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I finally figured out my sexuality, and started feeling comfortable with it at perhaps the most annoying time - JUST as I graduated from college. So after spending four years in a group of liberal, try-stuff-out people my own age...I ended up living back with my parents away from nearly everybody I knew.
Not too long afterwards, I took a job in a nowhere town. I was driving my way there in a 1973 VW Beetle. Just before I crossed California into Arizona, I picked up a hitchhiker. He was kind of beefy, nice, but not the swiftest ship in the armada. His name was Mike, and he was hitchhiking his way to Houston. (I think he told me why, but I've since forgotten.) We got to chatting, and he asked me if I had a girlfriend. I mulled over what to say - after all, although I'm six feet tall and fairly stocky, I don't know if I could've taken this guy in a fight if things went violent. But I decided to go for it, and I told him I was gay. He got really excited, and said that he was gay, too. Almost immediately afterwards, he asked if I wanted to have sex. (Although I believe his exact words were "you wanna, you know, do it?") I told him I was interested, but it was a fair way until we could find a hotel or something. He suggested we just pull over and have sex.
I mulled it over. There was no way in hell we were going to have sex in a VW Beetle - there was simply no room. But the highway there was somewhat elevated, and you could sort of go "down" into what was like a ravine. I figured if we set up there, we could have sex out of view of the passing cars. So I pulled over, got a blanket out of the back seat, walked down to the ravine, and spread out the blanket. Then I looked back up at Mike, wondering if we were going to just start making out or what.
He was already naked.
Mike was the first guy I'd ever seen naked "in the flesh"...well, not counting glances in changing rooms and whatnot. And he honestly gave me a lot to live up to. He wasn't quite "(American) football player build", but he was in the ballpark. Not really fat or muscular, but somewhere in between. Mildly hairy. And his cock was fully hard, and headed towards nine inches long. (In fact, with Mike being my first, I got the impression that my cock was "smaller than average", since, you know, I figured all guys were like Mike.
That only lasted until my next sexual experience, though.)
I decided "in for a penny", and ditched my clothes too. Then he got on his knees on the blanket with me, and we started making out.
...it was pretty much at that moment that literally all doubts I may have had about my sexuality vanished. THIS was what I wanted to do - hell, it felt like this is what I was BORN to do. Get naked with guys and do stuff. It didn't matter that we were both fumbling around, not really knowing what we were doing. It felt AWESOME.
We made out for a while, then I tried giving him a blowjob. "Tried" because he was simply too damn big for my inexperienced mouth to do much with. I probably wasn't all that great, but he seemed to enjoy it. Then he tried giving me a blowjob...and he was REALLY bad at it. Seriously, you shouldn't have to say "watch the teeth" more than once...let alone FOUR times.
But I figured hey, learning experience for both of us, right?
During the blow job, he started moving his hands towards my ass. This worried me. We had no condoms, no lube, he was well-hung, he was kind of "bull in a china shop", and I was an anal virgin. There was NO way in hell that I was going to let him top me. : ) But I didn't really feel like announcing that. So I decided to simply steer things in another direction.
I pulled him off my cock, and sort of pulled him up so we were back facing each other. Then I started making out with him in earnest....and he responded in kind. This was significantly hotter than the blowjobs had been, and we just kept that up, with our hands all over each other's asses. I heard him sort of gasp, which led me to think he was headed for orgasm. So I sort of gasped back and started humping my cock against his.
His orgasm hit just a bit before mine. It was pretty messy, although I have no idea how much of the cum was his and how much was mine.
We lay panting there for a while, then pulled apart. We started chatting as I wiped the cum off of us with my T-shirt. (I had more shirts in the car.) We agreed that it wasn't at all what we were expecting, but it was still awesome.
We got back in the car, I put on a new T-shirt, and we went back on the road.
We had sex in a hotel that night, but honestly, he never got any better at the blowjobs. We stuck with making out. Which was fine, since we kept getting off that way.
The next day, I dropped him off when our roads were going to diverge. We said goodbye, and I never saw him again.
Sum-up.
My first time was not romantic. It was with a guy I had known for about half an hour, and whom I would not see again after that encounter. He was not great at it, and neither was I. It was almost textbook "meaningless sexual encounter".
But I have absolutely no regrets. I enjoyed myself. I started my "how to have sex with a man" education - at least, the lab section thereof.
I started learning lifelong lessons - "give non-verbal feedback, and be attuned it from your partner", "feel free to move on if something isn't working", "if you're both enjoying it, there's no wrong way to have sex". I no longer had to worry about if I'd ever have sex, and if I could "do it OK". And, perhaps most of all, I realized "this is something I want to do more. A LOT more."
Lex