The One Where I Did Anal for the First Time [MF]

Admittedly, I’m an ass man. When I check out women, my first glance is almost always at their butts. Pretty much every woman I’ve ever been with has had a nice butt. Despite my dedication to the derrière, I’ve not had that much interest in anal.

This story takes place after my very first serious girlfriend and I broke up. We were the ones who lost our virginities together. We were going to get married. We were also young and dumb, but I digress. We’d talked about anal before. She was interested for a time. When we had sex, I would eat her ass. She said she really enjoyed it. Being young and inexperienced, though, I rushed into anal too fast. I wasn’t jamming my dick in her or anything, no. But I did stick my pinky in her ass one day, with no lube, and almost no build up. She yelled at me (rightfully so) and that was the end of sexy times for the day, and the end to our talks about anal.

The One Where I Took Her Virginity [MF]

This is gonna take a while to get to the sexy part. If you’re just interested in that, I’ll have a label in ALL CAPS RIGHT BEFORE IT STARTS.

In college, I worked at a toy store at the local mall. The job was boring but it paid for my food and alcohol for my junior and senior year.

I was the only guy in a store full of women. If someone needed help moving a display around the store, or they needed some tools that we didn’t have in the store, they called me. It was nice. I was like Hercules to these women.

Among them, two were married, two were engaged, and one had a boyfriend. Our boss was recently divorced and her mother, the assistant manager, was widowed. I’ve never been the type of person to knowingly go after someone who is in a relationship. With the pressure to make myself be desirable to them off, I actually made good friends with everyone.

Then Lynn was hired.