I remember really clearly the first time i ever had sex with a transexual.

It was, big surprise, in Thailand. I was there as part of a group and had started to become a bit obsessed with the ladyboys we had seen hanging around in some of the areas we had been to.

This night i had left our beach house to go to the only late night shop on this part of the island. i was pretty stoned and as i returned with a bag full of chips and cookies i spotted this girl walking in front of me.

The road was quite dark with little street lighting. She had very long straight black hair and long slim legs almost totally uncovered by a very short, but not tight. skirt. She was wearing very tall heels. As she walked she held an unlit cigarette pointing straight out from the ends of her fingers by her side.

As I said I had become obsessed with watching ladyboys, but with the group I was with had been unable to do or even say anything about it. Now I was on my own and could afford to give more than just furtive glances. I walked behind her almost in a trance (like i said, pretty stoned) just watching her hips sway as she walked. One of the things that had fascinated me about them was this walk. It was easy to spot as you could see it came from a lot of time watching and copying the way that women move, but it was always just a little bit too exaggerated, a little overstated. For some reason though this was what always got me excited. It seemed to be saying 'Look at what a sexy woman I am'. Not just the walk either. It was every movement, even down to the way she held that cigarette.

I was so deep in thought that I almost bumped into her when she stopped and turned. 'You got light?' she asked, striking an almost comical sexy pose with the cigarette held to her mouth. If I'd had any doubts, this sing song impression of a girl voice, as much a cartoon as the walk, would have given her away.

I held my lighter up to the cigarette, illuminating a very, very pretty face. A little make up, but certainly not overdone here, and she had looks that millions of girls would have swapped for without hesitation. I'm quite shy with girls but no hesitation here with an extremely corny 'You are very beautiful'. I could never have said that usually but it seemed the right approach. 'Thank you handsome man' she replied, liar obviously.

A few short sentences later she asked me 'You wan go with me?' She already knew the answer though. I was only wearing beach shorts and she had noticed that just standing with her had had given me an erection. As she asked me she made the point by just softly pinching the end of my cock through my shorts as she looked me right in the eyes. I wouldn't have said no anyway, but this clinched it. i remember that my legs went weak and i actually felt a little sick, that hit of adrenaline feeling.

We moved off the road into a side street and she backed into a little dark corner and sort of pulled me in. I was a little disappointed as I had wanted to go somewhere with her and watch her undress without worrying about people. She pulled me into her little corner though and started to kiss me and this knocked me sideways. Was i kissing a man? Different people have their own take on that but I know I wouldn't have been this excited by kissing an ordinary girl. She was a fantastic kisser, slow, unhurried, sexy and when I opened my eyes I was kissing a very beautiful girl. I was really loving this and didn't want to rush it so i asked her if she had somewhere to go. She hadn't but said if i wanted to hire a beach house for the night she knew somewhere we could go.

A few minutes later we were in one of those built on stilts type wooden beach huts a frighteningly short distance away from my friends. Looking back I assume this was hers anyway and just extra money for her as I paid but we never saw anybody to give it to. Never mind. only a few dollars.
I have never been with a prostitute anywhere else and don't know what it is like. I have always assumed it is very unfulfilling for both parties and that the hooker would put in minimum effort and push you out the door as soon as possible. I will always look back on this experience with a great deal of enjoyment. She was sexy, took her time, did everything more than once and even slowed me down several times. I loved kissing her. I loved the moment when I pretended to be surprised to find her lovely cock, and she immediately relaxed that i was into it and got an instant hard on as i stroked my hand over the little bulge in her panties. i loved sucking her cock, my first and it was such a good decision not to rush that. Most of all, I loved fucking her. I'd had a few drinks and smokes so i lasted ages and she seemed to get more and more into it. We were stood up with me fucking her from behind when i came in her. It was pretty obvious to her that it was near and she said 'slow' before craning her face round to give me long passionate kiss as I pumped it into her (don't worry I used her condom)

Altogether this was probably the best pure sex I have ever had in my life. Maybe she was trying to get a repeat or full week out of me, maybe she wanted to prove herself as sexy as other women, maybe she just even enjoys it. Who knows? There are lots of things about it that I remember well but most of all my head has two indelible full colour stills. One of her walking in front of me, long legs, hair flicking and one of my first proper look at her beautiful face illuminated by my cigarette lighter in the dark street. Unforgettable.