Love & Sex

My First Time

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Male • 16 years old • Houston

I was a girl-crazy junior in high school when I noticed a sophomore who was in two of my classes. She was a swimmer with a great toned body and sexy eyes. We started to hang out in the same group of friends and quickly it was clear there was a mutual attraction. The first time we went out ended in handcuffs, a misdemeanor charge for criminal mischief, and our parents coming to the police station to pick us up. Not the ideal first date, but I guess it was foreshadowing things to come.

Our parents did everything they could to keep us away from each other,


Illustration by Thomas Pitilli

which just fueled our determination to be together. We made out in the back stairwell at school and in parks after dark, and we'd sneak out to meet in the middle of the night. We couldn't keep our hands off each other, but neither of us ever had a condom, so we both remained virgins.

I finally bought some condoms and we agreed to meet in the parking lot around lunch and skip school that afternoon. Our options for privacy were limited. We couldn't guarantee either of our houses would be empty and my little Nissan wasn't exactly spacious, so we found an empty cul-de-sac in an abandoned development away from everything. I parked the car and spread out a blanket on the rough field grass. We took off our pants, and I fumbled with the condom until I was finally in.

In what felt like ten seconds later, we heard a car coming down the abandoned road — not just any car, but a police car coming to interrupt our little party in the middle of nowhere. Unlike Seth Rogen in Superbad, the female police officer had no problem cock-blocking me, and after we got dressed she took the swimmer in for truancy because she was under sixteen. After her mom got the second call from the police to pick her up, we had to get even more careful about tricking our parents. But we were able to stay away from the police, and the extreme efforts turned out to be worth it.