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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.)
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 email@example.com 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.