We were always together the two of us, practically raised together. We would do the “you show me yours” thing and even touched each other. One night I was spending the night with him, and when I came over, his sister went to his room, only a single bed, and we went to hers using her double bed. To be naughtly we’d often take off our underpants and be naked, sometimes touching each other. In an in-bed card game he lost the bet. He had to put my cock in his mouth and go up and down 30 times. I couldn’t take it and about count 38 or so (no he didn’t stop at 30) I shot my load, pulling out, and got it on his face and chest. He giggled about it, and moved it into his mouth. After he cleaned up I jacked him off onto his belly and he scooped it up and put it in his mouth also. The next day we’d touch each other as much as we could. Then that night he asked about doing it to me again. I let him get me hard and then I told him I needed more. He asked what I meant, that I could shoot in his mouth he didn’t mind, he liked it.
I didn’t say, I moved my hand to his ass and my finger to his hole. “this is what I want” I whispered so we couldn’t be heard. “No, no I can’t do that” he whispered back. “Sure you can” I said. With that I grabbed his sisters lotion from the nightstand and lubed up my cock, I put some on his hole and he moved away. I grabbed him, forced him over onto his stomach and got on top of him. He was of a smaller, thinner build and I easily held him in place. He kept whispering to please not do it, not to put it in. I stuck it about an inch into his ass and it felt so good. I slowly pushed the rest into him. I had 7 inches already at the time, to his 5 but I was finally inside someone. My cock was inside his butt, his body and I was going to fuck someone finally. I whispered to him how good it felt, he said nothing. I asked if it hurt too much and he said no that it didn’t. “Do you want me to wait a bit? let you get used to it?” I asked. His response was he wanted me to pull it out of him. “OK” I said and I slowly started pulling my cock out of my cousins asshole. I got about 5 inches out, and I felt it building. I pushed back in then half way out again. “Take it out, please, don’t do it like this” he whispered again. “Oh shit, I can’t help it, it’s cumming” I groaned back and pushed all the way in. As I was cumming, I told him I tried to pull it out but it started coming out and I couldn’t. He knew and just laid there and let me cum in his butt. He got up naked, going out into the hall to the bathroom not even trying to put on his underwear. I watched his cute boibutt as he walked out. When he came back, he told me that I came a lot, there was a lot up inside him. I asked if he wanted me to let him do it, or if he wanted me to jack him or use my mouth. I even offered to let him cum in my mouth. He just said NO, and rolled over onto his side. I pushed up against him, my soft, satisfied cock resting against his butt, and put my hand over to his front, on his cock. We went to sleep.
The next day I tried to explain and tell him that I was trying to pull out but it felt so good it made me cum and I couldn’t. We were talking about it in his basement, I asked if it hurt him, he said it wasn’t bad, I asked if he was sore now and he said he wasn’t. “Is there anything you want me to do for you?” I asked and with that, he said YES, and moved behind a wall of boxes. Back there I moved around and he was taking down his shorts and his underpants. He produced a small tube of vaseline and squirted some on his finger and moved it to his butt. “Put some of this on you and do it again” he said bending over so his ass was presented and his hands resting his weight on some boxes. I moved to him after lubing up, and pressed my cock to his pucker. I remember it looked so tiny, how could it take my thick cock? It did it the night before and here it was, when I could see his hole opening to accept my cock. I lasted about 10 minutes and came inside him. When I grew soft I pulled out, he stood up and pulled up his underwear and shorts. I pulled up my underwear and jeans. “OK, let’s go to the park and see what’s up now” he said. It was like nothing happened, he wanted to spend the regular day.
Afternoon, we were back in the basement, my cock was back inside his asshole and I was fucking my cousin getting my third nut within about 12 hours. He was moaning a lot, even telling me how good it felt. I apologized for fucking him the way I did the night before. “You mean you’re sorry for raping me?” was his response. YEAH I said I was. “I liked it actually, it felt good, and this feels real good” he said. Then he got me going. He was whispering back to me, “Fuck me, fuck me, make me a girl for you, make me take your big cock, I want your cock in my sissy hole. ” I couldnt’ take it and I came after about 20 minutes. That night we fucked twice, first time over 30 minutes over 40 the second. He was groaning and moaning so loud I thought he’d wake up his parents.
The next time I went to spend the night, both of us naked in her room, he stood up, went to her dresser and pulled out some panties and a shortie nightie. He put them on and came to bed. I came the first time in his mouth, then the next two times in his cute sissy butt. Then he got up, took off the nightie and panties and went naked to the bathroom again.
We are in our 30s now. I fucked him steadily until we were about 18, I was already getting girls pussies and mouths but I liked fucking him. Then I found out he was getting fucked by his high school teacher, and a football jock, as well as occasionally men he met in the park. He’s now a transgirl, B cup tits on top, hormones, shapely, thin body and lives with a man. I live with my wife and her sister (yes fuck them both)
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