[TM] Losing my trans virginity, age 21 *TRUE STORY* [crossdress] [convincing] [detailed]

So I’ll quickly give some background before I go into the story. At the time of encounter I was 21, living in *a city* while at uni, and was crossdressing very convincingly pretty much every free time I got. I even had a profile on a *well-known site* that was getting lots of positive comments and I was breaking into the Top 10 T-girls on that site- pretty impressive considering I have never taken hormones! So I got talking to a guy on that site about meeting up and one night I just went for it! Here’s what’s happened….

First, I chose my outfit. I didn’t have a lot of clothes but I had just ordered a white lace body con dress that came down to above my knees. I paired it with black heeled boots and black tights (denier 30 for all you fetishists out there ;)), and black lingerie. As I was going to have to drive across town, I put it all on in my dorm room and then put “boy clothes” over them. It was THE strangest feeling! For the past few months leading up to this point, I had been shaving and using hair removal cream all over my body so by this point I wasn’t just hairless, I was completely smooth and feminine all the way down. As I was putting my make-up into my bag, I realised that I had run out of eyeliner! I then had to go to *a local department store* and buy eyeliner- all the while pretending I was on my phone to my girlfriend so it looked like I was buying it for her :P. It was the biggest thrill I’d ever experienced walking around the shop knowing that underneath my jeans and hoodie I was wearing a fairly slutty dress and tights (although there were bigger thrills coming later that night…). I even bought a random magazine so I could hide the eyeliner underneath it until I got to the tills. When I got to my car, my heart was pounding and I emailed the guy to tell him I was about half an hour away.

At this stage, it was about 8 o’clock at night and it was winter so everywhere was very dark. I did a quick drive by his house to make sure I knew where it was, and then pulled up in what appeared to be a disused car park and got ready for my big night. I took off all my boring “guy” clothes until all that was left was the tight dress, tights and lingerie. I slipped the heels on, followed by my long brunette wig and just sat in the car with my heart absolutely pounding. It was so scary thinking that at any point someone could see me, but at the same time I was feeling an aroused, horny feeling that I had never experienced before. I didn’t have good lighting to do my make-up so I very quickly put a layer of foundation on my face and some BASIC contouring, and then decided it was time to head to his house. Driving in heels was the weirdest experience ever, but so empowering- and I kept glancing down at myself and looking at myself in the rear view mirror in disbelief, literally SQUEALING in excitement that after 10 years of dressing up and doing makeup I was finally getting out in public.

I pulled up at “Johnny”‘s house which was an apartment above some shops, and emailed him, telling him that I was in the car park and that I’d be knocking on the door very soon. I put the remaining make up containers that I’d need into my handbag (which I had stolen from a flatmate- whoops!) and took a deep breath. I looked through the windscreen and saw people in a tanning shop that were looking in my direction. I completely froze, thinking they’d caught on that I was a boy dressed as a girl, but then they looked away and carried on their conversation. I guess I was more convincing than I thought! I nervously left the car and walked about 20m to his front door. It was the longest distance I’d ever walked in heels and oh my god must I have looked like a baby deer. I was lucky that I had long, slender legs for a guy so I hopefully didn’t look too out of place.

Eventually, he answered the door. Johnny was about 35-40, dark hair, slightly taller than me and with just the right amount of stubble. He was well built, with a wide chest and good arms. I literally let out a slight scream of excitement when I saw him. He led me upstairs and into his bedroom so I could get the rest of my makeup on. He kept telling me how beautiful I looked and how much he loved my dress, and by this point I was very very wet with anticipation.

As I knelt on his floor looking in the mirror and applying the new eyeliner I had bought, I kept thinking that I was going to wake up and that it was all a dream. I was finally being “Niamh”- a 20 year old girl in a beautiful party dress with tall heels and smooth legs doing make up in a random guys house, with every intention of making out with him and doing “more”. It was a confidence I’d never felt before and never felt since.

After about forty minutes of doing my make up (it was SO hard doing my lipstick because I was trembling with nerves) I walked down his hallway and into his living room where he had made me coffee. He was wearing a tight t-shirt and jeans, and he stopped what he was doing and said to me “You look gorgeous!”. And, for the first time in my life, I actually felt it.

I took a seat on his sofa, being so careful to be 100% Niamh and not slipping into any “boy” motions. I crossed my legs, sat forward with my hands over my knees and fluttered my eyelashes. He brought the coffee over to me, but I was so nervous I don’t actually remember drinking it. We started talking- he was so sweet and interesting, asking me all about when my crossdressing started and about my interests. He kept complimenting me, telling me how much he loved my legs and lips. I must have been blushing right through my foundation.

