My First Time

Illustration by Thomas Pitilli

Female • 20 • Los Angeles

I grew up being told that men were horrible bastards, and that I couldn't trust them. Combine that with the fact that my mom and two of my aunts had children before the age of eighteen, I was definitely scared off of having sex. So, by the time I decided to just go through with it, I was twenty, and even more nervous.

My first time was with a friend who had initially told me straight up that he "didn't do virgins." Our friendship was built on a massive amount of unresolved sexual tension and four months of flirting. When we finally took an initial step toward a physical relationship, both of us swore that it was simply 'friends with benefits.'

He definitely wasn't the type of guy I would have seen myself with. I tended to avoid musicians and punks; my type definitely leaned more toward plaid-wearing, slightly hairy writers who listened to Vampire Weekend and Minus the Bear. I guess it was a case of opposites attracting. He teased me relentlessly for being a nerd, for my taste in music. He managed to make me angry and extremely attracted to him in the craziest way.

We were both fairly buzzed, having knocked out most of a bottle of vodka, and generally well on our way to enjoying a three-day weekend. Things were actually fairly relaxed, as we had just settled in to watch a movie. I decided to have a little fun, since he was spooning against me. I snuggled up closer to him, pressing myself against him, knowing I had his attention. He immediately took the bait and started grinding against me. By that point, the movie was pretty much forgotten.

If there's one thing I'll always remember, it's this: he actually warned me to stop. He told me that if I didn't stop, he was "going to end up tearing me apart" and that if I wanted to leave a virgin, I needed to quit. I'm definitely one to push limits, and seeing as my only other physical experience had been with a guy who was afraid to even touch me, I knew it was basically put up or shut up time.

It hurt like crazy. I expected pain, but I wasn't expecting it to hurt so badly, and for nearly the entire time. He was a bit rough, a biter, liked it hard and fast, and he wasn't changing his style to accommodate me.

I'm a dreamer, but thankfully I wasn't the kind of girl to have all kinds of romantic visions about losing my virginity. Because, if I had, losing it on the bottom bunk of a bunk bed in South Central, a little buzzed, with a friend who didn't go out of his way to make it special wouldn't have been in my plans. Still, even if it wasn't with someone I felt strongly about, even if it wasn't special, I don't regret any of it.

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."