My First Time

My First Time: “It’s not working. Why isn’t this working?”

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Whether it was in the back of a cramped car, with your pants at your ankles, or in your parent’s queen-sized bed, we want to hear 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.

My first time came a few weeks after my first kiss. The first semester of college found me more open and friendly than I’d ever been, and probably friendlier than I’ve been since.

The setting: one late night spontaneous dance party in a friend’s dorm room. A doe-eyed skater-type caught my eye with his uninhibited moves. I dove headfirst into my first sexy one-on-one dancing, first kiss, first make-out, first all night make-out, first 2nd base, first sexual nudity, first dick I’d ever touched, and definitely the first 3rd base performed on me and my bewildered and terrified cunt. It was exploratory and almost innocently sweet. I reveled in the freedom of a stranger’s touch (something I still seek and find intoxicating).

No one, I felt, was more ready than I — an 18-year-old virgin, hypersexual, sex-educated, chronic masturbator since childhood, and newly-discovered kissing-enthusiast.

I hung out with the kid more and we began dating, as much as college dorm room hangouts count, anyway. I remember walking around a photography exhibit of rainbows with a friend when I decided firmly that I wanted to have sex. With this kid, there was just enough trust and early love to feel safe, and just enough danger and uncertainty to feel exhilarated. No one, I felt, was more ready than I — an 18-year-old virgin, hypersexual, sex-educated, chronic masturbator since childhood, and newly-discovered kissing-enthusiast.

All of this context and backstory? …and I don’t really remember much about losing my virginity.

He bought the condoms, we did it on his elevated dorm bed, made sure I was all warmed up, and then…pain. “It’s not working…why isn’t this working, is there something wrong with me?” I thought. This memory is clouded with the pain. I’m not certain if we eventually achieved penetration or if it took two or maybe it was three more attempts. The whole affair was not sexy in the slightest. I do remember the color of the fresh blood that poured from my crotch for a day after the first time. God, it hurt so bad.

I described the hymen-break pain to my horrified virginal friends as: “similar to trying to pierce the upper cartilage of an ear, with the eraser end of a pencil.” I gained newfound envy of the horseback-riding soccer-playing hymen-less girls who escaped this bloody rite of passage.

After a hiatus for vaginal healing, the kid and I enjoyed a vigorous sex life for another couple of years. As I reflect now, I think several things: the lifetime of sex was worth that week of pain, and that virgins (and other people too, I guess) deserve safety and patience.

Female, 18, Massachusetts

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