My most recent time fucking a crossdresser [M28, T19]

I’ve always had a voracious sexual appetite that has led me into the rabbit hole on more than a few occasions. For my first story, I’m going to retell my most recent night with a crossdresser. This happened in February 2016 and is as accurate as my memory will allow.

I’m 29, tall, a fraction overweight, but I would imagine reasonably attractive. I am single, live alone and have no dependants. I did well at school and at university, and have found success in the financial sector. I am not objectively rich, but do make a six figure salary and have the toys to go with it. I only mention that as for the purpose of some other stories, I have managed to use it to my advantage to sleep with women very much out of my league. Sexually I am very much of a hedonist, but in my day to day life I am boringly ordinary. I do not drink, do drugs or smoke. My cock is just a hair over 7 1/2 inches, although it’s not particularly thick. It’s perfectly straight, something that has been commented on by lovers a few times.

For about 10 years I have been active on a couple of hookup sites online and have used them exclusively to meet crossdressers. I meet genetic women in the real world, but it’s difficult to find transgendered women outside the confines of the Internet. Anyway, about the start of February I was looking online and found a new user had registered, a crossdresser calling herself Rachel. Just one photograph of a slim, smooth, young looking crossdresser bent over her bed from behind. What drew my attention was the exquisite lingerie she was wearing. A sheer black thong disappearing between two very soft looking cheeks. A pair of opaque black hold up stockings smoothed up her legs, beautifully and instantly finishing at the top, not with lace, but just instantly finishing. She also wore black shoes – court shoes really – very attractive, with quite a short stiletto heel. I was drawn in.

I sent a very brief introductory message, explaining who I was, and importantly advising that I lived alone in a suburban but private detached house. I said that I would love to meet her for a drink at my house, and if she enjoyed my company maybe we could have some fun. She wrote back the next day giving some more detail about herself. She said she was 21, living in the city for university and had only recently started experimenting with dressing up. She said she’d been with girls in the past, but never with a man. Anyway, we chatted for a few days, and she eventually said she’d like to come to my house. Bingo.

I called my cleaner on the Saturday morning and on the pretence of having a party that evening, asked her to come and give my house a quick clean. She came round, changed the sheets, gave the house a once over, and I was ready for my guest. I had arranged for Rachel to come round at 7pm. Just after 7pm, I got an email from Rachel saying she would be a little late as she got held behind at work. She said she’d be about 7:45pm and apologised. I’ve done this enough over the years to realise that there was a good likelihood that she was going to flake, but at 7:35pm there was a knock on my door. I opened and in front of me stood a pretty young man with a rucksack. “Hi Rachel,” I said.

We went inside and exchanged pleasantries. We chatted initially about life generally, but then moved on to what we each wanted from this experience. I explained that I had been meeting crossdressers for quite a few years, and am well versed in how to treat a lady. She asked me for a drink in what was obviously her very feminine natural voice. As mentioned, I don’t drink myself, but do have a healthy supply of wine for guests. I allowed her to select her own bottle, and to open and pour it. Frankly, when you’re meeting someone from the Internet, anything to keep the creepiness factor down is very beneficial. We continued chatting, and eventually it became clear that Rachel was actually 19, and had been crossdressing from a very young age. She told me that she always wished she had been a girl. She said that she had lied about having sex with girls, but that she had received a blowjob and had had some other fumbling experiences. I’d bagged myself a virgin. At this stage Rachel was still dressed as a male, and so I sent her to the bathroom to get changed.

When she returned I felt a familiar twitch in my trousers. Fucking hell, she was hot. The face was still definitely male, in that cute feminine sort of way, but that body was unbelievable. Totally feminine, totally smooth. She wore a skater dress, with black stockings and no shoes. I had her come and sit beside me, where I put my arm around her and stroked her leg with my other hand. I whispered to her about how beautiful she was, and we soon moved into a kiss.

After a few minutes I dared my hand up her leg and under the dress. I rubbed gently up her thigh, and soon reached very smooth satin panties covering a very small nub. I pulled the panties to the side and honestly, this was the smallest cock I’ve ever touched. It was no more than 3 inches hard, and was uncut. As a result of the uncut foreskin it was extremely smooth to the touch. She also suffered from mild phimosis, so it wasn’t actually possible to retract the foreskin fully back. Very, very hot. I coaxed Rachel to move her hand down to my trousers. She was absolutely mesmerised and was gently moaning as I stroked her little cock.

I took off my trousers and shirt, all the while Rachel was closely watching. She took my cock into her hand and began stroking. It was strange; she stroked like a girl who had never touched a cock before. A sort of timid, unsure stroke that led me to think she was even inexperienced at touching her own penis. Eventually she started giving my cock some timid licks and bobbing it slightly into her mouth. Honestly, the blowjob was nothing special. It cried of inexperience, but she was trying her best.

I had her stand up in front of me, and pull her dress off. What was before me was a slim young man, wearing stockings, garter belt and satin bikini cut panties with a little cock poking out the side. I moved my head forward, and took the entirety of Rachel’s little dick into my mouth. I gently sucked while running my tongue up the underside, giving special attention to what little of the head was exposed when the foreskin was fully retracted. She was gasping and her breath was heavy. Her hand was in my hair, in an unsure way trying to get me to keep going. I pulled back.

I led Rachel into my bedroom and we got onto the bed. She sat on top of my chest, and I put some lube on her asshole and started gently pressing my finger into her entrance. I suspect she had plenty of practice with this hole with toys, as within a couple of minutes my finger was properly able to fuck her hole. All the while Rachel was stroking her cock. It was so small she was just rubbing one finger and thumb up and down. Unbelievably cute. It became clear at that stage why she was so unsure at stroking my cock with her whole fist!

