze for a moment, trying to come up with an excuse when Mary spoke again so quietly that it was almost difficult to hear what she was saying.
“What was he trying to do, just then, when you pushed him away?” Mary asked.
Cassidy’s blue eyes locked on mine, a mischievous look on her face, and she answered, “He was being very naughty and trying to shove his cock in me.”
I was caught completely off guard by the response, and was even more surprised when Mary said, “Oh, I thought it was something like that.”
Cassidy turned to face Mary, still waist deep in the pool water, and asked in a coaxingly sweet voice, “You weren’t going to tell on us, were you Mary?”
“Of course not” replied the little blond, a silly smile spreading across her face.
“Why ARE you still down here, Mary,” Cassidy asked, her head cocked in honest interest. “Were you going to watch us if we fucked down here in the pool?”
“I don’t know,” Mary replied, “I guess I thought you might do something… interesting again.”
“Have you had sex before?” Cassidy asked.
“What?” came the quiet reply.
“You heard me. Have you had sex before?” Cassidy asked again insistently. “We won’t tell anyone, just like you weren’t going to tell anyone if we had sex down here. You keep our secrets and we’ll keep yours.”
Mary’s blue eyes appeared genuinely thoughtful for a moment, and then she responded softly, “Yes, I’ve had sex.”
“You ever see other people have sex before?” Cassidy continued to pry.
“No,” Mary began, and then added, “Unless you count what you two did at the dinner earlier.”
Cassidy laughed, a light, sweet laugh. “So you did know what was going on,” Cassidy finally said.
“Yeah,” Mary responded. After another pause she added, “Why did you do that?”
“We were just fooling around and you happened to catch us,” Cassidy answered.
I had no idea where this conversation was going, but my hard on was starting to drain away and if I wasn’t going to get to fuck Cassidy in this pool then I was starting to lose interest. I began to consider gathering up our own things and seeing if Cassidy might let me fuck her back in our hotel room. Cassidy seemed to sense that I was losing interest, and she gently grasped my deflating cock under the water, playfully rubbing at my cock head with her thumb.
Cassidy’s eyes turned away from my cock and back to Mary as she asked, “Did it turn you on to watch him cumming?”
“Yeah, I guess a little,” Mary responded.
“Is that why you waited down here with us, you wanted to see if we would fool around again?” Cassidy asked.
“Probably,” Mary responded very quietly.
“If I let him fuck me in front of you, would you be willing to play with yourself in front of us?” Cassidy asked, again catching me completely off guard with the question. “I mean, I think it’s only fair. If you get to watch us fuck then we should get to watch you cum.”
“Umm…” Mary considered slowly while we waited. “I guess so.”
“You sure you okay with this, Mary?” Cassidy asked again.
“Yup,” Mary replied with little hesitation. “But what if someone comes in here and finds us?”
Cassidy laughed, “Then we’ll scatter.” Cassidy turned back to face me, my cock still in her fingers, and asked, “You good with this, sexy?”
Still a little foggy, I tried to reach deep into my brain to ask myself if I thought this was a good idea. The response that came back was, “Why not?” So out loud I said, “How are we going to do this?”
“However you want,” Cassidy told me, a devious look on her pretty face. “But first Mary has to let us see that pussy.”
Mary hesitated again, but eventually she stood and pulled down a pair of white panties and kicked them away with her foot. Once she had made the decision to play along, Mary was committed and sat back down with her legs spread. There was just a little strip of white blond hair running up from her pussy, but her lips were pale and very pink, completely shaved and looking a little wet in the artificial overhead lights of the pool room.
Cassidy was peeling off her shirt and stepping out of the pool. Little trickles of water ran down Cassidy’s smooth, shimmering skin, highlighting the channel between Cassidy’s big, round breasts and the swell of her smooth, toned thighs. I followed Cassidy out of the water. In my horny, playful state, once it became clear that I was going to get to fuck Cassidy here and now, my mind could focus on little else. But then I hesitated as my exposed cock came out of the water and I began to shed my shorts. Cassidy and I were not alone.
Again seeming to sense my hesitation, Cassidy turned back to delicately grasp my full, rigid erection in her hands. “Does seeing his cock turn you on?” Cassidy asked.
“Yes,” Mary replied a little breathlessly.
“Then play with yourself and enjoy the sight of this big piece of dick,” Cassidy teased with a laugh.
Mary’s hands actually dipped between her legs. I couldn’t quite see from the angle where I was standing, but I was guessing that Mary had indeed begun to play with her own pussy.
Reassured, my focus returned to Cassidy. There was a lot of stimulation hitting me, from Cassidy’s nearly naked body glistening with the last drops of pool water to Mary’s blue eyes on my manhood, but all of it was contributing to the overwhelming desire for my cock to get its release.
“How do you want to do this?” Cassidy asked me again.
Without I word, I grasped Cassidy’s hips firmly and steered her towards the near wall of the pool room. I then pushed between Cassidy’s shoulder blades and she bent over to place her hands on the wall in front of her. From this position, slightly bent at the waist, Cassidy’s firmly toned ass stuck out behind her. We were maybe six feet away from Mary’s chair, though Mary had to physically turn her seat to get a better view of us.
“You want to do this standing up?” Cassidy asked.
I replied by gripping Cassidy’s hips and placing my cock head at the wet entrance to her sex. I had to squat a little in order to get the angle right, but I was so horny that as soon as I did get the angle right I thrust my hard meat into Cassidy’s hot, wet snatch.
“Oohhhhhh,” Cassidy moaned as I pushed several inches of my throbbing, hard dick up into her pussy.
I hunched downward and withdrew a little, then thrust upward, slamming all of my hard cock home into her tight, wet tunnel. I could feel Cassidy’s soft and slippery pussy walls gripping me as I quickly built up a rhythm, thrusting my thick meat in and out of her pussy. Cassidy gasped and then began to moan as I fucked my meat in and out of her hole. I held Cassidy in place with a firm grip on her hips as I shoved my meat upwards, and then enjoyed the feeling of her pussy walls sliding against my member as I squatted and withdrew.
There were so many noises echoing in the little pool room. My balls began to slap against Cassidy’s clit as I slammed my thick meat home, which in turn caused Cassidy to let out little yelps of pleasure. Cassidy’s pussy began to make little squelching noises as I fucked my cock in and out of her. I also began to grunt as I fucked hard upward into Cassidy, feeling Cassidy’s tight little pussy milking my member. And even though Cassidy was still wearing her bra, the hard fucking caused her big, round breast to lift up and down over her chest, making a slightly wet, slapping noise.
But the noise that caught my attention was a soft moan from Mary. I turned to look at the little blonde, who was sitting with her legs spread wide, wantonly diddling her little clit with her blue eyes glued to our fucking. Mary’s pussy lips were red and dripping with her arousal, and her cheeks were flushed.
Watching Mary play with her clit gave me an idea, and I reached around with one hand and began to rub at Cassidy’s clit. She moaned deeply in response, while I continued to slam my cock in and out of her wet, slippery pussy channel. I was starting to feel the pleasurable burning of orgasm building inside my body, listening to Cassidy moan and stealing glances at Mary’s aroused face.
Then Cassidy said, “I’m going to cum.” Two short whimpers later, as I shoved my rigid pole deep into her tight hole, Cassidy loudly moaned, “OHHHHHHHHHHH” and her body shook as she came.
I slowed my fucking, thrusting upward gently with my hips, as Cassidy came hard on my cock. Her muscular legs shook as she orgasmed, her eyes shut tight while she bit her lips. I myself was close to cumming but not quite at the edge, so I didn’t want to stop.
When Cassidy’s eyes opened again, she turned to look at Mary. Mary’s little fingers were flying up and down as she rubbed at her clit, and she was panting like a Rocky(D) in heat, her pale cheeks completely flushed red.
As if answering a question from Cassidy’s eyes, Mary said, “I’m so close.”
“Would seeing his cock help you cum,” Cassidy asked, a little out of breath.
“Yes,” Mary replied, practically pleading.
“Show her your cock, stud,” Cassidy ordered.
Reluctantly, I withdrew my hard dick from Cassidy’s hot, tight snatch. My cock was so throbbing hard that it stood straight up, glistening in the pool light with Cassidy’s juices.
“Ohhh,” Mary moaned quietly, her eyes fixed on my dick and she continued to diddle her aroused clit.
“You want him to touch you with it?” Cassidy asked teasingly.
“No!” Mary replied firmly, still furiously rubbing at her sensitive little spot.
“You want to see his cock cum?” Cassidy asked.
“Yes,” Mary responded, then added, “Please.”
Cassidy dropped to her knees next to me and grasped my cock tightly in her soft fingers. She began to rapidly pump her closed fist up and down the length of my sensitive shaft, the cock head less than four feet from Mary’s face.
Cassidy’s fingers tightly sliding up and down my pole quickly started to feel very good, but that did not feel as good as her wet, tight pussy. I also enjoyed the sight of Cassidy’s round, firm breasts jiggling back and forth inside the confines of her lacy bra, but it wasn’t quite getting me to the edge of orgasm.
Mary on the other hand was moaning at the sight of the hand job just a few feet away. Her little fingers were flying back and forth so quickly over her pussy that I began to wonder how her arm could keep up the motion.
“Have you ever seen one so big?” Cassidy teased, looking at Mary.
“No,” Mary panted.
“Does it turn you on to think of a big cock like this slipping into your pussy?” Cassidy asked.
“Yes!” Mary pleaded.
“Are you going to cum?” Cassidy asked.
“Yes!” Mary moaned again. “Make that cock shoot!”
Cassidy’s bright, blue eyes looked up at me and she asked, “You close babe? You going to cum for us?”
“I’m pretty close,” I responded, Cassidy’s slippery fingers continuing to milk my sensitive rod.
Frowning, Cassidy knew that meant I wasn’t close to my orgasm. With her free hand, she reached behind herself and unclasped her bra. Cassidy’s big and impossibly firm melons spilled into view, her pink nipples bared for my eyes, Cassidy lifted one of her big tits obscenely and said, “You can cum on my tits if you want to.”
That caused a little spark of arousal to fire inside of me, sending me a little closer to the pinnacle of arousal.
Then Mary surprised us both by saying, “You can touch my breasts if it will help you.”
Mary’s blue eyes were on fire with her arousal, and her thin, delicate fingers were furiously working over her wet little nub.
I took a step forward, Cassidy careful not to lose my cock in her grasp as she slid up and down my sensitive pole, and I reached out towards Mary. The thin little blond did not flinch as my hand closed over her smallish breast, and I cupped it firmly in the palm of my hand.
“Ohhh,” Mary moaned in response to my hand firmly cupping her little tit. Between Mary’s moan and the erotic sensation of playing with Mary’s boobs while Cassidy jacked my cock, I felt more tingles bubbling up inside me.
I could feel Mary’s hard nipple poking out from beneath her wet t-shirt and bra, and I rubbed at it with my thumb. This elicited a sharper, “Ohh, yes!” from Mary, who began to writhe as I played with her nipple while she played with her clit.
“You going to cum, Mary?” Cassidy asked, her tight grip still milking my pole.
“Yes!” Mary panted.
“You going to cum, honey?” Cassidy asked me.
“Yes,” I replied quietly, enjoying the soft squeeze of Mary’s tit flesh and the insistent jacking of Cassidy’s hand.
“You going to cum because you like playing with Mary’s breast?” Cassidy asked.
I looked into Mary’s highly aroused face and saw the burning lust behind her blue eyes. “Yes,” I replied. Playing along, I added, “Her tit feels sooo good.”
Mary squeezed her eyes shut and squeaked, “I’m cumming!” Her thin little body quivered and her skinny legs shook back and forth with the power of her orgasm as it washed over her.
“Oh God,” I moaned, watching Mary cum beneath me, feeling her body shake through the little breast I cupped in my hand. The tingling sparks overwhelmed me and I felt the white hot pleasure of the orgasm explode in my body.
Sensing what was happening, Cassidy barked out, “Mary! Watch!”
I forced my eyes to stay open as Mary’s blue eyes flew open in time to see the first white spurt of cum spew out from my swollen cock head. The cum splatter landed wetly across Cassidy’s pale chest, coating the round tops of her breasts. Then Cassidy positioned her mouth obscenely over the head of my cock, looking out of the side of her eyes at Mary. My next three shots of cum spewed into Cassidy’s waiting mouth, and Cassidy smiled around my dick.
“Oh shit!” Mary cried out, her eyes squeezing shut again, and then her body was shaking in another orgasm. Mary’s fingers moved more slowly over her clit as the second orgasm flowed through her little body.
As my orgasm subsided, I looked down to find Cassidy already wiping her chest with a towel. “That was hot,” Cassidy said with a bright smile, “Super hot. I don’t think we could have timed or planned that better.”
As Cassidy retrieved her bra, Mary followed her lead and went in search of her discarded bottoms. “It was hot, wasn’t it?” Mary said with a giggle.
“Amazing,” I agreed.
We gathered up our things quickly and were soon tip-toeing out of the pool room. I never saw Mary again.
———–
The next morning I woke up naked with a nude Cassidy in the bed next to me. My mind was clouded by a slight hangover, but I also recalled the incredible memories from the day before.
As I stirred, Cassidy did too, the sheet and comforter sliding off of her large, round naked breast as she reached up to rub her eyes with her hands. Her pink nipple popped into view, capping her firm tit flesh, her skin glowing in the morning light. Waking up next to Cassidy like that, I felt like I had never been happier.
Cassidy leaned her head back to look up at me, her blue eyes sparkling in the morning light, and she said, “Good morning, sunshine” with a beaming smile.
“What was that all about, last night?” I asked her. It was the first thought to pop into my head.
Cassidy rolled herself onto my body so her big breasts were pressed against my chest and she looked into my eyes from just a few inches away. “You didn’t have fun with Mary last night?” The morning light set Cassidy’s red hair aglow behind her pretty blue eyes.
“Yeah, I did,” I replied with a smile of my own.
“So what’s the problem?” she responded.
“Why did we have to do all that? We could have just come back to the room and fooled around the two of us. Why did we have to mess with Mary like that?” I asked.
“Come on,” Cassidy replied, sounding slightly indignant. “Couldn’t you see it from the moment she watched you cum at the table? Mary WANTED that. She was looking to fool around, that’s why she stuck around at the pool.”
A moment of silence passed between us while I considered her response. Cassidy seemed to take that as agreement and continued, “I thought it was hot, and you had fun, and Mary looked like she came pretty hard. I bet that was the hottest thing sweet, innocent little Mary ever did. So where’s the problem with that?”
“I don’t have any problem with it,” I responded quickly. “I was just curious. Sometimes I like it when it’s just the two of us having sex. You seem to like it… spicier, and I was just wondering why.”
Cassidy’s arm slid down my chest, her hand found my cock and gave it a playful squeeze. “We have SOOO much time for just the two of us to have sex. We have sex all the time now, whenever you want. I want to have FUN! I want to do things that I may never get to do again, while I still can.”
Cassidy’s thumb was gently stroking the underside of the crown of my cock, distracting me a little. But I had rarely seen Cassidy speak so passionately. I felt like I had hit a nerve, and I wanted to know more.
“Why are you so insistent on doing all this crazy stuff?” I asked. “I mean, don’t get me wrong, I love it. I just want to know why you love it.”
Cassidy looked thoughtful for a moment, but then her blue eyes and her pretty face took on the mischievous look I had grown to know so well. “When I was growing up, I always wanted to be super good. I grew up in a very religious family and I loved it, and I still do. I think my family is great. But there were all sorts of things I didn’t do that my friends were doing. The biggest was sex. I’d get together with my closest girlfriends and they’d all be talking about sex, and pretty soon I was the only virgin. I thought they were crazy, fooling around like that. It was bad and it was dirty and you could get into serious trouble. And a lot of the time they didn’t enjoy it, but they would giggle and whisper secrets and it was like they were all in on something and I wasn’t.”
