Female • 16 years old • New York, NY
He was probably not the natural choice to deflower straight-A super-nerd me. His ridiculous primary-colored baggy pants actually fell down in the middle of the street on at least two occasions that I'd witnessed. He sold acid to my lunch-table companions. Most damning of all, he had been my best friend's boyfriend before she moved away.
I never really understood his appeal. He may have been attractive, but it was obscured by his flashy over-sized clothes. Nevertheless, I found myself spending more and more time with him once she was gone. He propositioned me over the phone one evening while claiming to be drunk. My sexual experience at the time was negligible, so I was morbidly curious.
We went to his house after school. On the way, he stopped in front of a drug store, and said he didn't have any more condoms. I rolled my eyes and went in alone. The man at the check-out asked if it was for a school project. Something like that, I said.
Illustration by Thomas Pitilli
In his room, I turned away when he tried to kiss me on the mouth. It didn't seem fitting somehow. I'd read that prostitutes don't kiss on the mouth so as not to get emotionally attached. I thought I was being worldly and sophisticated, but more likely I wasn't too confident about my kissing technique. I let him touch me and take off my clothes. My gaze wandered to the picture frame near his bed — it was of him and my best friend. He saw me looking at it and pushed it face down. I put it back the way it was. I missed her terribly!
The sound of his belt buckle hitting the floor snapped me back. Released from the confines of his pants, an enormous cock bobbed up. It was too big for his thin, sinewy frame, ridiculously so. When I put my hand around it, my fingers weren't even close to forming a ring. There was no way it was going to fit into petite little me! I demonstrated the impossibility as he lay on his back. It hurt slightly as the tip entered, but it would go no further. The pain didn't matter because the situation was just too deliciously ironic — he was so proud of his monster cock, but functionally it was useless in this case. I couldn't help but giggle at the absurdity.
Then I started to feel something different from the stretching pain. It was almost pleasurable. I looked down, and abruptly stopped laughing. Our pubes were touching! I hadn't been expecting that and didn't know what to say. Then he started rocking his hips and I began to feel dizzyingly pleasurable sensations I had never even imagined before. As I rode him, I figured it out — it was like getting a massage on the inside!
And I was in for another surprise. I'd done my research on the mechanics of sex and knew about the male refractory period. But at sixteen, he didn't have one. After we both came, we stopped for a second to change condoms and then just kept going. I kept that first condom, the one with a streak of my blood, as a souvenir of the our three-hour marathon and pasted it into my diary.
I got home at about eight that evening. My parents must've attributed my unmistakable glow to the joys of studying in the library. He and I later fucked on two other occasions. The third time he tried to get his best friend to join us, to my horror. It fizzled rather quickly after that. Then the pangs of conscience kicked in and I confessed everything to my friend long distance. Nearly two decades later, she is still my best friend and we still laugh about the fact that the same guy popped both of our cherries. We hear he's married now with two kids and makes a lot more money than either of us.