I saw someone begin a “diary” of their experiences as a sissy on here recently and it inspired me to give it a shot myself. The following will be true stories from my past starting from the first time I ever hooked up with a Tranny / Cross dresser / Sissy.
First things first, I consider myself to be a straight male; despite having had sex with all of the above. I am not attracted to men, rather the idea of complete submission; I see Trans, CD’s, and Sissies as a fetish, an object if you will (I suppose if it makes you, the reader more comfortable we can say I am bi). If this offends you, please do not read any further.
I have always been an avid porn watcher for as long as I can remember; as my love for porn grew so did my sexual spectrum. I found myself coming across new genres and fetishes that I never imagined I would be turned on by; I stumbled across a Trans pornstar named “Kimber James” and I couldn’t believe my eyes. She looked like every other big tit blonde bimbo I had seen before except she had a cock between her legs.
I was confused and borderline disgusted but slightly aroused; something convinced me to dig deeper. This led me to the sexual underworld of cross dressers, sissies, fembois, and so on. This was never my “go to” when I’d sit down and masturbate but every now and again, it would certainly get me going.
A few years later I ended up leaving my relatively small city and moved to Los Angeles; upon arriving I downloaded a dating app to meet women in the area and quickly realized there were far more CD’s and tranny’s in LA than there were where I was from. I only partially knew one trans person in my previous city and while I would flirt with her at parties, I never had any intention of actually hooking up with her or going any further.
Only a few weeks after living in LA I met a girl and that quickly turned into my first very serious, yearlong relationship. After a year, my girlfriend had cheated on me and our relationship went up in flames; a few months later we started dating again but we weren’t “officially” together again and we could both tell that it didn’t feel right. I stayed on dating apps and kept my options open as I knew my ex was doing the same; it was during this time that I came across a semi-instagram famous tranny (she had about 100 thousand followers at the time).
Out of respect for her, I’ll call her “L.”
Truthfully when I saw her online profile I wasn’t even aware that she was trans; she was a very tiny girl and had a gorgeous face. I shot her a text and figured what the hell, at the least I’ll just flirt around a bit; again with no intention of ever meeting up with her in real life. She turned out to be a genuinely interesting person and her social status piqued my interest to say the least; we chatted back and forth for a couple weeks and she would invite me to grab a bite to eat every now and again and I’d find an excuse not to meet up with her.
Besides, that wasn’t exactly what I was looking for. I didn’t want to date a tranny; I didn’t want to date anyone except my ex, even though that wasn’t working out. But, L was very persuasive; with her I found out just how flattering transgirls were when it came to men. I’m very fit and I work out constantly, so naturally I post gym selfies on social media; L would always message me to compliment me on my body and even go as far as telling me she wanted me to fuck her. Admittedly this was a bit uncomfortable at first.
I remember the night I agreed to finally meet her very vividly; it was December 23rd and I was alone while my ex (who I was still dating at the time) was celebrating Christmas with her family. Needless to say, when I got the invite from L to come over, I took it a bit more seriously than I ever had before.
“I’m house sitting for my friend.” She texted, “Come over, I have the apartment to myself.”
L facetime’d me and ended up convincing me to come over. This was the first time I had heard her speaking voice and it was much deeper than I had imagined it would be, which was a little off-putting as well; but I figured what the hell, she’s cute.
“I don’t have to do anything with her.” I remember telling myself on the drive over to her place.
“I’m here.” I texted her when I arrived, I stood outside the tall apartment building waiting.
“Okay, I’ll be right down.” She replied.
The first thing I noticed was, despite being 12 AM there was someone working at the front desk in the lobby of the apartment building; I was slightly embarrassed. L got off the elevator and made her way to the door; she had long bright pink hair and was much taller than I had expected. She was also wearing high heels; I’m not very tall myself, only standing about 5’7 and with her heels on she was all but towering over me. She welcomed me and gave me hug and we headed up to the apartment; I remember doing my best to walk through the lobby so that the desk clerk couldn’t see my face.
Once we were in the apartment, she offered me a glass of wine and I declined because I don’t drink; she poured me a glass of water and then made her way to the bed. I was quite nervous and she could tell.
“You don’t talk as much in person.” She noticed fairly quickly.
I laughed and tried to play it off, I didn’t admit that I was nervous; I also never mentioned that I was straight and had never been with a transgirl before. This was not exactly how I imagined my first encounter with one would be, I was only interested in the sexual aspect; the fetish. I did not want to get to know this person.
We talked for a bit but it was obvious she wanted sex as much as I did and she moved closer and closer until I decided to make the first move. I pulled her in close and planted a kiss on her lips; her mouth opened wider and our tongues slid into the others mouth and connected. We made out and things continued to escalate, with each deep kiss she moaned softly into my mouth until she decided to make the next move.
“Let’s get naked!” She said, excitedly.
