Trans man-a friend next door. Eventually he wanted to fuck in HIS pussy. I fucked him, then fucked him like a he was a gay man.
He lived on my floor, across a small courtyard. I could see him in his window he could see me in mine. On our balconies we’d talk at each other. We got to having some beers and watching games on TV. He was only about 5ft. 7, really thin, small goatee. One time over at his place I dropped in and he was in his boxers and a singlet tee. He changed shirts and I saw scars on his chest. I asked and he dropped the bomb. He was a transman. Born a girl and transitioning to be male. The scars were his top surgery and the body hair and facial changes due to hormones. I asked if he had cock and he said that no he currently wasn’t looking for bottom surgery he’s still got a vagina. He hadn’t really had much sex except with a lesbian woman he saw for a few months. She went her own way after that. I asked about that and the lesbian fucked him a few times with a strapon, but mainly oral or grinding between them. He said the big problem was that with the male hormones it made her crave sex and couldn’t get enough, but it’s difficult to get any as a transman without bottom surgery. He had sat down on the couch at the opposite end of me, one leg on the floor the other brought up on the couch I could see his pussy hair.
He asked if I wanted to see, he understood the curiosity and we got along so well he didn’t want to have anything lingering between us that might interfere with our friendship. I said OK and he stood up and pulled down his boxers. He had hairy legs, and a pussy in full bush mode. It was definitely a pussy. His legs were very hot leading to a pretty, firm, perfect ass.
“So when you get fucked, is it in your pussy?” I asked
“Yes, of course”
“So you don’t see yourself as a gay man”
“Not really, it’s just kind of split you know?”
With that I pulled down my pants and he got down sucking my cock. I got hard and he said he had to have it in him. In the bedroom he laid down and spread his legs, His pink inner pussy lips showing me the way to his fuckhole, his vagina. I didn’t want to kiss a guy, but once I was a few strokes into his pussy I needed to kiss. It was soft and feminine, his pussy was super tight. I asked and at 20 he’s only been fucked by 2 cocks before transitioning at 18 and 3 strapons, all pretty thin. It felt great and soon I was shooting my cum deep into his hairy pussy. I apologized not knowing if he was on birth control, he said it wasn’t a worry as he’d need to be off hormones for months to get pregnant. After we sat naked having some drinks and watching a game, then I took him to the bedroom and with him on his belly me in his pussy I pulled out and lined up to fuck his perfect little ass bubble. He balked and said he didn’t do that, and couldn’t. “Sure you can baby” I said. “All gay boys take it up the ass”. He was adamant, he didn’t want to get buttfucked, I insisted and as thin as he was it was easy to hold him down. he begged “Please don’t, I’ve never done this I don’t want to do this, DON’T” But by that time I had about 3 inches of my 7 up his super tight asshole. It felt good I couldn’t help it. “Don’t” he said continuing “Don’t, please don’t your raping me, it hurts, please don’t rape me”. I retorted by saying “Two guys together should have some gay sex too, I like your pussy but at times we do it like two guys do” He laid there quieted down and just winced as I was slowly fucking his ass. It was heaven and since I’d cum up his pussy about 40 minutes ago, it took me a good 40 minutes of ass fucking to cum again. I blasted up his virgin asshole with him grunting to my thrusts and shots of cum. “There baby, now you’ve been fucked like a girl and like a guy” I said, “nothing to worry about, you’ve crossed that off the list, go get me a beer”
He got up and we went to the living room to finish the game with two beers. I sat rubbing his pussy even made him cum once. I asked “How big were your tits?” “C cup, 34C” After an hour or so I asked if he was mad at me still for taking him that way. He didn’t say anything just shook his head. When he spoke he said “I never did that before, is that the way you like it?” “I like pussy and ass and mouth, you’ll have to do it all for me, IF you want me to keep seeing you” I said. Her sole response was “OK”. With that I got dressed, before pulling up my pants I dangled my cock in front of his face and he took it and kissed it.
So that’s how I introduced the transman into gay sex. I fuck his mouth, his pussy and his ass, just like I do with my girlfriend. Only HE can’t get pregnant, and HE has a much tighter pussy and ass than her used up cunt.
