First Timer

I was 20 years old, living in NYC. I had not had any time to find a girlfriends, I'd been on the road so much. I was horny, I had a week off, and couldn't seem to find anyone to have sex. So I went to a neighborhood bar that I knew was a tranny and crossdresser bar. I met Gloria who was a crossdresser, and very convincingly so. We met a few times, and I got the invite to her apartment. It was very close to mine, and we walked in and she turned on some music, dimmed the lights and went to change. She came out in some sexy lingerie. I was turned on, but had never had sex with a man before. I knew I wanted to fuck and I liked anal with girls, so . . .

She sucked me till I came, she made a big show of showing my sperm in her mouth before she swallowed and I liked it. We had a drink or two, I recouped and I pulled the see through panties down with her on her back and it was the first time seeing her 5" when limp, cock. When dressed she called it her clit. I stuck my cock in her ass and started fucking her. Kissing, sucking on the nipples on her titless little buds and she was rocking back into me, answering my every thrust. She reached down and started jacking herself while I was fucking her. I came, she finished herself while my cock was still inside her ass and growing limp. We repeated that a few times.

Then one Friday I stayed over with her the whole night. In the morning, I felt something cold on my butt and it was her lubing me. I asked what she was doing, and I got no reply, Instead I got her on top of me and her now 8" hard cock lined up to my butthole. I told her I didn't do that, and she answered with about 3 inches of it going up my ass. I wiggled and again said to stop that I didn't do that, and I felt it all go in with her pubic hair up against my ass cheeks. She waiting and was coaching me on getting used to it, and how to relax. The pain went away, and she started moving. Then finally getting to full fucking thrusts, and really slamming me every stroke in, I was grunting everytime she pushed it back in. She was whispering to me, telling me how good it felt and that she gave me pleasure, I needed to give her some. I was getting slam fucked, grunting every damn stroke she rammed into me. Then I felt the warmth. She was cumming in my ass. After I wanted to go to the toilet, and instead she pulled me on top of her missionary, and I fucked her. Then I went to empty out.

That was my first time getting fucked in my ass, only about 2 weeks after fucking my first guys ass. She stayed the "girl" and I the "boy" but I still got fucked a couple of times a week. I did it, and let a few other guys do it too, and I did them. She introduced me to sucking cock also. After a few different guys I finally found a couple of women to date. I really knew I was bi, and would fuck all their holes, and get fucked by them too.