My First Time

Illustration by Thomas Pitilli

Female • 15 • New York City

I remember it was a Friday because Cloverfield premiered, and we were late to meet up with our friends for the show. My boyfriend and I had half-planned the whole thing two months before, around Thanksgiving — I'd called him drunk drunk drunk (another first), from too much wine with my older cousin — when I told him I was, maybe, perhaps, I don't know, interested in doing the dirty deed. After Thanksgiving break, we talked it over while downing little bottles of chocolate liquor, only agreeing that it'd happen, but never stipulating when.

He bought condoms; I bought a new bra. We'd often gone to his house after school, usually empty until his parents arrived home from work, and cuddled, groped, and fondled beneath the covers. His room was a typical boy's room; you had to step over shirts and amps and folders and books to get to the bed. All this stuff felt like insulation against the world. If you looked up at the ceiling, there were tacked pictures of all his friends (me included) grinning like fools.

That Friday, we were doing the same cuddling-groping-fondling we'd been doing for the past four or five months, only now it was layered with serious intention. He supported himself on his left arm, kissing me softly, finding his way in. The first few thrusts were awkward, so he told me to get on top. The whole thing hurt and felt uncomfortable, and all I could think about was how bad giving birth would feel if this meat stick could spread apart my hipbones in a one-two-three.

After a few minutes of not getting anywhere, we paused, and I stayed seated on top of him, tugging the covers around our waists, my breasts pointed and bare, my shoulders curled in want of a shirt. We looked at each other and laughed. We were laughing the whole time, really. Switching positions, half kissing, half drooling on each other, laughing because my head had shimmied the pillow off the bed, or because someone's elbow had awkwardly jabbed someone's stomach.

"Thank goodness we're bestest friends," I said, after I slid to his side, tucking my head into the nook of his shoulder, lips reaching up to lightly peck his neck. "Otherwise this would be weird."

"It was okay?" he asked.

I nodded. "Yeah."

We'd taken so long to gain the courage (two hours, at least) that even grabbing a cab wouldn't ensure making the movie on time. I joked that he was the fuck 'em and leave 'em type of guy who couldn't even afford a little cuddling, and he laughed as we hurried to put our clothes on and go.

We got out of the cab on the corner by a bank, the red light glowing in the darkening sky. Our friends were across the street, waving, hurrying us over, but we didn't pay attention. Hand stroking my shoulder, he looked at me and said, his first time, "I love you." A pause. "And not just because we had sex. You don't have to say it back either. Don't feel pressured."

I didn't say it back. We walked across the street, sin written across our faces and babbling from our mouths. Our friends rolled their eyes and prepared for the movie (popcorn, soda, the works) that would eventually make us nauseous, walking crooked out of the theater in a post-tilt-a-whirl daze. He and I held hands through it all.

Months later (we'd broken up and gotten back together again), he asked me whether it had worked, whether he'd actually gone far enough in there, and I laughed and said yeah, there was blood and everything when I went to the bathroom that night; it was like suffering through your period twice in one month. He looked down at the floor with those glazed blue eyes and said, "Oh." I stroked his red hair, kissed his freckled face, my fingers playing with the buttons of his flannel. We've been together for three and a half years as of now, and so much has changed for better and worse: his family moved to Long Island, we're both going to different colleges, I love yous are like little presents exchanged at the end of a phone call. But I realize some things stay the same, because when, in that passionate scramble, someone's elbow awkwardly jabs someone's stomach, we still laugh.

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."