Again, I was hesitant but my cock was rock hard so I stripped down no questions asked and hopped back in the bed. She did the same and climbed on top of me to continue kissing me; unfortunately when she did, I felt her tiny limp cock rest on my leg. It must have been four inches or so, very small; I froze up. I don’t like dick and I didn’t want to touch or see hers but I kept kissing her.
“Suck my cock.” I instructed her.
L made her way down, kissing down my chest and abs until she reached my cock; I felt her limp member ooze precum out onto my thigh as she moved down and again I was turned off. She softly kissed around my thighs and around my balls before sticking her tongue out and licking her way up the shaft.
She then proceeded to give me one of the most mediocre blowjobs I’ve received to this day. I had always heard that guys and trannys sucked better dick than girls and I personally am a big fan of throat fucking but there was none of that. She could only take about a quarter of my cock in her mouth and didn’t try to go the extra mile. She sucked on the tip while stroking my cock for a bit before she stopped to take a break.
“Sorry, that’s just alot of dick in my mouth.” She said.
I wasn’t sure how to respond and I didn’t know what she expected from me within this sexual encounter so I gave her an awkward laugh and told her it was alright. She continued to suck on the head of my cock and I took over and stroked myself until I ended up cumming in her mouth; I was just ready to be over and done with this whole thing, my cock went limp almost immediately afterwards which never happens.
L collapsed on the bed beside me and snuggled up close; she continued to play with my limp cock with her hand, hoping to revive it.
“I think it’s done.” I informed her.
I’m still to this day not sure what she wanted; I don’t know if she wanted me to suck her cock or jerk her off. I’m sure she wanted me to fuck her in the ass, looking back on it and she did have quite a fit body on her; I should have done it but I never intended on fucking her. My thought process at the time was a mouth is a mouth; a blowjob isn’t “gay.”
We made some awkward small talk while the TV was on in the background; she asked me if I had ever been with a transgirl before and I told her no. She seemed off put by this answer but said “that’s cool, I guess.” I left as quickly as possible without being completely rude. I was disappointed to say the least.
On the drive home and the next day I remember feeling uncomfortable with myself about going through with it; it was nothing like I had hoped it would be. I never believed I’d give it another shot after that until…
My ex and I broke things off after realizing our relationship would never be the same again. While it was completely true, I was still extremely sad. I decided to cope with my sadness as any man does after a break up; with some emotionless, meaningless, kinky sex. So I took to the dating apps once more.
I scrolled and scrolled and I passed by several cross dressers and tranny’s until one specifically caught my eye; this time it was a cross dresser. She was fairly passable and had a decent enough face but her ass was the hook for me; ass is always the hook for me. I’m a sucker for a smooth fat ass. (I will always specify whether it’s a tranny, CD, or sissy but will always refer to them as “she.” This goes along with the fetish and humiliation aspect for me.)
I always use the same message when I message all of the above:
“I’ve never been with a _______ (CD/TS) before but I’ve always wanted to try.”
It works like a charm 95% of time. It helps that I’m pretty physically fit and fairly attractive. This CD and I never exchanged names but she informed me that she had her Dad’s house to herself until 4 AM and invited me over.
This time I was much more careful about negotiating what I wanted out of the encounter; I did not want to end up awkwardly snuggled up in bed with someone.
“Can you deep throat?” I asked. “You’re cool with me coming over and just sucking my dick?” I confirmed.
She was more than happy to do just that; she lived a good distance away so I headed over asap as it was already around midnight.
“Do you want to fuck?” She asked.
“Probably not, since this is my first time but we’ll see.” I hesitated.
It was at this point that she informed me that she didn’t have her wig which was a little frustrating but she said she would wear a hoodie. Whatever, I just wanted to fuck someone’s throat.
I arrived at her house and she instructed me to park a few houses down; then she told me to walk to her house and go around the back. I was already nervous and the adrenaline was pumping; I’d heard plenty of “craigslist” horror stories about people getting beat up and robbed so I was extremely cautious when entering the backyard. I carried a pocket knife with me for safe keeping.
I made my way down the long dark driveway until I reached the back of the house.
“Hey..” I heard a whisper. “Over here, come on. Hurry.” She instructed me from the garage.
I was even more nervous now as I was being led into a dark garage; what would be waiting for me on the other side of the door? Luckily, it was just her; dressed in nothing but a hoodie and a black thong. The garage was very dimly lit, damn near pitch black which was perfect for me. I couldn’t see her face and more importantly she couldn’t see mine; discretion was key for me.
She led me to a couch in the middle of the garage and then straddled the cushion cowgirl style with her ass facing towards me. She shook her ass in my direction and asked “You like what you see?”
I did indeed; her ass was even better in person than it was in pictures. I placed both hands on each ass cheek and rubbed it up and down; massaging it and spreading it. I pulled back and gave her a couple good smacks on the ass before placing my mouth on her ass cheek and giving it a little bite. My cock was solid as a rock.