“I really didn’t mind, I totally thought I was doing the right thing,” Cassidy continued. “But then I got to college, and one night I got a little drunk with this girlfriend of mine. And she was very cute and super sweet but also really super sexual. And one thing leads to another, and the next thing I know she’s playing with my pussy with her fingers, and then she just went down on me. And it was the dirtiest thing I could do! Not only was I fooling around, I was fooling around with a girl! And she had her mouth on my pussy!! It was SOOO wrong.”
“But she knew exactly what she was doing. I came so hard on her tongue, it was amazing. I don’t think my body ever felt that good before. She made me cum hard twice that night, and then the next day it just wasn’t a big deal to her. She did this kind of stuff all the time, and she was like, it happened and now we’re cool. But it was a SUPER big deal to me.”
“So then I started fooling around more,” Cassidy went on. “Sex was FUN. Sex felt GOOD. I wasn’t a slut or anything… you better NEVER think that I’m a slut. But I was more open to exploring that and letting sex happen. And I really loved it. Suddenly I realized all the things I had been missing. I didn’t get to do all the stuff my friends had experienced and I never would. And that’s why I don’t want to miss out on ANYTHING anymore.”
Cassidy’s fingers were still lightly rubbing up and down my cock, and my member was starting to slowly grow through her attention. “What do you want to do right now?” I asked.
“I want to fuck again,” Cassidy responded with one of her dazzling, bright smiles. “I want to fuck however you want to fuck.”
Moments later, Cassidy was on her back with her eyes closed, my head between her legs and my tongue intently lapping at her pussy. “Oh fuck!” she moaned, “You always know just how to stroke my clit with that tongue of yours.” I was rubbing the full length of my rough tongue over her most sensitive spot, lapping up her flowing pussy juices as I went, my fingers spreading her outer folds to fully expose her sensitive little button to my attention.
When I switched to very rapidly flicking just the tip of my tongue firmly against her wet clit, Cassidy cried out, “Oh, oh… I need your cock.”
Unwilling to stop my onslaught as my warm mouth closed over Cassidy’s pussy, I swung my body around so my knees were on either side of Cassidy’s head and my cock was right above her face. Cassidy quickly grasped my hard shaft and slipped the head of my dick between her soft lips, where her hot mouth went to work on sucking the head of my member. As we 69ed, I slipped two fingers into Cassidy’s tight pussy and began to finger fuck her deeply and quickly as my wet tongue continued to lash back and forth over her clit.
“Oh fuck, oh fuck,” Cassidy began to pant awkwardly, mumbling around my dick as my manhood filled her hot little mouth. “I’m going to cum.”
I bored down harder on Cassidy’s pussy, my tongue flicking quickly back and forth while my two fingers flew in and out of her hot, wet, hole.
“MMMMMMMMMMMMNNNNGG!!” Cassidy groaned loudly as she came. She had closed her lips around my member and her moans were vibrating my cock in one of the most erotic ways I had ever experienced. Her hips bucked a little against my tongue as she surrendered to her orgasm and tingled my member.
I was so turned on, as soon as she was done cumming, I flipped Cassidy onto her stomach and lined up my cock head at her pussy entrance, ready to fuck her from behind. Cassidy raised herself up onto her knees, then looked back at me from beneath her red hair with a smile. “Go ahead, lover,” she teased as she shook her firm, round ass at me.
I slowly and carefully worked the full length of my cock into Cassidy’s tight, wet hole, causing Cassidy to arch her back deeply as my thick dick penetrated her. But as soon as I bottomed out, I grabbed Cassidy’s hips and began ramming my cock in and out of her. Cassidy yelped as I fucked her hard, slamming my long cock into her hot little hole, her ass cheeks bouncing back and forth with my assault.
I could feel the pleasure of my orgasm building inside of me as Cassidy moaned from my hard fucking. Then I realized that beneath her body, Cassidy’s big tits were swinging back and forth from the force of my pounding. I could hear her nipples sliding back and forth across the sheets beneath us.
Close to the point of cumming, I wrapped my hands around Cassidy’s taut, young body and gripped her big melons with both of my hands. I pulled her up against my chest, burying my cock deep inside of her wet, slippery tunnel, as my hands mashed her big, round breasts against me. I felt her nipples pressing into the palms of my hands, and then I came.
The orgasm burst hard inside of me, and I blurted out, “Fuck yes!” as I felt my cock begin to deliver its hot load of cum deep inside of Cassidy’s pussy. I held her body close to mine with my firm grip on her full, round breasts, and my cock twitched deep inside of her and squirt after squirt of my cum emptied my balls into her tight, soft pussy.
We collapsed into a sweaty pile on the bed together, both wearing big smiles and panting a little from the effort. I leaned forward and kissed Cassidy softly on the lips. When I drew back, it seemed she was wearing a look of surprise on her pretty face.
———
The raunchy wedding weekend with Cassidy had seemed so absolutely perfect that I was totally unprepared for what came next. I settled back into my work week routine, but Cassidy was rarely around. We were both home only one night that first week, and while Cassidy wasn’t cold or distant towards me, she also wasn’t super friendly. With all the crazy sex from the weekend, I wasn’t feeling particularly frisky or in need of some alone time with her. But with all her talk about “letting sex happen,” I had assumed that we were headed to a wild, care-free level of hedonism that would make everything we had done before seem tame.
I might have caught on sooner that something was amiss, but my work was eating up all my time. As much as I complained, I kind of liked how busy I got. It kind of felt like being an adult for the first time, complaining about long hours and how exhausted I was when I got home late. My favorite part was the extra money, I started making a decent amount of overtime that padded my pay check nicely. It also helped that I was spending most of my work time with Kristen, as our bosses were working on the same project. In addition to being very cute, she was also a lot of fun to be around. She made the long work hours easier to bear.
Looking back, I think maybe I knew something was up after Cassidy and I didn’t have sex at all the weekend after the wedding. I thought maybe she was on her period, because she didn’t seem interested in being intimate and we had already established that pattern of never fooling around during her time of the month. But the alarm bells really started going off for me when Cassidy didn’t come home one night early the following week. I was a little worried and texted her around 10:00, and when she didn’t respond I started to get seriously worried. I was sick with concern, couldn’t sleep, until my phone finally buzzed at 2am with the message “Hey, I’m great, spending the night at a friend’s place.”
I didn’t see Cassidy the next day or night, I had to work late and she was already in her room by the time I got home. The next night I finally caught her in the kitchen when I came home. As soon as I walked through the door and saw her standing there, I blurted out, “Hey, I’m sorry if I come off as a little over protective, but I was kind of worried about you when you didn’t come home the other night.”
Then I stood there awkwardly, realizing that all the words had come out in one big jumbled rush. Cassidy fixed me appraisingly with her blue eyes, as if she was measuring me, and finally said in an even voice, “Sorry about that. I was hanging out with some friends and it got late so I just slept over at their place.”
I took a deep breath, focusing on trying not to sound like I was in a panicked rush, and replied, “I’m sorry,” even though I didn’t really know why I was sorry. “I know you don’t owe me a phone call or anything. I’m not in charge of you. I just got worried when you didn’t come home.” Trying not to sound too concerned, I left it there.
“Okay, I understand, that’s nice of you to be concerned” Cassidy responded, still very even in her voice. “If I can’t make it home for the night, I’ll try to give you a call to let you know. Is that okay?”
“Absolutely,” I responded quickly, even though the word “try” wasn’t really okay with me. “Thanks.”
I didn’t see Cassidy again for the rest of that week, the weekend, or the following week. I came home pretty late a lot of nights, so I know even now that she probably wasn’t purposefully trying to avoid me. I’d get home and Cassidy would already be in her bedroom. But that weekend I was home most of the day, and Cassidy wasn’t around. Friday night I went out to happy hour with my coworkers to unwind after a long day at the office. Both Saturday and Sunday Cassidy left early in the afternoon and didn’t get home until very late at night.
Having gone a full week without seeing Cassidy at all, I was in a strange mood that Friday. Four of my coworkers stayed with me until almost 8:00, working on our big project, before we finally called it quits. The one point of comfort was that our bosses were still in the office when we left. When someone suggested we all just go out to a restaurant and get drinks and dinner together, sort of like what we had done the previous Friday, it sounded like the obvious best thing to do.
Kristen was there, her chestnut brown eyes full of life and laughter. There was a lot of loud laughter around the table, unwinding after a very long week at work. We each had a couple of drinks before the food arrived, and a couple more drinks during the meal. We hesitated on ordering the second round of drinks for after the meal, but it seemed like the right thing to do. All those rum and cokes for me is why I don’t remember much of what we talked about. But I do remember Kristen’s bright smile, the cute little dimples in her cheeks, and the way my heart seemed to skip a beat when she was flashing that pretty smile and her eyes turned towards me.
After we settled the bill, we had that awkward moment of goodbyes where everyone stood outside the restaurant, chatting for a little too long and trying to figure out how we were all getting home. It turned out that Kristen and I lived in the same direction.
“I can walk you to your place if you want,” I offered, “I don’t mind.” I looked at my watch and was sur
prised to see that it was after 11. “Plus, it’s getting late.”
“You sure?” Kristen asked. “You’re going to walk the whole way home? It’s pretty far from here to your place.”
“Oh yeah,” I responded, “too expensive to take a cab, and I could use the walk.”
“Okay,” Kristen responded with a smile. “That would be great.”
I swear to you that I had no ulterior motive when I offered to walk Kristen home that night. I was fully planning to head straight back to my place afterwards, planning in my head to drink a little water before bed to stave off any hangover. The conversation was fun and pleasant, and I really enjoyed talking to Kristen. Still, it came as a surprise when we got to her building and Kristen said, “Hey, you want to come up and have a drink or something before you head home?”
The even bigger surprise was when I quickly responded, “I’d love that, if you don’t mind.” It felt like the words were coming out of my mouth before my brain even had a chance to register what I was saying. I’m still not sure why I said it. Part of me suspects that I was feeling lonely after spending all my time with Cassidy and then suddenly not having her. Part of me suspects I was just drunk and turned on by Kristen.
The biggest surprise (unless you remember where you are reading this story) was that five minutes after walking in the door to her apartment, Kristen was sitting on my lap and we were making out on her couch. It was an epic make out session: no words, no heading for second or third base, just 30 minutes of sucking face. Her lips were so soft and full, I couldn’t help but start comparing everything about her to Cassidy. I tried to drive those thoughts out of my head, and focus on Kristen, but I couldn’t help noticing all the new things that were different from Cassidy. For example, Cassidy liked to swirl her tongue around mine when we were French kissing. Kristen would dart her tongue between my lips and brush my tongue, and then pull her tongue back quickly, like she was playing coy. And Cassidy liked to move all over the place, sometimes she’d nibble on my neck a little and then go back to kissing me softly on the lips. Kristen held my face in her hands like she was trying to zero in on my lips and make sure she didn’t miss a single kiss on her target.
I reveled in nibbling on Kristen’s lips and kissing her deeply, so it took me a while to realize what we were doing with her grinding on my lap. What woke me up to all the naughty possibilities was Kristen grinding her pelvis against my legs. Somehow in all the frenching, Kristen had moved herself down one of my legs so her hips were really grinding downward against my thigh.
Right in front of me were her perfect, perky breasts. They were much smaller than Cassidy’s but fit Kristen’s frame very nicely and always seemed so impossibly shapely and round in her work shirts. I reached out with both hands and cupped her full breasts, daring to squeeze the firm flesh in my palms and feel the fullness of Kristen’s young melons.
I thought to myself that Kristen’s tits seemed just perfect for my hands, filling them completely with warm tit flesh while not providing much overflow beyond my fingertips. Cassidy’s tits, especially when she was naked, were such a handful that I sometimes felt they were overwhelming my hands or too much to hold onto while we were fucking. Then I immediately screamed at myself in my head, “STOP COMPARING KRISTEN TO CASSIDY! STOP THINKING ABOUT CASSIDY!!”
I rubbed at Kristen’s hardening nipples, feeling her little tips beginning to poke out from beneath the fabric of her bra and shirt. She responded by moaning into my mouth and grinding herself harder against my thigh.
I took that as a cue to let one hand slide down over Kristen’s body and feel for the waistband of her pants, but Kristen quickly broke our kiss. She pulled her head back and looked at me, cheeks a little flushed, with a combination of lust and worry in her eyes. “Not yet, okay?” she asked.
“Yeah, of course,” I responded.
We quickly went back to kissing and she seemed to have no trouble with me playing with her perky breasts through her top. I cupped the tips of her firm boobs between my fingertips and stroked her hardening nipples with my thumbs. That got Kristen grinding hard again against my leg, mashing her pussy back and forth over my thigh, through all of our clothes. She started whimpering cutely into my mouth as we kissed, almost mewling as my thumbs picked up their rubbing against her nipples and her hip thrusts became more frantic to match that speed.
Kristen broke our kiss, and I looked up at her pretty face as she moaned, “Oh… oh… ohhhhh,” in time with the grinding of her pelvis against my thigh. Her eyes were shut and her cute apple cheeks were totally flushed with arousal. I pinched her nipples through her shirt gently, and her eyes flew open in surprise as she yelled, “OHHHHHH!”
And then Kristen surprised me, letting out a high pitched squeak of, “Oh crap!” before her little body started to tremble atop me. Her arms embraced the back of my head and hugged me tightly to her chest as her legs shook and her mid section seemed to spasm atop me. She was cumming. As she trembled and panted, her little body lost in the bliss of orgasm, my cock swelled to full girth beneath her. I hadn’t had a girl cum from dry humping me since freshman year of college.
Kristen sat slumped against me for several moments, resting in my lap while half hugging me and half using me for support. When she finally looked up at me with sleepy, brown eyes, she said, “Do you want to sleep over?”
My thoughts at the time were all over the place. The evening had already gone in a direction far from the one I had expected. I probably should have ended it there, I told myself the best thing would be to walk home and then start again in the morning by trying to figure out what I should do or what I wanted to do next. But I was horny and my cock was rock hard, so of course I stayed.
Sadly for my throbbing dick, the most physical activity Kristen and I did after that was walk hand-in-hand to her bedroom. We lay down atop the covers, still fully clothed except for our shoes, and talked for a while. Just before we drifted off to sleep, Kristen said, “Sorry I couldn’t… you know… didn’t… let things go any farther… between us… earlier.”
“It’s okay,” I responded, eyes already half closed. “I still had fun.”
———–
I woke up the next morning to the sound of the shower running in Kristen’s bathroom, the door between the bedroom and bathroom was almost half open. Luckily I remembered instantly where I was, though I was slightly horrified to find my work clothes from the day before were horribly rumpled and smelled clearly like I had slept in them- which, of course, I had. I also quickly judged from the light coming in her window that it was still fairly early in the morning.
My two immediate problems were a combination of REALLY badly needing to take a piss and having one of the worst cases of morning wood I have ever had. My cock was a rigid pole, so hard it might have been made of metal.
It didn’t sound like Kristen was nearing the end of her shower, so I walked quietly to the half closed door and knocked tentatively on the door frame.
“That you, Kevin?” came Kristen’s voice.
“Yup,” I responded. “Sorry to disturb, but is there any chance that I use the toilet? I kind of really need to take a leak.”
“Ummm,” came a hesitant response, and then, “Sure.”
Cautiously I entered the bathroom. The shower was against the far wall, perpendicular to the bedroom I had just left. I should have expected that Kristen would have both a shower curtain and a shower liner. Although both were a little see through, combined I could see very little beyond the general outline of Kristen’s body in the shower. That was a big disappointment, because even that outline of her femininely curvy little body was sexy. But it also meant Kristen couldn’t see me, which was a good thing because I had been a little worried about getting stage fright and being unable to piss in front of her. Plus she hadn’t shown me any of her body and I wasn’t about to just show her my cock.
