How I lost my virginity with Mary [MF]

Kinda long. All participants 18+. Names changed to protect the guilty. This happened sometime in the 90s.

I didn’t lose my virginity until I was 18 and in college. I had a few girlfriends and I wanted to have sex, but I was scared to ask them because at the time I thought women didn’t want to have sex. I’ve never been good at reading signals from women (or men), and I’ve always been really satisfied pleasing myself, so I guess I just never pushed it. Once I realized how wrong I was, I began to understand why women didn’t stay with me as long as I wanted to stay with them.

I met Mary during my freshman year. She was musician student and a volleyball player, and super cute and flirtatious. We would joke with each other and sometimes hang out in when we were in a larger group, but we weren’t that close. I knew that she wasn’t a virgin because my buddy (and roommate) Alex had hooked up with her once after a party, but they weren’t dating.