For this story, I’m returning right back to the beginning. This was about ten years ago, but as with first experiences for many people, the vivid details have stayed with me to this day. I was 18, and at the time had begun partying. I live in a jurisdiction where the drinking age is 18, so as you can imagine, we liked to let loose at the weekends. I don’t drink now, and drank very little alcohol at the time, so my partying usually consisted of me driving my friends to a club, dancing a bit, try to get a girl and then head home. Obviously being relatively sober around drunk girls had its advantages, and many times I had girls hanging over me because I could make them laugh. Or more properly, I could speak coherently, while they couldn’t.
I’d already been into crossdressing porn for a few years. This was 2005, YouTube had only just started, and streaming video was very much in its infancy. In fairness, we already had broadband Internet, so it wasn’t terribly slow, I think in or around 2mbps. Despite that, streaming porn had barely taken off. I constantly fantasised about crossdressers, but usually I could only get that fix by images. Hardcore porn movies mostly featured so-called “shemales” in those days, which weren’t then and to this day aren’t my thing. The odd crossdressing video I could find left me cumming for days. I fucking loved it.
The one thing I hadn’t experienced at this stage was an actual crossdresser. Frankly, I didn’t know how to find one. Craigslist wasn’t really a thing yet in my country, and there wasn’t much in the way of social networking for sexual deviants like myself. That all changed in the summer of 2005 when one of my friends announced that we were going to go to a gay bar. All of us were fairly liberal and up for a laugh, and we’d heard the music was great so we took no issue. Some of my more adventurous friends had heard this was a great place to get ecstasy, but that didn’t interest me.
We headed to the club at about 10pm – relatively early, but we wanted to get there before a reputedly expensive door charge came at 10:30pm. When we went into the club it was quiet. Mostly groups of males, presumably gay, sitting round tables at the edge of the dance floor. Then there was us – final year at school, mixed gender, most definitely not a group of gays. What we thought going there I do not know! We all got drinks, chilled out and had a chat. The DJ was doing his best to build an atmosphere, but the place was pretty dead. Things picked up about 10:45pm, and my senses piqued when I saw a group of what were obviously crossdressers walking in. Fucking hell. My cock actually twitched in my trousers. I even got slightly dizzy thinking about them. They took a secluded seat in the corner, and aside from occasionally stealing glances, I had to move on with my night.
A while later I needed to get another drink. The place had filled out somewhat, so I decided to take a circuitous route to the bar so I could walk past the group of crossdressers. I walked into the area they were seated and glanced over, probably awkwardly. I looked again and locked eyes with a girl. She was tall, probably mid-twenties, with a long blonde wig. She was wearing a navy tight fitting dress that puffed out at the bottom, black tights and these wonderful silver heels. She smiled at me. I smiled back. Not being as confident as I am now, I walked on to the bar. While I was waiting to get served, she came up behind me and put her hand on my ass. She leaned in and said, “You’re straight.” I replied, “how do you know?” She said, “you looked at me with lust in your eyes, and I don’t get that from gay men.”
I replied and said that she hit the nail on the head. I told her she’s right that I’m not gay, and that I thought she was beautiful. She introduced herself, with a slightly masculine voice – moreso a gay lisp than feminine – as Kylie. I hadn’t touched her at this point, and she told me not to worry and that my friends hadn’t seen us together. She leaned in and softly kissed me on the lips. It was very strange. This girl was confident enough to kiss me about 20 seconds after we started talking. She lifted my drink and walked away. I was then left having to order another drink and pay for both. Honestly, that left me kind of pissed off, but I was absolutely mesmerised with Kylie. She was so naturally feminine, but it turned me on so much to know that in her day to day life she was probably just a feminine looking man. And that squeezed in under those tights was a cock. I wanted more, but in those early days I didn’t know how to get it.
I went back to my friends, and lost sight of Kylie. Later on in the evening I went onto a roof terrace and took a seat out by myself to check my phone and get some fresh air. Kylie followed me out. She sat down beside me and put her hand dangerously high on my leg. She talked to me about nothing in particular; I just remember her saying about moving home from university and having to keep this side of her a secret from her parents. I put my arm around her and we kissed deeply. We were all over each other. At this stage I didn’t really care If my friends saw us. This girl was hot, experienced and exactly what I wanted, and I was putty in her hands. She knew it. Kylie went into my ear and said, “so do you want to give me a lift home?” I pulled a complete dick move and accepted, despite knowing I was abandoning my friends. I sent a message to one of them and said if they all get a taxi home I’ll give them the money the next day for the inconvenience. Thankfully they realised what I meant and there was no drama.
