So this is a story that happened last year, but I still look back at it fondly as a great night that helped develop my confidence in the dating world. I’m 24, 5’11 and have not had too many experiences with girls. However, for the last year and a half, I had been having a lot of close encounters with one of my really good friends Lupe, she was 22, Latina, and had a pair of C cups and an ass that was unlike any other (it was seriously distracting when she would walk past me).
We had gotten really close over the years and this year, in particular, we had been hanging out a lot and texting every week. We would go for drinks, hang out, and she would come over to my place for movie nights. Looking back at it now, I was very much being an idiot and not catching a lot of hints she was dropping. Both of us flirted with each other, and a lot of times we would get very comfortable with each other but we never crossed that line and always remained “Just really good friends”. It was nice having someone to always talk to and depend on and hang out but we never called it dates, and I honestly didn’t have the balls to ask her out at the time.