Personal Sexual History - I

I suppose that I must have had some very early sexual experiences, but I don't remember them. When I was a pre-pubescent boy, hanging out with other nine year-olds in pup tents, when they got naked and cornholed each other (as happened, but infrequently), I always stood by and watched. There was a boy a few years older than we were who had developed, and he sometimes encouraged my friends to skinny dip in his pool, and the skinny dipping often led to some level of fondling, but, again, he never approached me. And, frankly, I don't remember anything more than some mild fascination in these activities. I don't remember any arousal.
I think I must have been thirteen or fourteen when I started having wet dreams. I was a late bloomer. I hardly ever played with myself, let alone full-on masturbation.

My best friend B. (who, years earlier had cornholed and gotten cornholed) was two years younger than I, but we were about the same developmentally, so our hormones were running at the same time. One weekend night, we were out camping, in the woods behind my house, and we were playing cards. At some point, I got bored and brave enough to suggest that we play strip poker. He agreed.

In the past, I've always thought of myself as the sexual instigator in my interactions with B. It's only recently occurred to me how readily he agreed to most of what I wanted to do. Maybe I was always just fifteen minutes ahead of him in suggesting things. It would be interesting to find out, and he probably still lives in the area, but I haven't spoken to him in probably twenty years, and I'd guess he's married with kids of his own now. Tracking him down to talk about this would be beyond awkward and would tell me nothing I really need to know.

Anyway, the poker game went on for a while until one of us (him, I think) was naked, and once that happened, the price of losing a round went from shedding a piece of clothing to performing a dare. At first, they were simple dares, like running out of the tent naked. By the time they got more, well, daring, I was out of my clothes as well. The dares proceeded to touching ourselves, and, eventually, to touching each other. I think the way I put it was, "let's turn out the lights and play with each other." After a minute or so of that, we played another hand, which he won, and he issued the same dare.

It would be generous to call our fumblings inept, but, really, when you're thirteen or fourteen, it doesn't take a great deal of skill to generate a great deal of pleasure. But we had soon exhausted our experience, and the evening ended without either of us ejaculating. I think there was probably some awkwardness the next morning, but I don't really recall. In any case, it can't have been too severe since we continued to hang out with each other all the time.

The next few times we managed to be alone together in a safe space, we continued to play, these times without the pretense of strip poker. We'd just get naked and touch each other. I think that I must have been the first one to take his cock in my mouth, but he always reciprocated. He was definitely the first one to cum.

His first ejaculation is something that will likely be imprinted on my brain until I die. We had been fooling around in his bedroom, and he was lying on his back, on his bed. I had started to suck on his cockhead, and I'd managed to keep going for longer than on the previous few occasions. I don't think he was making much noise, and I was getting tired of sucking on him, even though I didn't have any particular outcome in mind. The very moment I pulled my mouth off his penis, it was as if someone had turned on a faucet. He didn't spurt or shoot, but a thick stream of semen started to flow out of his cock, and it just didn't stop. I don't think that I've ever seen a bigger load in my life. Or another one that flowed in the same way. River of cum.

Because of the timing, I assumed that B. had cum because I'd stopped sucking on him. Sort of like taking my mouth off removed a cork. He assured me that the timing was merely coincidence, but I had no experience of my own to go by.

A week or two later, we were at my house, late one night. My bedroom was downstairs, and the rest of the family slept upstairs, so it was convenient, though we were out in the family room, adjacent to my bedroom. It was during the winter, and we'd been out playing in the snow earlier, and I was wearing sweatpants. We started playing around again, and I was propped up on my elbows, with my sweatpants around my thighs. We'd started out with fondling and jerking off, but just then, B. was sucking on my cock, and it started to feel different. Different good, different great. I started to feel an unfamiliar pressure building behind my cock, and just when it got to feeling so good that I couldn't stand it but didn't want it to stop, I began to cum. The ejaculation wasn't as dramatic as B.'s had been, but it was awesome, of course. What first ejaculation isn't?

