My First Time

Illustration by Thomas Pitilli

Female • 17 years old • Carlsbad, CA

I was the girl who people made cat-lady jokes about in high school. Three dismal years of being perpetually single without so much as a handjob or a kiss to brag about made me the kind of geeky, socially awkward shut-in who blends into the back of your Spanish class.

I had built up a sarcastic sense of humor and an incredibly frumpy wardrobe, and repeatedly pined hopelessly for the many boys who just saw me as a pal. One by one my friends told me about their first dates. Their first kisses. And then finally, their first times. I responded with weak smiles and various self-deprecating comments like "I'll let you know my own stories in thirty years or so." They laughed it off and patted me on the back.

This all changed in my senior-year chemistry class, when I fell madly in love with the most handsome, charismatic, charming, and intelligent boy I'd ever seen. He was born in São Paulo, and had an accent that drenched every word he said in romance. I loved every detail: the way he smiled, the way he brushed back his sexy black hair, and the way his smoldering eyes commanded my entire concentration, causing my grade to fall from an A+ to a C in about a month or so. He liked philosophy and quantum physics and comic books and old '80s bands — bands that I hated but pretended to like so that he'd love me.

And so he did. My first kiss came not too long after. When he finally asked me to prom, it was absolutely surreal, and my friends took me out shopping for clothes that would look "totally hot," meanwhile asking me all the most intimate things that I refused to tell.

For a stunning month and a half we explored each others' bodies with excitement and curiosity. Our make-out sessions were neverending, and I remember the day of my graduation he had about five hickeys on his neck that he sported with a trashy, goofy teenage pride.

Two days before his seventeenth birthday, we sat in his room, and he mentioned offhandly that his dad had given him some condoms. When I was brave enough to tell him to take one out, we realized that they were expired. I grabbed his hand and said, "Let's go buy some new ones," and we ran to the drugstore a block away. Looking at that huge wall of condoms was intimidating, and after debating whether we should invest in some of the more daring and exotic types, we decided on just the regular, light-blue box of three.

I remember how he shyly turned around and put it on, while I lay on his bed with my pants off, examining the little cartoons inside of the box, demonstrating how condoms worked. He turned on The Strokes before eagerly hopping on top of me, and I smiled and told him I was ready. After a few seconds I felt a searing pain that I wasn't fully prepared for. I lurched forward grabbing onto the small of his back, and I leaned my head back, watching how the rays of light hit the surface of his pool outside and reflected on the ceiling. After thirty seconds of nonrhythmic thrusting, he pulled out with one of the most satisfied sighs I ever heard. "That was amazing! Don't you think so?"

"I don't know," I said. "I guess so." My face was flushed and my head was spinning, and in that moment I felt dirty and sexy and alive and wonderful. I lacked only a feeling of physical satisfaction, as I admitted to myself that it wasn't nearly as fun as it seemed to be to the rest of society.

But we decided to have another go at it later. And again. And again and again and again. Rabbits don't fuck like we did. It got tolerable, then enjoyable, then mind-blowingly fantastic. That summer was the best of my entire life, and even though we've grown apart since then, not a day goes by that I don't miss him. I wouldn't change a thing.

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."