Where it happened: A friend's house
Langauge: English
Sex: Male
Rating: 5
Category: Straight
I lost my virginity to a high school friend’s mother. My friend was away at summer camp. I was doing yard work for the friend’s mother, I’ll call her Mrs. T, along with another friend, Greg. We were 15. When we were finished with the job, Mrs. T asked us to come in while she got the money to pay us. She asked us to follow her upstairs. We followed her upstairs to her bedroom. She was wearing a light cotton robe and she opened it, revealing that she was naked underneath. She said she wanted to give us a treat because we’d worked so hard. It was clear that she was propositioning us. She told us we’d have to shower first since we were hot and sweaty and dirty. I felt weird about it since she was my friend’s mother, but Greg was very eager and I didn’t want him to question my virility. So we went into the bathroom and took turns showering. Perhaps the most uncomfortable aspect was taking my clothes off in front of Greg. I was all the more embarassed when it turned out he was a lot more generously endowed than I was. But I felt there was no going back now. Greg took his shower first, and when I had taken mine and dried myself and gone back to Mrs. T’s bedroom, Greg was engaging in missionary-style intercourse with her. The sight of them disturbed me somehow due to the age difference, but it also aroused me greatly. Greg finished quickly and Mrs. T beckoned to me to take his place. I did so, and she guided me into her. I remember being surprised that her vagina felt so hot and wet. Also she had not provided condoms, so Greg’s semen was contributing to the slickness, which also creeped me out somewhat. I began to thrust rhythmically and soon found a comfortable posture and rhythm. Oddly enough, apart from the sensation of heat and slipperiness I wasn’t feeling a great deal, just slipping around somewhat wildly. She seemed to like my frenetic motion. We fucked like this for a relatively long time, several minutes longer than Greg had lasted, which made me feel more confident. Finally I came, with a sharp and vivid orgasm. Greg watched us the whole time. I don’t believe Mrs. T came but she was happy. She made small talk about the yard for a few minutes, then suggested that we leave. We pulled our clothes back on and she gave us the cash for the yard work. It felt like payment for prostitution, however–kind of a sexy impression for a couple of 15-year-old studs. I never did any more work for Mrs. T after that, although I could have, because I felt like it would be pushing my luck to have sex with her twice. What if my friend found out–her son? Greg went back, though. I didn’t have sex again until I got a girlfriend my own age, two years later.
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