My dick was so hard that it took a little maneuvering to get it pointed down at the toilet, but soon I was blissfully taking my morning leak.
“Holy hell, that’s a big dick!” came the exclamation from behind me.
I was so shocked by the unexpected outburst that I jumped, and Kristen was very lucky I was able to control my stream and keep from pissing all over the back of her toilet.
I turned my gaze to the side and saw Kristen’s wide-eyed face, black hair wet and clinging to the back of her head and neck, as she poked her head out around the shower curtain.
Kristen looked up at my eyes and smiled mischievously. “Sorry, I peeked.”
I had to go so bad, I was still sending a steady stream into the toilet when I replied, “Well that’s not very fair.”
“Is it because I didn’t… let you get off last night that it’s so hard like that?” Kristen asked, “Or are you so turned on that it’s hard like that even while you’re peeing?”
I chuckled a little, still careful to aim my piss, as I responded, “It’s just morning wood.”
“What’s morning wood?” Kristen asked.
“You don’t know?” I asked incredulously.
“No,” she replied quietly, “Am I supposed to?”
I began shaking off the last drops and putting my dick back into my pants while I explained. “Morning wood happens because, when you wake up, all the blood rushes to your extremities. In guys, it also fills up our dicks with blood and sometimes gives us a serious hard on.”
I was already washing my hands in the sink, and Kristen popped her head back into the shower. So I asked, “Have you never heard that before? And why did you feel like you needed to talk about how big my dick was?”
Kristen called back through the shower curtain, “Nope, I had no idea it did that. I can’t believe how little control you guys have over your thingies. And I haven’t seen many dicks before, other than like in science class, but yours is definitely the biggest… unless morning wood makes your dicks a whole lot longer.”
“Nope, it doesn’t do that,” I replied and Kristen shut off the water in the shower.
Her head poked back around the curtain and blatantly looked right down at my crotch. “How long does morning wood last?” she asked. “You’re still totally hard.”
“I don’t know,” I responded, as she grabbed her towel off the rack on the bathroom wall without revealing anything more than her slender, wet arm. “It might still be hard now because I fell asleep with blue balls and now I’m talking to you while you’re in the shower.”
“Ha!” she responded, sounding triumphant. “Blue balls. That’s one I know.” I heard a lot of rustling noises as she toweled herself off in the shower, and then she continued sounding playful, “So you’re still turned on by me, eh?”
“Yup,” I replied, “Why wouldn’t I be.”
“You don’t mind that I… stopped things where they stopped last night?” she asked.
“Well I would have loved if they had continued further,” I responded, “But I don’t mind that they stopped where they did.”
The curtain drew back and Kristen stood in the tub with her towel wrapped around her body and tied over her breasts. “You still look like you’re hard,” she stated almost matter-of-factly.
“You’re still sexy and standing there with just a towel on,” I responded.
She shot me a suspicious look, but smiled as she said, “Listen, I like you and I really enjoyed last night, but this is the first time we’ve even kissed or anything. I don’t feel like it’s right to do anything more together, but if you want to take care of yourself before you leave, I certainly wouldn’t have a problem with that.”
I knew what Kristen was suggesting, but just to be sure I asked, “Take care of myself?”
“You know,” she responded quickly, “jerk off.”
“What, right here in front of you?” I asked with a joking tone.
“Well,” she seemed a little flustered, “Wherever you want to do it or however you want to do it.”
“However, I want to do it?” I asked.
“Yeah.”
“Well I’d prefer to do it with you,” I responded with a broad smile.
“Well go ahead and do it right here then,” she responded. I could hear that she was trying to force an indignant sound into her response, but there was a little eagerness there, and her eyes kept dropping down to my crotch as if she was just waiting for me to show it to her again. “I’m not going to touch it or anything, but do it however you like.”
Instantly my mind flashed to so many things I had done with Cassidy, from jerking off into her hair that very first time to cumming on her face while she stood in the shower. And just as quickly as all those lustful memories flashed before me, a voice in my head shouted, “STOP THINKING ABOUT CASSIDY! Kristen is a beautiful and amazing girl, and you’re with HER now.”
Kristen looked at me questioningly, wondering why I was hesitating, but I collected my thoughts and finally responded, “It doesn’t seem very fair that you peeked and got to see my cock but I haven’t seen anything of you.”
“Well what are you suggesting?” she asked warily, her hands instinctively going up her body to grasp the top of her towel more firmly.
The old me would have hesitated further, maybe even told Kristen that it was okay and I was just going to go home. But the person who had done some amazing and wild things with Cassidy responded, “Well why don’t you help me out and show me a little of yourself?”
“What are you suggesting?” Kristen asked again
“Why don’t you… help me speed things along and make them more enjoyable by showing me those beautiful breasts I got to play with last night?” My response was carefully calculated to tell Kristen that I thought she was beautiful and remind her that I had already played with her boobs, all in the hopes she would show them to me. But the look she gave me was skeptical.
Finally she responded, “So you’re a boob man, eh?”
“What do you mean?” I asked.
“Well if you were a guy who loved asses, you would have asked to see my butt. Or maybe you would have asked to see as much of my legs as I’d be willing to show you. But you want to see my breasts,” she replied in another matter-of-fact voice, as if she was teaching me the birds and the bees.
“I’d prefer to see all of you, but since you don’t seem open to that idea, I thought I’d ask to see those lovely breasts I had so much fun with last night,” I responded teasingly.
“Go ahead and start stroking yourself, right there,” Kristen said quietly, “and maybe I’ll let you see something to help, if that’s what you want.”
Again, the old me would have hesitated, or at least been uncomfortable with the idea of just jerking off while standing there, still wearing all my work clothes from the day before. But the new me reached into my pants and pulled out my still mostly hard dick. Kristen’s big, brown eyes went right to my cock and stared as if she were transfixed, while my palm gripped my pole and began to slide up and down my shaft. It might have been my imagination, but I thought she sighed a little.
As I began to rub up and down my long pole, it didn’t take much for my erection to return to full strength. Kristen just silently watched my hand stroking my thick dick, the only sounds in the room were the last bits of water from the shower dripping into the drain and the soft sound of my hand sliding tightly over my cock skin.
“I showed you mine,” I teased, never stopping my jacking motion. Kristen’s big, chestnut brow eyes raised to meet my gaze again. “Will you show me yours?”
“You really think it will help?” Kristen asked half doubtful, half teasing.
“Definitely,” I replied with a smile.
As my hand continued to slide slowly up and down my pole, Kristen sighed. She stared at the bathroom ceiling for a brief moment, as if contemplating, then back down at my fully engorged dick where she watched my hand slide rhythmically up and down. Finally, her eyes met mine again, she bit her full lip in cute nervousness, and then she slowly let the wet towel slide down from her chest.
First the round tops of her smooth breasts slid into view, very perky and barely sagging as she released their weight. Then slowly her nipples became visible, a dark red almost turning to brown. They were small little nipple tips, but they capped her nice, round breasts perfectly. As the towel dropped to nearly her waist, I got to see the full exposure of Kristen’s firm tits, and I sighed appreciatively while I felt the sparks of arousal building in my groin.
They were much smaller than Cassidy’s big jugs, and the nipples were a different color, but they seemed so perfect for the curve of Kristen’s smaller, sexy frame. “STOP COMPARING EVERYTHING TO CASSIDY!” the voice in my head demanded once again.
“Does this help?” Kristen finally asked.
“Oh yeah, A LOT,” I said with a smile. “You have no idea.”
Kristen chuckled softly, but I could easily read the uncertainty on her young face. So I added, “Between last night and getting to see your… beautiful, beautiful breasts, I think I’m going to cum soon.”
“Really?” Kristen asked. “Is there something else I can do to help, without touching it or anything?” She quickly added on the last part to her question.
“Yeah, do you have any lotion or anything?” I asked.
“Right there on the edge of the sink next to you,” Kristen replied. She had so many bottles of stuff on the side of her bathroom sink that it took me a second to find the lotion.
I picked up the bottle with my free hand. The tingles were already starting in my loins, with Kristen’s innocent behavior combined with her full breasts openly on display. I wasn’t going to stop jerking myself off, but I needed some lubrication. The little squirt bottle proved slightly awkward in my one free hand.
“You mind helping me with the lotion?” I asked.
“Sure,” Kristen quickly and enthusiastically responded. “You want me to squirt it right on your… dick?”
“That’d be great, if you don’t mind,” I replied, handing her the bottle.
“Of course,” Kristen responded with a smile. She was very careful and deliberate with her attention, but soon a generous flow of cool body lotion was deposited onto the top of my cock and my hand was spreading it over my dick. The instant slipperiness and the ease of now tightly gripping my cock head had an instant effect. The view of Kristen’s full, round breasts hanging below her as she helped lubricate my cock also helped with my arousal.
“Oh yeah,” I moaned, “That’s so good. Thanks.”
“Anything else I can do, without you know, touching it?” Kristen asked again, a full smile on her face as her brown eyes switched back and forth repeatedly from looking at my aroused face to watching my lotion-coated hand slip up and down my hard meat.
“If you can’t touch me, which I don’t mind,” I began uncertainly, “Can I touch you?”
“Where?” Kristen asked suspiciously.
“Your breasts?” I asked.
“Sure!” She responded with a smile.
Just her happily willing reaction alone turned me on a little more. I awkwardly took a couple of shuffle steps towards Kristen, still standing in the shower, while never stopping the up and down motion of my tight fist milking my sensitive dick. When I got close, Kristen helpfully stuck her chest out a little bit, though I could tell from the way she was standing that she was ready to spring backwards if I tried anything she didn’t like.
When I reached up and my hand closed over her soft breast, the smooth, firm tit filling my palm, her hard little nipple poking into my hand, I felt the sparks inside me go haywire.
“Oh shit,” I warned, “I’m going to cum.”
“Already?” Kristen asked, keeping her chest stuck out so I could squeeze and fondle her tender tit flesh. “Just from that.”
There wasn’t much time. “Where do you want me to cum?” I asked breathlessly, my fingers playing with her bare nipple while my other hand rubbed firmly against my cock skin. The building fire of the orgasm was almost upon me.
“Ummm,” Kristen responded, trying to think quickly, “Can I see you shoot it for me into the tub drain over there?”
“You want me to shoot it for you?” I asked, looking down at her pretty face. Her eyes never left my cock and my hand insistently jacking it.
“Yeah,” she responded eagerly.
“You want me to cum for you so you can see it?” I asked, my voice shaking.
“Yeah,” she responded, almost moaning. “Cum for me.”
Her encouragement was the last spark I needed. I moaned loudly as my slippery hand slid up down over my pole, the orgasm bursting from deep inside of me and crashing like a wave over all of my senses. I never let go of Kristen’s firm, full breast, and may have squeezed it a little hard as thick ropes of my hot, white cum spewed out of my tip. The fat ropes of cum mostly pooled over the tub drain, but lines of it radiated outward along the bottom of the tub.
After I finally released Kristen’s firm tit flesh from my grasp, I quickly made my way over to the sink to wash the goo off of my hand. “Sorry if I squeezed your breast too tight there at the end.”
“No, that’s fine,” Kristen responded, quickly rearranging her towel to re-cover her breasts. “That was hot.”
I smiled broadly back at her, our eyes meeting. “I’m glad you thought so too,” I replied.
After splashing water on my face and running my fingers through my hair a few times, I decided I should try to walk home before too many people were out on the streets. Kristen agreed and dressed quickly, and I gave her a light peck on the lips while saying goodbye. Luckily Kristen’s roommate and most of the neighborhood were still asleep when I left. I got a few judging looks from older couples out walking the sidewalks, but they barely distracted me from the thoughts racing through my head.
I was pretty sure I was in love with Cassidy. At least, I hadn’t cared about someone as much as I strongly cared for her. But she was acting weird, almost purposefully distant. And Kristen was… well… all around wonderful. How the hell had I gotten so lucky to spend the night with her anyway? But I really did love Cassidy. Was I just being a typical terrible guy, chasing whatever new, hot thing appeared in front of me? Was I screwing up my chance with Cassidy? Or was Kristen really… something more like what I was looking for?
I was almost relieved when I got home to find Cassidy wasn’t there. I was pretty sure I didn’t want her to catch me in my work clothes from the day before. And I felt like I needed time to think things over before I tried to talk to her. Some wet dishes in the kitchen sink made it look like she had eaten dinner in the apartment, but there was no sign of her.
Over the course of the day, like a typical coward, I decided to see how things went that weekend between me and Cassidy before I tried to have any talk about what was going on between us, and definitely before mentioning anything about Kristen. I was being passive, but it seemed like the best thing to do.
Other than making a quick run for groceries and then stopping to pick up lunch on the way home, I was home all day. Cassidy wasn’t. I went to bed that night wondering again where she was, but determine based on our last interaction that I didn’t have to worry about her.
The next morning I did make a proactive decision. I called Kristen.
“Hey Kristen?” I asked, when she picked up the phone.
“Yeah?” she responded.
“It’s Kevin,” I informed her.
She laughed, a light chuckle. “I know.”
“Well… I was wondering if you might want to hang out some time this week,” I said, trying to sound as casual as I could muster with my heart pounding a deafening drumbeat in my ears. “Maybe we could grab dinner together or something on Wednesday.”
“Are you asking me out on a date?” she asked. I thought I could hear some teasing in her voice.
“If you’re okay with it being a date, then yes,” I responded, trying to keep my voice steady and even.
“Aren’t guys supposed to wait three days or something before calling a girl?” she asked.
“You definitely don’t know much about guys, do you?” I teased right back.
That drew a hearty chuckle from the other end of the line. “I’d love to,” she responded. “Anyplace you have in mind?”
“You want to talk about it at work this week?” I asked. “There’s some places near the office that I like, but I’d be open to picking a place depending on what kind of food you’re in the mood for.”
“Sounds good to me,” she replied.
“Great, I’ll see you tomorrow,” I said, ending the call. I couldn’t stop smiling for a long while after that call.
The smile was totally forgotten when Cassidy finally got home. It was almost 2:00 in the afternoon, but she walked in the door looking a little rumpled and wearing a tight little dress she often wore when going out dancing.
“Hey,” I called out as she came into the living room, trying to sound casual. “Crazy night?” I asked.
“I really just want to take a shower,” she told me over her shoulder as she headed to her bedroom. “You mind if I do that first?”
“Of course not,” I replied, confused by her response.
The sound of the shower ran for twenty minutes, but it was another twenty five after that before Cassidy emerged from her room. I pretended to be too engrossed in the tv show I was watching to notice. I didn’t want her to feel nervous around me, or appear too interested in where she had been all day. But I was surprised and apprehensive when she quietly began preparing some food in the kitchen without saying a single word to me. She didn’t even say hello, or ask how I was doing.
Some time later the noises in the kitchen stopped and Cassidy quietly came to sit with me in the living room. When I looked over at her, she was absently stirring a steaming bowl of food with a pained expression on her face.
“I have something I have to tell you,” she said softly without looking at me.
“Go ahead, shoot,” I said, muting the television.
“I’ve been avoiding saying it because I don’t know what you’re going to say,” she continued, still not looking at me.
I tried to make a joke in responding, “All the things we’ve done together and you’re afraid of just saying something,” but she didn’t even crack a smile. That made me really nervous. A thought flashed through my mind that maybe she was pregnant, and that terrified me. So I added, “Look, you’re the one who kept telling me that if I wanted something I should go ahead and ask for it. So tell me what it is that you want to say.”
Finally she looked up at me with those sparkling blue eyes. There was an unfamiliar emotion behind those eyes, maybe fear? Maybe sadness? But then she said, “I met someone.”
