My First Time

Female • 17 years old • Philadelphia

When I first saw The Boy, I wanted it to be him. He had these puppy-dog eyes that turned down slightly at the corners and he wore tight jeans and listened to indie rock and his brother was a famous TV star. It felt like the plot of a horribly quirky indie film just waiting to happen. Naturally, I assumed that simply because he was so ideal, there was zero chance of it happening. I was certain I would instead lose my virginity at a party, drunkenly half-raped by any pretentious cigarette-smoking English major who happened to wander my way. Luckily or not, it didn't end up like that.

The Boy was my best friend, and somewhere around ten-thousand Facebook messages after meeting him, two seemingly innocuous things occurred simultaneously. I got iChat, and downloaded "Gay Bar" by Electric Six. Those two things would change my life, because as I listened to the song, I typed, "I want to take you to a gay bar," into my chat with The Boy. Those stupid lyrics led to us discussing gay sex, which led to a discussion about Anaïs Nin, which somehow led to a discussion about pee fetishes, which ultimately led to a discussion about how horny both of us were getting from talking about how horny we were. In a fit of sudden sexual frustration, I took my chance. "I want to fuck you," I typed. "I'm tired of being a virgin :/"

Our relationship had always been completely platonic, and he resisted. But I begged and pleaded and argued. The Boy finally acquiesced. That was how I ended up at his dorm on a Tuesday night. ("We can't do it here," he said dubiously when I arrived. "This is the honors college. No one here fucks.")

Illustration by Thomas Pitilli

It was pouring rain. We walked quickly to CVS, where we argued momentarily about who would buy the condoms. He pressed ten dollars into my hands and pushed me inside. I wandered my way back to the farthest aisle, eyeing the contraceptives. The variety baffled me. I picked ones in a blue box. The man in line in front of me looked to be buying all of his groceries for the whole goddamn week from CVS. He seemed to take forever as I stood in the queue with my embarrassing purchase. When he finally left, I slid the condoms gingerly onto the counter. I bolted as soon as I paid.

We wandered around West Philly in the rain, looking for a good place. There was a little alley between two fences, and it was the best we could do. It was still raining. The ground was mud. We didn't say much. I led The Boy's hands to finger me first, to make sure I would be wet enough to get it in. He hurt more than he helped, and we gave that up quickly. He slowly undid his jeans and opened the box of condoms. I turned to glance at him behind me, but he grabbed my head and turned it back. "Don't look," he said. I closed my eyes. Then I was laid out on a tree stump, with my hips in the air and my hair pressed into the mud. My skirt was still on, but flipped up, and I was exposed and vulnerable beneath him. My panties were tossed somewhere in the dirt. The rain poured harder down on both of us.

With my eyes still closed, I directed The Boy inside me. He missed at first. He squirmed around on top of me, repositioning himself. I opened one eye a little bit, to watch him. He was so beautiful. My hands reached up to his lower back, to push him into me and I slipped them gently under his sweatshirt. We were still almost entirely clothed. He was nearly inside of me, and yet we were barely touching. It seemed so dismal, I wanted badly just to kiss him. Despite everything we'd promised about not having feelings for each other, I realized I loved him. I had always loved him. He pushed in and it hurt. I whimpered, "Keep going." He pushed deeper. "Okay, now fuck me — oh. Except you just pulled out."

"I know," he said. "I came." He got off me abruptly. "Now I know," he mused. "I don't like girls."

"Oh." I felt empty inside. I just lay for awhile on the stump in the fence-alley in West Philly staring at the sky. The rain came down on my face and my hair and my naked lower half where I still hadn't covered myself with my skirt. Then I cried.

Female • 21 years old • British Columbia

"I grew up in a socially conservative family; sex was never a topic of discussion..."

Male • 20 years old • Honolulu, HI

"I had an epically cool facade and no knowledge of how to make it work for me..."

Female • 18 years old • Washington, DC

"Between my shyness, low self-esteem, and identity as 'the smart one,' I'd never even been kissed..."