My First Time


Illustration by Thomas Pitilli

Female • 16 • Wilkes-Barre, PA

I never imagined losing my virginity in a car — let alone an Oldsmobile — but part of me wasn't surprised either. I was sixteen going on sixteen; naïve, half-baked, and horny. I had this boyfriend who cheated on me every other weekend, but I was in love with the fact that he was bilingual and cocky. (At sixteen, these attributes made it worth losing your virginity in a blue Oldsmobile in the cul-de-sac of a developing neighborhood, after soccer practice.)  

I was in love with the fact that he was bilingual and cocky...

Before we had sex, it was all fingering, hand jobs, and him going down on me. I only dished out one or two blowjobs before we had sex based on principle alone. You mustn't skip a base if you want to score. So for a few weeks it was just foreplay. He'd bitch about me holding out and I cleverly nicknamed his penis "The Pinto," which I thought meant "small" but really means "blotchy." Gross. 

So that night in his Oldsmobile, after a sweaty soccer practice, I let him finger me for a few minutes before he whispered, "You're ready." I didn't know if this was a question or a command, but judging by the way his fingers were flexing inside of me, I assumed he was trying to gauge the width of my vagina. A possible theory I have is that he was trying to formulate a satisfactory image of his penis sliding nicely inside, where it would fit like a snug glove instead of ripping. 

I was lucky again, to have a boyfriend thoughtful enough to give me a black-market pap smear before letting me know I was ready. The windows steamed up and The Pinto slid in. It didn't hurt and it didn't last long. Estimated three minutes later, he had pulled out and slithered the condom off. That was the first and only time we ever used a condom. It was all bare-backing it from that point on. As the smell of latex wafted in the backseat of his borrowed Oldsmobile, the windows steamed from his bilingual breathing, I noticed my panties dangling from my foot, which prompted a sole tear to streak down my face. I don't know if it was the overload of emotions or the fact that I had been wearing a pair of my mom's old underwear, but losing my virginity — in such a classy way — really did bring a tear to my eye.

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 (25 Comments)

Jan 25 11 - 2:14am

Frankly, it sounds like the two of them deserved each other. The writing is contrived, the protagonist seems detached and contempuous = I want my five minutes back.

Feb 18 11 - 4:21am

It took you five minutes to read this?

Jan 25 11 - 2:15am

(contemptuous, that is)

Jan 25 11 - 2:30am
Lady's a Man


Sounds like one of those girls who tries really really hard to seem different, quirky, and well read Like Juno.

But fail.

Jan 25 11 - 3:54am

man, people are so judgmental on these things. i like her--she sounds funny and actually pretty sincere.

Jan 25 11 - 4:00am

@LAC, it took you 5 minutes to read that?

Jan 25 11 - 2:37pm

@S Exactly what I was thinking.

Jan 25 11 - 2:54pm

@S: LOL, touché. In fairness, I read through it twice to see if I missed anything. No excuse for that, though, since when you see the phrase "bilingual breathing" it's time to pull the ripcord.

Jan 25 11 - 5:46pm


Jan 25 11 - 7:04pm

I'm pretty sure I know who the author of this is, and damn, that makes me feel weird.

Feb 08 11 - 8:56pm

I love that the author is from Wilkes-Bare! I think the story should include something about skiing at Montage and Old Forge pizza (a natural aphrodisiac, I hear.) :)

Jan 25 11 - 7:28pm

I like the contempt for her stupid 16 year old self. It's honest, sad, and funny.

Jan 25 11 - 8:25pm
tom wants to comment

@Scrantonite: Do tell us more.

Jan 25 11 - 8:31pm

@S: @Scope: The illustration is pretty clever. That's worth an extra minute of lingering.

Jan 25 11 - 9:24pm

lol @ "the pinto"

Jan 26 11 - 7:35am

I was just about to say that the illustration was remarkably tacky.

Jan 26 11 - 12:40pm
Under Where

Do tennyboppers frequently wear their mothers' panties?

Jan 27 11 - 12:21am

I never understand why people are so harsh to these things. Is it out of the realm of possibility that of the 6 billion people on the planet (and about 80% have had sex), some of them are going to have less-than-perfect stories and may involve socially strange circumstances? I appreciate everyone of these, but maybe that's just me presuming they're genuine and candid.

Jan 27 11 - 4:53am

That's the thing, though -- this doesn't feel genuine and candid, it feels self-conscious, contrived, and poorly written. As for the less-than-perfect stories, if anything the comments are harshest on the stories with happy endings and smooth sailing. Or at least, people will say a story's fake if it involves (a) a girl who has an actual orgasm, (b) a guy who doesn't ejaculate after ten seconds and knows where the clitoris is, or (c) two people who treat each other with love, respect, and compassion. (So I guess this one's real, then.)

Jan 28 11 - 12:15am
what the

Ok, who would wear their mother's old panties? That is beyond disgusting, and I'm gonna say it, especially if her mom liked to bareback too. GAH.

Feb 15 11 - 11:32pm

this is 100% true. glad to see some of the story itself stirs enough emotion for comments, seeing this was written on a summer day when the sun had gotten too hot and time needed to be wasted under the shade. then again, we waste time always, especially as 16 year olds losing our virginity in a car. alas, cheers to those who have a monumental "first time" story.

Feb 15 11 - 11:42pm

Ha i think the story is clever and has a very funny spin to it. I like the fact that the author takes something that is meant to be sacred and puts a rather emotionless and "eh" kind of attitude to it. She makes the concept and hype of losing ones virginity not so scary and "important.." More like a "weird event thats just weird." well done.

Jun 15 11 - 6:02pm

How nice if yls (8/9/87) give her first time to me. I, shp will love and take care of her till end of our life...........

Jun 23 11 - 4:03pm

Weird story told with weird attitude. Enjoyed it nonetheless, including the bilingual breathing. Thanks for telling.

Jun 19 12 - 7:31pm

pengen sich ngerasain perawan.........