Where it happened: college
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Alison was my friend’s girlfriend first. At least that’s what he said. But he was probably just fucking her, because when I invited her to visit me at college she said yes.
I was eighteen, but I was still a virgin. I had almost fucked my first girlfriend, who I had been with for over a year including two summers, but that’s another story… Well, the short version is that we had a long distance relationship and were only together a lot over the summers. We did everything you can do except go all the way, and when she was about to go home at the end of the second summer she asked me to fuck her. But I didn’t have any condoms, so I said no. She went home and dumped me a month later, because she said she had fallen in love with another guy. I was so jealous. I still can’t get the image out of my mind of them fucking. I’m still jealous. If only I’d fucked her she would still remember me as her first. But now she probably doesn’t think of me at all.
Anyway, Alison came to visit, and though she was very nice and quite good looking I was nervous. It was clear we were going to go to bed together, but I was a virgin, and I knew she wasn’t. I wasn’t ashamed of being a virgin, not at all, and I told her. She said she was happy to teach me.
We undressed and got in bed together. I played with her body—I was experienced with that, and she got very wet. I was hard, and I lay on her, and she helped put me into her. That was itself an education, though it made perfect sense that a woman would know how to put me in her better than I would.
I started stimulating her, and myself, and it felt great, but because I was nervous about doing a good job I lost my erection.
I was embarrassed, though not devestated, but Alison was just so nice. She was really a wonderful first partner. She said, “That happens someteimes Matt. We can try again later.”
That she told me we could try again later relieved me. I knew my first time wasn’t over, and I could try again.
We went out to eat, and we talked. Before that I hadn’t talked to her much. I’d only been with her when my friend was around. As we talked we got to know each other, and I realized what a nice person Alison really was. After dinner we went back to my apartment and undressed again. Because we had gotten to know each other and developed an emotional connection I was relaxed. She started to put me in her, and I said I’d do it. We pretended to argue about who was going to put me in, and we laughed about it.
She had an orgasm first, and that was another learning experience, because that’s the first time I realized that if I had come first she wouldn’t have been able to. Luckily that’s never been a problem for me, and it kind of goes along with losing my erection. I’m slow to arouse and last a long time, which can itself be a problem, for if I wait too long, like much over a half hour, my orgasms aren’t as strong. For me, it’s all in the timing.
I didn’t know about that then, except that I learned it was good not come first, which seems obvious but wasn’t at the time.
We stayed together for three days that weekend and had sex again and again.
When my friend found out he got pissed, but as I said, according to Alison she had never been his girlfriend. I still think of her fondly. Wonder where she is now. Wouldn’t mind doing it with her again. What with all my experience over the years… LOL
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