I started with ads on craigslist just to get guys to fuck me while I crossdressed. I'm 5ft. 9" tall weigh only 132lbs, and always had no body hair except on my legs and very little on my forearms. I never had to shave. I got fucked my first time by another boy who was 17 when I was 15. He took me almost everyday, many times twice a day for two years when he transferred to a college out of town. He still came around to fuck when he was home from school. I did do it with two girls, one girl only once the other probably 20 or 30 times. I got more turned on fucking her in her butt than anything. She hated that and we split up. I went back to being the one getting fucked, and one of my friends got me into crossdressing gradually. It was first as a turn on for him, but then I really liked it. I started with undies, stockings graduating to nighties and lingerie. Whenever I could spend the night I'd add make up and style my long hair like a girl. After college I just couldn't find anyone, I was never a drinker and didn't like the thought of trying to pick up a man in a bar. I was crossdressing all the time, even in outer clothes.

I put an ad on craigslist as a tg crossdresser looking for a man to have sex with me. The pictures were real and I got a few men that came over. One older guy was super great to be with, he was a good fuck, took his time, was in no rush. Only when he left, he put $100 on my nightstand. He came over many times, and even though I told him he didn't need to, he kept leaving the money. I wasn't hurt, even though I explained I wasn't asking for any money, he said he knew, he wanted me to have something from him to buy myself a gift. By this time I had over $2000 stored up of his $100 bills. Ken, the older man, eventually stopped coming around, though after buying me a ton of clothes, lingerie, undies, stockings, make up, and even taking me on a few island trips for 4 and 5 day weekends, where I totally rocked out some pretty tiny bikini's (no I don't have a big one, it's very very small).

I started putting an ad for generous gentlemen, and I actually got more responses that when I was wanting to get fucked for free. I was making between $ 200 and $ 600 a day for as many days during the week as I wanted to "work". Considering "work" sucking cocks, then lying down and getting fucked . . . I did it every day. Eventually I found a few sites for tranny escorts and they started getting me much more business and for more money, even after their finders fees. After about a year on hormones, I bought myself B cup boobs and the nude pictures got me even more business, and about a year after that I went for broke. I told some of my regulars, and they all lined up to fuck me (2 would suck my little clit/cock) because I was getting the final operation. As of 4 months ago, I now have a pussy and a totally female body. The agencies let guys know that I'm a post-op tranny and I don't get fucked as many times, but I make a lot more money. I take it in the butt as I've done since I was 15, pussy and my mouth as I have done since I was 14. One agency put me on the girls side of their group too, I'm totally passable.

I don't know what I'm looking for, and I don't want to be a hooker for too much longer, but the money is really good and there isn't much use for a woman, who was a man, who was a crossdresser, then a pre-op tranny who has a degree in fine arts!!!!