Fucking a cute virgin crossdresser [M29, T27] [MT]

It’s been a while since I last posted a story. The truth is that I haven’t had anything worthwhile to post. I’ve had a few sexual encounters in 2017, but none have been noteworthy. That changed on Saturday night.

I had been browsing a well-known alternative lifestyle website during a break from work for Easter and had noticed a new user had joined in my area within a 5 mile radius. The user had registered as a crossdresser called Lara, aged 27, slim and mentioned in a very brief profile that she was passable. I moved on as it read like the profile of a fantasist or someone just on to chat. A few days later I could see that this user had added a few photos. They were exceptional. So smooth, all in the same outfit that comprised white Converse, black tights and a pink dress. None of the photos showed anything explicit, nor was there anything above mid-chest. Her legs were very cute though, super feminine with small feet.

I sent a message just sparking conversation and asking what drew her to the site, as well as complimenting her photos. She replied that she liked mine as well, and that she was just on to see what was out there and to maybe try something new. Reading between the lines I took it that she wanted to be fucked by a man for the first time. We chatted by private message for a few days and I sent through some more pictures of myself. I learnt that she had been crossdressing since she was a teenager, always in private, and seemed to be fairly religious. I became bolder and suggested we meet, but I was rebuked quite sharply but Lara said she was happy to talk to me on the phone. I gave her the number to my “sex SIM card” and got a call a few minutes later. We had phone sex, basically me telling her the things I would do to her and she moaned and wanked herself until she came.

After the call I – being the deviant I am – Googled her phone number. Bingo. I first found the number on the Church website for a men’s fellowship group, along with a first name. I then searched on Facebook for the name along with the name of the Church. Tagged in a photo I found my girl. Definitely the same build, but decidedly less feminine than I’d seen in the waist-down photos. Not a particularly masculine face though. Very soft features, despite the jeans and shirt. I was satisfied I knew this person was who they said they were, and indeed were located very close by. Now, how to fuck her.

Luck was on my side, as on our next call a few days later Lara told me she wanted to suck my cock. I told her we’d get it arranged, and we set up a mutually agreed time of 8pm on 6th May. We were on. I booked a hotel about half an hour away from where we both lived and built myself up for the night.

At the hotel, time seemed to stand still. I checked in at about 7:45pm, and watched the minutes go by extremely slowly in the room. I’ve met with lots of women and crossdressers over the years, but there always is that pang of nervousness about meeting a stranger for sex. Lara knocked the door just after 8:00pm and I let her in, wearing her male clothes but wearing the same converse from the photos. She went straight to the bathroom, emerging about 20 minutes later in the same outfit from the website. White converse, matched with black tights on her long slim legs, with the dress that in real life was more red than pink and a blonde wig. She had made a pretty mediocre attempt at makeup, succeeding only with the lipstick and blusher. But fuck was she hot. The thought of a 27-year-old virgin crossdresser, a totally untouched ass. I didn’t even know at that stage how far we would get.

I sat down on the bed, motioning for Lara to join me. We went into an embrace, with me holding her tightly as we kissed in an upright seated position. She had barely spoken a word to me at this stage, and was visibly nervous, shaking slightly as we kissed. Eventually I reached my hand down to her thigh and rubbed it around her very soft nylon legs. As I raised higher I could feel Lara becoming more rigid, until eventually I reached a large but very soft cock squashed under her tights and panties. I rubbed my hand around it, expecting it to harden, but nothing happened. It was totally soft, just curled up and neatly packed away. I directed Lara’s hand to my chinos and pressed it onto my hard cock. She gently rubbed, with that look of total amazement. She’d clearly dreamt of this day for a long time. I unbuttoned my chinos and took them down. Lara took my cock out from my boxer shorts and started stroking gently, always looking and she was seemingly in awe at a real life dick in her hands.

We stood up and I turned her round to face the mirror. She was looking at herself with me right behind her, pushing my hard cock up between her ass cheeks. I was enjoying rubbing my dick up along her crack, feeling that soft sensation of skin on tights. After doing this for a short while, I turned her round and pulled down the front of her tights and panties. I pushed my cock to hers and rubbed my head on hers. She was quite large. In my experience most crossdressers seem to have a below average size, but this was a good 6 inch, and fairly girthy. It had stiffened as I rubbed my cock around her head over and over. I put both of our cocks side by side and stroked both at once. We kissed. Her cock leaked pre-cum like none I have ever seen before. It was literally wet, not just a few drops.

