Well, it’s been a while since I shared a story. Unfortunately since the summer I’ve had a lack of interesting stories, particularly about crossdresser encounters. But this experience was so hot it would be a shame to keep it to myself.
Way back in August I noticed a new profile had come up on a well known scene website. The profile gave very little away, but what I could see was one photo of a crossdresser wearing only black panties and black stockings bent over from behind. The photo was black and white and deliberately didn’t give much away. The girl called herself Poppy and was aged 19. As I said, this profile was pretty much bare. Usually I don’t bother with profiles like this, as from experience they are usually the flakiest people, but this girl was so smooth and slim that I had to introduce myself.
At first we began talking a little over private message. She was a first year undergraduate, living about 20 minutes from me. She was of Asian heritage and kept herself smooth. Poppy had been trying to build the courage for a couple of years to meet with a guy, as she was a total virgin with both males and females. Things progressed and we had a couple of voice chats on Skype. Totally unremarkable voice, she just sounded like a young, if slightly effeminate man. As you may know from my other stories, I travel a lot for work and we kept missing opportunities to meet. I had got Poppy to the stage where she clearly trusted me and we’d exchanged a few more pictures. This girl was beautiful, so cute with a boyish figure. She sent me a picture of her cock poking out of her panties, and fuck it was so small and smooth. When not erect it was so small it protruded horizontally from her body, not even enough weight to weigh itself down. Every one of the pictures was taken from her dorm room which turned me on even more. The thought that this young guy would retreat to his room to dress up as a girl got me hard more than once.
Finally a couple of weeks ago I messaged Poppy and said I would be at home until the New Year. She was pretty eager to meet and asked could we meet that day. Well, I’m not going to be one to turn down that offer, so I called her on Skype and asked where and what time. She didn’t drive, so I had to go and pick her up and bring her to my house. She didn’t want to have sex, nor did she want to suck me, but she wanted us to wank each other. Honestly, I was hoping for more, but a meetup is a meetup so I agreed I’d pick her up from outside the university halls at 7:30pm. I told her to wear her stockings and panties under her clothes.
When I arrived she was standing under a lamppost. I could just make her out in the darkness and gently pressed the horn to get her attention. She walked over in full boy-mode, but still had that underlying femininity that most crossdressers ooze to those of us who like it. When she saw me she smiled – a cautious smile – and I leant over and opened the passenger door. She got in and we started talking just as we had been for the past couple of months. I could tell she was seriously, and I mean seriously nervous so I tried to inject a bit of humour. She liked my car, so I showed her around some of the cooler features, including the massaging seats which she loved. I put my hand across onto her thigh and could just feel the lacy stocking tops through her jeans. I rubbed my hand up and down and she closed her eyes. This continued for a while, with me trying to be careful not to go too close to her cock as she seemed very, very nervous about the encounter.
About half way back to my house she became more relaxed and confessed to me that her heart rate had been so high when she saw my car. She said she’d never done anything like this before and asked me if I had. I laughed slightly and said I had been meeting with crossdressers for over a decade and said that I liked women as well. I confessed I’d also had sex with a couple of transsexuals abroad. Poppy was absolutely intrigued and if there had been any nerves beforehand, they were gone now. She asked me all sorts of questions, about why I liked crossdressers, did I think she was cute, what I liked to do with them. It was all very naïve, and glancing across at this fine featured boy I couldn’t help but think I was throwing Poppy in at the deep end.
