Jesse and Me By Trace Archer
There I was, queening the fuck out every night when it finally happened. I was sixteen years old and I had become a regular at a local coffee shop called Javasphere. Even though I was (and still am) a butch, at the time I didn't know that gay men could be anything but Jack from Will and Grace.
To be fair, even then I was too butch to really enjoy being a femme and I would fall into occasional "lapses" of acting like what I would eventually realize is my true self - a guy. That's the mood I was in when I finally got laid for the first time.
I can't honestly remember the name of the guy who I had sex with my first time. I had been trying so hard to lose my virginity for so long that that night I just picked one that would do what I wanted him to do. I'll call him Jesse.
Jesse was a bisexual guy that I had met before at Javasphere. He was probably about three or four years older than me. About five foot ten with curly red hair and the complexion of a teenage boy, he wasn't really the best looking guy ever, but he was okay. I knew he was interested. He never made any pretense about wanting to get in my pants. I, however, wasn't interested in him. He one of those dirty, stinky, pagan guys who might have been cute if he had ever bothered to take a shower or cut his hair. Don't get me wrong. He was good enough in a pinch... and I was in a pinch. I needed my cherry gone!
I propositioned him at the coffee house. I told him that I wanted to lose my virginity and I needed a ride home, and that if he'd supply the second then I'd let him have the first. He literally jumped at the chance. No, literally.
So we're on our way back to my parent's place about fifteen minutes away and I pull his cock out of his (black) jeans. I'd never sucked a cock before and I wanted to see what all the fuss was about. I stroked him until he got hard -- that is to say I pulled his six inch cock out and ran my hand over it once -- and began to give him road head. He wasn't trimmed and I must have flossed more that night with his red pubes than I did for the next year combined. He moaned and groaned all the way back to my place.
Once we got to my parent's apartment building he stopped. We both knew that road head wasn't the best I was going to do that night, but since we had nowhere better to be he was at rather a loss for what to do next. I told Jesse that we would be heading to the dugout of the baseball diamond behind my house where we would continue our tryst.
We walked back to the dugout in the very cool October air. It was late and the sun had set hours ago, so what was left of the heat of the day had already dissipated. I knew that we'd have to keep most of our clothes on to make this work. When we got back to the baseball diamond, I pushed him down onto the bench and we kissed for a few moments. I wanted to say that I'd kissed a guy, I pushed up his shirt and played with his nipples for just a moment, and I resumed sucking his cock.
As I said before, Jesse wasn't the cleanest guy ever and he smelled pungently of body odor. I wouldn't be surprised if he hadn't showered that day. I'd be even more surprised if he owned a stick of deodorant. Even though I wished at the time that he had been clean, in retrospect this was probably the beginning of my love affair with the scents of a man.
After sucking his cock for a few moments, he told me that he wanted to suck mine. I stood up and undid my pants so that he had access to my cock. He began sucking my eight inch dick greedily. Like I said before, I wasn't really into Jesse; he was just the guy that I was condescending to let take my virginity. Needless to say, I didn't want to look at him any more than I had to, so after I let him suck on my cock for a few minutes (he wasn't very good, though he moaned and groaned and praised the hell out of the job I did on him) I told him to fuck me.
"I don't have anything to lube my cock with," was his response. I didn't care. I just wanted to get this over with. Not that I wasn't turned on at some level. My sexual side was being allowed to surface, after all. It was more that I had done everything else (all the basics anyway) and wanted to go all the way. I sucked his cock for a moment longer to lube his cock with my spit; I undid my pants, and slid them down enough to expose my virgin-pink asshole to him. I got down on all fours and told him to "do it."
Jesse spat on my asshole and began to push his cock into me. In all seriousness, it didn't hurt nearly as bad as I was expecting. While it didn't feel nearly as good as I was later to learn that ass-fucking can feel, it didn't feel bad, either. It just felt full. Jesse pushed his cock into me and began to pump, slowly at first, but then as I began to push my ass back onto him he sped up.
Even with my nose at the other end of my body from Jesse, I could still smell the scent of his day old body-odor as he pumped into my virgin asshole. He began grunting and panting as he neared his orgasm. I was futilely stroking my own dick, but the sensation in my ass was so new that I couldn't concentrate on my own pleasure.
Soon enough, he told me that he was getting close and asked me where I wanted it.
"Just shoot it up my ass," I told him. I didn't want any mess to clean up, and besides, that's what a good fag does. It's too bad that since then, I've learned better. I'd rather take it that way every time. Either way, it was my first time and I was naive enough to believe that it was safe -- lucky for me, that one time, it was.
Jesse grunted as he unloaded up my previously virgin hole. He took my cherry and planted the flag that would let all the other guys know that I was now, officially, open for business. We stood and made out for a moment longer before we hiked up our pants and walked back to his car.
Jesse began making some comments that I can't specifically remember about how he was some kind of super-stud and how he had just "taken" me and all that other macho shit. I knocked him right off that high horse.
"I brought you here. I told you to do it. And I'm the one who took it," I told him, "If anyone is the stud here, it's me." He agreed. Indeed, what else could he do? It truly had been me doing all the hard work.
Jesse and I smoked a cigarette (a filthy habit that I have since quit twice) and then I told him that I would be going in. We made out again for a moment -- I think he was more into the whole event than me -- and I went in.
I was sure that my parents would be able to smell the sex on me. Jesse was pretty pungent, after all, but they never said anything. I grabbed a towel and went to shower off. I stroked myself off in the shower and thought "come hell or high water it's done now: I've lost my virginity." My ass had a satisfied burning as I finally pumped out my load. I hadn't been into Jesse, per se, but I was truly a cocksucker now and no one could take that away from me.
I pushed out one more load that night, thinking about what had happened. I wasn't into Jesse then, but now, nine years later, I'm grateful for what we did. That night might not have been the most romantic or perfect, but it was mine. I got to do everything that a gay man needs to know how to do. I got to learn with someone at least as naive as me, and, though I hadn't gotten off with him, he was nice enough to make sure that I enjoyed myself. And I did enjoy myself.
I'm twenty-five years old now and I haven't thought about that night in a long time. I wonder where Jesse is now. I wonder if he "grew out" of his "bisexual phase" as so many guys claim that they do. I wonder if he ever got fucked himself. But most of all, I wonder if he remembers that night and if it was as special for him as it has turned out to be for me.
This is my first submission to Nifty. It is an accurate portrayal, as near as I can remember, of my first time. I've been an avid reader for some time and have decided that I'm ready to finally post some of my own work. Please feel encouraged to comment. I respond well to criticism if it has a point and is not simply negative for negativity's sake. I would truly love to hear what you think. You can contact me at: trace.archer@gmail.com
Happy reading guys! Trace