After frotting for a bit, I put her down on the bed face down and started toying my fingers into her ass. It was tight but not uncomfortably so. I suspected she had tried a bit of fingering before or maybe even a dildo, but I didn’t ask. She was super timid and very nervous. During this time I could see that she was playing with her cock, but aside from the occasional increased breathing rate she was completely silent.

I put on a condom and lubed my cock and gently pressed it at her entrance. I fucking love a nice closed ass and that first ever so slightly painful sensation of pushing in. Once your cock is past the rectum it feels amazing, the tight ring around the shaft, but anyone who enjoys anal knows the first inch or two can be slightly painful. I enjoy that. I pushed in, and could see her hole opening to accommodate me. She was totally silent. I pushed in and over a couple of minutes got myself right in to as far as I could go. A good 5 inches.

I was whispering to Lara that she was being a good girl and she sought my confirmation that I was inside. She said it wasn’t sore and so I started gently rocking back and forth, moving in and out perhaps half an inch per thrust. After a few minutes of this I started fucking her harder. All this time she was face down on the bed lying there. I pulled her up into a doggystyle position and fucked her hard. My pelvis was slapping off her ass and my cock was spreading her right open. It looked truly fantastic. I reached down and could feel her cock was still very hard. I stroked her and she moaned slightly while I continued to fuck her from behind. She told me she was going to cum and I stopped. Totally stopped. I told her I didn’t want her to cum yet, and I placed her on the bed and started fucking her in missionary position.

After a couple of minutes of this I resumed stroking her cock but very gently, more like rubbing my finger around her head. It was a weird angle as she still had her tights and shoes on, so the tights were sort of at thigh level, so as I stroked her cock I could only see the head from the angle I was fucking her. She moaned again that she was going to cum and I stroked her harder. She shook slightly and just at that point I pulled my hand away and fucked her hard. She tried to put her on hand down to stroke her cock but I pulled it away and held her hands down as I told her I wanted her to cum. Just a few seconds later her cock shot out a rope of cum almost at right angles across the room and off the side of the bed. It must have shot 3 feet. She shot another 3 or 4 ropes up onto her dress which by this stage was hiked up around her chest. Her cum was like water, very little consistency to it.

I couldn’t help myself. Looking down at this sexy crossdresser, who just 2 hours previously had never even touched a cock just cum from having me deep in her ass pushed me over the edge. Within a couple of minutes I was ready. I went rigid and moaned as I emptied my load into the condom deep inside her ass. Right in to the hilt by this point she loudly exclaimed that she could feel my cock throb. I was totally empty, my balls drained. I pulled out and took the condom off.

Lying down beside her I asked her if she enjoyed it. By this stage she had noticed that there was some blood on her ass – oops. She said she loved it and it made her feel like a girl. She went to the toilet to clean up and I lay back on the bed and contemplated what had just happened. The room was filled with that tell-tale smell of totally debauched sex and I was well satisfied.

Lara came back from the bathroom and told me she would have to get back to her fiancée. What the fuck. During all of our discussions there had never been any discussion of a woman. In fact, for all I could tell Lara was into men only. She came over and told me she’d only wanted to suck my cock but hadn’t had the opportunity yet. I obliged and she took my soft but ready for round two cock in her mouth. I caressed her tights covered ass with satin panties underneath, remembering that I had just fucked this perfect ass 15 minutes before.

I’m not ashamed to admit I didn’t last long. Maybe 7-10 minutes on round two before I erupted into her mouth. My load was smaller, but shot out with significant force, with Lara looking at me as I again emptied my balls. She got up, went to the bathroom, presumably spat it out and came out a few minutes later in male mode. Makeup gone, wig gone, dress gone. “Thanks for fulfilling my fantasy. It was a one off, but I hope you enjoyed yourself. I doubt I’ll do it again but thanks.” With that, she turned around, went out the door and was gone.

The next day she had deleted her profile from the website. Lara was hot, but what I haven’t conveyed is that she was very inexperienced and I effectively led the session 100 per cent. I’m more one for the chase, and so ordinarily I’d not be too bothered if we didn’t meet again, but Lara left me wanting more. It’s been a few days now since we met and I can’t get her off my mind to the extent that writing this story is therapeutic.

Anyway, onto the next experience. In that regard I’m going back to Phuket next month for a week. You know what that means.

Please leave any feedback or comments. I enjoy reading them. Check my other submissions for some other experiences I’ve had with crossdressers over the years and one or two with women.

Source: reddit.com/r/gonewildstories/comments/69y7hc/fucking_a_cute_virgin_crossdresser_m29_t27_mt