I (44/m) had a gf in college who insisted that I use a condom every time we had sex. I was a junior/senior in high school and my gf and her roommate were a few years older in college. They lived in an apartment together and I was there a lot.
They were best friends and I got to be good friends with the roommate since I spent so much time there. We drank a few nights a week like a lot of people during that phase of life. There were plenty of times when just the 3 of us would drink. One of those nights my gf said she was horny and wanted me to fuck her. I playfully said, “I will but only if I can hit it bare.”
We laughed, but it sparked a conversation and her roommate said, “wait, you mean you make him wear a condom?!” I said something like, “I know right!?”
Anyway, a couple of weeks later my gf left for class before I woke up. I was pleasantly surprised when I woke up to her roommate (totally naked) crawling into bed with me. She said she knew how fucked up this was, but she couldn’t stop thinking about me having to have sex with a condom all the time. She said she preferred it bare. As she was talking, her hand found its way through the sheets to my cock.
She didn’t ask. She didn’t hesitate. She wanted to fuck right then. She pulled the sheet off of me and threw her sexy leg over me, grabbed my hard cock and dropped herself down onto it. She rode me hard. She came even harder. It didn’t take long for me to finish inside of her because I was so used to using a condom and her bare, soaked pussy felt incredible.
We had sex many more times over the next several months until she finished her semester and moved away to another college. She’s the reason I’ve hated condoms ever since and very rarely used them after that gf.
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