My first time, I was 19 in the Marine Corps. The Gulf war ended and a group of us use to hang out in Oceanside doing stupid stuff and listening to Depeche Mode.
On the night in question, my best friend decided to pay for sex, so we ended up talking to this Black Prostitute I thought she was a cop. I didn't know why but I felt the situation was a bit off. She made the deal with him, and made it a 2 for 1 deal. So we ended up at her place. I really had no desire but I was asked to go first so I did, I am sure it didn't last very long. But the strange thing was she preformed in sexy clothing, and commented on I didn't pay to see. So I shrugged my shoulders and did the deed.
The next weekend libo we were out on town during the day and went to the Mexican fast food place by the pier, she was there with her roommate, in the day light I realized why I felt uneasy. She was a transgendered Prostitute, I found out later she was sort of famous because she was once a Marine Drill instructor. 0.o Of course this caused me no end of internal questions mainly because I never felt male inside, but I wasn't ready to admit it out loud so I proceeded to sleep with every woman I met for the next year. (it was a large number)