The silence hung between us, stretching onward painfully. I was pretty sure what she had meant, but I had to ask anyway, “What do you mean you met someone?”
She sighed, eyes dropping back down to her food. “I’m seeing someone. I met a guy and we’ve been seeing each other… you know, going out and stuff… doing things together.”
It felt like someone had stabbed me through the heart with an icicle while the ground suddenly dropped out beneath me. And I was falling, no sense of where I was, no bearings, just tumbling inside.
Cassidy continued quietly but steadily, as if once she had started talking there was no stopping the words. “I kind of felt like I hadn’t been doing anything new in a while, so the weekend after the wedding I went out with some friends and they introduced me to this guy. And we hit it off pretty quickly, and I don’t know really how it happened but… we’ve been spending a lot of time together.”
She looked up at my face and then winced. Before I could even realize that my mouth was hanging wide open, she went on, “Us at the wedding got… kind of intense for me. And I didn’t plan things to happen this way, they just did. And I knew you were going to be upset about it, so I didn’t know what to say, and then the longer it went on the harder it became to say anything. I hope you know that I didn’t mean to hurt you.”
How had she not known it was going to hurt me?! What was all the stuff we had been doing before?! Why had we done so well and everything gone so great, and then all of a sudden this? Those were the thoughts that leapt to the front of my mind, but somehow I didn’t want to say anything. I just wanted to curl up into a ball in my room by myself and never go anywhere.
So the silence stretched between us again, until Cassidy finally said, “Do you want to say anything?”
Somehow what came out was, “Are you happy with him?”
“Yes,” she replied without hesitation. A few more seconds crawled by in silence before she said again, “I’m sorry,” and then took her bowl and went into her room.
I turned off the tv, went into my room, and lay in bed staring at the ceiling. All night I lay there, trapped alone with my thoughts, feeling as if someone had replaced my beating hear with a bundle of razors that was cutting up my insides. I tried at first to go back through my thoughts and justify to myself that Cassidy wasn’t really going to stick with this guy. She was going to come back to me. We had too much fun together and the sex was too good.
Then I tried to rack my brain to see if there had been any clue that this was coming. I accused her in my thoughts of deceiving me. But the more I thought about it, the more concerns did come to mind. There was her cool reception after the wedding. There was the guys she flirted with at the bar. There was the fact that she had never wanted to be openly affectionate with me when we were with other people.
I barely noticed when the dim light of morning began to spread across my ceiling. I still felt like I was falling inside, tumbling down a hole with no bottom. I felt a little like crying, but tears wouldn’t come out.
Sometime around mid-morning, still lying on my back on my bed, another painful truth dawned on me. I thought that Cassidy and I were in a relationship, but at the same time I had happily fooled around with Kristen. I wanted to be the one who decided what was going to happen between me and Cassidy, but I didn’t really want it to end. Slowly, over the course of the day, I clung to the thought that maybe I had known all along that Cassidy wasn’t going to stay with me, and maybe I wanted Kristen. The idea that I might be better off with Kristen felt like the only thing that kept me from going insane that night.
Heading into work Monday morning was tough. I had eaten just a bowl of cereal since Saturday night, and not slept much Sunday. The worst part was feeling like something had died inside of me, but the world continued on. Happy people passed me as I headed to my office, people going about their lives, even though I was hurting because part of my world had ended.
I thought that seeing Kristen would cheer me up, and it did, but not as much as I hoped. She greeted me with a smile when I walked in, while we both played it coy and hid the fact that anything had happened between us. Somehow I stumbled through the next couple of days, the brightest moment in my week coming on Tuesday when Kristen and I were alone and she said, “I’m looking forward to dinner tomorrow night.”
I saw Cassidy once during that time, as she walked from the front door into her room on Monday night, without saying anything to me.
———-
At first, dinner on Wednesday was like a band aid on stab wound. It held me together but barely did anything for the pain. After we had ordered but before the appetizers arrived, Kristen shook me out of my melancholy.
“What’s wrong?” she finally asked. “You’ve been kind of down all week. Is it something to do with your roommate or are you disappointed that you asked me out on a date?”
I was so startled by Kristen’s question that I almost hit my knees on the underside of the table. “What do you mean my roommate?” I asked.
“So it is your roommate?” she responded. “That’s a relief I guess. I was starting to be sure that you regretted asking me out.”
“No, of course not,” I replied emphatically. “I’m really happy you agreed to this dinner.” I decided to be a little honest with her. “Honestly, I’m really glad I’ve had this to look forward to, it’s been helpful. But why do you think it has to do with my roommate?”
Kristen searched my face skeptically, as if she was trying to decipher if I was telling the truth that my depression had nothing to do with her. Finally she responded, “You used to talk about her all the time, and tell everyone stories about funny things you two did together or that she did. If I didn’t know you better and know that you would have told me that something was going on between the two of you, I would have thought that you two were dating or something. But in the last few weeks you’ve barely said anything about her, ever since you got back from that wedding out of town. And this week you haven’t mentioned her at all.”
Women could be frighteningly perceptive sometimes, and Kristen scarily so.
“It’s a bunch of things,” I lied, “But us being roommates is one of the bigger ones, I guess. I don’t know if we’re going to work out as roommates after all,” when I said it then, it was the first time I had seriously allowed myself to consider that possibility, “We haven’t been getting along. And that kind of makes me sad, I thought we were going to be good roommates.”
It was close enough to the truth that it seemed to have convinced Kristen. “I’m sorry to hear that, really,” Kristen said consolingly, “She sounds like fun. Do you want to talk about it.”
“Not really,” I told Kristen, “I rather talk about happier things, like finally getting a chance to get to know you outside of the office.”
It might have been bald faced flattery, but Kristen’s smile told me that it had worked. Deciding to focus on happier thoughts also helped with me. By the time the dessert arrived I was laughing for the first time in several days, and Kristen and I were having a great time together.
I swear, I didn’t plan for anything to happen that night. I had gone into the evening in such a sad funk that I told myself I’d be pleased if Kristen and I both left smiling at the end of the night. But we walked out of the restaurant laughing, her arm around my arm. And then I was walking her home. And then I was going up to her apartment for a drink to cap off the night. And then we were making out again on Kristen’s bed.
Other than sitting on the bed in her room instead of the living room, it was a remarkably similar set up. We were both still wearing our clothes from work, and she was sitting on my lap showering me with very soft and precise kisses. I loved the feeling of her soft, full lips pressed against mine, the feel of the tip of her tongue brushing wetly against mine. I loved the feel of her soft breasts in the palm of my hand, even if I was searching for the nub of her little nipples through the covering of her bra and shirt.
This time, Kristen’s shirt dr*ped loosely over her midsection. As our lips pressed insistently against each other, I ran my hands down the side of her firm, young body and easily slipped both beneath the bottom dr*pe of her top. My hands found her skin beneath her shirt to be smooth and warm, and I slid my hands slowly upwards over that soft skin.
Kristen broke our kiss just as my fingers made their way to the tantalizing bottom edge of her bra. “No sex tonight, okay?” Kristen asked, her dark eyes looking seriously into mine from just a few inches away.
“Sure,” I said, “If I do anything you don’t like, you just tell me and I’ll stop. Okay?”
After another couple seconds staring searchingly into my blue eyes, Kristen seemed to decide that was good enough for her because she went back to kissing my face again.
It didn’t take long after exploring the surface of Kristen’s lacy bra for my eager hands to get bored. I moved quickly to Kristen’s back and appeared to have her bra unsnapped even before she realized what I was doing. Though she let out a little squeak into my mouth as the clasp sprung free, she didn’t stop kissing me and lifted her arms to help me get the bra straps over her shoulders.
That may have been a mistake by Kristen because I lifted up with both hands and she soon found her bra and her shirt both going up over her head. Her beautiful, firm breasts popped into view just in front of my face, and as soon as I spotted her dark, little nipples, I was leaning forward to suck one into my mouth.
“Ohhhhh,” she moaned as my hot, wet mouth closed over the top of her teat, and the tip of my tongue found her rapidly hardening nipple. I sucked a little harder around her firm tit flesh as I ran the length of my tongue over her nipple tip, eliciting an “Ohhh God,” from Kristen.
One of my hands, now free of her clothes, reached up to grasp the full, firm breast in my mouth. As I suckled on her nipple and swirled my tongue wetly all over the smooth top of her breast, my hand filled with the firm but yielding fullness of Kristen’s tit.
Kristen responded by pulling the back of my head against her firm bosom, and her hips began to grind downwards against me again. I switched my mouth to her other breast, grasping that boob with my other hand and guiding the excited little nipple into my warm, sucking mouth. While I slathered my tongue all over the new nipple, my hand squeezing the firm, smooth flesh further into my mouth, I grasped her other breast firmly in my other hand and rubbed her wet nipple back and forth with my thumb. This brought another deep moan from Kristen, who started furiously grinding herself downward against my leg.
I was a little tired of being grinded against, with no attention to my penis, so in a fairly fluid motion I lifted up my hips while simultaneously grasping Kristen and spinning her in a turn. We landed as I had hoped, with her underneath me and her bare breasts against my chest, my growing cock squarely between her legs. My manhood was still confined in my pants, but as I began to thrust my hips downwards against Kristen’s body, she quickly got the idea. The length of my dick was now rubbing against her pussy through her pants, and she was quickly grinding her hips back up against me.
I kissed my way up Kristen’s bare chest, my fingers now toying with both of her wet nipples, as my soft lips found the underside of her neck and began kissing and licking her wetly there. Kristen went wild, shoving her hips upwards against me as I tried to ride her body while grinding back against her.
Eventually, Kristen’s hands pressed against my shoulder, and she pushed me upwards a little so she could look me in the eyes once again. Her hips never stopped moving up and down against my body as she said somewhat breathlessly, “You promise, no sex, right?”
“I promise,” I said, smiling broadly as the feeling of my penis pushing against her had gotten my dick up to full size.
“You promise,” she repeated. “No slipping it inside of me or anything like that?”
“I promise,” I repeated, wondering where this was going.
“We can make it feel a little better than this,” she said, as she quickly slipped her hands between us and began to unzip her work pants. “Take yours off too,” she instructed, as she hooked her thumbs under the back of her pants and began to slide them off of her pale, round ass.
I was so excited, I had everything off only a heartbeat or two after she had tossed her own pants aside. My shirt, belt, pants, socks, underwear- it was all gone. I looked down at Kristen’s completely nude body, her legs were slightly spread apart with her feet planted on the edge of the bed, and her slightly moist pussy was completely shaved. She was skinner than Cassidy, less toned but also less curvy, and yet she had all the right curves in all the right places. Seeing the slight apprehension on her face, I spoke the truth to her. “My God, you’re beautiful,” I said. She smiled widely in response, flashing her pretty, white teeth.
As I settled my body atop her, I noted that she was also much shorter than Cassidy. “Stop comparing her to Cassidy,” the voice in my head feebly complained, but this time I did not care as much. The shaft of my full, hard cock was nestling between the folds of her soft pussy lips, and that was all I cared about at the moment.
“If you slide it up and down against me,” Kristen began, looking at me with eager but uncertain big doe eyes. But I didn’t need instruction for this. I slid my hands behind her shoulders for leverage and began firmly and rapidly pushing the length of my cock up and down over her pussy lips. Kristen’s legs flew out to the side as she spread herself wider for me, and her hands gripped my shoulder as she moaned again, “Oh God.”
I had done this before, and it was the exact same hip thrusting motion as fucking. The only difference for me was that I also pushed my hips downward so my hard, thick cock slid along Kristen’s soft pussy lips, which were rapidly growing wetter. And since I wasn’t inside her, it was just the underside of my shaft being rubbed by her wet skin. For Kristen, I made sure that my cock head and the bottom of my shaft both ground against her little clit, and with the right stroke my whole shaft would rub over her very sensitive spot.
I had been humping against Kristen for less than two minutes, my most sensitive skin rubbing against her most sensitive skin, when she started whimpering, “Oh God… Oh God… Oh God… Oh God!” I looked down and her face was flushed, and she was biting her lower lip.
“I think I’m going to orgasm,” she warned as my full, hard cock slid up and down over her wet little clit, her juices now dripping out of her pussy and coating the length of my eager, throbbing rod.
“Good,” I told her, looking down into her excited brown eyes as my hips thrust downwards against her little body. “Cum.”
“Ungh!” she moaned, closing her eyes briefly, “If you want to do anything else before…” her voice just trailed off.
I was struck by how sweet she was trying to be, she wanted to make sure I was enjoying myself too before she came. “Just cum for me,” I told her gently. “Don’t you like feeling my hard cock sliding across your pussy?” I teased.
“Oh God yessssss!” Kristen hissed, and then her eyes were shut firmly and she was biting hard on her lower lip. Her back arched deeply off the bed and then her body froze as I continued to press my thick, hard dick back and forth against her soft pussy lips and wet little clit. She let out a high pitched little moan like a balloon deflating, “eeeeeeeeee!” while her arms and legs shook and I just kept grinding my hips downward against her. Then she slowly let her body ease back down against the bed while groaning and gasping for air, a broad smile spreading across her face.
My cock was rock hard and coated with Kristen’s slippery juices. Grinding my sensitive dick against her wet pussy had felt good, but I was not quite close enough to coming. Not wanting to bother her in case she was too sensitive, I stopped thrusting my hips back and forth, and let my hard cock rest against her pussy lips.
Kristen didn’t fail to notice my condition, looking down at my thick member as soon as her eyes opened. Her smooth, feminine body was laid out before me, legs spread wide, covered in a slight sheen of sweat. I could have penetrated her right there and there was nothing she could have done to stop it, and as our eager eyes met I believe the same thought crossed her mind. But I did not move, I simply stood there panting a little with my aching cock nestled against her womanly folds.
“How can I help?” she asked, her big brown eyes eager but uncertain.
“Well there’s lots of ways,” I teased, and I began to thrust my hips back and forth once more. Her pussy was now positively dripping with her wetness, and my cock slid easily back and forth across the top of her folds.
Kristen reached down with her flat hand, pressing it against the top of my hard dick. The added pressure of her hand sliding along the top of my shaft while also pressing my cock against the soft, wet skin of her pussy caused some immediate sparks to ignite in my aching rod. All the visual stimulation of Kristen’s sexy, naked body and the view of her pretty face as she came had been foreplay, and now her soft palm was rubbing against the sensitive top of my cock and my bare cock skin was sliding against the wetness of her outer lips. The increased stimulation was pushing me rapidly up towards the peak of arousal.
It felt so good that I slowed down my thrusts just a little, wanting to deliberately feel the pleasurable sensation of my cock rubbing against Kristen’s body, wanting to enjoy the sight of her firm, bare breasts beneath me, wanting to relish the feeling of her soft hand purposefully encouraging me towards orgasm. But all combined, with my throbbing pole thrusting back and forth between the tight tunnel of her outer flesh, I was quickly close to orgasm.
“I’m going to cum,” I moaned, trying to warn her.
“Go ahead,” she encouraged with a smile, “Shoot it.”
Two more quick thrusts and I felt the delectable burning sensation of overwhelming pleasure explode out of my loins. I closed my eyes and groaned loudly as I absently felt my cock spray it’s hot load of cum all over Kristen. The orgasm lifted me and shook my senses as I spurted again, and dimly I became aware of Kristen carefully covering the tip of my dick so that the rest of my thick, creamy load spurted harmlessly against her hand.
When I opened my eyes and looked down, there was a thick line of white cum laying the in valley between Kristen’s breast and another that had shot up onto her right breast almost to the point of her dark little nipple.
“God, you look beautiful,” I said, taking in the sight of her womanly body decorated with lines of my spunk.
“Thank goodness you didn’t cum harder or you might have gotten me in the face,” Kristen responded with a chuckle. If only, I thought.