Then it happened, she moaned louder and said “sorry”, before leaning back slightly and moaning again. She moaned a third time and with that she shot out two large strings of cum, one hitting the top of my leg, and one shooting almost vertically up my cock. Fuck, it was hot. She was shaking slightly, and almost immediately her tiny dick began to shrink into an impossibly small thing. I pulled her panties over it, and brought her down close to me. She said she was sorry again, and I stated that there’s no reason to apologise.

Part of me at this stage was a little frustrated. Many people lose motivation for sex once they’ve cum, and I desperately hoped this wasn’t going to happen. She seemed a little unsure of whether to continue, but eventually she put her head down onto my chest and started licking her cum off my cock. Gentlemen, this was a sight to behold. Something you should know about me is that I like a long sex session. The shortest I have ever cum was about 20 minutes of penetrative sex, but usually I like to fuck for at least 45 minutes, and often over an hour. With this one though, it was so fucking hot that I could already feel my balls working up to a massive cumshot.

Rachel then got up on top of me, and tried to lower herself down onto my cock cowgirl. She got a good deal in, but she said it was a little sore, so we changed to missionary. I lay her down on the bed, and gently began pushing my cock into her ass. I could tell that it was hurting her, but she was a real trooper, and soon enough most of my cock was inside. For those who enjoy anal sex, you’ll know that unlike a vagina, the asshole tends to feel relatively alike in different people. The only real difference is the tightness of the rectum itself, and fucking hell was this tight. It was squeezing my cock in further.

I began taking slow strokes in and out, watching Rachel’s face whimper with each push. She wasn’t moaning, but was breathing heavily. It was obvious she was in a little pain, but I think over and above that I could see in her face a satisfaction that she had finally gone through with it. That she had wanted this moment for years, and she was being fucked.

After a while I picked up the pace a bit and started fucking a bit harder. Her asshole was very slippery by now, as I’d kept adding more lube for comfort. I leaned down for a kiss and she did something very hot. She wrapped her legs around my back. Few things in life are hotter than having stocking clad legs wrapped around you while you’re fucking. After 15 minutes in missionary, we moved onto doggystyle.

I have a mirror at the end of my bed, and I positioned us in such a way that Rachel and I could see the action in the mirror. It was fantastic. I could see this little smile on her face as she watched herself get fucked from behind. A few minutes later, Rachel asked me to take my cock out and I moved her to lying down on the bed. I got between her legs with my cock and I began frotting her soft little dick. It did the trick, and soon enough her dick had grown to it’s full 3 inches. She kept commenting on the size difference, which of course turned me on very much. We rubbed cocks for a while, until I moved on to giving Rachel a handjob. I stroked her cock gently, pulling back the foreskin as far as it would go, before gently moving the skin back over the head. She kept moaning, and after a few minutes she told me she was going to cum again. I kept stroking her through her orgasm. I could feel her little cock spasming in my hand as I stroked, and just one little dribble of cum came out. Honestly, I don’t know if I’d even call this cum – it was basically entirely see through, but was very hot anyway. I moved my hand up to her mouth and she licked off the cum like a good girl.

Time had gone on a bit, so I motioned her to go down and lick my cock. We were in sort of a 69 position at this time, except laying on our sides. My cock was in her mouth, and she was giving it a much better blowjob this time than before. Her technique had improved substantially, probably just with a building up of confidence. All the while I played with her legs and feet. She had her toenails painted red, and I could just see them through the stockings. Unbelievably hot.

I could feel my orgasm building, and told her I was just a couple of minutes off cumming. I got my biggest surprise of the night when she said she wanted to swallow my load. Those exact words, “I want to swallow your load.” She kept sucking and I let my orgasm build and build. All the while I was playing with her little feet. The first throb from my cock told me this was going to be a huge orgasm. I told her I was cumming, and Rachel proceeded to gently milk my balls with her hand while continuing to bob my cock in and out of her mouth. I could feel a good 6 strong shots of cum shooting out of my dick, but my orgasm must have lasted a good 30-40 seconds. I was absolutely fucking spent. Right into her mouth.

Rachel raised her head up slightly and smiled, as she made a slightly strange face while swallowing my cum. She came up beside me and we chatted. She told me all about how long she’d been fantasising about, “making love to a man”, and how she watched porn all the time imagining she was the girl. She thanked me for the experience, but said she should really go. She went into the bathroom, got cleaned up, got her clothes on and came out. Looking down I could see her shoeless stocking feet poking out from underneath her jeans. Fuck me, so hot to know this cute little thing was going home wearing the lingerie I just fucked her in. She put her shoes on and off she went. I gave her a quick kiss and said we should do this again. She was fairly non-committal; probably the guilt had set in that she’d just met and fucked a stranger.

I had a shower and contemplated what I’d just done. I’d fucked probably my 30th crossdresser in 10 years. She was definitely in the top two or three in terms of looks. Very inexperienced, but the hotness made up for that in buckets. I went into my bedroom and lying on the floor beside my bed was her dress.

I got onto my laptop and sent an email.

“Thanks for tonight, I enjoyed that. I hope you had a good time. You’ve left your dress. How about you come round next Saturday and I’ll give it back to you? ;) Bring something to sleep in and you can stay for breakfast. x”

She didn’t get back in contact immediately, but we are meeting for the second time this Sunday. I intend to use this account to catalogue my many different experiences with both genetic and transgendered women from around the world. I am absolutely not an author, so please leave any feedback on how I can improve my writing for future stories.

Source: reddit.com/r/gonewildstories/comments/4asmbh/my_most_recent_time_fucking_a_crossdresser_m28_t19