They were best friends in high school. And they remained best friends ever since.
Even as they were adults living in the big city, with their own careers and their own busy lives, they still made time to meet at least once a week at a downtown cafe, where they shared updates on their lives.
They were still dressed in their office clothes as they made conversation over coffee.
“So, my 5 year anniversary is coming up,” Ashley said, referring to her marriage to Rob.
Candice sharpened her gaze. “You know, 5 years is a big deal, especially nowadays. You know what that means, don’t you?”
“What?”
“It means you’ll have to get him something extra special this time, and vice versa too.”
Of course, Candice was the authority on this. She worked for a dating website and was a professional matchmaker. She was also a relationship therapist and a marriage counselor.
No matter how dubious Candice’s career seemed to Ashley, there was no doubt that it was effective. Candice had a great reputation for bringing people together and making difficult relationships work. In the big city where they lived, people were more than willing to pay Candice big bucks for her guidance.
“At this point, it’s tough to get something nice for Rob,” Ashley complained. “He’s a low key person and he already has everything he wants.”
“Then do something special. Cook him a great meal. Throw him a surprise party. Anything.”
“Unfortunately, Rob is a far superior cook than I am. And he hates surprise parties. He thinks they’re childish.”
“Good sex always works,” Candice said in a joking manner, taking a sip of her coffee. “Men always appreciate a good blowjob whenever possible.”
Ashley blushed, “Goodness, keep it down, would you?”
“Look, all I’m saying is that 5 years is a big freaking deal. Especially these days. You might want to think of something special.”
“You’re right.”
“I’m always right,” Candice winked.
***
The advice itself wasn’t bad. Ashley thought about it on the way home. As she undressed in her bedroom, she realized what a lucky woman she was.
She was married to a great guy, she had a great job, and she had a wonderful group of friends to rely on. At 33 years old, she was doing well.
But what was she going to give Rob for their 5th anniversary? He already had everything he wanted. He wasn’t a picky guy. He was simple in his taste. He worked as an insurance salesman, and in his free time, he enjoyed sports and hanging out with his buddies. That was it.
Normally, Ashley loved the fact that he was so low maintenance, because it gave him more time to focus on her needs instead.
Now, more than ever, she wanted to make things about him. She wanted to please him. And she was determined to make their marriage last.
She looked in the bedroom mirror. She still kept herself in decent shape. She was an athlete in high school & college, but since becoming an office girl, it was harder to maintain the same form. She’d put on a few pounds around her hips and thighs. Most people wouldn’t have noticed it, but she was always self-conscious about her appearance, and kept track of every change her body made.
Time to cut a few carbs, she thought.
Otherwise, she looked great.
She slipped into her comfortable and casual home clothes- sweatpants and a large tshirt. With the big anniversary coming up, it was time to be a good housewife and prepare dinner.
***
Work was interesting the next day. Ashley worked for a mid-sized advertising agency, where she got to do a job she loved. She loved collaborating with her colleagues and being creative.
But in the back of her mind, all she could think about was her upcoming anniversary, and the conversation she’d had with Candice.
With everything being ahead of schedule in the office, Ashley used her break time to go to the private bathroom to call her best friend. The free relationship advice was always welcome.
After all, if Ashley was right, she knew that Rob must have been planning something special on his own. It was easy to do something special for Ashley. She had plenty of things she enjoyed, including- surprise parties, fancy dinners, and of course, expensive jewelry.
Anniversary gifts were something Rob never forgot about. Each year, he made sure to get her something very nice. Each year, he always managed to outdo the previous year’s gift, which was why Ashley had to come up with something extra special.
She went inside the bathroom and made the call using her speed dial. Thankfully, Candice had free time as well, and they chatted briefly before getting straight to the point.
“I think you’re right,” Ashley said, sitting in the bathroom stall with the phone in hand. “Something romantic is probably the best idea.”
“Now you’re getting it. Good for you.”
“The problem is that I don’t have any ideas.”
“How about sexy outfits? You know, lingerie, see-through bra and panties, that sort of thing.”
“Rob wouldn’t be into that,” Ashley replied. “Everytime I buy something sexy, he wants me to remove it as fast as possible. He just likes the nudity.”
“How about role play? There are plenty of hot scenarios out there.”
“Too tacky.”
“Oral sex?” Candice asked. “Where are you with that?”
“No troubles there.”
“Do you swallow?”
“It’s practically a habit,” Ashley replied with a hint of embarrassment. “There’s the problem, it seems like we’ve covered all the bases.”
“What about anal sex?”
The question stopped Ashley cold. She was dumbfounded for a moment and in a state of slight disbelief. Anal sex? Was that really the answer? Candice was the expert and she mentioned it for a reason.
“We’ve never done that,” Ashley replied.
There must have been something about Ashley’s response, because the tone of her voice caught Candice’s attention.
After all, Candice was a woman who specialized in dating, relationships, and sex. She made a successful career out of it, which not many people can.
