My First Time

Illustration by Thomas Pitilli

Male, 18, New Jersey

From what I had heard, sex was supposed to be fun. All I knew was that I wanted to do it. A year of college had passed up in Syracuse and to tell you the truth, it wasn't much like I'd expected. I mean, I knew it wouldn't be exactly like the movies, with the orgy-esque parties and girls all over campus basically begging to have sex with any guy with a pulse. But, like many a man, I had this misguided idea that I'd be able to reinvent myself at college — transform myself from nervous to confident and be able finally to get the girls I wanted.

What I soon realized was that college didn't so much allow you to reinvent yourself as it simply allowed the real you to come to the forefront. Writing this now a handful of years later, I'm perfectly fine with that reality. But at the time, with one year of college down the tubes, I could count the amount of girls I'd even hung out with on one hand, and I hadn't come close to having sex with any of them.

A few days later, I got a message from her on Facebook, saying she was sorry...

With some time to kill after arriving home for the summer, I took a weekend to visit a friend of mine at Northeastern in Boston. The first morning on campus, before heading to get breakfast, I ran into my ex-girlfriend from high school, who also happened to go to the school.

"Wow, you look terrible," she said. That stung. Could I argue with the point, though? Not really. I hadn't shaved in weeks, was wearing a ripped t-shirt and the baggiest sweatpants I had. I looked, well, terrible

"It's nice to see you too," I said back. She, on the other hand, looked really nice, better than I had remembered — so nice in fact that she was all I thought about on my bus ride home the next day.

A few days later, I got a message from her on Facebook, saying she was sorry. I told her it wasn't a big deal, that I did look like trash. She laughed (or rather, LOL'd). We agreed to hang out when she got back home, which would be in a few weeks.

Mind you, all I had in mind at this point was to see her again and maybe make out, maybe get a blowjob. Crass, sure. But, I hadn't really thought, "I'm going to have sex with my ex!" I mean, to say "sex wasn't at all on my mind" is obviously untrue, as I was an eighteen-year-old male. It's always on my mind to some degree, even to this day. But let's just say it wasn't hogging the space.

That summer, I worked during the day representing my Italian heritage (which is to say delivering pizzas for Domino's) and she worked at night. On a Thursday night, she drove from her job straight to my house. She stepped out of her car and I saw her all at once. She wore a straight, plain black dress with shoulder straps. Stunning.

Now, obviously she was there to hook up, and sex was something we'd both obviously thought about without actually discussing, as both of us were first-timers. Because I lived with my parents and they (along with my Grandpa and little brother) were all home that night, we headed downstairs to the spare bedroom. It was in this very room that we had first kissed two years prior. All very sentimental. Standing in the room, I sat down on the edge of the bed as she stood in front of me near the mirror.

"So..." she said.

She wasn't one for words.

"So..." I said.

It was all I could do to not jump on the bed like a giddy five-year old. I stood up, pressed her close to me, and we started to kiss. Her hands moved down my sides, mine on her breasts. Quickly I moved to the zipper on the back of her dress. As that happened, she lifted my shirt over my head and undid my jeans. I sat back down, keeping her close to me as we continued to kiss and grope around. She pulled away from me and dropped to her knees, taking me in her mouth. I leaned back, in pure heaven.

Moments later, she came back to me, and now we found ourselves both lying on the bed, naked besides my socks. I'm not sure why I kept them on.

"Do you have a condom?"

I did, I told her. At this moment, I realized they were all the way upstairs, two floors up, in my room. Everyone was asleep at this point, but I still had to stealthily head upstairs, massive hard-on and all, to get the condoms. A mack truck wasn't stopping me. Once I got back downstairs, I hopped back on the bed and ripped open the packaging to apply the condom. She asked how I wanted to do it, a question I wasn't at all prepared for.

"Like this?" I said, motioning for her to get on top. She straddled me, taking me inside of her very slowly. I began to thrust, and we were having sex. I expected her to moan, not because I was good or bad, but because that's what women did during sex, or so I'd heard/read/seen. Moaning wasn't exactly what came out. It was more of an "Oww," or at times an "Ahh, ehhh." Generally, sounds of discomfort.

So I asked, "Are you all right?" She said she was, that it would get better, and that I should just keep going and try to block her out. While I thought that last part sounded a bit off, the idea of keeping going sounded good, and considering I was enjoying the feeling of being inside her, I didn't exactly beg off.

So we kept at it, determined to make this work. But, the noises on her end only got worse. Telling her it wasn't worth it to me if she was in pain, I pulled out. At first I didn't notice anything out of the ordinary, bringing her close to me. She felt terrible about it — it was her first time too, after all. Then, I looked down at my penis. The condom still stood there, but it was covered in blood. Stifling a "What the f —" under my breath, I saw that there was a stain the size of a golf ball on the bed

Thankfully, we had a dog with a predilection for urinating on the carpet. I grabbed the Nature's Stain Remover we had in the laundry room and went to work. Obviously, that was the end of that night.

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.
According to just about every pre-college advice manual, floorcest is a bad idea.
"So no, I didn't lose my virginity in the most traditional way."
"He looked like if Ian Somerhalder and Gerard Butler had somehow created a baby."

Commentarium (12 Comments)

Dec 21 10 - 11:49am

Nicely done

Dec 21 10 - 12:46pm

Excellent story! Totally authentic.

Dec 21 10 - 2:19pm

Beautiful illustration.

Dec 22 10 - 12:12am

I agree. I love the illustrations for these stories.

Dec 22 10 - 10:21am

haha, i logged on to comment on the art but i see someone beat me to the punch. wonderful illustrations. kudos.

Dec 22 10 - 10:05pm

Realistic, but boring as hell. Just because it is authentic and ordinary doesn't mean it should be published online for others to read..

Jan 23 12 - 10:25am

Boring is subjective...and obviously it should be published in order to get these opinions. Your argument is flawed.

Dec 28 10 - 6:05pm

great story, beautifully written, but anticlimactic. i guess most first times are though...

Dec 31 10 - 5:54pm

I wasn't expecting the ending.

Feb 08 11 - 4:58pm

Haha. Here I thought everyone that had a year in college at the very least knew about the hymen. Or a period. Protip: If you're unsure, bring a towel to put underneath. May seem creepy, but hell, it'll save you the odd laundry hours.

--And now you know!--

Jul 02 11 - 2:40am

and knowing is half the battle

Jun 23 11 - 4:50pm

Touching story. Thanks.