After a night out I regretfully went home with a friends sister. One of those think with your dick now, think with your head later moments. She wasn’t even attractive. Not ugly but stick thin and no tits and a very plain face. Back at her place we got into it. The making out was fine but she went to go down on me and inserted my cock into her mouth and sort of sucked on it like a pacifier. I thought she’d work up to other techniques but didn’t. Just kept sucking it like she was sucking her thumb. Then I laid her on the bed and stuck it in missionary and fucked her a while and she was so unresponsive and made no sound. It was awkward so I asked her to get on top but she said no just keep going. I eventually came and we fell asleep. The next morning as I was leaving she said how she wanted this for so long and was looking forward to seeing where it goes. I had to let her down that it was a one time thing. She cried. Her brother and I drifted apart basically because I was avoiding her. So that’s probably the worst sex I’ve had.
But I can’t claim to be perfect. There was a night I was able to land a gorgeous girl at a bar when I was in my early 20s. I’d only had sex with a previous girlfriend and didn’t really have any skills at it. This girl was so out of my league I couldn’t believe we were going to fuck. Well she straddled me and slid my cock in and between my hands on her ass, her tits in my face and her pussy enveloping my cock it was all too much and after maybe twenty seconds I had to push her off of me as I came. And it all happened so fast I couldn’t maneuver myself so I just sat there jerking cum onto my stomach. She wasn’t comforting at all about it like a girl typically would be. She was disappointed and basically asked me to leave. Humiliating.
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