“Have you ever experimented with anal before?” Candice asked in a suggestive tone. “I mean, without Rob. Have you done it with past partners before?”
As best friends, Ashley & Candice have discussed their sex lives before, of course, but never in such detail. The level of specifics was beginning to make Ashley feel uncomfortable, but she couldn’t complain. After all, she was the one who called for the free advice.
“I’ve never had anal sex before.”
“Not even a finger?”
“I’ve had a finger,” Ashley admitted. “Nothing more.”
“Really? When?”
“Some guy I briefly dated in college?”
Candice became intrigued. “Really, college? Who was it? Mark? Dave?”
“That’s not important right now,” Ashley replied, shaking her head. “The important thing is me and Rob.”
“I think we’ve found your answer.”
“Anal sex?”
“Yep.”
“Sex in my butt?” Ashley asked again for confirmation.
“That’s pretty much the same thing.”
“And how’s that supposed to work for our anniversary? Should I just spread my butt open and tell him it’s time to fuck?”
“That’s a good start.”
“I was being sarcastic,” Ashley sighed.
“Well it was a good idea nonetheless.”
“I’m being serious, Candice.”
“So am I. This doesn’t have to be rocket science. Men love sex. Sometimes, it’s that simple. Wear some sexy lingerie, give him a hot blowjob, and offer your anal virginity. I guarantee Rob will fall in love with you all over again. Heck, he might even marry you again.”
Ashley was quiet for a moment. Her best friend had a point, no matter how lewd it seemed to be.
“I’ll think about it,” Ashley said.
“There’s something you still haven’t told me.”
“What’s that?”
“Has Rob ever asked for anal sex?”
“Never,” Ashley replied.
“Do you think he wants it? I mean, has he ever massaged your butt? Does he compliment your bottom? Does he look at your butt at all?”
“Yes, to all of the above. Do you think that’s a sign that he secretly wants to have butt sex with me?”
“It could be,” Candice said. “Maybe he wants it, but he’s too shy to ask.”
“I don’t know. If Rob wanted anal, he would have asked.”
“Maybe he doesn’t want to freak you out. Or he’s afraid that you might think he’s some sort of pervert.”
Ashley nodded. “Maybe.”
“Now for the final question, which you haven’t mentioned either.”
“What’s that?”
“Have you ever fantasized about anal sex before?”
God, it was a good question. One that Ashley instantly knew the answer to, although she was slightly embarrassed to discuss it, even with her best friend of all people.
“Sure I have,” Ashely admitted. “Not recently. But it’s crossed my mind. I think it’s crossed every girl’s mind at some point.”
“Then what’s been stopping you all these years?”
“What do you think?”
“Tell me.”
“It’s not complicated,” Ashley replied. “To put it bluntly, cocks are large, assholes are small. In my case, tiny. It’s that simple. That’s why I’ve ever taken the plunge. I’m not made of rubber. I’m a human being.”
“Honey, lots of women these days have butt sex. And lots of women enjoy it, a lot.”
“Including you?”
“Definitely me.”
Ashley smiled, “Figures.”
“Why?”
“You seem like the anal sex type. No offense.”
“None taken,” Candice replied. “The pain is worth the orgasm.”
“Does it really feel that good?”
“I could tell you. Or you could experience it yourself, on your anniversary with Rob.”
Ashley paused for a moment. “How will I know if this is right for me?”
“There’s only one way to find out- ask him.”
***
That night. With their anniversary only a few days away, Ashley tried her hardest to be the perfect wife.
She wore a nice dress and cooked dinner from a recipe she had learned online. Naturally, the food didn’t turn out very well, but at least she tried.
After relaxing on the couch in front of the tv, it was finally time for bed.
They kissed passionately and Ashley unzipped the back of her dress. As they prepared to make love, the topic of anal sex was continuously on her mind. It was all she could think of while they kissed.
She didn’t want to spoil the surprise, but she couldn’t help it either. She just had to know if Rob would think it’s a good idea or not. The worst case scenario would be to offer anal sex on their anniversary night, only for him to be disgusted. Then it would be too late. The night would be ruined.
So she had to ask now. She ended the kiss and looked her husband straight in the eyes.
“I’ve been thinking,” she said. “Our 5th anniversary is coming up, as you probably already knew.”
“How could I forget?”
“Then why not do something special?”
Rob smiled, “Anything in mind?”
It was the moment of truth, and she tried to appear as confident as possible when she made the proposal.
“Do you want to try anal sex on our anniversary night?”
Her eyes were locked to her husband’s face, waiting for any sign of reaction so she could analyze it. She wanted to know his every thought and his openness to a new sexual adventure.
Sure enough, through the subtle shifts on Rob’s face, it appeared he was interested in the idea, and Ashley felt a strange sense of relief, like she had found the perfect gift for their anniversary.
“Anal huh? That sounds interesting. Have you done this before?”
She shook her head. “Nope, never have.”
