This is the most cliché first time story ever, with a little twist because what is my life without a twist. So there we were, two 16 year olds leaving their first prom. Technically it was my prom and Freakin’ Puerto Rican, was my date. Freakin’ Puerto Rican, was a grade younger than me, but had more game than Michael Jordan, so naturally I asked him to prom. Fast Forward to us leaving the prom, we went to a friend’s house who’s parents were out of town, and I knew what was in store for the rest of the night so I started chugging a delightful mixture of blue gatorade and gold tequila. Now, I know what you’re thinking, “that’s disgusting” “didn’t you want it to be special?” hell yeah it was disgusting, and at my Catholic High School I was one of maybe ten juniors who had not had sex at this point, so I was ready to be done with it. I don’t think we stayed at our friend’s house long, mainly because Freakin’ Puerto Rican and I didn’t have any mutual friends, and he was ready to take this virgin to pound town. We only had to stay long enough for his grandma to be asleep by the time we got back to his house.
Here comes the good part. We are walking up stairs to Freakin’ Puerto Rican’s room, he makes sure I’m “ready” by saying “this is going to be great, I’ll go slow.” He proceeds to set the mood by turning on the Celtics game, and rubbing my back. If this didn’t do it for me already, him saying, “I’m going to need you to suck it, I’m not hard enough,” sure put me in the mood. Me being the unexperienced 16 year old that I was, happily obliged and when he was finally ready, we started having sex. No bare in mind I had never been with a boy before, yes kissed many but not in a sexual way. I went from zero to 100 real quick. Keeping my lack of experience in mind, I have to tell you, I felt nothing. There was no pain, no pleasure, no nothing. ( My now fully experienced self is aware that Freakin’ Puerto Rican, had the smallest penis I’ve ever been with/ seen in real life) At this time of course I had no clue what was supposed to be happening so I did what I saw in movies and fake moaned and moaned and moaned. Boy he may not be working with much, but shit the kid and stamina. I mean this went on for at least 30 minutes. I can’t recall if he ever finished, I know I didn’t. I just know my friends waited outside of his house for me and picked me up afterwards.
I wish there were more Freakin’ Puerto Rican stories I could share with you, but sadly (for my self esteem) after we had sex, he told me if I would have waited a little longer, he would have dated me. Oh boy. I totally wish I would have waited… Bummer to my 16 year old self, blessing to the rest of my life.