Sarah Silverman Loses Her Virginity

"As it turned out, there's a reason thirty-year-olds sleep with nineteen-year-olds."

BY SARAH SILVERMAN

Like in Every Young Girl's Dream, My Delicate Flower Is Taken by a Gruff Thirty-Year-Old Comic from Queens Who Is Emotionally Indifferent to Me

Kevin Brennan was the emcee on open-mic nights, Mondays, at the Boston Comedy Club on West 3rd Street in the West Village of Manhattan. I had a job passing out flyers for the club every Thursday, Friday, and Saturday from 4:00 p.m. to 2:00 a.m., and besides my ten-dollars-an-hour payment, I could go up on open-mic night without bringing two friends (a prerequisite for open-micers was that they had to bring two paying customers).

Kevin was tall with dark brown hair and a white-and-red blotchy Irish face. He wore a long army-green trench coat and carried a briefcase, which, at nineteen, I found very impressive. And he was thirty — a grown man. He stood outside the club smoking a Merit Light. I went outside and bummed one. 
 
kevin: So, you go to school?
me: Yeah. NYU.
kevin: What — are you a freshman?
me: Mm-hm.
kevin: What — are you, like, in a sorority?
me: Yeah, but you can only be in it if you're really cool.
kevin: Yeah? Who else is in it?
me: Just me.
He laughs. 

Let me take a moment to describe myself here: big curly perm, black polyester shirt with long shear sleeves, black miniskirt, and Doc Martens with thick black socks. It was 1990.

I did my five minutes and stayed for the rest of the night until the show was over and Kevin was going home.

"You wanna see my apartment?" He chuckled, I assume at his paper-thinly veiled offer. "It's in Queens."

"Sure. Yeah."

And off we cabbed to Astoria, Queens. We walked up a stairwell and through a hallway to his apartment. It smelled good to me. It smelled like first grade for some reason. Something industrial but sweet, like old paint and licorice. Inside there was a small living room, a bathroom, and two bedrooms — one his and one his roommate's. On the coffee table was a Best of Chicago tape. He also had a stack of records, with the Go-Go's Vacation on top.

"Wanna see my bedroom?"

"Okay."

He led me to his bedroom — a bed, a dresser, and an ashtray. He kissed me while he laid me back in his bed.

"Have you ever had sex before?"

"Yes, I've had sex before," I said, insulted.

Here's the thing. I thought I had had sex. My senior year of high school I visited my sister Laura at Boston University, and she fixed me up with a friend who was from all accounts very good-looking. I knew he was the kind of guy girls in my school would think was really hot. He was in college; he was tall and lean and had long hair and a long beard — like a sexy Jesus. We sat on my sister's tiny living-room couch and watched Dead Ringers, a creepy Jeremy-Irons-as-twin-gynecologists thriller and fell asleep before anything really serious happened. The next morning my sister and her roommate left early for the AIDS Walk, and this guy and I — yipes, I can't remember his name, maybe Brooks or something like that — moved into my sister's bedroom. He put on a condom and pushed against me, but there was honestly no hole there. I figured that was it. The guy just pokes hard between your legs for a while. Sex. When he finally gave up, he said, "It's not like it is in the movies, Sarah. Is that what you thought?" Which was a weird thing to say right after watching Dead Ringers.

"No," I said defensively.

So when Kevin asked me if I was a virgin, I answered honestly: no. Somehow I think he knew better than me, because he pretty much instructed me through the whole process. He talked me through my first blowjob (that, I admitted I had never done before), what to do with my tongue, what not to do with my teeth, and so on. And then, slowly at first, he pushed inside me. All the way inside. And all I could think was,

Holy shit, THIS is sex, Dummy.

He sat up on the side of the bed to smoke another Merit Light, carefully ridding the end of any excess ash, molding the red tip of it into a constant point. He put out his cigarette and pulled back the sheets to get up, revealing a Rorschach-like pattern of blood. Like a red butterfly stamp, getting lighter and lighter with each imprint.

There was a long moment of silence before I worked up the moxie to say,

"That came out of you."

"Um. No it didn't."

Another long pause, broken by him,

"It's okay. Just buy me new sheets."