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Story When were you the closest to having sex?

When I was around 18 I lived with my brother (let's call him Hank) and his girlfriend (let's call her Jessica) for a few months. They had been together for a couple of years but their relationship was deteriorating at the moment when I joined them. Jessica was flirting with other men and generally acting like a bitch towards Hank. Maybe my presence was adding fuel to the fire? I'm sure Jessica was disgusted by me and my awkwardness, and didn't want my ugly presence around her. Maybe she was disillusioned with Hank when she learned he has dysgenic trash like me for a brother. Anyway, after a few months of me living with them, they finally officially broke up. Hank and me moved out to a different place, but their car still belonged to the both of them, so they shared it and Hank let me use it sometimes. One day I was finally moving out to a different town and I needed a lift to the train station but Hank was away. So the plan was: I take their car to Jessica's place and Jessica drives me to the train station. I didn't want to miss the train, so I departed a good hour earlier. When I arrived at Jessica's place, she invited me in and offered to cut my hair. I was just as confused by this random offer as you and I tried to refuse at first, but she really insisted on cutting my hair. So I agreed, then it hit me. I had to take my shirt off. I was really meek and not assertive at all back then, so I didn't back out of it, I just thought well whatever, this wouldn't be the first time she'd see my bare chest (beach and stuff). So she cut my hair and told me to go take a shower. Then I finally realized what was really going on. Jessica had set up the context for revenge sex with me. Or maybe she was feeling so trashy and so hungry for cock that she'd consider even someone like me? I don't know, women are weird. But I was a horny 18 year old and she was kinda hot, so I actually wanted to do it. But I had absolutely no social skills so I didn't know how to handle that situation. There were moments of silence when Jessica waited for me to say something, but my mind was empty. So I took the shower, she gave me a lift, and that's the end of the story. Now that I think about it, the whole situation feels creepy and disgusting. She wanted to use me as a means to her plot. It's probably for the best that nothing happened.
Never in my whole Life
When I was around 18 I lived with my brother (let's call him Hank) and his girlfriend (let's call her Jessica) for a few months. They had been together for a couple of years but their relationship was deteriorating at the moment when I joined them. Jessica was flirting with other men and generally acting like a bitch towards Hank. Maybe my presence was adding fuel to the fire? I'm sure Jessica was disgusted by me and my awkwardness, and didn't want my ugly presence around her. Maybe she was disillusioned with Hank when she learned he has dysgenic trash like me for a brother. Anyway, after a few months of me living with them, they finally officially broke up. Hank and me moved out to a different place, but their car still belonged to the both of them, so they shared it and Hank let me use it sometimes. One day I was finally moving out to a different town and I needed a lift to the train station but Hank was away. So the plan was: I take their car to Jessica's place and Jessica drives me to the train station. I didn't want to miss the train, so I departed a good hour earlier. When I arrived at Jessica's place, she invited me in and offered to cut my hair. I was just as confused by this random offer as you and I tried to refuse at first, but she really insisted on cutting my hair. So I agreed, then it hit me. I had to take my shirt off. I was really meek and not assertive at all back then, so I didn't back out of it, I just thought well whatever, this wouldn't be the first time she'd see my bare chest (beach and stuff). So she cut my hair and told me to go take a shower. Then I finally realized what was really going on. Jessica had set up the context for revenge sex with me. Or maybe she was feeling so trashy and so hungry for cock that she'd consider even someone like me? I don't know, women are weird. But I was a horny 18 year old and she was kinda hot, so I actually wanted to do it. But I had absolutely no social skills so I didn't know how to handle that situation. There were moments of silence when Jessica waited for me to say something, but my mind was empty. So I took the shower, she gave me a lift, and that's the end of the story. Now that I think about it, the whole situation feels creepy and disgusting. She wanted to use me as a means to her plot. It's probably for the best that nothing happened.
Never
 

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