I headed with Kylie to my car and once inside we were all over each other again. It was fantastic. I am a huge leg fan, and have always had a thing for tights, so my hands were all over her legs. She was loving it. Her hand was caressing my crotch, while her tongue was deep in my mouth. She tasted so feminine. In these early days, despite being fairly experienced with girls, I didn’t really know what to do with an infinitely more experienced crossdresser. I didn’t know what the etiquette was; can I touch her cock?
Kylie answered that question for me, and she guided my hand right to the gusset of her tights, through which I could feel soft panties, but more importantly my first ever cock. I stroked her through the panties, giving me a weird sensation. I was actually touching a dick. It was hard and warm and there was definitely a little bit of precum soaking through Kylie’s tights. Just when things were getting good, Kylie let out a cute little moan and said we should head somewhere more private. I drove us to a nearby car park, looking out onto the lake, with my cock like a fucking steel rod in my trousers. It’s been the case from then on for me that genetic girls get me hard, but crossdressers get me totally solid.
When we arrived in the car park, Kylie gave me this sexy smile, and she pulled her tights and panties down to her knees. Now all that was between me and her cock was her dress. I unbuttoned my trousers and pulled my boxers down. I’ve always been quite well endowed, about 7 ½ inches, and I could tell Kylie was impressed. That made me even harder. I took my hand and lifted the dress. In front of me was a 5-inch cock, quite thick and cut. Just right there. The head was glistening with precum under the car park lights. It was so inviting, but I was slightly apprehensive. At that point in my life I had watched a lot of crossdressing porn, but never considered the repercussions on my sexuality of actually playing with a cock. Of actually fucking a boy dressed as a girl. Today I fully accept that it puts me somewhere outside the heterosexual norm. I don’t consider myself bisexual, because I am not attracted to men, nor have I ever had sex with a man. But I do accept that fucking a crossdresser is not entirely heterosexual.
Anyway, I put my hand around her cock. It was soft to the touch. The skin was unbelievably soft, but it was rock hard. She was enjoying this. I gently began stroking up and down on Kylie’s dick, enjoying the feeling of a warm cock in my hands. She continued to kiss me, and now and again would let out a little moan into my mouth. I started getting more confident with my stroking, and gave a bit of variation in my technique. I tried to replicate on Kylie what I’d done to myself while masturbating and what girls had done to me. It was working.
Kylie began to squirm slightly in the seat which looked very, very sexy. She pulled away from the kiss and started breathing heavily. She started trying to push me away slightly, but I whispered in her ear that I wanted to make her cum. She took me at my word and with one loud and very feminine moan, Kylie started shooting rope after rope of cum onto my hand and dribbling down onto her belly. Fuck, I can still remember it now. It was a huge amount of cum, at least equal to the most I’ve ever shot. I continued stroking her through the orgasm, and even continued while she squirmed from over-sensitivity. Kylie came in for a kiss and whispered to me that I was the first man that had made her cum. She said that most of her lovers had been very selfish and hadn’t even touched her cock, and the ones that had just awkwardly groped at it before shortly losing interest.
It was at this stage that I realised that Kylie was actually quite drunk. I had originally seen in her a very confident girl, but I realised after her orgasm that it was alcohol-fuelled bravado rather than confidence. That was when my own confidence fully returned. I’ve always been quite dominant with women, but initially I was more reserved with Kylie. After making her cum like that my confidence was back. I told her it was my turn to cum. Despite an almost complete lack of touching my cock for at least 10 minutes it remained totally solid, such was my level of being turned on.
I told her we were going to go for a walk. She was apprehensive, but eventually agreed we could go for a walk around the lake. It only takes about 10 minutes to do a full circuit of the lake, but Kylie told me this was her first ever time outside as a girl not at a house or gay club. I took her by the hand, and we walked like a couple, hand-in-hand. Eventually my hand made its way round to her ass and began caressing her lovely nylon covered cheeks. They were opaque tights, very, very soft. I could feel that underneath her full cut panties had little bumps covering them. I was lost in a world of feeling this amazing ass. All the while we talked about normal stuff – what we did, where we were from, what we wanted to do in the future. Normal stuff, but deep.
