I went over Reddit's post character limit, so this story continues in the comments since I don't like breaking stories into parts.
Before I begin, I'd like to point out every single part of this story is 100% true. Consequently, there aren't any fantasy moments amongst the lines of, "She pulled my pants down and laughed hysterically. Then, she invited her friend to have a look. They both held out their pinkies and laughed while I shriveled up." So although this story has an erotica feel to it, there's no climactic over-the-top moments involved. Also, my dick is approximately five inches long – not too small really. But size queens will let you know: if it's not big, it's small.
Up until the age of twenty-three, I never thought about my penis size. Mainly, I didn't have to. Only a couple women had seen it until that point. Throughout high school, I was the third wheel. I'd watch as my friends picked up beautiful girl after beautiful girl. Perhaps I set my standards too high, but simply put, I wasn't getting laid until my early 20s.