I was just getting ready for my third date with Kassandra, or Kass as everyone called her, and I was excited about the prospects of the evening. She lived about forty minutes away, but happened to be in my neighborhood that day visiting with a friend of hers, so when she was done hanging with her she had called me asking if I wanted to get dinner. I was loopy about this girl – she was smart and witty, she had a real affinity for literature and writing like I did, and whenever we talked time melted away and we ended up just picking each other’s brains for hours. That was mostly what our dates up to that point had been, bar one night where we shared a brief kiss. Kass had warned me when I first made my move that she was a shy person when it came to intimacy, and to make matters a bit more complicated, I had been dating another good friend of hers when we met at a Halloween party that previous October. Shortly after that the relationship had ended, and when my paths crossed paths with her again a few months later, I had made sure to clear things with my ex before I asked Kass out. My ex said she didn’t have a problem with it, but Kass still had some apprehension, not wanting to step on her friends toes and risk harming their friendship. This level of consideration only made me like her more.
Author: BoysbythePool1
[MF] I embarrassed the clerk at a novelty store, made it up to her with sex
This all happened about 5 years ago, when I was about 19 and working at a shitty retail job where I had made some close friends. It was around the holidays, and in my group of friends we had an in-joke that we were going to buy my friend Chris a flesh light for Christmas (hilarious, I know). My other friend Andrew and I decided to go out to this record/novelty store in our town that had a smoke shop and sex toy section on the second floor. It was a favorite place of the semi-popular punk scene in our town, and so the store had tried to cater to all sorts of weird demographics. We headed upstairs and, sort of awkwardly, lingered around the smoke shop kind of drifting towards the beaded curtain that hid the adult section.
One of the two clerks at the smoke shop was an extremely cute brunette with a ponytail that help up her already fairly short hair. She was about 5’7″, and had a body that was just my type. Her breasts were small but obviously perky under her tight grey top, and her slim body widened out into some great hips and a small but shapely ass. She also had a really cool nose piercing that just did it for me.