I helped her clean up, her hand was totally covered in my cum. And then we cleaned up a bit in the bathroom, and she offered to let me spend the night. I told her I would love to stay, but we had work the next day and I couldn’t show up wearing the same clothes. I fell asleep alone in my bed later that night, and had dreams filled with Kristen.
———-
This next part of the story is the whole purpose of me telling you this long tale. The rest are all very fond memories that I deeply treasure and still enjoy, but they serve most importantly to provide the background and the context to this ending. I could have skipped to the end and you may have still enjoyed it, but this simultaneously sweet and sad portion is better with the long introduction.
I didn’t see Cassidy at all on that Thursday, and we barely saw each other on Friday. She didn’t try to speak to me and I didn’t try to speak to her. I was still hurt, but my mind was continuing to wake to all the signs that we weren’t meant for each other and she hadn’t really been interested in me in the first place. And of course, Kristen was a happy possibility that chased most of the sad thoughts away.
Kristen and I met for lunch on Saturday, but she was busy with plans for most of the weekend. We gave each other a long, lingering kiss goodbye in front of her building, and on my walk home I made my decision. I’m not sure what I would have decided without Kristen in the picture, but that doesn’t really matter because the fact was that she was very much in the picture.
I sent Cassidy an e-mail as soon as I got home, telling her I was planning to make a nice dinner for myself in the apartment on Sunday. I said it would be easy to make it for the two of us, and I would love for her to join me so we could have a chance to talk. Cassidy responded early that evening that she thanked me for the offer and would like to have dinner with me on Sunday.
I didn’t expect to see Cassidy at all before then, but I was up late flipping tv channels that Saturday night. She came stumbling in around 2 am, wearing a tiny little cocktail dress that made her breasts look enormous, her red curls a mess and spilling all over her back. She was clearly drunk, stumbling into the living room in high heels, and it looked like she had hickeys running down her neck.
Seeing the hickeys hurt more that I would have expected, but I still felt very close to her. “Need any help?” I asked from the couch as she kicked off her heels.
“Can you, maybe, get the zipper going down the back of my dress?” she asked, slightly slurring her words. “It would be a bitch to try to get at that little thing, and would be so awesome if you could just zip it down a little.”
I stood up and she turned around, using one hand to pull her mess of red curls out of the way. I located the zipper easily and pulled it down maybe an inch, and then said, “Is that good?”
“That’s so great,” Cassidy replied, and then she shocked me by pulling the zipper all the way down her back. I thought she might just step out of the dress right in the living room, but she stopped with the zipper undone and took a deep breath, and then said, “Phew, that feels so much better.” With that, she headed into her room, and I heard the water in her shower starting shortly after her bedroom door closed.
Maybe fifteen minutes later, I was still watching tv when Cassidy reemerged with a towel wrapped around her, dripping wet red hair guiding little streams of water down over her shoulder.
“I’m sorry if I’m bothering you,” she said in a hushed voice, as if she risked waking some third person in our apartment. “I’m starving.” Her last words came out slurred, sounding more like “ssslaarving.”
Cassidy headed straight for the snack food cabinet and soon after had plopped herself on the couch happily munching on a box of wheat thins.
“This okay?” she asked, mouth half full of cracker. “Us hanging out on the couch together?”
“Of course,” I lied, “Why wouldn’t it be?”
“I don’t know,” she replied honestly, looking as thoughtful as a drunk person could look. “You know, stuff between us recently.” Then she added quickly, “I am looking forward to talking over dinner tomorrow.”
I looked at the clock and guessed that the program I was watching had another 15 minutes, maybe a little less. I decided to watch to the end and then politely excuse myself for bed.
Ten minutes later, a soft snoring sound caused me to glance back over at Cassidy. The box of crackers was almost on its side on the couch next to her, her head was leaned far back over the top of the couch, and her mouth was slightly open. But the absolutely worst part was that her towel had fallen part way open.
Somehow the corner that had been tied up over her ample bosom had flapped free and taken a big corner of the towel with it. Her right breast was completely exposed, her large, round, creamy melon wide open to my incredulous eyes, her puffy pink nipple on full display. Most of her left breast was also open to the air, though a bit of the towel still clung to her nipple.
It wasn’t fair at all, I decided. How could a girl look so hot with cracker crumbs on the corner of her mouth? I had almost forgotten how toned her belly was, the way her red hair and pale skin made me think of strawberries and cream. I forgot how full and big her boobs were, and now all of it was on display in my living room.
Sighing, I stood up and went over to shake her gently by the shoulder. “Cassidy,” I whispered softly, “you’re passed out in the living room.”
Cassidy batted at my hand like she was acting out some drunk comedy sketch. “I’m too tired Danny,” she complained very groggily, “You do what you want but I’m going to sleep.” Who the fuck was Danny?
I tried shaking her gently again, and this time when she swatted at my hand the whole towel fell open. Other than the little bit over her lap, covering her pussy and upper thighs, her whole, voluptuous body was on display.
I debated just leaving Cassidy there on the couch, but eventually hooked a hand under her arm pulled her very slowly to her feet. I left the towel on the couch. If she woke up and came back to her senses, it was not like I’d never seen her naked before.
“Come on Cassidy,” I tried to encourage her, “time for bed.”
She threw a still damp arm over my shoulder, her big, free swinging boob pressed against my side, as she began to shuffle with me towards her bedroom. “Okay, thank you,” she mumbled, “but no playing with my ass this time, Danny, it’s not funny.” Seriously, who the fuck was Danny?
Cassidy flopped into her unmade bed when we got into her room, her big, firm breasts flowing up and down over her chest as she hit the mattress hard. I’m not very proud of it, but at that moment my cock was rock hard from al the exposure to Cassidy’s beautiful nakedness. I grabbed the front of my shorts, feeling how hard I was, and briefly considered jerking off to the sight of her. Her pretty face looked so peaceful, red hair fanning out behind her. And her hard, pink nipples were right in front of me, begging for my attention.
Instead, I covered her with her blanket and went back to my room to jack off. I came in less than three minutes.
———-
Cassidy and I were both in the apartment for most of Sunday, though we barely talked to each other and spent most of our time in our rooms. It became especially awkward when I started making dinner and Cassidy remained in her room with the door slightly open. It appeared she didn’t want to talk until the time for talking arrived.
But once the food was spread out and she was sitting across from me on our tiny little dining room table, she had barely finished complimenting my cooking with the first bite of food before she decided to dive right in.
“I think I have to move out,” she said quietly, poking at the food in front of her.
I was happy I had a big chunk of food in my mouth that I had to chew, because it kept me from choking in surprise. I hadn’t expected her to be so direct, or to come to the exact same decision I had reached.
It also allowed her to continue sharing her thoughts. “I kept trying to tell you that I wasn’t in this forever, I was just having fun. But I guess that wasn’t fair of me, and I definitely didn’t mean to hurt you.” That last bit sounded painfully genuine and helped soothe my hurt a little. “I certainly never thought you were going to fall in love with me, which is very touching, I promise, but I can’t return those feelings for you.” Her words were speeding up, beginning to rush together. “And I realize that would always be between us here, and something stupid would be bound to happen because, believe me I’m telling the truth, the sex with you was always amazing.” That certainly helped my wounded pride, “And I don’t think either of us would be comfortable with me bringing Chet here or having him spend the night, that’s the guy I’m seeing, Chet.” So who the hell was Danny? “But now I feel like I’m just babbling so I’m telling you I think I should move out but what do you think?”
“I think you’re right,” I began slowly, “We can’t both stay here. But you don’t have to be the one to move out, I can leave.”
“No, don’t be silly,” she cut in quickly, “You were living here already. It totally makes sense that I’m the one who leaves.”
I had thought the same thing, but admitted it was me with the hurt feelings so I had to offer to be the one to go “If you’re sure,” I said quietly.
“I’m sure,” she said firmly.
We both looked at each other, and it was like a big boulder had been sitting between us, blocking us from talking to each other or really seeing each other, but that boulder had been rolled mostly out of the way.
“You going to be okay?” Cassidy asked, her blue eyes searching mine.
“I am,” I said with a smile.
“Because I’ll help you find another roommate if you want,” she said as she began loading more food onto her fork, “But she better not be as pretty as me.”
I laughed at the unexpected joke. “I think I’m done with female roommates,” I said. She looked at me questioningly as she chewed, and I continued, “How could they ever top you?”
“So you’re going to be okay,” she asked again when she had finished chewing. “I mean it. You’re a great guy and maybe we can’t be best friends but I’d love if we could at least stay friendly. And I want you to be okay.”
“I’ll be okay,” I assured her, “I think I might have found someone myself,”
“Really?!” Cassidy asked excitedly, “Who is she? Are you two dating? How did you meet?”
I turned my head to look out the window in order to avoid the intent look from her pretty blue eyes. “I just found her,” I said vaguely, “and I think she might like me too. That’s all.” Then I added, to avoid further discussing the topic, “You going to be okay moving out?”
“Yeah,” she replied. “I wanted to make sure you’d be okay with it first, but a girlfriend of mine needs a roommate. Her lease starts on the 15th, and I’m paid through the end of the month here, so if it’s okay with you I was thinking I’d move to the new place next Saturday.”
The suddenness caught me off guard, and Cassidy must have been able to tell from the look on my face so she added, “I know it’s soon, but it could be the best deal for both of us. I can move almost all of my stuff, especially the big stuff, on Saturday, but have the rest of the month to move the little stuff over and settle into my new place. And I know it’s not a lot of time for you to find a new roommate, but I can help with the search and they can move in before the first if they want. It’s pretty ideal with my girlfriend needing a roommate, but she would need me to start paying rent on Thursday.”
“No, that’s great,” I said, trying to wrap my mind around the idea that Cassidy was leaving the apartment in a week. “It’s lucky your friend needed someone and I can see how this makes things easier if you can cover both rents for half a month.”
“You sure?” she asked.
“Yup,” I agreed, then added to show my support, “You need help moving?”
“Actually, that would be great if you could help a little,” Cassidy said. “Chet is busy next weekend and a couple of my girlfriends said they could help but I could really use a couple of guys to help me with the big stuff.”
“No problem” I assured her, “I’ll be happy to help you with the move.”
———-
Cassidy spent almost all her free time for the next week frantically packing up her belongings and creating little piles of stuff all around our apartment. But the ice between us had melted and that made it especially nice to be in the apartment again, after the previous few weeks. I even helped her pack up her stuff.
When the moving day arrived, I was very concerned that I was in deep trouble for two reasons. None of Cassidy’s other friends showed up to help. Also, Cassidy was wearing the same short shorts and tank top over sports bra combination that had gotten me so turned on the day she moved into the apartment. The only thing worse than being tempted by her tight little ass, snugly encased in her shorts, and the big swell of her firm breasts visible whenever her tank top flapped open was remembering all the times I had gotten to play with and cum on those delicious naughty bits of her body and knowing it was all off limits to me now. I cursed her friends vehemently both for sticking me with most of the work of moving her stuff and also for leaving me alone with the sexy hot body.
Although Cassidy had been smart enough to rent a big moving van, which made moving her furniture much easier, my predicament of being stuck alone with her got worse and worse over the course of the morning. First we began to sweat, hauling all of her stuff around. She looked so sexy with the slight sheen of sweat on her smooth, flawless skin. While we were riding down in the elevator with her dresser, I think she caught me watching a tiny little drop of sweat run down her neck, over the middle of her chest, and disappear into the deep fold between her pale cleavage.
The next constant problem became that we kept bumping up against each other while maneuvering her big items out of our apartment and into the van. To help her hold her overstuffed chair upright for the elevator ride, I had to lift from under her and my right arm dragged up and across her big, round breasts. I could feel the firmness of her ample tit as I lifted the chair. At one point, sliding past me while I lifted something into the van, Cassidy’s hand brushed against my ass. And then, in the moving van, trying to lift part of her bed frame to position it on to of her dresser, Cassidy had to slide in front of me while I held the frame over her head. Her tight little ass brushed right against my crotch and pushed into my groin a little as I hefted the bed frame forward.
Riding back up to the apartment in the elevator, my cock was at more than half-mast and aching for a little attention. I tried to keep my focus on the floor numbers as they ticked by, so I wouldn’t look at Cassidy’s tight little body or the way her big, round breasts moved up and down on her chest as she breathed heavily.
I thought I had escaped notice, but Cassidy turned to me as soon as we were back in the apartment.
“You need to take care of your hard on now, or you want to take a little break to catch our breath and let that thing calm down?” she asked matter-of-factly.
“What are you talking about?” I asked.
She laughed, a deep, sincere laugh. “Don’t try to play dumb with me, mister. I know all about your big dick there, I’ve had lots of experience with it, remember?” She walked closer and actually pointed at the bulge in the front of my shorts. “You’re too big to notice,” she continued, “and it sure looks like you’re most of the way hard now. Don’t think I didn’t feel it poking into my backside when we were in the van. So since you’re doing me a favor, I’m trying to do you one now. If you want to go in your room and rub one out now, I’ll be happy to give you the time to take care of your little problem. If you rather we just take a break and let your little friend calm down, we can do that too. But it’s going to awkward if you’re walking around with a big hard dick while I’m trying to move, especially if someone sees us in the elevator or one of my friends finally shows up. And I wouldn’t want you to bump into something and hurt it, so one way or another you have to take care of that.”
With my hands on my hips in consternation, still breathing a little heavily from the effort of the move, I responded honestly, “Well given those two choices, I guess I have to take care of it, because I don’t think it’s going away.”
The door to our apartment was still propped open for the move, so Cassidy walked over and shut it. “Totally fine with me,” Cassidy responded, “I don’t know what’s gotten you so worked up like this anyway, I’m already exhausted from all the lifting. Just please be quick about it so we can get back to the move.”
I laughed my own sincere laugh, remembering all my fun times with the fiery and bossy Cassidy. “You want me to just whip it out here?” I asked.
“Whatever gets us back to moving quickest,” she replied, shooting me a daring look with her sparkling blue eyes.
“Fine, then if you really want me to get it done with quickly, just stand there like that while I do it,” I dared her, pulling down my shorts and exposing my hard dick for good measure.
Cassidy crossed her arms defiantly under her big breasts, but didn’t walk away. “I don’t see how that will help,” she responded.
“You really don’t know what’s got me so turned on?” I asked. I had no idea what I was doing, no plan. I was just running on instinct as my right hand closed over the top of my dick and started sliding up and down over my hard cock meat.
“No,” Cassidy spat back at me.
“Seeing your body like THAT!” I exclaimed almost accusingly, my hand loosely pumping up and down over my cock. “Your ass is just… there! For everyone to see how tight it is! And your breasts… I mean come on! They’re so big and just the whole curve of them is visible in that sports bra.”
Just talking about it, and the sexy defiant look on Cassidy’s face, and my hand helping a little bit, my cock was at maximum length and girth. Cassidy’s blue eyes were also fixed on it, which helped make me even hornier in some weird way.
Arms still crossed under her ample breasts, without taking her eyes of my big dick, Cassidy demanded, “You’re saying THAT is my fault?!”
“I’m just saying it’s a compliment to you,” I tried, which didn’t seem to make her any happier. But I was starting to not care about her judgment of me. She had seen me jerk my own hard dick like this several times before. We’d done so much stuff that there was little shame between us. And after her ridiculousness the previous weekend, drunkenly exposing her naked body to me, this was going to make me feel better. I was going to openly ogle her hot, young, curvy body and get myself off in front of her. I thought it might even be a fitting end to our sexual shenanigans, especially considering how they had begun.
“So you want me to just stand here and watch you play with yourself?” she asked, but the angry had gone out of her voice.
“That would help, yes,” I said, spitting generously into my own hand to provide a little lube for my excited rod.