“Has this been something you’ve wanted for a while?”
“Long story,” she replied. “But kind of.”
He continued smiling, “Why wait? You look gorgeous in that red dress and we’re both in the mood. Why don’t we do it now?”
“Now?”
Shit, she thought.
She wasn’t mentally or physically prepared. But what’s the problem? If Candice could do it so easily, so could Ashley. As Candice had mentioned, plenty of women do it nowadays.
It was time to stop being a wimp and finally lose her anal virginity.
“I’ll get the vaseline,” she said with a sense of self-defiance.
“Are you sure you want to do this? You look so…uneasy.”
“I’m fine. Believe me, I’m fine.”
He rubbed her shoulders. “I’m okay with, you know, regular sex. We don’t have to do this if you’re not comfortable.”
Ashley took a step back and dropped her red dress to the floor.
“I’m serious. I’m fine.”
She was almost in a robotic mode as she grabbed a small container of nearby vaseline and handed it to her husband. Then she pulled her panties down and bent over the bed.
The mood suddenly felt cold & unromantic, like she was in a doctor’s office preparing for a prostate exam. While she waited in the bent over position, she realized that her husband must have been dumbstruck by the awkwardness, and that she’d forgotten to be seductive about their first anal adventure.
But it didn’t matter anymore. Rob had the lube. And her bare ass was pointed outward, ready to go.
The sound of the vaseline cap opening made her more nervous than she’d expected. Deep down, she felt the same nerves she did when she lost her virginity. And in many ways, it was the same thing. She was losing her virginity again, except this time, it was the virginity in her ass.
A shock went up her spine when she felt Rob’s vaseline covered index finger push inside her ass.
“Yikes!” she gasped.
Rob’s finger immediately pulled away from her butt.
“Are you okay?”
“I’m fine.”
“Do you want to keep going?” he asked.
“Of course I do.”
Rob tried again, this time a little more gently. He pushed his index finger back in her butt, and it was the most uncomfortable sexual feeling Ashley had ever felt.
It was so unnatural and awkward having a lubed finger in her butt. Worse, it just felt unsexy.
When Rob pushed his finger all the way in, Ashley’s toes curled on the carpet floor and her body tensed.
“Take it out,” she ordered.
Rob pulled his finger away and gave his wife a concerned look, as she stood upright.
“This was probably a bad idea,” he said.
“No, it’s a decent idea. It’s just, I’m not prepared for it right now. That’s all. We can try again later, on our anniversary night.”
Rob looked confused. “You want to try that again?”
“Why? You don’t like it?”
“I don’t know. We haven’t even done it. But you look so uncomfortable when my finger was in your butt.”
For some reason, that only made Ashley feel more determined to have anal sex with her husband. Maybe it was because it would be the first time for both of them. It would be like losing their virginities together. His cock in her butt. What a romantic thought, in a very odd way.
“Then it’s settled,” she smiled. “Anal sex on our anniversary night.”
“I’m serious, Ashe, we don’t have to do this.”
“And I’m serious too. We’re doing this. I just need a little more time. In the meantime, let’s make love the proper way.”
They held each other and kissed.
Ashley was disappointed with herself that she couldn’t go through with it. She considered herself to be a strong career-minded woman who could overcome any obstacle, but anal? That was something out of her realm.
She definitely didn’t want to rely on Rob either, because that could be dangerous. There was no way she was going to trust her delicate little anus to an inexperienced man with a semi-large cock. That was out of the question.
No. What she needed was an expert. Someone who’d know what to do in a critical situation like this.
Luckily, she knew just who to call.
Part 2 of 3: The Sexually Enlightened Best Friend
The next day in the office, Ashley’s mind was consumed with her sex life. All she could think about was sex. And whether she could actually go through with taking it up the butt.
While she was at her desk, she texted her sexually enlightened best friend. When Candice was free to chat on the phone, Ashley headed to the bathroom for a quick moment of privacy.
After making the call and sitting on the toilet seat cover, Ashley spilled all of the details. She told Candice about the brief conversation with Rob, his willingness, and the finger that went inside her butt. She told Candice about all of her feelings regarding the personal matter.
“I don’t see how a normal woman could handle that?” Ashley wondered.
“It’s 2016, honey, plenty of women are into that.”
“I’m sure it’s just to please the guy.”
“Hang on,” Candice said. “Let me send you a link. Watch it, then call me back.”
“Is it porn?” Ashley asked, knowing her best friend.
“Actually, it is.”
“Is it going to put a virus in my phone or something?”
“Doubtful. I look at that porn site all the time on my phone, while I’m supposed to be working, and my phone is just fine.”
Ashley sighed, “Send it over.”
“Call me back when you’re done watching.”
Ashley waited for the link. It was boring and lonely sitting in the bathroom stall waiting for a porn link. It was a sad reflection on the state of her personal life.
Finally, three links arrived.
