My relation with male gay sex has always been... complicated. I started putting things in my anus at a rather young age (at beginning of puberty) I think before I first had an orgasm, and I really liked the feeling.
I tried to bottom with a guy I met at university, I admired him a lot, but I went too fast on his penis with my tight anus, and it was really painful. He first stroke our 2 penises one against the other, and I was not at ease. I was really ashamed to be with a guy, very stressed and had not much pleasure. He wrote me after that this first time for him too has sealed his desires for guys.
I tried several other times, but was very nerdy at that time - I only had one girlfriend at that time, and I was very immature. She thought I might be gay, which was an idea that seemed strange to me. I never really felt attracted to boys at that time, but loved the idea of gay fucking.
I met a gay boy, and we had sex a couple of times, in both directions, I guess it was one of the 2 times I managed to top, but we did not see each other for long - I was unable to communicate, too shy, and beside sex, I had no idea what to do with him. I found him really cute (I have always been into young Asian guys, and used to look like one myself at that age). Last time I saw him, he came to help me recover after I was victim of an attack, and I fucked him without a condom for the first time, which created a terrible fear for me, because AIDS was something I really feared at that time (mid 90). I got scared and I guess it's one of the reason we did not see each other.
The other reason is that my (older and only one) brother came out at that very time, and while I was wondering if I should do it too, I felt we would both be ridiculous if did. So I kept it for me, but I told to myself the same crappy childhood that we shared seemed to lead to the same consequences.
I then tried a few times again, with a huge difference between what I imagined and what I actually felt.
I met my wife after many years of therapy. I've really loved her, we got a boy, but now, 15 years later, I don't feel much pleasure penetrating anyone, to my great surprise because I have loved that so much... and I started appreciating bottoming for real, this time.
I told it to my wife, who told me she was not attracted to me anymore either, and that she cheated twice... we're still together, because we very much like each other, but I'd love to be fucked more often, which I don't allow myself because I don't want to hurt her or look like the real whore I can be 😃 . I don't really like the idea of telling my teenager that I'm probably gay.
I have a(n Asian) sexfriend who fucks me real good, but once a week at best, and I still can't reach orgasm from that only, I have to masturbate at the same time. I had a period where I became way more a sissy, buying pink T-shirts and female underwear, but it passed (but it'll come back) - it seems I have "gay crises" which then vanish, but I'm always game for anal sex. I kiss him, too, he's almost the first one I felt like kissing.
I'm really sorry not to be the one to my wife anymore, but I've changed gradually; I was far from thinking it'd end up this way. Sometimes I feel it's not really me, that it must be some kind of hormonal disorder or that there must be something... But still, I like male sex like this, and I'm looking for harder things now (with tons of fetishes inviting themselves in my sexual life).
But I really feel sorry I was unable to enjoy a crazy sexual life when I was that cute thin guy; now I'm way older, things are getting tough, because gay community is véry youth-centric. So many regrets... so much time lost... and I still lose lots of it 😢 .