My first time was actually fairly recent, about 6 months ago, more or less. I was 19, he said he was 27, but he was really 34. I didn't really care about his age though, maybe the lying would have bothered me if he had meant more to me. It was only our second time hanging out. He had asked me over to watch a movie and have drinks that night, which my friends all explained meant sex. I hadn't had much experience with the opposite sex up until this point, so I was a bit naive going into it. But I decided that either way I was ok with whatever was going to happen. I wanted to get it over with, and I had always had a thing for older men, so I figured why not.
He didn't really push anything at first. We just played a drinking game and listened to music, I got a bit tipsy of course. Then came time for the movie. We sat down on his rather uncomfortable couch, and as the movie started he remarked how he was tired and asked if I wanted to lay down next to him. At the time I knew exactly what this meant, but I went along with it. I wasn't even really that attracted to him. I mean, he was attractive but not in the I want to jump your bones and bang you sense. I think it was just because of his age. But anyway, I'm laying down next to him and he starts making out with me, and soon his hands are down my pants and I'm like alright, so this is really happening then. He asks me if I want to go to the bedroom and it's then that I mention that I'm a virgin, and he says it's ok and that we don't have to do anything I don't want to do. So he carries me to the bedroom, undresses me, goes down on me, and then I ask him to grab a condom. Then we have sex for what seems like forever. It hurts of course, and the fact that I'm really not that into it doesn't help at all. At one point he even tries anal, which was painful of course, but for some reason I didn't tell him to stop. I think it was a mixture of the alcohol and the fact that he was so much older that kept me silent. And plus now I could tell my friends that not only had I lost my virginity but I'd also tried anal in the same night, ha. So he then finishes and we lay there for a while. I didn't really feel much of anything afterwards. I guess I was just happy to have gotten it over with. Then I got up and got dressed and he drove me home.
We had sex a few more times after that, but each of those experiences ended up being pretty much the same as the first. I think at the time I was just desperate for the attention he was giving me. I wanted to believe that he really cared about me, but I doubt he ever did. At first I was impressed by his clean apartment and his nice things, things that no guys my age could afford to have. He also treated me differently than guys my age did, but I understand now that it doesn't really mean he liked me anymore than they did. I don't know if I really regret it or not though. I definitely learned a lot from it, and it completely got me over my interest in older men. Now when I think about the whole situation it leaves me feeling a bit sick, hope I never run into him again.