Up to that point, I had still never fully jerked myself off. But one night, I was taking a bath, and I started playing with myself. Not surprisingly, it felt good. I started using soap, and rubbing harder, and it felt better. I kept at it for a long time, and by the time I got around to ejaculating, I had rubbed my cockhead so raw that after the initial rush of the orgasm, the soapy water made me sting badly. The next day, my foreskin (I am circumcised, but the doctor who did it was not overly aggressive) was swollen to four times it's normal size. I remember thinking that the tip of my cock looked like a club on a playing card. I was scared, but only enough to wait for the swelling to go down. I was hooked, and my technique improved so that it was all pleasure and no pain. To this day, though, it takes a lot of effort for me to get myself off, and if I get carried away, I get sore.

B. and I continued to play regularly, when we got the chance, which was never often enough for me. He had some guilt about it and sometimes wanted to quit doing it, but then he'd always decide he liked it too much to give it up. I only wanted to be sure that we never got caught, which we never were, though there were one or two mildly close calls at his house. Over time, our play evolved into a fairly set pattern that involved each of us going down on the other (sequentially, not in a sixty-nine) and then lying down next to each other, head-to-foot, so that we could jerk each other off. Most of the time, he would cum first, but there were periods when I'd regularly be the first to shoot. I didn't like that as much. Neither of us had anything approaching a hair trigger, though, so sessions would regularly last the better part of an hour, start to finish.

We did experiment with other things. I tried kissing B. once or twice, but he wasn't having any of it. He thought it was wrong for two boys to kiss. He was more amenable to having his ass licked and licking my ass, and he didn't mind having his ass Vaselined and fucked if I was willing to do the same. I mostly remember being fucked as being painful and fucking as not as much fun as being sucked or jerked off. We didn't fuck more than a few times before settling back into the oral and manual routine. It worked pretty well for us.

We got older and things changed, of course. He was a jock, and I was a nerd, and since I was two years older than he, by the time he got to high school, we didn't hang out much. We were still friendly, though. I remember coming home once when he was a junior in high school, and we hung out and played tennis. We seemed to have forgotten entirely about sex, though, at least with each other. I wasn't having sex with anyone else, either. He was dating girls, but I doubt he was getting much.

I was home again once when I was probably twenty-one. He would have been nineteen. We hadn't seen each other in a year or two, and one afternoon my sister came home saying that she'd run into him, and he came with her. We hung out again and talked some more that evening. Then the next day neither of us had anything to do, so we got together for some tennis and talked into the evening. The same thing happened on the third day.

That night, it was late, and we were hanging out, and I scraped together my courage and said, "Do you want to fool around?" and B. said "Sure!" He excused himself to use the bathroom, and then we both went into my bedroom. It was pretty much status quo. We got undressed, got on the bed, got hard, fondled, and sucked. I asked him if he was up for getting fucked, and he said he was, so I got out the Vaseline, and we did that for a while, but it wasn't all that hot for either of us. He didn't try to fuck me. Eventually, we ended up on the floor, head-to-toe, stroking each other off. That worked.

After we'd both cum, I was suddenly a bit wistful. He said something like "that was fun," and I said something like "it's been a long time." Maybe it wasn't the reaction he was looking for, but in any case, he did have to work early the next day, and it was already very late. He left without either of us saying anything about talking or getting together again, and I had to get back to Boston a few days later. He didn't call or come back, and I didn't call him. I haven't seen him since.

I can't say that I really missed him. By that point, we had little in common and were mostly just a way for each other to pass the time. But of course I miss the sort of friendship you have with someone you knew from the ages of eight to eighteen. And the sort of sex you have when you first realize it's a possibility. Luckily, though, I got another shot at that when I was considerably older.


(See, that last line was a teaser for part II. But Part II may be a while coming since I still have to get through my "What I Did on My Summer Vacation" posts. Because I know that nobody wants to read about sex when they could be looking at pictures of wildflowers or tales of amusement park madness. Right?)