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I confess I did have my first sex at 15 inside another boys butt. I did fuck him a few times when I could, got a couple of BJ’s from him but he never wanted to try to fuck me. I’d suck him sometimes but not to cumming, he used it a prep sort of, before getting fucked by me. At 16 I had my first, what I’ll call “real” lover. She was a granny at 64 and widowed. She gave me her mouth, which was much better than the other boys had been, taught me to eat and fuck her pussy. I loved the taste of pussy so much that after buttfucking, eating pussy became my second favorite sex act. She reluctantly let me fuck her in her butt after about a year. She’d done it when she was a teen and hadn’t had it since. So as promised I took it really slow and easy. She would let me do it probably once every couple of weeks, sometimes more. As I grew and got out in the world I traveled for work a lot. I traveled all over the US and outside in many countries. Sometimes I was gone a long time, but moving around so much I didn’t have time to meet women. I found it was much easier to find a guy to fuck.
I prefer other men like my women. I like petite, feminine looking, attractive, with nice feminine bodies, and great looking legs and hot asses. About a year ago I met Dan. I thought he was cute, feminine looking, petite and very femme body, so maybe a decent mouth and especially his hot little butt to fuck. He was a bit elusive to move forward, and eventually he told me that he was born a woman. He still had his small tits, and pussy, but was on hormones so looking more and more male, with body hair and facial hair. He did keep his facial hair (very little of it actually) shaved all the time, his chest hair wasn’t much at all and he did have hairy legs but there was also a fully hairy pussy. He didn’t like sucking cock but I got him to do it, even cumming in his mouth and swallowing a few times. I was looking forward to fucking a HOT HOT “boibutt”. However; his pussy was available for sex, he had never had anal and didn’t want it. After about 2 months I basically told him that if SHE wanted to be a HE, and be with other guys, then not always but “gay” sex would have to happen. In other words I wanted to fuck his butt. Staying away for a couple of weeks, I got a call from him. “I’m naked in bed, I’m lying on my stomach. Key is in the mailbox, come in and do what you want to do. Just please, PLEASE remember it’s my first time and I don’t want to be hurt”. Within an hour my cum was up HIS ass. He has had sex with a few other guys, nothing too much but experimenting and always with them they have to use condoms.
In turn I intentionally went out to find out about the reverse trans role. I was going to trans friendly bars, especially this month long trip to Amsterdam. I met Trude. She was a male to female transgirl. I was a little nervous, for some reason I didn’t want a transwoman who had a big cock. Not sure what that was about, but Trude was again, petite, very pretty with a knock out body and of course GREAT legs and even GREATER ass. When after our third date we were together, she took off my pants and got on her knees as I sat on her couch and started a BJ. I came, she swallowed then told me that was so I’d last longer when we fucked. She stressed again that she had a penis and that it would have to be anal sex. I told her of my love of buttfucking, and off to bed we went. We were together the entire trip which got extended by two weeks.
When I came back, Dan had stopped seeing other guys, wanting instead to be with me solely. No committment on my part, just that he was wanting one man only and especially wanting to feel the cum inside him. He willingly let me buttfuck him, pussy fuck him, eat his pussy and he started regularly letting me shoot my cum in his mouth and readily swallow all. He told me about his encounters, and then I found out an encounter with two drunk men that turned into rape rather than sex. That is why he wanted to be with me only. I told him about Trude, eventually he got over the jealousy and through constant talking about it, and pushing his boundaries, I got the two of them together. I even got to see Trude, fuck Dan in all holes, and then Dan spread my butt for Trude to fuck for my first time.
That was over two years ago now, I really miss those times. I did have those unique experiences, I don’t think too many others have been able to have. My current girlfriend is a cis woman, and actually can cum from getting buttfucked. I’m in heaven.
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