I (M27) lost my virginity to a much more experienced 20 year old and I think it rewired my brain

NSFW

To set the scene I had one girlfriend before aged 21 but we were never able to go the whole way. We masturbated each other and I went down on her - but never the other way around. When I tried to penetrate her were both anxious as fuck, she would tense up, I would go limp and then we would give up. We broke up after a year, I had told myself since my teens I wanted my first time to be with another virgin so I insisted to myself and anyone who asked that we lost our virginity together.

Fast forward to 27, and still painfully virginal now figured we probably weren’t evenly matched after all. The next time we met she had invited me to her house. She was still living with her parents but they were both out. I arrived and we went upstairs to watch a movie. Within minutes of the movie starting she was on top of me, kissing me. Her shirt came off and I tried to fondle her breasts. She unzipped my jeans, released my penis and started sucking on it. It felt amazing but due to nerves I couldn’t get hard. She asked me if I wanted to fuck and I said yes. All the clothes came off, she threw me a condom and any doubt about this not being her first time was gone. I managed to get the condom on but still couldn’t get hard enough. She got on top of me and tried to lower herself onto my penis but each time she tried it just flopped to the side. After a few minutes despite this I came and we stopped. She was very kind about it and assured me she thought it was in. I went home thinking I had blown it but I got another chance.

This time she came to my apartment. I tried fingering her on my bed, between her moans and a handjob I was able to get hard and penetrate her in missionary position. It went on only a couple of minutes and I still couldn’t cum but it felt like a success. I cherished that feeling of finally being inside someone though I suspect the noises she made were fake for my benefit. Third time started similar except she asked me to eat her out. I did so gladly and again got hard from her moans. This time after penetrating I was able to cum, perhaps quicker than I would have liked but E was pleased. When we talked later I found out she wasn’t even close to a virgin, her count was over 30. She was cool about my lack of experience, said she felt powerful and enjoyed seeing me experience things for the first time. If E didn’t judge my inexperience how could I judge her experience?

I did for a while wonder how I felt about this. The first vagina of a girl I had entered had seen a lot of penises before mine - this was nothing like I told myself it would be. On the other had I had lost my virginity to someone who had been patient and never judged me. It was surely not the most thrilling sex E had had but she seemed to have enjoyed making me feel good about myself. We split up after about 6 months and I haven’t seen her since. Despite my feelings when younger though I think this was as good as the situation could be. On the wholesome side I liked that I had lost it to someone who made me feel safe and respected and gave me confidence for several more relationships in the future. On the kinky side I love the imbalance… A much younger woman had this power over me and had made me the vulnerable one. I found it confusingly sexy thar she shared what was a huge moment in my life was a routine moment for her. I live hundreds of miles away now but I love that this girl will always carry my virginity around with her.

Posted Aug 5, 2025, 10:03 PM UTC

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