Male, 18, Pennsylvania
It was 1966. I was eighteen, and it was the summer after my freshman year at college. I was the youngest person in my class all through school. I've just found out recently that I have and had ADD, though I don't think anyone knew what ADD was back then. Everybody just knew I was immature, impulsive, and socially way behind my peers. My sex education consisted of an excruciating ten-minute talk with my obviously very embarrassed father, who somehow thought talking about how dogs do it would convey to me the mechanics of human intercourse. He was quite a prude.
I'd had one girlfriend in high school. I was a senior and she was a sophomore and much more mature than I was. The furthest we had gone was kissing and a little breast-kneading through her sweater. In college I did manage to actually touch a girl's bare breasts, once. She wasn't a girlfriend — just someone I was set up with.
One of the guys in my ROTC unit was going to training that summer and got me the job that he had had for the previous three summers at a girls' camp in NH. I was to teach riflery and sailing. I knew I could handle the shooting, but I didn't have a clue about sailing. He told me the owner wouldn't let anyone on the water if the wind was blowing anyway, so I just needed to read up a little and I'd be fine.
It was my first job. I lasted three weeks and then got fired for kissing one of the campers. She was seventeen, and we were crushing big time. I caught a bus by the side of the road that took me to the closest town, where I caught one for New York City and then on to Philadelphia. From there I caught the train to my home town. The two-mile walk from the train station to my house was one of the longest of my life. I'd spent the whole night staring out the bus window, trying to figure out how to explain what happened to my parents. When I got there, I discovered that they were away for the weekend. It was a Saturday morning, and they wouldn't be back until Sunday night.
Adding this latest fiasco to the fact that I had managed to basically flunk out of college (they wanted me to go to summer school, which we couldn't afford), I was feeling like a complete failure. At loose ends, I called a guy I had grown up with. I called him a friend but he was really just someone who, once we reached puberty, would only spend time hanging out with me if he had nothing better to do.
He came over and talked me into raiding my parents' liquor supply. Then he called a girl he knew who was a "sure thing." Out of the goodness of his heart, he was going to help me lose my virginity. She was a bit older, perhaps twenty, and had been at a wedding that day so she'd already been drinking. He had a car. On the way to pick her up, we stopped to buy condoms and he made me go in alone to do it. I still don't know how I managed it.
She was actually rather attractive, very friendly, and more than a little drunk. We all sat in front while he drove to a secluded spot that he knew of. Once there we drank a little and he joked around with her. Then he told me to give them some privacy while he "warmed her up for me." I had already told him I didn't want to be the second guy and he had sworn he wouldn't "do her." So I went and smoked a cigarette and pretended everything was cool.
A little later he got out of the car and told me to go to it. She was already naked and seemed perfectly okay with it all. She helped me undress while we made out. I was surprised to feel how wet and hot it felt inside when I put my finger in her. I clumsily tried to go down on her (from some instinct I suppose), but being in a back seat made it all very difficult and awkward. Finally I managed to get the condom on and entered her. I'll never forget the feeling of heat that surrounded my cock and how overwhelming it was. I doubt I lasted more than thirty seconds.
I took the condom off and tossed it out the window, only to have my "friend" lean in from where he'd been lying on the trunk and make some crack about it joining the one that was already there. I took that to mean that he had in fact had sex with her despite his promise.
I joined the Marines a couple weeks later, a day before my notice to report for a draft physical arrived anyway. I saw her a couple times while home on leave after boot camp. We had sex again both times, but I'm sure they were equally unsatisfying for her. And I just felt bad about it all. Guilty about even doing it and frustrated that I didn't really know what I was doing and couldn't make it good for her. She was really very sweet, but I was so caught up in the whole "good girl/bad girl" thing that I never really thought of her as someone to be in a relationship with. I've always felt bad about that — not so much that I didn't get involved with her, if she'd even wanted that, but that I didn't treat her better, with more respect.
And that's the story. I still cringe a little when I think of it.