Years later, finally hooked up with my high school crush [MF]

There was this girl that I had a crush on all through high school but nothing ever happened. I was too shy with women to go for her at the time, and meanwhile she went through several boyfriends. She would often tell me about her escapades. I got a little jealous but always just acted like a “nice” guy hoping to get my chance without making a move. We hung out all the time but I was solidly in the friend zone. After high school we gradually fell out of touch for a few years.

Fast forward several years to when we are both in our mid 20s. She is just finishing music school and has her final recital at the same school I went to. I attended the concert, and afterwards, as we hadn’t seen each other for years, she asks if I want to hang out. We go back to my place – still living at my mom’s lol.

Just to describe her, she is medium height, fit looking, thin but curvy, medium length black hair, amazing natural tits, and the cutest face you have ever seen. Always done up and looking particularly stunning this evening in a beautiful red dress.

The night I lost my virginity and came down her throat 3 times. [MF]

Like most 20 year old virgins, I was absolutely desperate to get laid. It’s not that I didn’t want to earlier, I was just really terrible with girls, mainly because I was incapable being forward. I was perfectly social, and had lots of friends. I just wasn’t getting any.

Anyways, at this time there was a group of friends I was hanging out with regularly. At some point, one of the guys in the group started seeing a girl that I’ll call Kristin who started hanging out with the group. She was 19. She was cool, she partied and drank with us, and one night we were staying at this guy’s cabin a little bit out of town for the weekend. We were all getting hammered, and Kristin ended up making out with and eventually going to bed with another girl at the party. Sometime in the night (it is all hazy because of the alcohol) I somehow ended up making out with Kristin in the bathroom, and she told me she really wanted to fuck me, but she couldn’t because she was still with her boyfriend. “I want to but I can’t” is all I remember her saying. The rest of the night is basically a blur.