Ashley opened the first one, which was a link to a porn site. The video was a brief professionally done clip which showed a woman being plowed in her anus by a huge cock. She fast forwarded through it, watching only the main parts.
The second video had the same content.
The third video was much the same.
She felt a slight embarrassment sitting in the bathroom stall, in her office attire, watching porn on her phone, when she was supposed to be working. She used to complain when men did it, now she was doing the same thing. At least she had a legitimate reason for it, she thought.
After skimming through those porn clips, she called back Candice.
“What did you think?” Candice asked when answering the call.
“I meant normal women. These are porn stars.”
“What’s the difference?”
“Porn stars are performers,” Ashley explained. “They’re made for sex. It’s all they do. And they can spend all day getting in shape and preparing for sex. I’m an office employee. It’s different.”
“Fine. Hold on. Call me back in a few minutes. Let me show you something else first.”
“Wait…hang on…”
The call ended and Ashley sighed. She waited patiently, finally two links arrived from Candice.
Ashley clicked on the first. It was from the same porn site, except this time, it featured a normal couple instead of porn stars. Ashley watched as a plain looking housewife was receiving anal sex in her bedroom, by a man presumably her husband.
The next video was similar. It featured a plain (slightly nerdy) looking college student having an anal orgasm, courtesy of a guy from the college football team.
Ashley was no stranger to porn. She’s watched softcore stuff on cable with her husband. Occasionally, they would watch hardcore porn by ordering it on-demand to spice up their sex life.
But she had never watched amateur porn before. It was odd watching “normal” people fuck. It was like being a voyeur into their sex lives. It was even more surreal watching the videos of those “normal” women having anal sex, and absolutely loving it.
Ashley understood the point of the videos and called her friend back.
“Okay, I get it,” Ashley said. “Normal women can do it too.”
“And you’re a normal woman, right?”
“Last time I checked.”
“Then why can’t you do it?”
Ashley sighed, “I don’t have a clue.”
“Sorry for sounding like a condescending bitch. Honestly, at this point, Rob is probably right. Maybe try something else? Ask him if he has any other fetishes. There’s gotta be something.”
“I’d rather stick with the whole anal thing.”
Candice’s relationship sense kicked in. “Really. Why is that? Now I’m starting to think that a part of you is actually looking forward to this, no matter how hard you try to fight it.”
“I think it’s hot. My guess is, Rob thinks it’s hot too. And frankly, I’m a little curious. I’ve always been sort of curious. It’s the one part of my body which I haven’t explored sexually. So it would be nice to kind of see what the fuss is about.”
“Sounds like we have an important mission ahead of us.”
“So you’re willing to help?”
“Of course I am,” Candice replied. “There’s no way I’m ever going to miss this.”
“Any ideas for what to do?”
“Actually, I have plenty of ideas. I’ve never told you this, but I’m also a sex therapist, in addition to the relationship advice I give.”
“Now isn’t the time for jokes.”
“I’m deadly serious,” Candice said with an undeniable firmness.
It was enough to convince Ashley. “Okay then, how do we start, assuming I get to use your sex advice for free.”
“My payment is watching you have a powerful anal orgasm. In other words, I have to be there and participate, okay?”
“You want to play with my asshole?” Ashley asked in disbelief.
“Uh huh.”
“Is this some sort of lesbian thing? Or is this purely based on our years of friendship?”
“Both.”
Ashley’s eyebrows raised. “Okay, this isn’t weird at all.”
“This is about you, okay? Do you want my help or not?”
Ashley took a breath. “I do.”
“Then let’s get straight to the point, shall we?”
“Fine. How would you normally proceed with this? I mean, if I were a client, a total stranger, what would you do with me?”
“It depends on what you would allow,” Candice replied. “Maybe I would meet with you one-on-one for a crash course on anal. Or maybe I’d do a couples session, where I would assist your husband in claiming your bottom.”
“You, me and Rob, at the same time? A threesome?”
“It’s a viable option.”
“Does it normally work?” Ashley asked.
“Everytime. But I screen carefully though. It has to be the right couple. Only people who are sexually secure with themselves and their relationship. After all, as a sex therapist & counselor, the last thing I want to do is drive a wedge between the couple. Jealousy is a very dangerous thing.”
“Interesting.”
“Any thoughts so far?”
“Rob has always joked about having a threesome. Plus, I know that he thinks you’re very pretty.”
“Leaning towards the threesome I see,” Candice said playfully.
“Sort of.”
“If it makes you feel any better, it’s technically not a threesome. Remember, I would be in an assisting role. That means, I would prep your anus for penetration, and Rob would do the rest.”
“That actually sounds pretty hot.”
“Oh, it is,” Candice replied.
“Would you actually be doing anything with Rob though?”
“I won’t be fucking him, if that’s what you’re afraid of.”
“Then what?” Ashley asked.
“Like I said, I’ll be prepping your anus. I’ll lubricate you and begin with some light stretching. Then, to put it bluntly, Rob will fuck you right after.”