“You’re ridiculous,” she said accusingly, but she didn’t move an inch and her eyes remained glued to my hard cock.
“You going to miss playing with my big dick?” I asked teasingly.
Cassidy scoffed in response. “You’re ridiculous,” she repeated, and then retorted mockingly, “You going to miss playing with MY amazing body?”
“Oh yeah,” I answered honestly, “I am.” Something about the way she mocked me but still stood there in front of me, firm ass and creamy tops of her breasts just inches away, got me excited. I could feel the distant tingles of orgasm beginning inside me as my hand pumped up and down my throbbing cock. I decided if she had worked so hard to make me bolder, then my boldness was her own damn fault. “You maybe let me touch those breasts one last time, for old times sake?”
Cassidy’s voice grew serious and she replied, “I shouldn’t.” But she didn’t say no.
“You know full well it will make me cum quicker and then we can get back to moving faster,” I tried. “I’ve played with those beautiful breasts of yours so many times, what’s one more time?” I asked.
“We shouldn’t be doing this stuff together anymore,” Cassidy said quietly, but after a moment of hesitation she pleasantly surprised me by taking a couple of steps towards me. She sighed resignedly as she uncrossed her arms. “We should really get back to moving,” was all she said.
One hand still steadily working up and down my fat dick, I reached out with my other hand and brought it tentatively up to Cassidy’s breasts. When my hand made contact with the round swell of her big tit, even if she was still wearing her clothes, I felt a little jolt of arousal shoot through my penis and I sighed. Cassidy just laughed at me, a little laugh, but even as she shook her head as if she couldn’t believe my reaction I could see the sparkle back in her light blue eyes.
“I love your breasts,” I said as I gently began squeezing her firm tit through her top. “They’re just so… BIG, and so… FIRM.”
“Are they now?” Cassidy responded teasingly, her hands moving up to her tits but making no move to stop me. “Are they helping you get off?”
“Yeah,” I said, it did help feeling naughty in playing with her boob. I squeezed a little at the tip of her big breast, found the hardness of her nipple beneath her sports bra, and rolled it gently between my thumb and forefinger. Cassidy closed her eyes and bit her lip in response.
“You like that?” I asked.
“You know I do,” she responded, opening her eyes to look up at me. I could see a little of the fire of arousal beginning to warm her face and eyes.
“You want to touch my big dick one last time?” I asked, voice catching a little as the arousal built in my loins.
“You close to cumming yet?” Cassidy asked.
“Yeah,” I responded.
Cassidy spit into her hand and then reached out to grasp my dick. She squeezed me tight with her soft little fingers, my hand still lightly squeezing her breast, and she said, “Then cum for me.”
“Oh God,” I said, eyes closing reflexively. Her wet hand was tightly squeezing my man meat and pumping rapidly up and down my pole, just the way I liked it. “I’m going to cum on the floor or the wall,” I managed to say in warning.
“Oh shit!” Cassidy replied. She dropped rapidly to her knees and warm mouth closed tightly over the tip of my rod. My eyes opened in shock, looking down at Cassidy’s head on my dick, her red hair in a pony tail trailing out behind her. I felt her tongue lapping at the underside of my shaft as her mouth sucked on me, and I came hard.
It felt so good, so unexpected, that I moaned loudly with the pleasurable release. Cassidy didn’t miss a beat as I pumped spurt after spurt of my hot cum between her soft lips, spraying my orgasm into her mouth. Her cheeks slipped back and forth over my rod as she bobbed her head up and down just a little, and her tongue continued to slather against the underside of my dick while she swallowed my load. “Oh fuck,” I moaned as the orgasm subsided.
Satisfied that I had stopped pumping cum, Cassidy released my cock from between her lips with a loud pop. She looked up at me with a smile and a twinkle in her eyes as she said, “I don’t know how I’d explain a fresh cum stain on our floor to my friends, if they ever get here.” She rose to her feet, walked over to the kitchen sink to rinse out her mouth, and then said, “Now can we get back to moving?”
I was very happy after that, even the heavy lifting couldn’t bother me. Some of the furniture was difficult because Cassidy, as strong as she was, couldn’t hold up her end as easily as I could. We had to stop and take little breaks along the way. And she still looked super sexy in that tight sports bra and little booty shorts, but she had very much satisfied me in the living room.
Cassidy started to get almost playful soon after I came in her mouth. At first I thought she was only realizing that she was going to miss me, and was being affectionate. She slapped my arm at one point and laughed. At another, I had to squeeze against the wall of the van so she could get by and she swiped at my ass as she moved past.
I thought it was wistful thoughts because she started talking about funny or treasured moments from our relatively brief time as roommates. But then I began to wonder when she started saying things like, “I loved how surprised your face looked that first time I just got in the shower with you. You were shocked!” She laughed loudly at the memory.
Later she added, “I loved going into work right after you had eaten me out, knowing that I already came once in those clothes that day. I’d be turned on all day just thinking about it.”
We had finished with big furniture and were moving the heavier boxes when I bumped hard into Cassidy. I had just put my box down in the van and turned around to start to walk towards the loading ramp and Cassidy was standing right behind me. Our midsections collided, her big breasts squishing against my chest. She started to fall back from the impact, so I quickly wrapped my arms around her and held her against me.
As we stood there, our sweaty bodies pressed against each other, Cassidy looked up into my eyes and said, “Don’t go getting all hard again, I already helped you take care of that,” and with another of her light laughs she turned around and walked away.
I thought the moment had passed but as soon as we got upstairs, Cassidy closed our apartment door again and turned to me. “Alright, playing with your dick and you cumming earlier clearly turned me on a little, and now all the bumping into each other has got me a little bothered,” she stated, the tone in her voice implying that this was at least partially my fault. “I can’t focus anymore and before my friends get here I need a little relief, and since I helped you earlier I think it’s only fair to ask you to help me.” Her blue eyes were filled with uncertainty.
“What did you have in mind?” I asked casually.
“I don’t know, I’m all sweaty,” she said, “but the quicker the better because some of my friends have got to show up soon if they weren’t all lying to me.”
With a shrug, I put my hands under Cassidy’s arms and firmly lifted her off her feet. Her skin was wet with perspiration, which I admit was a little bit of a turn off, but after hefting all the furniture it was not hard to gently deposit her on her back on the kitchen counter. As I hooked my fingers under the waistband of her shorts and pulled them down, along with her underwear, Cassidy feebly protested, “Wait, what are you going to do?”
Her question turned into a gasp as I leaned forward and my tongue made contact with her outer pussy lips. The sweat made her taste very salty, and there was a little tanginess present as I explored between her folds with the tip of my tongue. But there was still not much flavor to Cassidy’s sex as my tongue began flipping up and down over her sensitive little bump.
“Ohhhhh,” Cassidy moaned deeply, and then in a high pitch, “Are you sure?”
I answered by closing my hot moth over her pussy and sucking her little clit between my soft lips. My tongue flicked slowly but steadily up and down over Cassidy’s little button while my mouth rubbed against the edges of her folds.
Cassidy’s hands went to the back of my head and pulled me against her and I rubbed hard against her clit with the full length of my flat, wet tongue. She wanted this to go fast, so I carefully slipped two thick fingers into her hot pussy, coating them with my saliva as they slid past my sucking mouth. I probed against the top of her tight, slippery pussy walls, and it may have been my imagination but her pussy felt even hotter than usual.
Soon my tongue was flicking rapidly up and down and then back and forth across her hard little clit while my two fingers pumped in and out of her wet hole. Cassidy began panting with the thrusts of my thick fingers while my lips trapped her clit in my mouth and rubbed against the edges of her nub.
“Oh shit… oh shit… oh shit…” Cassidy began to pant, my fingers fucking faster and harder into her pussy while my tongue kept up its wet assault on her clit. “Oh shit.. don’t stop… don’t stop…”
Her pussy was positively dripping juices as my fingers flew in and out of her hole, the tip of my tongue flicked rapidly over the top of her sensitive button, and Cassidy screamed, “OH YESSSS!!! CUMMMMMMMMMINNNNNNGGGGGGGGGGGGG!!!”
Cassidy’s strong thighs clamped down around my head as I carefully continued to lick gently up and down her slit and my fingers slowly slid in and out of her pussy hole. Her tight little body shook a couple of times, and then her hands and thighs released their grip on my head.
“Phew,” Cassidy said as she dropped off the counter top and back onto her feet. “You were always really good at that.” She collected her shorts and started putting them back on as she said, “Thanks, I really needed that.”
Now it was like all the barriers were broken between us once again. Well, maybe not all of them. I had several lingering concerns swirling around in my mind. One of the main ones was whether this was a bad idea considering how I was supposed to be trying to move on and get over Cassidy. The other was Kristen and whether we even had a relationship status, and the certainty that she wouldn’t like knowing what I was doing with Cassidy.
But when we were down at the van again and Cassidy openly grabbed my ass, I felt like it was fair to give her tight, round bum a squeeze as she was bent over with a box. On our way back up in the elevator, an older woman got on with us on the ground floor. Cassidy made sure to leave plenty of room for the woman by backing up almost right in front of me, and when the woman got off the elevator just before our floor, Cassidy rubbed her toned ass up against my crotch while the woman exited. Cassidy looked over her shoulder with her devious blue eyes as she exited herself and laughed at me.
So when Cassidy picked up a light box in the apartment and began to walk back to the door, I threw some of her pillows on top which temporarily blocked her sight and reached between the pillows and box to give one of her big, firm breasts a squeeze. “Hey, watch out for my stuff!” Cassidy whined in mock protest as the pillows toppled to the floor.
Back down in the van, I had just put my box down when Cassidy boldly grabbed at my crotch with her hand. Her little fingers wrapped around my semi-erect cock through my shorts and squeezed. Without letting go, Cassidy stuck one hip up and put her free hand on that hip. “Yup, you’re hard again,” she said. “I knew you would be just impossible after earlier. Think we should take care of it?”
“What do you have in mind?” I asked in response.
Cassidy let go of my cock, took one step towards the opening of the van, and pulled down the heavy rear door with us still inside the moving van. She ignored my protests of, “Hey, don’t get us stuck in here,” and walked back over to the nearest stack of boxes. She leaned forward while keeping her legs straight and pulled both her short shorts and her underwear down her shapely legs. Resting her arms on the top of one of the boxes, Cassidy stuck her smooth, round, bare ass towards me and wiggled it while winking one of those dangerous blue eyes at me.
“Aren’t people going to hear us?” I asked, very skeptically.
“Only if YOU’RE loud,” Cassidy whispered.
That was really all the invitation that I needed. I completely shed my shorts and boxers, pulling them over the shoes I was wearing and discarding them on some furniture near me. Cassidy smiled when she saw my cock growing stiffer and starting to point straighter, and she wiggled her ass again. I spit some saliva into my hand and then coated the fat head of my dick with the lubrication as I walked up behind Cassidy. Again I had to hunch down just a little to get the angle right, but we had done this before. Less than thirty seconds after Cassidy had closed the door to the back of the van, my fat cock head was pushing against the tight outer folds of Cassidy’s wet pussy.
Cassidy pushed down against my invading cock, and my cock head popped past her tight outer opening. It had been a while since I had felt the slippery, hot, wet embrace of Cassidy’s tight pussy walls against my thick pole, and I had missed it. As I thrust deeply inside of her, Cassidy sighed, and I withdrew again almost to the tip. I loved how tight her little pussy managed to squeeze my hard rod, and the feel of her pussy lips pulling against my sensitive skin as I slid back and forth inside of her. I ran my hands over Cassidy’s smooth ass cheeks, squeezing just a little to feel the firmness in her ass, while my throbbing cock slid in and out of her hole. Then I grabbed her hips and started really pounding my long, thick meat in and out of her tight little pussy hole.
Cassidy actively muffled her moans, I could hear her voice catching in her throat or hear her moan inside her closed mouth as I plowed hard in and out of her. I wanted to remember this fuck, so I grabbed Cassidy’s hips and speared her hard and deep, shoving my thick meat into her and feeling her wet pussy walls gripping me as I pounded back and forth. Unfortunately, the heavy moving van began to rock back and forth a little with my steady and hard fucking motion. The movement was barely noticeable, but something, possibly the shocks, started squeaking. Cassidy turned her head to look back at me over her shoulder, her red pony tail swaying back and forth in rhythm with my thrusts. Her blue eyes burned with desire but her face showed concern.
To lessen the rocking, I slowed my thrusts and alternated my pace. I continued to shove my thick dick into Cassidy’s dripping wet pussy hard and deep, but not always at the same speed so the van wouldn’t rock further and further side to side with my movements. Although the squeaking mostly went away, there was still a little noise from the movement of the van. I slid my hands up over Cassidy’s taut stomach and under her tank top. I slid my fingers beneath the underside of Cassidy’s sports bra and firmly pulled both the sports bra and tank top up and over Cassidy’s big smooth breasts. As my cock slid slowly but firmly in and out of her hot, wet snatch, my hands closed over the front of Cassidy’s ample breasts, and I squeezed the firm globes in my palms, the smooth tit flesh overflowing between the spaces in my fingers. As I switched to pulling gently on Cassidy’s hard, pink nipples, Cassidy began to whimper in arousal. She turned back over her shoulder again, and as my cock pushed in and out of her slippery tunnel, she bit her lip to show me she was desperately trying not to cry out, her eyes sparkling with her lust.
Then we heard voices just outside the van and Cassidy’s eyes shot wide open. She tried to pull her tank top back down over both her big, pale breasts and my hands, but I just kept slowly working my excited cock in and out of Cassidy’s tight pussy walls. The voices seemed to get a little closer, and Cassidy’s eyes wet a little wider, now turning towards the closed van door. I got a devilish idea and slipped one hand back down her body to probe for the top of her slit between her legs. When I found her wet pussy lips, I quickly located her sensitive little clit and started rubbing gently against that little wet nub. Cassidy bit her lip in earnest and then turned back to look at me and mouthed the words, “You fucker!”
The voices seemed to be lingering outside the van, and my cock kept up is steady pace of withdrawing several inches and then forcefully plowing those inches back up in a long thrust into Cassidy’s tender, wet pussy. My finger began to rub circles more quickly and insistently around Cassidy’s wet little clit, and Cassidy arched her back deeply in response. Cassidy grunted deep in her throat, trying to stifle a loud moan, and then as my cock pumped in and out of her womanhood she began to shake her head back and forth as if saying, “No, no, no, no.”
I leaned forward, my other hand still gently rolling her nipple between my finger tips, my full, thick cock sliding wetly in and out of her pussy, and I whispered softly into her ear, “Cum for me.”
“No!” she whispered back, but the voices began to sound fainter.
My finger kept up its insistent circling around the edges of her super sensitive clit, and with my cock completely filling her little pussy I whispered, “Cum on my cock for me, those people are gone.”
“Oh yeah?” she asked breathlessly. I couldn’t see her face as she was turned away from me, but I could feel the heat burning through her body.
I began thrusting harder and faster again, my fingers toying with her hard nipples, my fingers rubbing over her wet clit, and I whispered, “Do it Cassidy. Cum on my dick!”
“Oh God!” she moaned softly, and then she was squealing as quietly as possible, her legs shaking as my big, hard dick continued to slide in and out of her wet channel. My fingers kept rubbing on her nipple and her clit as her little body shook beneath mine. And then with one loud sigh she lay her body down on top of the box she had been resting against, and she let out a little murmur as if she was purring.
The feel of Cassidy cumming for me, with my cock inside of her tight little pussy, had driven me close to orgasm. My thrusts picked up speed as I pushed myself closer and closer to ultimate release, the pleasurable fire building inside of me. Cassidy knew me well enough to know what I was doing and pushed herself back up on her elbows so she could turn and look back at me again over her shoulder.
“You going to cum for me now?” she whispered as my cock pumped more and more quickly in and out of her wet slit.