She dropped to her knees on the floor and yanked my shorts down; my cock bobbed up and down in front of her face and before I knew it, she had taken my cock down her throat all the way to the balls.
“That’s more like it.” I thought to myself.
She aggressively bobbed her head forward and backward taking my cock all the way down each time, gagging on it and spitting everywhere. She slid her hands up my thighs until she reached my ass and grabbed herself a handful of my ass; she spun me around and pushed me forward on to the couch and proceeded to dive face first into my asshole.
Again, she aggressively ate my ass; essentially tongue fucking it. She asked me to sit on the couch so she could get on her knees for me and slowed things down a bit. This was easily the best part; she happily showed off her deep throat skills slowly moving up down my cock with her throat, occasionally using two hands to stroke it into her mouth. She really enjoyed bringing me to the edge of an orgasm and then stopping.
I was fucking loving this; this is exactly what I expected my first TS encounter to be like.
“Do you want a popper?” She asked.
I declined but she decided to do one anyway. Apparently a popper is quite popular in the gay community though I had little knowledge of them; she informed me it makes you super horny and loosens you up for anal sex.. Which is when she asked.
“Do you want to fuck me?”
She continued to suck my cock and I hesitantly declined. She could tell I wasn’t fully comfortable with it.
“C’mon just let me sit on it.” She said. “You don’t have to do anything but sit there.”
I won’t lie; in the heat of the moment the thought of her ass bouncing up and down on my cock excited the shit out of me but I searched for excuses.
“I didn’t bring a condom.” I said.
“That’s okay, I have some.”
She was persistent but ultimately I couldn’t bring myself to fully commit. Like I said before, a mouth is a mouth but fucking is a different story. Though she seemed a little let down, her enthusiasm never changed; she continued to suck my cock like a champion and when she could tell I was ready to cum, she asked:
“Will you film it for me?”
“Umm.. Sure?” I answered.
She pulled out her phone and handed it to me; I turned on the camera and began recording. The light from the phone was blinding. She brought me to the edge a few times to really drive me crazy and get me going and then finally let me have it; she sucked it deep all the way down her throat and stuck her tongue out to lick my balls. When I started cumming she pulled back and stroked it until the cum exploded out onto her lips for the camera to see; she then put my cock back into her throat and swallowed the rest of the cum.
I thanked her and quickly said my goodbyes. She gave me 5$ for gas money and I was on my way.
On the drive home I started to reflect on the situation as I did the last time and I was a little uncomfortable with the fact I basically just let a guy blow me but whatever, at least it was an incredible blowjob this time.
I had accepted it and it wasn’t so bad. I figured if every blowjob from here on out was that good, I could really enjoy myself. I kept my eye out on the dating apps for more TS/CD’s while also searching for new girls to date. I enjoyed the “forbidden” rush I got from the first two encounters; it was like a huge secret that no one would ever know and I was sneaking around at night to do it. It was a part of the thrill.
The next one I contacted was another CD and again we did not exchange names. This one I wasn’t 100% sold on. She was Asian and looked cute in one of her pictures but the rest were questionable and she didn’t have the body of the first two. After chatting for a bit I came to the conclusion that I wasn’t interested.
That is until one extremely long day of work; I got off around 3 AM and I really wanted to bust a nut. I knew this CD didn’t live far, maybe 10 minutes so I decided to see if she was still awake.
This was one of the stranger experiences I had during this time. I drove over to her apartment and she instructed me to wait outside the door, again I’m nervous and a little paranoid so I had my pocket knife with me for protection. After waiting outside for at least five minutes she finally opens the door and tells me to be quiet.
I suppose she didn’t live alone and had roommates who were unaware she cross dressed; so she grabbed me by the hand and quietly led me up the stairs to her bedroom. I stripped down and laid in the bed; she crawled onto her knees behind me.
She sat on her knees between my legs and started to awkwardly worship my cock (and by “awkwardly” I mean she started smelling it). The scent of my cock must have aroused her because she started breathing heavily and started touching herself. She sucked on my balls for a while and made her way up the shaft.
This was by far the worst experience I ever had on this adventure I was on. The blowjob was worse than the first one; she had a small mouth and could barely take the head of my cock. She stroked it and suckled it a bit before asking me to get on top while she laid down.
I obliged and squatted over her face on my knees and dipped my cock down into her mouth. She asked me if she could play with herself and I allowed it; then she told me she wanted me to jerk off onto her face while she jacked herself off. I was more disappointed than you probably are reading this.
I stroked my cock until I came on her face and when she felt the cum on her face she started cumming; fortunately I never saw her cock. I rarely ever saw their cocks other than the first encounter; it seemed to ruin the fantasy for me.
Anyway, I got dressed and she quickly snuck me back down the stairs and out of her house.
“What a fucking waste of time.” I thought to myself on the drive home this time. Completely unsatisfied.
“Maybe this really isn’t for me after all.” I said to myself, once again.