A few of my different "firsts"...
I my first time ever fooling around in any extent with another guy was around 2.5 years ago when I was 23. My feelings of attraction to men had only surfaced a few months prior and while I thought it may be a phase, the feelings weren't going away so I decided that it was best while young and single to experiment a bit, rather than finding myself older and married to a woman with this bit of regret and curiosity in my head about being with another man (cheating is not an option for me), so I gave myself permission to explore a bit. After a few months of misfires and a lot of uncertainty and confusion about how to even go about doing such a thing, I met up with a man from craig's list for my first gay experience. I was more nervous than I could ever remember being. I was practically shaking. My stomach was queasy and I was just alternately petrified and excited. We met up, made out, felt each other up and gave each other head. It was my first time feeling another man's body, kissing another man or having a prolonged hug with one even. It was my first time seeing another man's dick. After it was over, knowing it was my first time, he asked me if I felt weird. I told him "strangely, no". I was really surprised that I wasn't as freaked out as I thought I'd be. After I left, it was very matter of fact. It did sort of feel odd though walking around that day, at the store or at home and just thinking that only a few hours ago, another man's dick was in my mouth. I felt relieved at having done it, at having finally after months of curiosity had this experience and at the time, thought I was done with it. My thirst had been quenched and my curiosity satisfied. Then however, I decided to meet up again with him, thinking that it would be a better experience the second time as my nerves would be far less. I did, and was again sort of satisfied for another few weeks before the desire came back again. Long story short, I'm still "experimenting", something that I thought back then would would be complete after one experience.
My first time having anal sex with another guy, as a top, was several months after the above experiences and with the same guy. In between my first hook-ups with him and this one, I had hooked up with I believe three other guys. Two of the experiences were horrible and I was sort of convinced that I was "off" men and really done, when another guy sort of fell into my lap and I found myself enjoying my time with him and my curiosity reignited. I got back in contact with the first guy and we met up. I'm not one to have anal sex with strangers; and not that he was a good friend or anything, but in having met up with him before, I felt a certain level of comfort with him. I decided that if I'm gonna really experiment with men, I should try anal sex and he was willing to be my first. I had never had anal sex with anyone, male or female before. I was sort of clueless as to what to do and I remember I actually came on here lurking and looking for tips beforehand. It was very basic when we got around to it. He slipped a condom and some lube on me and got on all fours and we did it doggystyle. As I was doing it, glancing down and seeing an ass, a man's ass bouncing up and down on my cock, I just couldn't quite believe that this was happening, that I was in this situation. When it was done with, he said he was impressed for an anal sex virgin that I lasted as long as I did. Looking back on it, I am too, since as i've posted in later threads, since then I've had a very difficult time getting hard enough to penetrate with anal sex. After this experience, I thought that I had reached sort of another level of "gayness" so to speak. This was no longer a one or two time "experiment". I had now been fooling around for months and had done so with a few guys and had now had anal sex with one. It became harder and harder to deny that this was just experimenting. To this day however, I have only had anal sex a handful of times, all with this same guy with me on top. We had a good long fuck buddy relationship but I'm pretty sure that's come to an end. I haven't had anal sex with him or anyone, with me on top, in well over a year.
My final "first" was my first time being a bottom. This happened only around two months ago. A different guy I had met on craig's list a few months before. We had met up a few times and got along really well in addition to being physically drawn to one another. Were circumstances different, I actually would've entertained the notion of dating him, something that I up until that point, had no interest in ever doing with another man. The bottoming was sort of spontaneous. He recommended it while we were in the middle of fooling around and I agreed. I was extremely nervous since his dick was so large and I had never had anything up my ass minus a finger, and even THAT hurt. He used a lot of lube and went very slow and was gentle and responsive to me when I winced or told him to hang on. While it was going on, I wasn't giving it much thought that I was a bottom but rather trying to just concentrate on not being in pain if that makes any sense. The experience was okay, pleasureable in a few random spurts and with a mind-blowing orgasm, but as a whole, painful and not too pleasureable. After it was done, I remember just being shocked that I had fit such a large object in my ass. I half wanted to look at my asshole but I was afraid to. Afterwards, in the days afterward, I felt really strange. REALLY strange. Physically, I was sore for a few days which I guess was to be expected given the size of his dick and my anal virginity, but had me freaked out for a bit. Emotionally and mentally, I felt odd too. Part of me was happy at having completed sort of the last "first" and having experienced all that I could with another man. The other part of me was incredibly disappointed and angry at myself for it being so spontaneous. I had thought that if I'd ever give up my ass, it would be well-planned, I'd have gotten more use to anal play, and I would've been with a partner for a long time whereas none of this held true for this situations. These feelings of doubt and guilt intensified when I didn't hear from him for awhile afterwards. I was really hard on myself. I felt used and disgusting, and was kicking myself for being an idiot. I regretted doing it. That was over two months ago. I still talk with the guy but we have yet to meet up and he gave an explanation to his vanishing and I sort of came clean about my feelings of disappointment and anger at the situation and he understood. It was the first time I felt any sort of emotional attachment to a person or had an emotional response to sex. So where it stands now, do I regret bottoming? I'm not sure. I'm not a natural bottom and don't see myself doing it again, so I guess in that respect it was good to have of done it, but I do partially regret the timing of it.
Lately, I've felt my curiosity about men and sex with them supremely satisfied. I feel like I've moved on from one phase into another. As I stated in another thread, there was a sort of slut phase that I went through and now I'm at the other end of it. I feel sort of like sexually I've done it all. I don't know what form my "gay life" will take. I know that I'm no longer as hard up and perma-horny as I once was. Now being sexually fulfilled, perhaps it's time to have other firsts like the first date and the first relationship, or conversely, perhaps my attraction in men will diminish as there is no longer the exotic allure there. I'm not sure what form my sexuality will take in the coming years. It sure does like to switch it up and keep me on my toes though.