“Oh yes,” I said, focusing on my thrusting and the wonderful sight of her smooth, round ass in front of me.
“Anywhere but my pussy,” she said.
“What?!” I exclaimed with surprise, the slippery feel of her wet pussy walls on my sensitive cock skin bringing me closer and closer to the peak of arousal.
“Don’t cum in my pussy,” she whispered quietly, her blue eyes looking intently into mine. “You can cum anywhere else.”
“On your face?” I stated more than asked, feeling the fire of orgasm begin to overtake me as I thrust in and out, in and out of her sweet, wet, womanhood.
“No, we’re in a van!” she harshly whispered back. “How can I clean that up and go back upstairs?”
“Cassidy!” I hissed in near desperation, almost unable to stop the hard thrusts that were bringing me inevitably closer to the edge.
“Anywhere else,” Cassidy asked, her blue eyes full of concern. “I’ll owe you one on my face,” she pleaded.
Sighing with exasperation, I pulled out. My hands flew to Cassidy’s shoulders and I spun her around forcefully. Uncertain what to do, she stood in front of me for a moment with her hands up, looking at my throbbing and twitching dick, which was ramrod straight and covered with her juices. I pushed her down onto her knees with one hand while the other just managed to retrieve my discarded boxers. Holding my boxers in one hand, I pushed Cassidy’s big breasts together and shoved my hard, aching cock up into the smooth, tight tunnel between her big, firm breasts. I just barely managed to lay my boxers over the top of Cassidy’s big, round melons, covering the opening of the valley. Quickly catching on, Cassidy reached up to help press her firm tits together. Then it was one thrust, then two thrusts into the tight but soft tunnel of skin formed by her cleavage, and I felt the orgasm burst from my loins all the way down to the tip of my toes and out of my cock.
I moaned uncontrollably, eyes shut, as my cock spewed its hot load of cum deep between Cassidy’s round melons. I thrust once more with my hips, feeling my cock twitch again and again as it pumped out my sticky, white spunk. I opened my eyes and saw that my boxers were serving their intended purpose, catching my cum and preventing me from spraying Cassidy’s face with my cum. She was looking up at me with a big smile while holding her firm breasts together, and it was a remarkable sight. Her blue eyes looking at me, red ponytail sticking out behind her, with my red boxers laying over the top of her creamy, round breasts, her hands pushing together to keep my dick firmly inside the tunnel formed by her big cleavage.
I took my boxer shorts and tried to wipe down the middle of Cassidy’s big bosom, hoping to collect most of my spunk before it ran anywhere else on her body. For some reason, that made Cassidy giggle, but she just knelt there with her sparkling smile on her face, watching me carefully try to clean up her chest. Unfortunately, when I finally pulled my shrinking dick out from between her smooth globes, a little cum trickled down her chest and I had to chase it with the boxer shorts. But for the most part, I was able to catch all the mess in my boxers.
Cassidy and I both redressed carefully, my boxers wadded up as neatly as I could manage in my hand, and rode the elevator back up to the apartment in silence but full of smiles. I was smiling because she had told me that she owed me a chance to cum on her face, right at the end of our fucking. And I was hoping to cash that in.
But we were both surprised when we got back up to the apartment and found two of Cassidy’s girl friends waiting for us in the living room.
“Hey, is that your van out back?” One of them asked, “It didn’t look like you were down there so we came up here to wait for you.”
“Yeah,” Cassidy said quickly, “Had to close the door for a tricky bit of loading. Thanks for coming to help!”
While Cassidy caught up with her friends, I hurried into my bedroom to hide my cum filled boxer shorts in my bathroom and quickly throw on a fresh pair. Unsurprisingly, little else of the move was eventful, especially in the hanky-panky way I had been hoping for. I cursed Cassidy’s two girlfriends for showing up when they did. Not only had they ended my chances for fooling around, we were almost done with carrying Cassidy’s stuff down to the van.
I rode with Cassidy in the van over to her new place while her two friends drove over in one of their cars. The mood was light and friendly between us, which I enjoyed. We shared a lot of jokes and told a lot of old, funny stories from our time living together. I kept thinking I was happy that our time as roommates was going to end this way, with us enjoying each other’s company, since it had come so close to ending very poorly between us.
I’ll admit that I appreciated having Cassidy’s two friends with us for unloading the van. Getting things up to the new apartment went much quicker with four people, and carrying the furniture was much easier. Cassidy started unpacking some of her stuff while her friends and I carried the last of her things up to the apartment, but for the most part she just told us to leave things in one room or another and she would sort it all out with her new roommate.
When the van was empty and Cassidy told us she didn’t need us for anything else, one of her friends offered to drive me back to my apartment.
“Oh, he’s going to help me return the van,” Cassidy told them. “I’m just going to unpack a couple more things here and then we’ll be taking the van back.” That was news to me.
“You sure?” the friend asked.
“Yeah, thank you so much. I’m really grateful that you came and helped, it really helped me a lot.” And with that, the friends were saying goodbye and closing the apartment door behind them.
“So no rush,” I said, “But how long do you think until we take the van back?”
“Oh, I don’t need your help returning the van,” Cassidy responded, placing the random items in her hand down on the coffee table.
“Then why did you…” I started.
But Cassidy interrupted. “Because this is it,” she said with what looked like a rueful smile. “My new roommate is out of town for tonight, which is why it was so great to be able to move in today. I can take my time unpacking everything and not worry about being in her way. But more importantly, we have the whole place to ourselves.
“So this is how I’m going to say goodbye to you. I mean, not goodbye forever, but… goodbye to us. At least what we used to be,” she said as she began walking towards me, and I detected a little extra sway in her hips as she crossed the room towards me. “You know, not jut the roommates but all the other extra stuff too.
“I know I told you earlier that I’d make it up to you for in the van and you could cum on my face. And don’t think I didn’t notice in our little deal that I probably still owe you at least half a dozen times getting you off.” She was standing right in front of me at that point, looking up at me. And I could see the happiness and the sadness combined, both in her twinkling blue eyes and written on her face. “So this is how we end it. This is how I say goodbye to us. You can have me one last time, for all the times I owe you, and I’ll do whatever you want.”
I wrapped my arms tightly around Cassidy’s toned little body and hugged her close against me. As her firm breasts pressed against my chest, she began to say, “What do you want to do?” but I cut her off by pressing my lips firmly against hers. Immediately she was kissing me back, our tongues twirling and dancing almost frantically in each other’s mouths.
I let go of her long enough to grasp the bottom of her tank top and pull it, along with her sports bra, over her head. She lifted her arms to accommodate me, her big, round boobs falling free but barely sagging, so perky and firm on her chest. Then Cassidy was reaching for my shorts and pulling them quickly down my legs. There was a brief moment of comedy while we both tried to shed our sneakers and socks as quickly as possible, and we laughed, Cassidy naked from the waist up and me now naked from the waist down.
When the last of our garments were removed, we practically lunged at each other, our bodies colliding with naked flesh slapping into and enveloping naked flesh. Cassidy’s hands were all over my hair, my hands pulling her naked chest against mine, and our lips pressing insistently against each other.
Cassidy tried to drop to her knees onto the carpeted floor while holding me, and with our arms wrapped strongly around each other she pulled me down with her. Her smooth skin was still covered in a light sheen of sweat, and it was already driving me crazy that her soft skin was sliding against mine all over my body. Her firm tit flesh slid against my chest, her nipples poking into mine. Her toned thighs slid against my legs.
I landed atop her, with my growing cock already nestled between her open thighs. She was smiling up at me, her blue eyes sparkling with desire, her red hair splayed out behind her head. But I didn’t just want this to be me fucking her missionary on the floor. She had already said I could have whatever I wanted.
So I swung myself around, sliding over the top of Cassidy’s curvy body, until her smooth, bare, pink pussy was in front of me. I looked between our bodies, past the big mounds of Cassidy’s perky breasts, and saw my cock pointing down at Cassidy’s face. I thrust my dick into Cassidy’s hot, eager mouth and she immediately began sucking on the head of my rod.
Resting on my elbows, I used the fingers of my right hand to spread Cassidy’s soft pussy lips apart. Her hard little clit poked out proudly from the top of her folds, and I flicked at it twice teasingly with my tongue. Cassidy moaned around my cock, her soft, slippery cheeks vibrating against the sensitive skin of my rod, sending tingles of pleasure rippling through my body.
I licked up and down the length of Cassidy’s pussy lips, keeping her wet sex carefully spread with my fingers, and then dove in on her sensitive little nub. My hot, wet mouth closed over her button quickly, and I sucked her clit up between my soft lips. With my lips gently rubbing back and forth around the edges of her clit, while it was trapped in my wet mouth, I flicked my tongue eagerly over the top of her pleasure spot.
Cassidy almost choked on my dick in her throat, and then she squealed a high, loud squeal deep in her throat while still swirling her wet tongue around and around my cock head. I began sucking her little clit into the tight, soft space between my lips, then letting it slip almost out of my mouth, then sucked it back hard between my lips. When the hard little nub was in my mouth, I flicked rapidly at it with just the tip of my tongue, lashing at it wetly.
Cassidy released my cock from her mouth with an audible pop and yelled, “HOLY SHIT, YOUR TONGUE!” Her words dissolved into another squeal of pleasure as I sucked her clit back between my soft lips and flickered the tip of my tongue just over the top of her sensitive button.
Cassidy’s soft fingers closed firmly over my wet cock and slid up and down my shaft, but even without looking I could tell she was only stroking me absentmindedly. She was too distracted by the sensation of me suckling then releasing and then suckling her clit, my tongue rubbing furiously at it whenever I sucked it up into my hot, wet mouth.
Cassidy began babbling as her hand slipped slowly up and down over my rigid manhood. “Ungh… HOLY FUCK!… Oh… Oh… I don’t know what you’re doing but… SHIT… it feels AMMAAAAAAZZZIIIIIIINGGGGGG,” Cassidy clenched so hard getting out the end of that last word that I was glad my excited dick was no longer between her lips.
“Don’t stop,” she instructed me. “Don’t stop… just like that… I’ll do anything… don’t stop… oh God… oh God…” Her strong, smooth thighs began to tighten around my ears as her voice rose in pitch, “Oh God… Here it cums… oh yes… OH YES… OH YES! OHHHHHHHHHHH!!!”
I could feel Cassidy’s body coming hard from everywhere. Her toned thighs clamped tightly around my ears, but then her legs were shaking too, vibrating my head as I kept her clit trapped between my teeth. Her hand stopped at the base of my cock and squeezed hard on my solid pole, almost a little too hard. As I slathered my tongue back and forth across her clit, I could feel Cassidy’s scream in her flat belly as she moaned and shook beneath me.
Cassidy squeaked continuously for what had to be at least 30 seconds, and then suddenly the pressure disappeared from her smooth thighs on my head, and her hands were shoving me off her body.
“Okay, stop, stop, stop,” she was panting frantically as I released her clit from my mouth.
When I turned back to look at her, Cassidy’s body looked like she had just run a marathon. Her chest was heaving up and down, her big, round breasts swaying back and forth slightly from the effort. Her chest was also flushed red, as were her cheeks, and her blue eyes were twinkling with a mixture of delight and exhaustion. Her entire, mostly pale, naked body was covered in a light sheen of sweat, down to the tips of her little toes. And she was smiling broadly at me.
“Holy shit,” she said quietly, pausing to suck in a deep breath, “I don’t know what you just did but.. phew. That was crazy.”
When she threw me forcefully off her body, I ended up on all fours near her feet, facing her. Cassidy looked down my body, and when my eyes followed hers I saw that my cock was still rock hard, coated in Cassidy’s saliva, and pointing straight up my body at Cassidy.
“I know, I know,” Cassidy sighed, “This was whatever YOU wanted. But I can’t help what you just did with that fucking tongue of yours.”
Slowly I crawled over to her smooth, sweaty body, until I was on all fours hovering over her midsection. Cassidy laughed, she knew very well what I wanted. She accommodated me by pressing the bottom of her palms into the sides of her big, firm tits, then pushing her boobs together and interlacing her fingers across the tops of her light pink nipples. Then she smiled up at me, almost questioningly, as I drank in the sight of her big, smooth tunnel of tit flesh just waiting for my use.
I positioned my long cock at the bottom of Cassidy’s cleavage and purposefully took my time slowly sliding my rigid rod through the tight tunnel between her breasts. My fat cock head’s passage was lubricated by Cassidy’s sweaty chest, and I delighted in the feel of smooth, slippery breasts sliding against the achingly sensitive skin of my cock. The firmness of her breasts and pressure she was using to keep her tits locked together squeezed deliciously at the full length of my hard dick as I thrust in and out of her tits.
Just as amazing as the sensation was looking down at Cassidy, squeezing her big, round breasts together to pleasure me, and looking up at me with a smile. As I thrust slowly back and forth, dragging my engorged cock through the valley bet
ween her boobs, Cassidy’s huge melons were pushed up and down by my motion. I had never tit fucked Cassidy in this position before, and the sensation and the visuals were firing up my libido.
Cassidy probably could sense the building arousal in eyes as she egged me on by saying softly, “Cum for me.” When I smiled broadly in response, she said, “Go ahead lover, cum for me. Cum deep in between my breasts like that. Or if you want, push that tip through the top and shoot your load all over my face.”
But this was probably going to be the last time for us, and there was so much more I wanted to try. Although my cock was ready for release, I wanted more than that.
“No,” I responded, pulling my cock out from between Cassidy’s round, delightful mounds, “not yet.” I lifted my leg over Cassidy’s body and stood next to her, looking down past my throbbing, twitching, fully erect cock at her pretty face and questioning blue eyes. “You said I could have whatever I wanted.”
“So what do you want?” she asked me, releasing her big, round breasts and rolling onto her side so that her mountain of smooth tit flesh flopped slightly down to the side.
“I know you have a toy that you use on yourself. I want you to get it right now and then get on all fours on your bed,” I instructed.
“You sure?” Cassidy asked me, “My toy?”
“Yes!” I snapped. “Right now.”
“Yes sir!” Cassidy replied with a giggle, and she was quickly on her feet and running into her bedroom. I watched her toned, round bottom as she disappeared into her room and I slowly followed her.
When I got to the room, I remembered that we had set down the frame and the mattress in the middle of the room, but we hadn’t moved it against the wall yet or put any sheets on it. Oh well. I entered just in time to see Cassidy toss a big, rabbit style vibrator onto the bed and then leap onto the bed after it, landing on all fours with a bounce.
I was proud that my cock was still rock solid, and walked to a spot behind Cassidy, whose toes were hanging down over the edge of the bed. She looked back at me over her shoulder, and I could read a wide range of expressions in her blue eyes and on her face: excitement, nervousness, eagerness and fear. They were all there, in her soft lips and her twinkling eyes, as she shook her firm, round ass at me.
“Play with yourself,” I instructed. The toy was just barely within Cassidy’s reach, and as she leaned over and her big boob hung down below her body, she looked back at me questioningly.
“You mean stick this inside of me?” she asked.
“No,” I responded with a sigh. “Use the vibrating part on your clit.”
“I don’t know,” Cassidy responded hesitantly, but she flicked on the vibrating rabbit ears as she continued, “I’m a little sensitive down there.”
“Good,” I told her, “Remember that you said this could be whatever I wanted.”
I could barely hear the vibrating and guessed that she had it on a low setting. But I was still getting what I wanted, and I laid my hands on either cheek of her toned, bare ass. “Play with yourself,” I said again, and was rewarded with a little gasp from Cassidy as I could hear the vibrating ears making contact with with the wet skin of her sex.
