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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.  n°



We're looking for stories about the first time you had sex. Email with 300-800 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.

 

20 Comments

finally, these are getting closer to MY first time... i don't think i trust people whose first time was magical and lasted eight hours.

cb commented on 11/17

First decent, first time story.

aj commented on 11/17

Grim.

DJC commented on 11/17

How sad, yet realistic. Why does it have to be so soul crushing? I wonder if they got over it.

mwc commented on 11/17

I think that most have been realistic and fun to read. The only magical, bullshit story being the one at camp, on the beach, with the sunset, etc. This one was good though, very entertaining. However, I still prefer the nose bleed story.

PNC commented on 11/17

This would be some awful melodramatic crap a teenager wrote without that great twist.

GH commented on 11/17

to be fair about the camp story, the author did come back in the comments and say that she ended that story right at the point where it was still magical, and how the aftermath was as crappy as one would expect.... As for this story, I'm want to know if they ever spoke to each other again, and if he was nice to her after he made her cry.

alr commented on 11/17

My favorite was the girl from CN who claimed she had been raped which then spawned a massive comment thread in which almost everyone pointed out that she was as culpable as he. https://hooksexup.com/regulars/my-first-time/010-female-16-connecticut/

NN commented on 11/17

without wanting to reignite that whole thing... she didn't "claim" she'd been raped, she WAS raped!

tmp commented on 11/17

You see the world too black and white...it was more complicated than that.

@tmp commented on 11/17

it may have been more complicated than that, but she certainly wasn't "as culpable as he," and by my recollection that was hardly the conclusion of the majority of commenters at the time.

tmp commented on 11/17

I loved this

M commented on 11/17

I'm with tmp. That's not my reading of the comments either.

JS commented on 11/17

The comments have kept up over these last few months, you might see something you missed if you revisit.

NN commented on 11/17

Called it. By sentence 10.

SG commented on 11/17

omg, i DIDN't call it! wow. that is so sad. on a stump? in the rain? DAMN.

sofi commented on 11/17

DAMN that was dark! and so sparse and amazing. i like that the writer didnt bother to od the story with superlatives to drive it in. dope dope imagery girl.

soso commented on 11/18

Even I didn't see the ending coming, and I wrote this! haha We are still friends. I suppose that would've been apparent, had I not ended it where I did, because even right after, we went back to his dorm and I gave him a boomerang I found in my purse. It is interesting that I still speak to him, because he is now upset that I wrote this. It makes me wonder if anyone else's first times have read their story here....

JH commented on 11/19

the answer is the same as the answer to "how do i get to carnegie hall?"

dwp commented on 11/20

It was rape, both because she was drunk AND because she said "I can't do this." Legally, it's VERY much rape. Where are you from? Afghanistan?

NN commented on 11/20
 

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