When we got to my house we got up and went inside. We sat down on the sofa and I put on some music. Poppy enjoyed looking at my (rather unimpressive) vinyl collection, and picked out Lorde, Pure Heroine and put it in the player. She came and sat beside me and I asked her to take off her shoes and trousers. She very timidly pulled off her shoes and I could see within were her size 6 feet in sheer black nylon, with a slight run on one toe. Underneath I could see that she had painted her toenails black – very sexy. Next off were her jeans, and what was left was Poppy in a long white t-shirt, black cotton panties and lace topped sheer black stockings. I pulled her in close to me and we sort of cuddled for a minute. I whispered how cute she looked and she smiled and said she found me sexy. This sounded totally out of place for someone so innocent. I went in and kissed her. It was all a bit awkward, but we kissed while I stroked her legs and moved my hands up towards her ass. I cupped a cheek in my hand and squeezed, while rubbing my fingers under and inside her panties. I watched her face in front of me change to shocked as I rubbed my finger around the outside of her very smooth hole.
But that wasn’t what I was getting tonight. I grabbed her hand and directed it to my slightly hardened cock. She gently rubbed around the outside of my jeans. It wasn’t working so I slipped my jeans and boxers off and her face looked amazed. She reached out and grabbed my cock and held her hand around it. She whispered to me that it feels amazing and I went in and kissed her again. While our tongues darted she rapidly stroked my cock up and down. When I was fully hard I put my hand across and untucked her cock from her panties. It was fully hard and fairly small. Not as small as it looked in pictures, perhaps 5” long, but very thin. I would say it is probably about average for an Asian guy but slightly thinner. In pictures it looked very small indeed. I began to stroke her cock up and down. After we wanked each other for a couple of minutes while we kissed, Poppy began to whimper. She told me to keep stroking her. “Keep going, ugh, that feels nice.” She made a very cute little noise, a sort of high pitched groan and out came her cum, all over her t-shirt. It squirted in defined lines, one, two, three, four shots launched out of her little cock, perhaps 8 inches up her t-shirt. It was a lot of cum. Poppy had told me that she tasted her own cum so I raised my hand to her mouth and she sucked her cum off my hand. I then kept Poppy laying on the sofa and I got up and straddled her, rubbing her cum covered cock on the tip of my own. She jolted as I rubbed the slippery heads together.
After a few minutes I lay down beside Poppy and had her keep wanking me. I’m always concerned that post-orgasm guilt will set in, but with Poppy she kept her enthusiasm up right to the end. My own cock was beginning to build up at this stage. She stroked me and stroked me, looking and trying different techniques. She told me it felt nice and warm. Odd, but yeah, those words happened! I got her down on her knees in front of me and I stood over her. I asked her did she want my cum on her face. She knodded enthusiastically and continued to stroke my cock over her face while looking up at me and smiling. Few things in life could be hotter than this. Looking down at a crossdresser covered in her own cum, stocking covered legs with a softened cock squeezed between her milky thighs and her panties. The thought and sensation began to push me over the edge. I tensed up and took my cock into my hand and stroked. I groaned “fuuuuck, good girl” as I let out a massive load over her face. She opened her mouth to breath and a shot went right in. I sat down on the sofa and she took off her t-shirt and used it to wipe off my cum. She swallowed the little that had gone in her mouth.
Poppy got up beside me and smiled. She said it was amazing and was everything she’d hoped for. I asked her if she wanted to go further than handjobs and she said she did, but not yet. She was nervous about sex, blowjobs, anything more really. I went and got her a clean t-shirt and drove her home. On the way back she was clearly glowing. We chatted very openly about sex and our interests. She was into femdom porn and particularly loved crossdressers being dominated by men or women. As I left her off, I leaned over and gave her a kiss, right outside the halls. We confirmed we would be in touch with each other and I drove off, leaving her to return to her room, almost certainly to masturbate to what had just happened. Certainly that was my intention when I got home!
And that was my first meet with Poppy. There has now been a second, and tonight there will be a third. I can’t get enough of this girl. So, so cute.
Please leave any feedback or comments. I enjoy reading them. If you’re interested I’ll share the next meet, where we progressed to mutual blowjobs and some rimming while watching porn.
Source: reddit.com/r/gonewildstories/comments/5jw2kq/mutual_handjobs_with_my_new_crossdresser_friend
I would love to read more stories of this nature.
This is so cute! I love it
What a great experience!