Transsexual First Time

I've always been a fairly normal guy. Except for the fact that since I was around 12 I first found my love for cross dressing. I'm someone that always considers myself reasonably straight, but fascinated with lingerie. The fact that women get to wear such sexy items and we didn't really made me jealous. Just the feel of lace or satin against my body was awesome. Starting with my sisters lingerie, a cute little set of black panties and bra, I felt so sexy, and instantly wanted to try more.

Over the years I built up a large collection of lingerie which I would spend hours dressing in. Of course, after a while I realised that the thought of being with another guy or transsexual was something that turned me on immensely. Even though women were the thought of every second minute of my life. For many years I would dress myself up. My favourites were black lace, starting with a small sexy g string, topped with a garter belt and black thigh high stockings. A tight mini skirt that just covered my ass for the bottom, and a black lace bra and halter top with black satin gloves to finish the effect. After a while I finally had the guts to buy a brunette wig and a pair of sexy heels, and a nice realistic vibrator.

Over the following months, I would get gamer and gamer, sneaking down to the local park, where the toilet block had endless graffiti from guys looking for someone just like me. Nothing ever seemed to happen though. Until I found the opportunity of the internet. After all, it was a fairly dangerous option stealthing around parklands in womens attire, hoping for the right person I was interested in.

I met my first transsexual on the internet and organised to meet up. This was the most daunting experience I have ever contemplated. We chatted for a while and found we were into the same things and got along beautifully.

We met in an apartment in Surfers. So nervous. Whe she answered the door, she peeked around the corner without showing herself to me. I thought, well now or never. As i walked around the door, my breath was taken away. She was dressed in a sexy black really short dress with knee high boots, a sexy blonde wig and as she turned around, the faintest bottom of lacy panties showing underneath the skirt. Wow I was nervous, but so excited about the chance of fulfilling my fantasies.

We sat down to chat with the most awkward small talk I have ever been involved in. I moved to the bathroom, and took my bag of goodies with me. Here I would change into my favourite outfit that I mentioned earlier. All black lace, starting with a sexy small g string, garter belt and stockings, a really short satin skirt that showed off my ass beautifully, lacy black bra with fake inserts and a halter top. To cover myself up I was wearing a long leather coat, my brunette wig and a pair of sexy sunglasses

As i entered the room, she gave me a nice smile and a small sigh. We instantly grabbed each other like a pair of horny teenagers. This was my first time and I was almost ready to cum, just at the first touch. I took the lead and started kissing her nipples and all over her sexy chest. Much as I call her "her" throughout this story, I still couldn't get out of my mind that I was with a guy. Something I thought would be completely weird, but felt so natural. I worked my way down and lifted her short skirt to find the sexiest pair of lacy panties. I couldn't even wait to get her panties down, and started to suck up and down her beautiful cock outside her panties. Slowly and teasing I removed her panties, and finally tasted my first cock. So salty with her precum and a musky flavour all over. I worked my way slowly from the tip to the balls with the tip of my tongue, spending time teasing up and down, before that overwhelming urge to take it in my mouth. I hope I was doing a good job, and she clearly started moaning within moments. After a few minutes of swallowing as much cock as I could take, I could sense she was ready to cum. I wanted more than this, and after years of playing with a vibrator, the urge to feel a real cock inside me was all I could think of.

Please fuck me, was all I could say. I was too excited to say anything more. Boy was she happy. I bent over and pulled down my panties over my stockings and started fingering my ass. She was around 8 inches and reasonably thick, much bigger than my vibrator. She said that she would try to be gentle and slowly fuck me. After getting three fingers into myself I knew I would be ready. The anticipation was incredible, but that first feeling when she was pushing into me was surreal. I was quivering from my toes to my ass as she slowly pushed into me. First the head would push halfway in and slowly loosen me up. After a few minutes getting used to the swollen head I started pushing back slowly onto "her" cock. After taking around 4 inches in it just slid all the way in. Oh my god. What a feeling. I'm glad I prepared with my vibrator for this day, because it hurt a little, but was so satisfying. She began pumping in and out of me doggy style with long thrusts all the way in and out. I thought I would cum within seconds but managed to hold off. She started fucking me harder and harder and I knew this was what I always wanted. " Fuck me harder", " I love it". She kept pumping and pumping and after a few minutes I started cumming. I never even touched myself, just cumming like I've never cummed before. But yet she still kept pumping away. I was in heaven. After 10 minutes of practically screaming my head off, she told me she was about to cum. Only one thing would make my fantasy complete. I turned around and put my face in front of her cock and ordered her to cum on my face. Within seconds she exploded all over my face. I opened my mouth wide and received 2 long streams straight into my mouth. It tasted so good, so warm and so good and only a little bit salty. What a turn on. I slumped on my back and felt so relieved that I had finally fulfilled my fantasy from head to toe.

Since then I have only had the luxury of doing this once again, but looking forward to repeating everything, maybe even with a couple of trannys or guys. Imagine all that multiplied with a number of people.