-
Dating Disasters
-
Straight Male / 45
My First Time
We were late teens (19-ish), just out of school. Both virgins who had only met a few days ago randomly on the bus. She was a bigger girl—actually cute—but had some body image and self-esteem issues. She also had a great rack I could have played with all day long. I was average or just a bit over, but super shy and socially awkward. She thought I was maybe the catch of a lifetime, but I was so shy that if she hadn't hit on me, it never would have happened.
We had no friends in common, and she'd just been hanging at my place—making out, stroking me, and letting me play with her huge tits. The only thing that pissed me off was that she refused oral, both giving and receiving. I don't know why. Since it was summer and no one was home, and we both didn’t have a lot of friends, I dry-humped her, fondled her, and got jacked off for almost two days straight but was too shy to ask to fuck her.
Finally, at the end of the second day, she was like, "Buy some condoms before I come over tomorrow," and I thought I was gonna die of shock. But you bet I did, and I had them in the open when she got there.
It was painful for her and just okay for me. Mish. I banged her good—I had seen enough porn. I was finally in a real pussy, so I was gonna fuck it good. It was wet, felt great being in it, and since she was a virgin, it was hard getting in. But once I was in, she didn’t have as much grip as I thought. I pounded it as best as I could, but I couldn’t cum because she was hurting too much. While it felt good to me, she was near tears and totally suffered through it for me. I think this is where my sadist kink came from, lol.
She kept telling me to keep going because she had a crush on me and wanted the sex to keep me. I felt bad, and not knowing what was wrong with her or why she was in so much pain, I worried I had really hurt her, so I stopped. That made her feel bad. Later (a few hours later), she got me off by letting me titty fuck her huge cans, and honestly, it was actually better than fucking her.
I fucked her a few more times that summer. She used sex to keep me interested, but it backfired because she never got better at it or even wanted to enjoy it. Let me be clear—I was no better at it than her, but she kept throwing it at me, wanting me to fuck her. She just wanted me to get what I needed as a carrot to keep me, so she lay there like a dead fish and duty-fucked me. Bad sex didn’t bond us. I got off, but not by much.
She came over less and less because I’d just fuck her, and we had nothing to talk about. The last time she came over, she didn’t want to fuck (likely on her period), and it was so awkward. I was an ass and said something like, "Maybe you shouldn’t come back if you’re not gonna let me fuck. This is awkward."
She, of course, was hurt, and I never saw her again.
I feel bad. I was an ass, but we were kids. I hope she had better boyfriends than me after that. I think of her sometimes but can’t even recall her name, lol. Sorry, whoever you were.
We had no friends in common, and she'd just been hanging at my place—making out, stroking me, and letting me play with her huge tits. The only thing that pissed me off was that she refused oral, both giving and receiving. I don't know why. Since it was summer and no one was home, and we both didn’t have a lot of friends, I dry-humped her, fondled her, and got jacked off for almost two days straight but was too shy to ask to fuck her.
Finally, at the end of the second day, she was like, "Buy some condoms before I come over tomorrow," and I thought I was gonna die of shock. But you bet I did, and I had them in the open when she got there.
It was painful for her and just okay for me. Mish. I banged her good—I had seen enough porn. I was finally in a real pussy, so I was gonna fuck it good. It was wet, felt great being in it, and since she was a virgin, it was hard getting in. But once I was in, she didn’t have as much grip as I thought. I pounded it as best as I could, but I couldn’t cum because she was hurting too much. While it felt good to me, she was near tears and totally suffered through it for me. I think this is where my sadist kink came from, lol.
She kept telling me to keep going because she had a crush on me and wanted the sex to keep me. I felt bad, and not knowing what was wrong with her or why she was in so much pain, I worried I had really hurt her, so I stopped. That made her feel bad. Later (a few hours later), she got me off by letting me titty fuck her huge cans, and honestly, it was actually better than fucking her.
I fucked her a few more times that summer. She used sex to keep me interested, but it backfired because she never got better at it or even wanted to enjoy it. Let me be clear—I was no better at it than her, but she kept throwing it at me, wanting me to fuck her. She just wanted me to get what I needed as a carrot to keep me, so she lay there like a dead fish and duty-fucked me. Bad sex didn’t bond us. I got off, but not by much.
She came over less and less because I’d just fuck her, and we had nothing to talk about. The last time she came over, she didn’t want to fuck (likely on her period), and it was so awkward. I was an ass and said something like, "Maybe you shouldn’t come back if you’re not gonna let me fuck. This is awkward."
She, of course, was hurt, and I never saw her again.
I feel bad. I was an ass, but we were kids. I hope she had better boyfriends than me after that. I think of her sometimes but can’t even recall her name, lol. Sorry, whoever you were.
