My First Time

Illustration by Thomas Pitilli

Male • 15 years old • Pennsylvania

The unceremonious throwing away of my virginity ended up being quite memorable, due mostly to venue: the stairwell of my neighborhood's YMCA. By the time I reached ninth grade, I'd had access to my fair share of pornography. I knew (in my mind) how to pleasure a lady, because I'd seen foreplay and penetration from every single angle you could ever imagine, thanks to the invention of the internet. It was time for me to put what I'd seen to the test. How hard could it really be?

I'd been IM'ing with a girl named Ashley from a nearby school, and we had decided we should have sex with each other. She didn't take a lot of convincing. This shouldn't be surprising, since her screen name was "ThongCutie" followed by a few random numbers. (I'm not joking.) We had no place to go to have sex, being that we were both too young to drive and lived with our parents, so at some point, the YMCA became our most viable location. There had to be some place in that gigantic, three-story building where we could successfully pull off some teenage fucking. You don't encounter a lot of suspicion from your parents when you tell them you want to go to the YMCA on a Wednesday night.

I did some recon during one of my frequent trips to the YMCA to play basketball, and found a convenient spot at the bottom of a stairwell that seemed to lead nowhere but to an emergency exit. I figured nobody would come there, and reported back to Ashley that I'd found a place. Classy.

We met at the basketball court. She was in gym clothes with a lot of make-up on and I was in a t-shirt and basketball shorts with three condoms tucked into one of the pockets. (I've noticed that you always either bring superfluous condoms, or stumble upon the opportunity to get laid when you weren't expecting to, when you have none.) She went down the stairs first, and I followed approximately thirty seconds later, when I was sure nobody was watching.

It was all business. She didn't have to ask if I'd brought condoms, because we'd worked it all out online beforehand, along with the color of thong I wanted her to wear (lime green). We barely even talked, but just began kissing and groping each other. I remember how glossy her lips were, and I remember pulling mine away from hers to take a good look at her, like people always seemed to do in movies. This was as close as I got to being passionate during the whole process, and I kind of regretted doing it. We made eye contact, and it was actually more awkward than later, when part of me was inside her.

She wasn't exactly a knockout. She was a bit heavy-set, but she had some larger-than-average breasts and that cute, round face a lot of curvy women possess. The thing was, though, she just exuded promiscuity. This was not her first time. I had to remind myself that I was here to be rid of something, and she would do just fine for that.

The undressing was easier than what you might expect for a first-timer. There was no bra-unhooking, because sports bras don't have them, and the entire experience was completely devoid of buttons and zippers.

Once I had put a condom on, she guided me into her. No foreplay necessary. And then I began to hump on top of her quickly, which was what I'd seen from the veterans online. This girl probably didn't feel any pleasure during the thirty to forty seconds I lasted. She probably didn't feel any pleasure for the next two minutes I stayed inside of her and continued before rolling off, so as to avoid complete embarrassment.

There was no post-coital cuddling, and neither of us wanted it. She was probably disappointed with my performance, and I just wanted to get out of there to go and think about what I'd just done. I quickly dressed, and sat down on one of the steps while I waited for her to do the same. "You don't have to wait for me," she said, and added that it'd be better if we left separately anyway, so I did.

I'd left the condom on when I got dressed, for whatever reason, and went immediately to the bathroom once I returned from the stairwell. I took it off, threw it into the garbage, and then looked at myself in the mirror to see if I looked any different. As expected, I did not.

Then, I went into the gym, where I grabbed a basketball and started shooting around, just like I did most Wednesday nights during my teenage years. Nothing had changed, except that my shot seemed to have improved slightly. But this could've been my imagination. I only spoke to Ashley one more time after that, on the internet, where I apologized for my poor sexual performance, and was told I'd get better with practice. I like to think I have.

We're looking for stories about the first time you had sex. Email with 500-1000 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.