Cassidy’s back arched, and with her body resting on two legs and one hand, her thighs were spread apart for me. I teased the outer folds of Cassidy’s now dripping wet sex with the fat head of my cock and got an arousing and unexpected feedback from the vibrations that were just inches away on her clit. I teased open Cassidy’s wet folds, enjoying the sensation of her skin buzzing with the vibrator, and then I sank the first few inches of my pole firmly into the tunnel of Cassidy’s sex.
It felt good to be back inside of her, warm and wet on my manhood, as I thrust back and forth a few inches. Her pussy was dripping with her juices from her earlier orgasms, but her tight, wet pussy walls still gripped my sensitive cock skin as I plowed back and forth inside of her. The vibrations added a little extra sensation, and I grabbed her hips to pull her back onto me as I sank the full length of my long, rock hard rod into her body.
Cassidy was panting and moaning from the combination of my cock fucking her pussy and her vibrator on her clit, but I got the feeling she was barely touching herself with her toy.
“Press that thing into your clit,” I instructed her, shoving my meet deep inside of her sex and feeling my hanging balls slap against the vibrator next to her clit.
“Oh… it’s sensitive,” Cassidy complained in an almost whiny voice.
I reached back with my left hand and slapped hard against the smooth skin of her ass. The slap sounded much louder than it felt, but it had the desired effect as Cassidy yelped and then pressed her vibrator more firmly against her clit.
I began to pound my cock hard into Cassidy from behind, and could hear her hanging tits sliding over the bare mattress beneath her as her body was rocked by my hard fucking. In and out I thrust rapidly, sliding the full length of my wide, excited dick inside of her wet, squishy tunnel, and I slapped her pale ass again hard.
“Ow!” she yelped, but the muffled sounds of the vibration made me think she had pressed the vibrator even harder to her clit.
“I told you to press it right against your clit,” I said as I pumped my hips frantically back and forth, ramming my thick meat into her tight hole.
“I am!” she pleaded, her voice begging and moaning at the same time. “Oh FUCK! It’s right on my clit!”
“Keep it there!” I demanded, punctuated by another flat slap on the soft skin of her bottom. My big pole was flying in and out of her hot snatch, juices dripping down her thigh as I fucked her hard.
“Oh God… it’s RIGHT THERE!” she yelled back at me. But despite the protest in her voice, Cassidy was rocking her hot body back and forth in rhythm with my fucking, and the vibrator stayed on her clit.
“You going to cum like this?” I asked, my hips shoving my hard meat deep inside of her tight, wet hole.
“Yes!” she practically shouted in response.
“You going to cum with my dick in your pussy and your vibrator on your clit?” I demanded.
“YES!” She practically screeched. “Oh FUCK… YES!”
The tingles of my own orgasm were just starting, but the sight of Cassidy’s sweaty, pale, naked body practically electrified with desire in front of me was driving me wild. “Then cum for me,” I said softly.
“Oh… oh… I don’t…” Cassidy panted in rhythm with my hard pounding.
“Cum on my cock for me, Cassidy,” I said, never slowing down, just pumping the full length of my hard cock in and out of her hot, dripping wet womanhood.
“OH FUCK, OH FUCK, OHFUCKOHFUCKOHFUCKOHFUCK… YEEESSSSS!!” Cassidy screamed, her words blurring together as her back arched deeper than I had ever seen it and she orgasmed on my hard and pounding pole. The orgasm was so strong that I could feel her insides slowly contracting back and forth around the fullness of my dick, and her thighs shook violently. She froze with her big, round tits thrust out from her chest, the vibrator still gently buzzing her sensitive and over stimulated clit, and then she collapsed in a sudden heap on top of the mattress, practically throwing her vibrator off the bed.
My hard cock slipped from inside of her as she crumpled to the bare mattress, my manhood tingly and desperately aroused. But I knew there was nothing I could have done to stop her, she was fully spent.
I spent a moment admiring Cassidy’s toned body and womanly curves. My eyes drank in the way I could see her bottom rib pushing out from her body, and then her frame curve gently inward to her waist, and then flared back out again to her very pale but toned hips. I admired the way her pale, round breasts were so full and so firm that, with her body lying partly on her side, it was like she was resting atop two big cushions of tit flesh.
When Cassidy finally opened her eyes and looked at me, her full lips curved upward into a sleepy smile and she looked almost exhausted. Her first words were, “Oh God, you’re still totally hard.”
“You look like you’re ready to sleep for the night,” I teased, still standing at the side of the bed.
“That was amazing..” Cassidy said softly eyes slowly closing as her words gently drifted off. “It was almost… too intense. Too much sensation.” I let her lay there for a moment in silence, her chest gently rising and falling, her smooth, naked skin glistening with her perspiration, until I thought she might have fallen asleep.
Just when I was about to say something, Cassidy slid off the bed and stood on her feet. “I know you’re probably aching to finally get off, but I need a minute to recover. And I need to clean up a little.”
With that, Cassidy walked out of the room and I slowly followed her. She went into the bathroom, closing the door most of the way behind her but leaving it clearly ajar. I decided to stand outside of the bathroom and give her some time, though my excited cock slowly began shrinking on me. I heard the sink running, and then a toilet flush while the sink was still running, and then what sounded like splashing in the sink. When the door finally opened, Cassidy looked generally the same except that she had clearly splashed some water on her face and the edges of her red hair were wet.
“Okay lover,” she said with a tired smile and one hand again on her hip. “You’re the one who wants to be in charge all of a sudden, so what do you want?”
“I suppose you feel a little too worn out to keep fucking?” I asked more than stated.
“I’m a little worn out down there right now,” Cassidy responded with a hint of sarcasm in her voice, “so if we could find something else to do I would prefer that.”
“I can think of something else I might want to try?” I said slyly.
Cassidy’s red eyebrows went up and she looked at me suspiciously. “What did you have in mind?”
I hesitated, but then said questioningly, “You willing to try anal?”
“Umm… maybe,” she responded. Her blue eyes dropped to my half-hard dick and then she looked back up into my eyes and said, “It’s really a compliment to you, lover, but I think your dick might be too big for my ass.”
‘We can take it very easy,” I tried to convince her. “We’ll go slow and as soon as it starts hurting you just say so and I’ll stop.”
“Well that thing is going to hurt at least a little,” Cassidy said skeptically, eyes returning to my dick. But I could tell I had won when her hand dropped back to her side. “But if you PROMISE me that you’ll stop if I tell you to, then I’m willing to try taking that huge dick of yours.”
“Amazing!” I blurted out, followed by, “I promise, you just tell me if it hurts too much.”
“So how do you want to do it?” she asked.
Moments later I had Cassidy resting her elbows on the bathroom sink, bent over at the waist with her legs spread. With her body in this almost L shaped position, she was looking into our reflections in the mirror and her round, toned ass was sticking out behind her.
Her blue eyes watched me apprehensively as I tried to get my dick all the way hard again. I had taken some baby oil we found in Cassidy’s new bathroom, poured a generous amount into my hand, and then carefully lubricated the length of my long shaft. I was squeezing my pole tightly, my closed fist still sliding easily up and down my pole, getting myself hard and slippery. The sensation was pleasurable, especially after all the earlier excitement, and the view of Cassidy’s smooth, pale ass just waiting for me also helped. But my cock was also getting a little sensitive from all the rubbing and stimulation, and it took me a little while to get my erection to full steam.
Once my cock had returned to a rock hard stiffness, I applied another big dollop of oil to the tip of my dick and then carefully positioned my fat cock head right up against the tightly puckered sphincter of Cassidy’s ass hole.
“You ready?” I asked, looking into Cassidy’s blue eyes in the mirror.
“As I’ll ever be,” she responded. I noticed for the first time that she had taken a hand towel and wrapped it tightly around one hand while holding the other end.
With my hard cock head practically dripping lube, and pressed right up against her tight little bung hole, I pushed. And nothing happened. I put a little more pressure, thrusting a little bit with my hips, and my fat cock head pressed hard against Cassidy’s closed opening. And still nothing happened.
I was about to give up and ask if I was doing something wrong when Cassidy, looking into my eyes in the mirror, said, “Go ahead, you’re going to have to push a little harder.”
I thrust with my hips like I was trying to bury my dick in her pussy, and FINALLY my cock head popped past the resistance and through Cassidy’s tight ass hole. The sensation as I slipped inside Cassidy’s ass was remarkable. Her tightly packed sphincter muscles squeezed my cock head almost to the point of being painful, and yet squeezed it so arousingly and delightfully as I slipped into her rear entrance. Cassidy gasped loudly as the first inch of my thick cock slipped into her poop chute, so I pulled out just to the tip of my head and then thrust two more inches slowly past her ass hole.
Cassidy cringed a little in the mirror, biting her lip, but I was lost in the new, stimulating sensations. Once inside of her ass, the sensation of her ass passage around my dick didn’t really feel that great. She felt looser through her back door than in her pussy, and I kind of missed the way her tight, slippery pussy channel slid against my sensitive cock skin. But the sensation of her asshole was amazing. That tight little bundle of muscle squeeze whatever cock skin I slipped past it. As I rocked my hips back and forth to send a few inches at a time sliding in and out of her rear door, her bung hole milked my thick rod so tightly it caused pleasure on the border of pain.
Added to the sensations in my dick, the view was just plain naughty. Cassidy’s sweet, round bottom was right in front of me and there was my big dick, being shoved up the wrong hole. I slipped my slippery cock back and forth through Cassidy’s tight sphincter, and I knew just from the sight of my dick disappearing up her ass that I was being bad and it felt really good.
The physical sensations and the mental feeling of naughtiness were starting to get my overworked cock back on the path to orgasm. I could feel the tingling starting in my groin and building up through my toes, and I was actually contemplating if I wanted to try the sensation of cumming deep in her ass. But then I looked up from Cassidy’s round, firm ass and into her face in the mirror. She was gritting her teeth and had the towel wrapped around one hand so tightly that her knuckles were turning white.
“You okay?” I asked.
“It kind of hurts,” Cassidy managed to say through her grimace.
“You want me to stop?” I asked, my cock still slowly sliding back and forth out of her ass.
“You mind?” she asked.
I immediately withdrew my cock from Cassidy’s ass chute, my cock head sticking inside for a brief second and then sliding out through the very tight hole with a pleasurable little pop. “Of course not,” I said, though popping my cock head out of her hole had provided a little burst of sensation that had brought me even closer to cumming.
“I’m sorry,” Cassidy said, turning her body around and standing to face me, “but that is easily the biggest thing that’s ever been up in there. Were you close?”
I looked down at my cock and seeing that it looked generally clean I closed my right hand over the tip and began to stroke up and down. “Yeah,” I responded.
“I’m sorry,” Cassidy repeated. “You want to cum now? I’ll do whatever else you might want.”
Seeing the towel still wrapped tightly around Cassidy’s hand, I got a weird idea. I put my free hand on her waist and guided her hot little body until she was standing next to the tub. Then I took the free end of the towel and threw it up so it went over the top of the bar holding the shower curtain. Cassidy looked at me confused, with one end of the towel wrapped around her hand and the other dangling way over her head.
“You said you’d do anything, right?” I asked, as my hand continued to slide up and down my excited cock.
“Yeah,” she replied skeptically.
“Reach up and wrap that other end of the towel around your other hand,” I instructed. Cassidy did what she was told, and in order to wrap both hands in the towel, she had to stand right under the bar with her hands up a couple of inches above her head.
When she turned back to face me, I could see in her twinkling blue eyes that she was starting to catch onto the idea. Her hands appeared bound above her head , and her full body was on display for me, from her red hair still tied in a tight pony tail to her pretty face and dazzling blue eyes, to her big, full tits sitting proudly on her chest, down to her shapely, toned legs and her little toes.
“You may want to step into the tub for this,” I told her, and she dutifully obeyed, stepping backwards over the edge of the tub while keeping her blue eyes focused on me.
“You said anything I want, right?” I repeated, as my closed fist continued to pump steadily up and down my hard, slippery pole.
“Yes, sir,” she responded in a soft voice, and the “sir” sent a spark of pleasure shooting up my cock that drove me wild.
“I’m going to cum on your face, Cassidy,” I informed her, walking so I was a little bit closer to her. As my hand slid up and down my still slippery dick, I realized there might be a little problem with the angle. Cassidy was shorter than me, but my cock was still at a level below her boobs.
“Yes, sir,” Cassidy repeated, sending another little tingle up my spine from her submissiveness.
“I want you to beg for it,” I told her, still trying to figure out how I was going to get my load on that pretty face. Her encouraging words and her beautiful, curvy, naked body just hanging there in front of me for my use was quickly driving me towards orgasm.
“Please sir,” Cassidy begged, “Please cum on my face.” He voice was so meek and yet hungry, her blue eyes looked up at me pleadingly. Her beautiful, creamy breasts swayed back and forth in front of me as she purposefully shook her chest slowly from side to side. “Please give me your cum, sir. Right on my face.”
Her voice was driving me wild, and I finally decided to just go for it. I stepped up on the edge of the tub and looked down from well above Cassidy and she kept her eyes on mine.
“Please sir, cum on my face. Shoot that cum right on my face. Cover my face with your cum sir,” she pleaded softly.
My whole body was a live wire and the energy was pouring straight into my cock. It was the build up from all the fucking before, and sliding inside her ass, and watching her hot little body in her tight clothes all day. It was her looking up at me with a little smile, begging for my cum.
When I finally burst, my hand tightly milking my dick, it really felt like a flame was shooting out of my penis. I had never felt something so sharp or intense from sex before. Maybe it was the crazy strong sensation or maybe it was the fact that I had cum so many times before, but as the orgasm tickled me to my core, I kept my eyes open easily for one of the first times in my life.
And as that orgasm blew out of me, I was treated to a lovely sight that I will never, ever forget. The first blast of cum caught Cassidy partly by surprise, probably because I had warned her almost every time before. It splattered very wetly right onto her smiling, pink lips, the excess dribbling down her lightly freckled chin. Her light blue eyes widened in surprise, and then she shut them tightly just before my second spurt hit her squarely over her right eye. The cum was so forceful that it splattered down her pale cheek, and the white cum made the red of her eyelashes stand out even more. At this point the orgasm was so overwhelming that I was just pumping my cock with my hand, and my cum was going wherever my cock happened to be pointed at the time. So the third spurt started at Cassidy’s forehead and then went back over the top of her head. With her red hair in a pony tail, my cum seemed to be a glowing white line of contrast. My fourth spurt hit her weekly in the cheek, the jizz flowing down her neck. I was just beginning to recover my senses, and was surprised that I was still coming, but I had enough sense to point my dick squarely at Cassidy’s face. The last spurt hit her directly on her little nose, the spunk running down over her lips.
As the orgasm subsided, Cassidy started to laugh with her eyes still closed. “You proud of what you did there?” she asked me, smiling through the white jizz covering her pretty lips.
“Oh yeah,” I responded.
She laughed again and said, “Mind turning on the shower for me?”
Maybe fifteen minutes later we were both looking fresher, though I was back in my sweaty clothes. I paused awkwardly in front of her apartment door, turning back to look at her before I opened the exit.
“You are amazing, I hope you know that,” I said, trying to fight back the emotions that were trying to bring tears to my eyes. “You’ll always be special to me.”
“You too, of course,” Cassidy said with a sad smile, her blue eyes looking deeply into mine. “Thanks for everything, I really mean it.”
I leaned forward to say goodbye, and Cassidy caught me off guard for one last time by planting a soft, light kiss on my lips.
We were never as close after that day, which surprised me a little at the time but looking back doesn’t surprise me at all. I moved on to Kristen and Cassidy just moved on. We still saw each other while out with friends, but we never really got into each other’s lives after that. We also had to be careful when out drinking together, because we would get really flirty. We even “rebounded” once a couple of years later and had sex one night. But that goodbye at her doorway was the real end to the story of me and Cassidy. She was simultaneously the best and worst roommate I ever had.
Hot And Horny Red Headed Roommate
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