Stories | 2016

This happened about 15 years ago when we were in our early 20s. My senior year of high school I moved to a new school and connected with a girl in my graphic arts class due to a shared interest in ska/swing music. She was my only friend that year even though I was cool with lots of people. She's white with short brown hair and bangs, skinny, killer ass and cute as a fucking button. We hooked up once and realized that relationship wasn't going to happen and we were better friends. We graduate, I moved away and lose contact for a couple years then reconnect later.

All right everyone, let me tell you about the time I lost my anal virginity. This happened just over 24 hours ago with my [22/F] boyfriend [29/M] of a few months. For some background, he has had anal sex before but I hadn't ever - only some light anal play, maybe a finger on occasion, that sort of thing. For some of the cute background on our relationship because I'm sappy and have an emotional approach towards sex, we've both said one of the main things that attracted us to the other is that we're both equally goofy and silly.