My First Time

Illustration by Thomas Pitilli

Male • 18 • Massachusetts

I can tell you a good deal about the first time I had sex, even though I'd drank enough so that when showtime came around I couldn't perform. Freshman year was coming to a close, we were all drinking recklessly, and this beautiful, smiling blonde girl and I were making vague plans. She listened to what I was saying for a long time, which made me say some stupid stuff. I wasn't thinking about what was happening, and the deciding point came when I gave her my sweatshirt outside so she could stay warm. I remember it smelled like melting snow. She started kissing me.

Previously I'd only had one serious makeout session and never touched boobs or any other lady parts. The warmth, touch, and smell of another body that close: I never could have imagined what these things would feel like. After I made out with her in front of the dorm, one of my dude friends had given me a high five as she and I walked up to her room. She didn't seem to mind. In her room, we watched like six episodes of The Office because I had no idea how to start off.  Finally, I made a move, and eventually, I had a condom on, which seemed about as far as things were going to go for me, anatomically.

"Are you sure you're comfortable with this?" I said, because she didn't seem like she was.

"No, wait." She sat up and held her head in her hands.

"It's totally fine if you don't want to."

"No. I'm sorry. This is so embarrassing."

"Can I still stay here?"

"Of course." I couldn't sleep because the bed was so small. I lay awake most of the night with my eyes open, euphoric and delirious. She fell asleep almost instantly.

The next morning I lied and said I wasn't a virgin when she asked, and she did the same when I asked in return. Only virgins would believe these things. Absurdly hungover but feeling triumphant, I walked around without my shirt on and told all my buddies I'd gotten laid last night. Something unpleasant occurred where I went temporarily blind in one eye, maybe from staring at a ceiling in complete darkness for hours and then being next to a window letting in full sunlight. Maybe dehydration. I don't know. After breakfast I threw up and took a nap, and first thing after my nap I walked down the hall and gave her a hug and an RC cola, as a gift to put me in good stead for the future.

So I didn't have sex that night. But a year later, I finally, officially, sealed the deal — it was with her anyway, and truthfully it was pretty forgettable. Even so, four years later and a year apart in between, we're still together, and I love her a lot.

Female • 16 years old • Israel

We became friends right from the start. We found that we had the same cynical and sexual sense of humor.

Female • 22 years old • New England

"I can't tell you how glad I am that I never signed that 'True Love Waits' pledge."

Male • 15 years old • Washington DC

"I had never planned to lose my virginity to a guy—let alone Rob. I planned to pretend to be straight for as long as possible."