“Sounds…well…adventurous.”
“It is,” Candice acknowledged. “But I might have to touch Rob a little bit, if necessary. I’ll guide his penis inside of your anus to ensure that it’s not too painful. Anal penetration requires a fully erect penis, so if he’s not erect enough, I may have to stimulate him in some way. Most likely with my mouth.”
“So you’ll be giving my husband a blowjob?”
“Only if necessary.”
“That’s reassuring.”
“Hey, you called me. Don’t forget it. I’m helping you the only way I know how. Going by my record, I do a good job at this.”
Ashley sighed, “Thanks, seriously. I mean it, you’re the best.”
“Don’t thank me yet. You can thank me after your first anal orgasm.”
“All of this sounds like the perfect sexual experience for an anniversary. But I’ll admit, it’s very daunting.”
“It always is. And it’s not for everyone.”
“I’d like to try it,” Ashley said. “I’m interested. I really am.”
“You have to be absolutely positive, or else we can’t go through with it. Our friendship is too important. I would never want to ruin your marriage.”
“Then I’ll have to ask Rob and see how he’ll feel about this.”
Candice laughed, “What’s Rob going to say? No? Of course he’ll be fine with this. He won’t be fucking me. He’ll be fucking you.”
“True, but still, I better call him and see what he thinks.”
“I have a better idea.”
“Which is?”
“I’ll call Rob,” Candice said. “I’ll work things out with him, then it’ll be sort of like a surprise for you. I don’t want you to keep stressing over this. The first rule of anal sex is to relax. And that includes mental relaxation.”
“That makes sense. So are you going to call him now?”
“Yes, and I’ll need one more thing from you.”
“What’s that?”
“I’ll need a picture of what I’m working with,” Candice said. “Send me a picture of your bare butt, and a clear picture of your anus. Right now.”
“You want me to start sexting at work?”
“It’s not sexting,” Candice insisted. “It’s advance preparation for an important and delicate medical procedure involving your marital health and sexual well-being.”
“Candice, it’s sexting.”
“Call it whatever you want. I need those pictures to determine how to proceed with the anal process.”
“In other words, you want to know how small my anus is,” Ashley jokingly clarified.
“Exactly.”
“Fine,” Ashley sighed. “I’ll send it in a moment.”
“Perfect. In the meantime, I’ll give Rob a call to work out the details. I have a great feeling about this.”
“So do I. This is by far the kinkiest and craziest thing I’ve ever done, but for some reason, I think it’s going to work.”
“That’s because I’m an expert in this,” Candice reassured.
The two friends said their parting words, and the call ended.
Ashley got off the toilet seat and took a long hard look at herself in the mirror. She had never taken nude pictures of herself before, but if there was ever a good reason to do it, this was it.
She removed her office skirt and panties, placing them on a countertop. She stood only in her buttoned up top and shoes. She was naked from the waist down. Fashionably speaking, it was a very odd combination seeing herself like that, especially in the office bathroom of all places.
After turning around, her butt faced the mirror, and she pointed her phone camera to the mirror also. She took a snapshot of her butt reflection, and it was officially the first nude photo she had ever taken.
Next came the more awkward picture. She thought about how she was going to take a picture of her anus, then came up with the solution. She crouched down and put the phone between her legs, under her body. Once she was in the right position, she took the snapshot.
She stood upright and looked at the picture of her anus. It was the first time seeing it so clearly. She noted the light brown color, shape, and lines of her anus. It definitely looked tiny, and taking Rob’s cock in there was going to be a challenge. Luckily Candice knew what to do.
Ashley texted the explicit pictures to Candice, and suddenly the situation was taken to a whole new level.
***
That night, as Ashley and her husband cozied in front of the tv, all she could think about was the anal fucking she would soon receive, and how Rob felt about it.
Even with all the action on Boardwalk Empire, which is Rob’s favorite tv show, Ashley kept wondering the same things. Especially since neither Rob nor Candice had mentioned anything. Ashley wondered if Candice had even called Rob or not. There was only one way to find out.
“Did Candice call you earlier today?”
“Yes,” Rob said with an unusually coy tone.
“And?”
“And I think you’re in for a special treat,” he said with a faint smile, which he was clearly trying to hold back.
Ashley was semi-ticked off that she was being left in the dark regarding the outcome of her own bottom. She needed answers, and it was clear that neither Rob nor Candice would be giving any.
“Can you at least give me a preview? What should I expect?”
“I promised I wouldn’t say.”
“Are you absolutely sure about that?” Ashley said with an over-the-top seductive voice, as if it were going to work.
“I’m absolutely positive.”
Ashley made a sexy voice again. “Please, darling? I’ll do that thing with my tongue. All you have to do is give me a hint.”
“I can wait,” he smiled. “Just trust me on this. Candice has something special in store for us.”
“You think so?” Ashley replied in her normal voice.