After about half an hour, he asked if I wanted to take my shoes off and put my legs up on the sofa over his. I was so nervous, but I did it. As soon as I put my legs over his, he began stroking them like I was his girlfriend. I remember thinking over and over again- “This can’t be happening, this is too perfect.” I felt like a total woman and it was amazing. His hands were getting further and further up my legs each time, and I remember looking down my legs at his hands and thinking “I don’t just feel like a girl, I look like one too- and he’s treating me like one!” I was even flirting with him, which took me by surprise as it’s something I was never particularly good at as a boy. Eventually, I told him that if he wanted any “action” he was going to have initiate it, because it’s the guys job. He laughed, and then told me that he wanted to taste my lips, and then he leaned in and kissed me.

OH MY GOD. My first kiss as “Niamh”. With a guy.

It was everything I thought it would be. He was putting lots of pressure into my lips, but I was kissing back- allowing his tongue to enter my mouth and search around. I ran my hands through his hair and under his shirt while he began to slowly caress where I tucked my penis between my legs. I was in absolute heaven. We stopped and pulled away a few inches, and he asked “Is this okay for you?” I didn’t even answer, I just pulled him in by his t-shirt and kept kissing him. I remember that I was rubbing my legs together and making moaning sounds while kissing- I didn’t even mean to, it just came so naturally.

Eventually, my hands found my way down to his belt, and his moan of approval meant that I knew he wanted what I wanted. I slowly unbuckled his belt and reached in, for the first time feeling a cock that wasn’t my own. In this moment, I was completely a girl for the first time in my life and I wasn’t going to let the feeling end.

Gently, I pulled it out of his boxers so it was completely exposed, and as I slowly masturbated him I began to kiss him. This time, he was really REALLY into it and for the first time I felt what it was like for a man to take control. And the weirdest thing happened- I didn’t just feel aroused in my own penis, but I felt that, ahem, “something else” was crying out inside me to be touched….caressed….penetrated. Maybe it was a mix of the perfume I was wearing, and the soft feel of the clothes against my completely hairless body, and knowing that I was wearing surprisingly convincing make up. Or the fact that I was with a guy who only knew me as “Niamh”, a surprisingly confident human being passing for a beautiful girl who in this moment, was completely wanted by a real man. And I completely wanted him.

As I masturbated Johnny, I could feel a little bit of pre-cum coming from the tip of his penis. I stopped kissing him and said “Is it okay if I put this in my mouth?” I didn’t know WHERE this confidence was coming but I thought “Hey, I’ve kissed a girl for the first time and wanked him off, might as well keep these new experiences coming!”. He murmured yes, and I slid off the sofa very seductively until I was on my knees in front of him like a little slut. I had seen girls on TV and in real life in this pose and often felt so jealous of what they were about to do, and now I was finally getting to experience it myself.

I put my hand around it and brought it towards my mouth. It smelt and looked so good- and no joke, it must have been at least 6.5 inches erect. I looked up at him through my brunette fringe and eyelashes and ran my tongue from the base of his throbbing cock to the tip of it, running my tongue along the tip. I could taste the saltiness of the pre-cum, and it tasted SO GOOD. After letting my saliva run over it for a few seconds, I took the plunge and placed the entirety of his shaft into my mouth. I felt the tip hit the back of my throat, but rather than gag I kept going up and down, up and down. He was making moaning sounds, which made me make moaning sounds as well. The whole time, I was getting wetter and harder myself, thinking “Oh my god, I am giving a blow job. I am a complete slut.” He had his hand on the top of my head directing me, which was every bit as hot and amazing as I had imagined it would be. He was saying dirty things to me, like “You are the perfect slut” and “You are so fucking good at that”. I guess the universe had conspired together to make me a real fucking pro at giving head for the first time :P

It must have gone on for about five minutes, him playing with my hair and me going down on Johnny. Eventually, I pulled away from his cock. It was covered in my burgundy lipstick and I was literally salivating, with a mixture of my saliva and his pre-cum swirling around my mouth and down my chin. I looked up at him, and he looked at me. There was only one place where this night was going.

I asked him “Do you have protection?”, which he said he did. I stood up, straightened my dress and kneeled beside him on the sofa, kissing him again on the lips. I was completely Niamh- there was no going back now. This was all I wanted, and it felt like it was all I had ever wanted. So I asked him, “Then, can we take this into the bedroom?”

And if you want to find out what happened next, you’ll have to upvote me and write nice comments about me below :)

Feel free to ask any questions about the night- like what I was wearing etc. I know what I’ve written sounds a bit like a fantasy story, but I promise you, it was 100% true.

much love :)
Niamh xxxx

Source: reddit.com/r/gonewildstories/comments/58oicz/tm_losing_my_trans_virginity_age_21_true_story