Worst. Sex. Ever.

Bad sex, writers admit, is often in the eye—or the Bed—of the beholder

Consider the worst sex you've ever had, the kind that made you want to crawl out of your own skin, or perhaps devote yourself to celibacy. Think your tale's bad? Have I got some stories for you.

Last year at a reading called "Worst. Sex. Ever.," the capacity crowd at P.S.122 yukked it up at organizer Chris Hampton's tale of trying to have sex in the bathroom of a group home for men with developmental disabilities where her girlfriend worked (while patients knocked on the door), Brian Grosz's attempt to bed a woman while his foot was bleeding ("I quickly scrubbed the blood off my hands, tossed the trash in the bathtub, and went back into the hallway with that Al Green 'gonna get me some' dip in my hip"), and Choire Sicha's first and last gay trick turning. Clearly, bad sex is funny, and the show became a monthly event, the WYSIWYG Talent Show (wysiwygtalentshow.org). February 15, also at P.S.122, saw a follow-up with more worst-sex tales, though, Hampton admits, "Originally, it was little more than a self-centered excuse to get onstage and tell a horrifying story about an ex-girlfriend."

In honor of this series, I've been pestering people to tell me about their worst sex ever. What's been fascinating are the tales that didn't make the cut: I heard so much about falling asleep mid-coitus and post-blowjob vomiting that such stories started to lose their luster (unlike the tale of an allergic reaction to a man's cherry-laden jism). One woman pursued a guy for months, finally landed in the sack with him, and found a dick so small she couldn't be sure they were having sex (sadly, they were). For the winners in the "worst sex ever" category I wanted anecdotes that stuck in my mind, made me laugh or cringe, or best of all, left me wanting to repeat them incessantly.

Thankfully, my friend Anna has countless tales of sex gone wrong. Anna is hot. Tall, blonde, and busty, she wears tiny shirts that barely cover her boobs, and glasses that make her look like the consummate naughty librarian. She exudes sex and, in fact, works in a sex-related field, yet her stories make her sound like sexual poison. Once, after a very brief sex session, her lover propped himself up on the bed and, instead of complimenting her on her efforts, said, "Has anyone ever told you you have a spacious vagina?" Another time, a girl asked her, "Are you sure you've really been with girls before?" A boyfriend's friend told him, "Anna's the least sexual person I know. How do you think she would reproduce? By budding? Like a plant?"—a line which said boyfriend then repeated to her.

Were these people socially awkward losers? What gives? I asked Anna. "Because I'm open about sex, people in turn feel comfortable being open about sex with me. The result is, I've been known to set the stage for a little too much honesty. Not everyone has the ability to distinguish between a healthy level of openness and being brutally and unnecessarily truthful."

Cheryl B. gave me a preview of the story she read at WYSIWYG. "It's about a guy with a really big cock," she gleefully recalled. What could be so bad about a guy with a big cock? "He didn't know how to use it," she explained. "What made the experience so horrible was his obsession with the size of his penis and his lack of interest in doing anything that didn't include it. I wondered if it was my fault, but realized later that it was his problem, not mine."

I asked Hampton why bad sex is so compelling. "Everyone has had bad sex at some point or another," she said, "and it can be pretty comic once you get a little distance from it." It's certainly ripe territory for laughing at oneself. Peter Hyman, who recounts some of his worst sex in essays like "Menage à Faux Pas" in the collection The Reluctant Metrosexual (Villard, 2004), has an interesting take on the topic. "Bad sex is bad for a lot of reasons, one of which is that you've probably cleaned up your apartment in anticipation of an event that really did not call for such tidiness. No sex at all is much better than bad sex, because with the no sex option, you can at least be alphabetizing your DVD collection, or catching up on your bill paying." Neal Pollack, who writes the Bad Sex With Neal Pollack column at nerve.com, says the only redeeming quality of bad sex is that it "can sometimes lead to good sex if talked about in the right way."

What's most interesting about hearing people's bad-sex stories is how many of them involve not the mechanics, but the aftermath. One woman, whom I'd forgotten to contact, eagerly reminded me that she had a story to share. But when she finally told it, her story didn't seem that awful: a half-hearted round of sex with a guy with a small dick. It wasn't until the next day, after he was long gone, when she found herself locked out of her apartment because he'd flipped a lock she never used, and had to divulge to both her neighbors and roommate what she'd been up to, that things started to disintegrate. "I would say it was the worst sex I ever had because in addition to the sex being really bad, I had to admit to other people that I'm a big slut." On the other hand, a really dirty, explicit message left on the apartment's communal answering machine by a paramour was just "embarrassing" for her.

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