“I am. She gave me several tips over the phone. And she told me what she plans to do with you. I honestly think this is going to add something special to our sex life. Something we’ve never done before.”
It was intriguing to say the least. Deep down, a little jealousy kicked in.
“Are you going to fuck her too?” Ashley asked in a soft feminine tone.
He patted her thigh. “Of course not. Don’t be silly.”
“Then what’s the big secret?”
“You’ll find out soon enough,” he replied, then pointing to the tv. “You’re missing the best parts.”
With that, Rob focused his attention back to the tv. Meanwhile, Ashley kept her mental focus on her soon-to-be sore bottom.
Part 3 of 3: Anniversaries & First Times
It was a Saturday morning, which meant that none of them had to go work.
Ashley followed the instructions which Candice had emailed her the night before. The instructions were mainly about cleanliness and beauty.
She took a nice long soapy shower. There was special emphasis on cleaning her anus & rectum. Ashley followed the special instructions in the shower. In fact, she did it twice to be sure.
Following the shower, Ashley sat in front of her dresser mirror with an assortment of beauty products. She took her time making herself look more desirable than she already was. There was equal emphasis on her hair.
By the time she was done, the professional office girl was long gone. It was the new, anal friendly Ashley. And she looked as gorgeous as ever.
She topped off her appearance with matching white bra & panties, followed by a white negligee.
Everything she did was according to Candice’s advice in the email.
Speaking of which, the doorbell rang. 10 am. Right on time.
Ashley and Rob went to open the front door together. There stood Candice, the sexually enlightened relationship therapist, with a sassy hair style and two shopping bags.
Candice held up the bags and smiled, “Are we ready to begin?”
Suddenly, what appeared to be an ordinary Saturday morning turned into the beginning of something special.
***
The couple waited anxiously in their bedroom while Candice prepared herself in the bathroom. One of the bags Candice brought was for her special outfit. After all, she couldn’t go out in public dressed like she was ready for an anal encounter.
But that raised the question, what was in the other bag? They would find out soon enough.
When the bathroom door opened, both Ashley & Rob were shocked to see Candice’s transformation.
Candice’s casual clothes were all gone. Instead, she was barefoot in a red negligee, similar to the one that Ashley was wearing. Candice also had her make-up done glamorously, and her hair was styled as well.
“Are we ready?” Candice asked, striking a playfully sexy pose.
Ashley was slightly jealous of her best friend’s beauty secrets and fitness routine. She made a mental note to ask for tips later.
“Ready as can be,” Ashley said.
Rob agreed.
“The first step is to look the part,” Candice said. “We’ve already done that, obviously, along with the necessary cleaning. Now the next step is for you to get comfortable, and for me to loosen you up.”
Ashley felt her pussy twitch.
“I’m ready.”
Candice looked around the bedroom. Then she placed a towel on the couple’s marital bed, spreading it neatly.
“Before you lay on the bed,” Candice said. “You’re probably wondering what’s in the other bag.”
Ashley nodded. “I have a pretty good idea.”
“It’s the anal kit we’ll be using.”
“Sounds intimidating.”
Candice reached in the bag and held out a small pink dildo. “Not really. It’s mostly a few small stuff and plenty of lube. Enough to get you ready for Rob’s penetration afterward.”
“I’m starting to feel butterflies in my stomach.”
“Then we better get started.”
Ashley & Rob gave each other a big long hug, followed by a series of kisses to the lips. It was almost like saying ‘goodbye.’ But actually, it was the welcoming of something new to their relationship.
“Panties off,” Candice said.
Ashley reached down and pulled her panties off, tossing them away. She was naked from the waist down, with the thin negligee covering her bottom and pussy, but that wouldn’t last very long.
She got on the bed exactly the way Candice had instructed. With her knees on the towel, and her face pressed on the bed. Her butt was up in the air, and she was keenly aware that her asshole & pussy were fully exposed to her best friend and husband.
It was an awkward moment. In many ways, it felt like a visit to the doctor for Ashley. Except instead of a typical gynecological examination, a thorough ass pounding would soon be in her future. But first, there would be the foreplay. Oh god, what kind of foreplay? Ashley thought.
A pair of hands rubbed both of Ashley’s bottom. Not just any hands. Soft feminine hands. The kind which only Candice possessed.
Oh god, it’s beginning.
“Here comes your surprise,” Candice said. “I know you’ve been bugging Rob about my plans. Well, here it is. I find that a good female rimming is the best way to stimulate anal virgins. Now relax.”
Oh god, a rimjob. From Candice?
Before Ashley could say a word, she felt her butt cheeks being spread even further by the soft hands. She knew that her asshole was spread wide open for her husband & Candice to view.
Then came the tongue. Oh god, the tongue. Her little brown anus was being licked by her best friend. Licked up and down. Licked side to side. Licked in all directions. Then came the kisses. Then the licking again. Then a few more kisses to her anus.
