Love & Sex

My First Time

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Male • 17 years old • Massachusetts

It was my junior year of high school and my parents were out of town. A bunch of friends came over that afternoon, including one girl I'd always thought was cute. She and I hung out a lot, but it was always in a group, always firmly in the friend-zone. That day we all smoked weed, and we dipped into my parents' liquor cabinet as the night wore on. I remember vodka shots, though things get hazy after that. I had a turntable and a bunch of vinyl records in my room upstairs, and this girl said she wanted me to play some music for her. Oddly, I think she wanted me to play one of the classical records, although our group was mostly into hip-hop at the time.


Illustration by Thomas Pitilli

So, we went upstairs. Crazily enough, at this point, I had never actually kissed a girl. I was Michael Cera, just a skinny, nervous mumbling dude when actually one-on-one with a lady. But that night, all the vodka and weed and music somehow made me loose and uninhibited. I was feeling warm and confident (what I'd later recognize as the perfect state of drunkeness). I put a record on and we sat down on my bed. I leaned in for a kiss. I honestly would have been happy just to get that first over with, but things kept going.

It wasn't long before we had stripped down to our underwear. ("Dude," I kept thinking. "Dude.") Then — amazingly — she went down on me. I went down on her, pretending I knew what the hell I was doing (thank God for pornos). I couldn't believe it, but eventually we got to the point of wondering who had a condom. That would be: neither of us. I don't know how or why I came up with this idea so soon, but I immediately suggested that we try anal sex. And she agreed. I ran to the bathroom to grab some Vaseline. Where this "expertise" came from — considering that only half an hour ago, I had never even kissed a girl — I don't really know. We tried anal for a bit, which I count as the loss of my virginity. I didn't have anything to compare it to, but she wasn't enjoying it, so we stopped.

I wonder whether technically this counts as losing my virginity. Does virginity have to be vaginal sex? Does penetration suffice? Does there need to be climax as well? Whatever the definition, in my mind this night takes the prize.