Love & Sex

My First Time

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My First Time - Illustration by Thomas Pitilli

Illustration by Thomas Pitilli

Female • 18 years old • Burlington, VT

He was my best friend's boyfriend's best friend. The plan, orchestrated by our friends, was for the two of us to hook up. It seemed convenient, and I was coming off of a bad breakup and looking for something with no strings attached.

But my parents shipped me off to my grandparents' house in Oregon over spring vacation, somehow suspecting that if I was left at home unattended, I would wreak havoc. So instead of having a no-strings-attached hookup, the boy and I ended up talking on Facebook for hours, as I sat in my grandparents' cold basement while it rained and their cats twined around my wool-socked feet.

Although I woke up each morning to a text from him asking how I slept, the conversation never took the abrupt left turn that I had come to expect from guys. He never asked for pictures. He never made creepy sexy insinuations. I was confused, to say the least.

When I got home, we hung out. We went hiking; we kissed. He made me laugh harder than any guy I'd ever known. But my ovaries got the best of me, and in the back of my mind, I wondered incessantly what we "were."

The third time we hung out, it was the four of us — he and I and the two people responsible for us being together. We drove around, doing a lot of nothing. My best friend attempted to pierce my ear in the parking lot of a pizza place while I lay in the back seat of the car and he held my hand, stroking my hair and complimenting me on my bravery. Finally, we ended up in an abandoned quarry. In a display of true friendship, our friends generously offered to take a walk, even though the bugs were swarming outside.

I have always been impatient. I got into the back seat knowing exactly what I was going to do. He didn't expect it, but luckily I had a condom in my glove box that my friend had left there as a joke — so when I said, "Want to share another painful piercing experience in the backseat of my car?" everything was covered.

It's like ripping off a band-aid, I thought. Just get it over with. I was glad he knew what he was doing, but it hurt. I scrunched up my face and looked out the window, tried not to whimper. Eventually, the pain dissolved, and I was left with a strange and mildly pleasurable sense of invasion. I enjoyed it, but eventually I began to wish it would just be over. Soon, it was.

We chucked the condom on the ground (classy, I know) and walked out to find our friends. "I guess now is when I ask the awkward question," he said. His voice cracked, and my heart melted. "I know we're leaving for college, but do you want to be together, or just like… friends?"

We found our loyal, bug-bitten friends, and went back to the car. They aren't together anymore, but my voice-cracking devirginizer and I still are.