Love & Sex

My First Time

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Female • 16 years old • Woods behind Papa Playground

I had been with my boyfriend for four months when I started to feel trickles of panic; we were growing distant from each other and I was desperate for us to stay together. His name was Michael and he lived pretty far from me, on the other side of the city. He was always the one to come and visit me at least once every couple of weeks. It was during one of these weekends that I brought him to meet my friends.

When it was about time for Michael to leave, I put on my best pout and shuffled my feet, and my friend Dan and I walked him to the bus stop. When he asked what was wrong, I told him I felt we hadn't gotten to spend any alone time together. He understood the emphasis on "alone" and offered to make a detour through Papa Playground.

Illustration by Thomas Pitilli

Michael and I had spent plenty of time in the woods behind Papa Playground, making out and practicing manipulating our clothes to get to the goods without exposing too much flesh to the winter wind. Today however, I felt a different type of apprehension when we left Dan behind to wait for us at the edge of the woods. Inside the woods we started our routine of kissing and fondling, stopping at third base. But this time, when Michael begged to go all the way, I surprised him by agreeing.

It was the most awkward encounter I've ever had, doubled over with my jeans pulled down enough to expose my behind, holding Michael's calves behind me as he banged unapologetically hard into me. I was screaming with the mix of pleasure and pain — pain, mostly — and when we were done, I walked back to meet Dan stony-faced and not at all happy with my decision.

Later on, while walking back home with Dan, as I looked at the mud stains left on the bottom of my jeans, Dan said he'd heard me screaming and yelling, and that he saw a guy parked across the street in his car looking into the woods fixedly and eating a bag of chips. So apparently my first (and worst) time was spent entertaining some pervert with a free show. Perfect.