Virgin Voyages: Want To Be Best F**k Friends?

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On Tuesday’s episode of “Guy Code,” the cast will talk about losing your virginity. Some of us here at Guy Code Blog are sharing our stories. #Don’tJudgeUs

I had a couple drunken oral forays my freshman year of high school, then I quit drinking and getting anywhere with girls. I kept smoking cigarettes though, which meant I hung out at the edge of school property with a diverse bunch of f**k-ups.

One night senior year, I’m talking on the phone with one of said f**k-ups, Jessie, a junior who I made out with at a New Year’s Eve party a week earlier. She’s implausibly hot–way out of my league–but I don’t understand how low self-esteem affected decision-making back then, so I feel like this is happening because I, too, am hot.

The girl has the voice of a developmentally delayed gangster, and she starts telling me how she wants me to be her “Best F**k Friend.” I don’t know if physicists can measure the increment of time it took me to reply, but five minutes later, I’m driving to her house to pick her up. You don’t make gangsters wait, you know?

She reminds me to get condoms, so I go to the gas station where Joe, the night guy, sold me cigarettes underage, and I try to play it cool, buying cigarettes and then condoms as an afterthought. But when I ask for condoms, Joe shouts my name to the heavens and hugs me tight. How did he know I was a virgin?

We drive to the only secluded place in my town, a place I found thanks to years of hotboxing my car with friends. We smoke cigarettes, letting all that January air in. We start making out, but now we’re too cold to be both naked and able. Pretty sure my parents had gone to a movie, I invite her back to my house.

My room’s about to become a kinky doctor’s office: we take off some of our clothes, lie on the bed, and then very methodically try each position. Rather, she teaches me each position because she’s lapped me (and most other people) around the block. But this is before porn videos were all over the internet, so I don’t know how to make even a sleazy effort at pleasing her.

Not being used to condoms, I have to finish the way I’ve had to since seventh grade. We put our clothes back on, go to leave, but as we walk downstairs, my parents come in. They see an attractive girl they’ve never met, and their son who smells vaguely of semen, which they’re definitely used to. They try to be polite but are too embarrassed for me to drag it out, so they let us go.

I went two years before I had sex again, and again it was from a girl who wanted to be dirty BFFs. And again I was bad at it.

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Charlie Kasov (@charliekasov) is a comedian and writer based in Brooklyn, New York.