Getting a rimjob was never on Ashley’s sexual bucket list, but she was so glad she felt it. If she had known it was this good, she would have asked Rob to do it years ago on their wedding night.
Now, here she was, on her knees, face down, getting her asshole licked by her best friend. She had always known that Candice was a very sexual person, and an expert in sexual matters, but this? She couldn’t have known that Candice was an expert in perform oral sex on a woman’s anus. The technique which Candice was doing was simply too good to be true.
Then came the final piece of the rimjob. Candice’s tongue went inside. Oh god, it went in. Ashley felt her anus being slobbered on, saliva running down her ass, and inside the entrance of her rectum.
It tickled a little, but mainly it felt sensational, stimulating nerve endings she hadn’t known existed.
“Goodness,” Ashley moaned, face down on the bed. “That tongue of yours…my god.”
Candice briefly stopped. “It’s why I get paid the big bucks.”
And with that, Candice continued with her anal licking. Her tongue licking the ring of the anus, followed the entrance to the rectum, then she stopped.
“Are you ready for the next phase of your licking?” Candice asked, still holding the ass apart.
“There’s more?” Ashley asked, still face down.
“Yes. Here it comes. Now relax, honey.”
Candice said something to Rob, which was so brief and short that Ashley wasn’t able to hear it. All she heard was the sound of shuffling. She couldn’t see it since her face was on the bed. Sure, she could have simply turned around to look what they were doing, but why bother? She loved surprises, and she was in for a special oral surprise.
The next thing Ashley knew, Rob was eating her cunt from below. Meanwhile, Candice returned to her rimming duties.
Ashley experienced a full oral assault on both her pussy & anus, at the same time, from the people she loved the most.
Her eyes widened and her lips curled while she released a short moan. It was double the oral pleasure. Rob sucked her pussy like never before. Candice picked up her anal licking pace.
Deep down, Ashley cursed herself for never doing this before. Oh well. She was a young 33 year old woman, there would be plenty of time left in her life to continue enjoying double oral sex.
She felt a climax approaching when Rob focused his tongue on her clit. It was exactly the way Ashley liked her pussy eaten. Start at the center, then orgasm with clitoral stimulation.
“Oh god,” Ashley groaned, face down, eyes rolling back. “I think I’m getting close.”
Candice briefly pulled her tongue away. “Girl, go for it.”
With that, Rob continued licking the clit faster, and Candice performed an oral whirlwind inside the virgin anus.
Ashley unleashed an orgasm for the ages.
She screamed out loud and her body tightened. Thank goodness they had recently purchased a home, where they could have some decent privacy. In their old apartment, a scream like Ashley’s would have certainly caught the neighbors attention, and maybe the attention of the police.
Now, in the privacy of her own home, Ashley was able to let it all out. Her pussy & asshole received powerful oral stimulation, which resulted in a wet powerful orgasm.
When it was done, Rob moved away from under the pussy, and Candice removed her tongue.
Ashley collapsed on the bed, a wet soaking mess, with a post-orgasm smile on her face.
“Rob was right about you,” Candice said, admiring her bare bottomed best friend. “You’re quite the cummer.”
“Ho..ly…shiiit…” she groaned.
“Girl, now we’re only halfway done. They key to good anal sex is lubrication and arousal. I’d say you’re more than aroused. And you’re nicely lubricated from my saliva. But we still have work to do.”
“Still?” she slurred.
“Yes, now back into position you lazy bitch.”
Candice gave her best friend a powerful slap on the ass. It was enough to get Ashley back on her knees with her butt in the air.
While her mind was still reeling from the intense orgasm, her face was pressed onto the bedsheet, and she felt her butt cheeks being spread again. This time, the hands were much stronger, which meant that Rob was the one holding Ashley’s butt wide open.
Which meant that Candice had both hands free.
Suddenly, Ashley heard the familiar sound of a lube bottle being opened.
Then, Ashley felt the small pink dildo being pushed inside of her butt. It was only a few inches long, but it felt massive inside of her tiny butthole. The pink dildo was pushed in and out.
It was removed, leaving a gaping feeling in Ashley’s butt.
Next, something a little bigger was pressed against her hole. Another dildo from Candice’s bag. It was pushed harder, entering the virgin hole. As it continued being pushed, Ashley knew that this toy was much longer (and thicker) which gave her a much more stretched feeling.
She felt the ring of her anus and rectum being pushed to its limit. Then, it was held in place there, allowing her anus time to get used to having something that sized in her ass.
Then, the larger dildo was pulled away, leaving a gaping feeling in her delicate asshole.
Suddenly, in the background, there were these sucking/slurping noises. It took a second for Ashley to realize that Candice was probably sucking on Rob’s cock, getting him hard and lubricated for the anal fucking. That bitch, Ashley thought.
The sucking noises stopped.
“Happy anniversary, girl,” Candice said in a teasing voice.
“Happy anniversary, darling,” Rob said.
