My interest started when I was about 35 or so, in 1995. Long before the Internet. At the time I was married and my wife was dying. (She had Systemic Lupus.) I had been without sex for about three years and the only release I allowed myself was going to a nearby adult arcade and whacking off. (I couldn't bring myself to cheat on my dying wife. I wasn't that scummy!) The way the arcade was set up, you paid four dollars and walked into the arcade area. In the area was a display that showed which movies were on which of the 12 channels they provided and they always had two tgirl movies playing. There were about 20 rooms and I always chose one of the five or so that didn't have gloryholes in them.
I never paid much attention to which movie was on which channel, so I'm surfing the channels and come across a hot blonde in a bikini sucking off a guy by a pool. She really turned me on, so I settled back and watched. After a 5 minute suck-off, she started taking off her bikini bottom. As she slowly pulled them down, I noticed a small heart-shaped spot at the top of her crotch area. She was very tanned but had apparently put a heart-shaped sticker there while tanning, resulting in a non-tanned area shaped like a heart. I thought that was pretty hot and was really admiring it when she pulled down her bottom completely to reveal a small cock! To say that I was shocked was an understatement, but I was also VERY turned on. I knew what a shemale was at that point, but I haad never been interested in them.
Anyway, she obviously couldn't achieve an erection, even with her partner sucking it, but all the while I was fascinated. I started jacking off, thinking about phrases I had heard like "the best of both worlds" and "boys will be girls" and trying to convince myself that being with a shemale wouldn't be cheating because she wasn't a "real woman". I exploded like crazy and watched the whole movie through several times.
I lived in Houston, so a few nights later, I drove through the Montrose area, looking at the shemale hookers and getting SO turned on! I never picked one up, but I had a lot of nights whacking off to the image of them parading down the streets of the Montrose.
I never cheated on my wife, but after she died in 1996, I waited about 6 months and started calling the phone sex lines which were popular at the time. One lady I talked with told me that she was a shemale and that while she wasn't interested in sex on the first date, she would teach me about transsexuals and take me out to the clubs. It was a fun night and I couldn't believe all of the hot, sexy ladies at these clubs. My date, Michelle, told me that most of them were hookers and to stay away from them. I did, but boy was I excited!
Michelle and I never did get together. She had to leave town about a week later to take care of her sick mother back in Baton Rouge (where, coincidentally, I had lived for 17 years). By then, I knew where the clubs were and I began hanging out there. I'll admit that I tried a few TS hookers, but I quickly learned that I was no bottom and stuck to the girls who were not tops from then on, which pretty much ruled out the pros.
I lived with a sexy tgirl for a couple of years (she was a nurse), but we argued so much that the relationship didn't go any farther and when I lost my job and moved to Atlanta, I pretty much dated genetic women from then on. I'm married now but I really miss the tgirls.
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