The lake was totally deserted. I told Kylie I wanted her to suck my cock. We walked just off the main path, onto a grassy clearing. It wasn’t a great idea as Kylie’s heels started sinking into the grass! I got her down on her knees and pulled out my cock. Looking down at a very feminine older man, dressed as a sexy blonde, lips wrapped round my dick was absolute heaven. At this time in my life I’d only been with females my own age. What I found out that night is that a crossdresser sucks better cock, and someone with a few years experience sucks much better cock. It was fantastic. Sexy slurping noises, and soft moans came from Kylie as she rapidly worked my cock. She fucked her mouth with it. I said nothing, just watched this spectacle from above. It was to this day one of the hottest experiences of my life.
After what seemed like only a few minutes, but in reality was probably about 15 or 20, I was ready to cum. I told Kylie, and she dropped a bombshell on me. She didn’t like the taste of cum. I told her I didn’t mind, and asked if I could cum on her ass. She said I could, and went to pull down her tights. I said I had a thing for tights and wanted to cum over them. She laughed and said, “each to their own.” She was bent over a tree, dress pulled right up and for the first time I could see this amazing bubble butt. It was unbelievable. Looking down I could see the sexy black tights go right down her legs to her silver heels. I was properly, properly throbbing by this point. I rubbed my cock on her ass and told her how amazing it was. I could see that she was actually stroking herself from the front at this point.
I recall being so hypnotised by her moaning and thrusting her ass back towards my cock, that I didn’t even feel the orgasm building. It just fucking hit me. I shuddered and groaned loudly. I slapped her on the ass and then started spurting cum. It came out pretty gently at first, but built up into a good 4 or 5 long ropes splattered across her bum. Kylie turned round, still holding her dress up and told me she was going to cum. She asked me to stroke her cock again. I rubbed it literally for about 10 seconds and she shot out a second load, much, much smaller than the first, over the grass. A couple of dribbles went on the crotch of her tights.
Kylie laughed and said we’d made a bit of a mess. She could feel my cum seeping through onto her lower back and ass. Then she did one of the sexiest things I have ever seen in my life. She walked back to the tarmac, dress still pulled right up. She daintily stepped out of her heels and pulled her tights off. She put her heels back on and handed me the tights. She said I’d made a mess and she couldn’t be expected to walk around like that. We laughed together and I put the tights in my jacket pocket.
We walked back to the car, continuing to chat about life generally, and honestly, we really clicked. Rarely in life is it so easy to talk to a stranger, but with Kylie it was great. I drove her to her friend’s house and I could see them peeking out the window at us. I gave Kylie a kiss and asked for her number. She said she didn’t have a mobile phone; in 2005 that was unusual but not yet weird. Instead, she gave me her MSN Messenger address.
I drove home, got into bed and let’s be honest, I took those tights with me. I stroked my cock thinking about Kylie and what we had done and blasted another load over them. I looked at my phone and saw I had a text from one of my friends from the club. He said that he’d seen me leaving with a hot girl and that I’d done well. Fantastic. My (drunk) friend thought it was a genetic girl.
I regularly met Kylie until 2010. We were never exclusive, but we did have a lot, and I mean a lot of sex over the years. During this time I ended up getting with a couple of her friends, which eventually started to drive us apart, but I think the final nail in the coffin was Kylie’s relationship status. Around 2008 she started dating a female, as a male, and in 2010 they got engaged. I’m not one for drama, so I totally cut it off. I knew his fiancée would not have known about his other side, or if she did, I’m sure she didn’t expect her husband to be to regularly fucking a man.
I had a lot of firsts with Kylie. We had a very adventurous sex life. Like a lot of “fuck buddy” type relationships, things were a little bit toxic beneath the surface, but I believe we both enjoyed it for what it was at the time. I have enough stories about this girl to write a novel, but this time will always be most special to me. Kylie was my first crossdresser, and my first trip down into the rabbit hole.
Source: reddit.com/r/gonewildstories/comments/4azbgw/my_first_experience_with_a_crossdresser_m18_t25