My Trans Cousin

At 14 I fucked my 14 year old cousin in his ass while staying over one night. Whenever I was over, his sister stayed in his room and we shared the double bed in her room. One night we were playing around with each other and he rolled over on his stomach saying he had an itch in his ass. I stuck in a finger and wiggled it around for a while, then pulled out. He kept saying it itched and with some cream from his sisters dresser I inserted 2 then 3 fingers and wiggled them around. Still on his stomach he said he needed something bigger, and told me to get on top of him. Naked me, got on top of naked him and tried to get my cock into his ass. I had it lined up and asked if that was what he wanted. He was almost moaning the word "yeeesssss" . I couldn't get it in, trying as I could, using the cream didn't make it, and he told me to get off. I've now got a rock hard 7 thick inches and I have to get off him. In all honesty being on top of his smooth butt felt really good. He got up and went to get vaseline. He already had it in and on his ass, rubbed some on the head of my cock and laid back down and spread for me. I laid on top of him, and put my cock to his hole and again asked him if that was what he really wanted. Again YES. I pushed in slowly, my head glided in and stopping half way asked if he was OK, he wanted it all. I pushed into his ass till my hair was up against his ass cheeks. I moved left to right and asked if that was helping his "itch". No, try something else he said. So I slowly moved my cock out till just my head was in his ass, then slowly moved it back in. I repeated it 3 times and stopped. "Is that what you want" i asked. "YEAH" he answered, I moved in and out and started fucking him, and he asked for it faster. "Really" I asked, "faster". I held still with my cock all the way up his ass and told him that he had to ask me to do it, do what he really wanted me to do. "fuck me" was the answer. "Fuck me, as much as you want". So I fucked and after about 10 minutes told him if I kept going I was going to shoot inside him. He told me to do it. I came inside my cousins asshole. It was the first sex for us both.

I fucked him that whole weekend. He couldn't get enough, he would show me the vaseline and say he was ready, and at night in bed, daytime in the basement, or even in his mom and dads bed when everyone was out of the house for several hours. That time he put on a pair of his moms stockings, garter belt, and a black see through shorty nightie. I fucked him face to face that time, and he pulled up his legs wrapping them around me. We were getting used to it and I could fuck for about 30minutes now the first time, 45 and more for second and third times. this continued for some years, at 17 I started fucking a girl, and he didn't. I fucked him once or twice in the next year, and he was wearing panties and stockings. My cousin was gay, he wanted to suck and get fucked.

At 21 he started transitioning and living as a woman. He actually was pretty, small framed, not too tall, smooth body, no facial hair, and tits that were naturally occuring with hormones and I and his sister would still see him at this time, his parents wouldn't come around. Eventually I would address him as a woman and called him by his chosen name. I also would stay over and fuck him. He sucked me, I fucked him and she was GREAT. I fucked her for a year and a half, we were kissing now as a man kisses a woman and hated having to move for work. She would visit some, and I'd get back when I could but I did admit that I was fucking a couple of women from work and my neighbor.

Then she went for bottom surgery and I was the first guy to fuck her after all was repaired and ready. Kissing, making out, eating pussy, her sucking cock, fucking, and still buttfucking. She didn't want to buttfuck anymore because she had a pussy, but I said with cis women I still want to buttfuck. After all that was my first taste of sex for almost 3years, his mouth and his ass from 14 to 17.

So I fucked my male cousin, I fucked my trans cousin, and now I've fucked my woman cousin. I was the first in his mouth, first in his butt, the first to suck and titfuck, and the first in her pussy.