This time, Ashley felt something else pressed against her asshole. It was hard, yet it had a soft feeling. There was no doubt about it. It was Rob’s cock. Her husband was about to fuck her in the ass.
She squeezed the bedsheet and braced herself for what was to come.
Rob pushed. His cock entered. The penetration was slow and gentle. It almost felt like an expert penetrating her, although she wouldn’t have known, since she had never been fucked in the ass before.
She then realized that this was from the tips which Candice had given Rob. That was why Rob was able to fuck her ass so easily. And it was also thanks to all the anal stimulation & orgasm which Candice had provided.
Everything was working to perfection. Rob’s semi-large cock was able to penetrate her rectum effortlessly, although her ass did feel very full.
Finally, it went all the way inside, and Rob rested himself in his wife’s tiny little rectum.
“That’s it girl,” Candice said, who moved up to caress Ashley’s hair in a loving way. “The hard part is over. It’s all the way inside. Now enjoy yourself and the orgasm to follow.”
The best friends held hands and looked each other in the eyes, while Rob slowly pulled his cock back, then giving a thrust.
“Oh…” Ashley gasped. “God…”
“Easy, girl. You’re doing just fine.”
The throbbing cock inside her ass repeated it’s motion. Rob pulled back, then gave another thrust, this time a little bit harder, which Candice had privately instructed him to do earlier.
More thrusts came. With each thrust, Ashley body was pushed deeper into the bed. Her face pressed harder on the bedsheet. The bed rocked. Her hair waved back and forth. Her small breasts swayed.
Soon, Ashley found herself taking a full on ass pounding. The bed shook and Ashley began to cry.
“It’s okay dear,” Candice said in a reassuring tone, wiping away the tears. “You’re doing so good. Your ass was made for this. You’re going to be addicted to ass fuckings by the time your husband is finished.”
Ashley wondered how that could be true as her ass continued getting plowed. It hurt, but it also felt good. It was like the perfect contrast of pain and pleasure. She was being stretched beyond belief. But also, her rectal nerve endings were being stimulated in ways she hadn’t thought possible.
“Oh my god” Ashley cried. “My asshole!”
Tears rolled down Ashley face as the pounding continued. She could have asked for it to stop. She could have begged for it to end. But she didn’t. She was venturing in new territories of her body. She was experiencing new things with her sexuality. And she was loving every second of it.
It still hurt like hell. But there was an undeniable satisfaction to it. Candice sensed the pleasure that Ashley was feeling, and she gave a slight nod to Rob, which was their signal.
Suddenly, Rob began fucking at full speed. Ashley cried out loud, tears rolled down her face, as her delicate little asshole was being plowed with a force she didn’t know she could handle.
“Oh god!!!!” she cried for dear life.
Then she came. She came for the second time that morning. It was different orgasm from before. It wasn’t free flowing and enjoyable.
No. It was raw. Pure. Untamed. It was an orgasm which came from her primal lust. And it made a serious mess all over the place.
Thank god Candice had put that towel on the bed.
The orgasm was so intense, that Ashley hadn’t noticed that Rob had ejaculated inside of her rectum already, flooding her little hole.
For the second time that morning, Ashley was face down, collapsed on the bed, with her bare butt exposed.
Both Rob & Candice admired their work: A dazed Ashley, laying in pure orgasmic bliss, completely wet between the legs.
Epilogue:
When Ashley had come home from work, a small shopping bag in one hand, a purse in the other, she was in a great mood.
She put her purse down near the stairs and she approached her husband in the kitchen, who was still in his work clothes as well.
“Sorry I’m a little late,” she said, kissing Rob on the lips while still holding the small shopping bag.
“What’s this?”
She smiled, holding out the bag, “This…is a nice little gift which Candice gave me. We had coffee a while ago.”
Ashley took out a small bottle and tossed the bag onto the kitchen countertop. The bottle was see-through and it contained a clear liquid fluid. But what stood out the most about the bottle was that it clearly indicated that it was for anal purposes only.
In fact, the substance in the bottle was made specifically for anal sex. It was a new product made to make anal sex a heck of a lot easier.
“Oh my,” he said, eyebrows raised.
“Your cock. My ass. Right now.”
Ashley handed her husband the bottle. She turned around and pulled her panties off, tossing it to the floor. She spread her legs and bent over, lifting the back of her office skirt. Then she placed her hands on the kitchen counter, ass pointed outwards.
While Rob poured the new bottle of lubrication in her asshole, Ashley stared out into the garden. It was a beautiful day and the sun was going down. She realized what a lucky woman she was. She was married to the love of her life and they had found a way to take their sex life to the next level. She also had the perfect best friend, the one who made this all possible.
Life was good.
A simple push, and Rob’s cock entered her little asshole. At that point, Ashley had become accustomed to having her butt stretched by his cock. This time, it seemed easier. Candice was right, that new bottle of lube was awesome, which meant there would be plenty more anal sex in Ashley’s future.