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Illustration by Barry Bruner

Bad sex stories

Readers recount their worst sexual experiences.


Magic hell
My first boyfriend and I fancied ourselves the experimental types. One night, in a fit of giddy inspiration, we bought a bottle of Magic Shell syrup—that stuff that hardens into a candy shell the minute you squirt it onto your ice cream. We were both so excited at the prospect of turning my nipples into candy-coated chocolate treats that we totally whiffed on the logistics. Magic Shell works on ice cream because it’s cold. When applied to room-temperature flesh, as we soon learned, all you get is runny, weird-tasting chocolate syrup. I was disappointed by the results, but my boyfriend was devastated. He tried blowing onto my Shell-covered nipples to cool them. He even tried icing them before applying the chocolate, but nothing would coax the syrup to solidify. It was a rude reminder of the laws of physics. —female reader, Wicker Park

Not that kind of dirty
One night my girlfriend and I are making out, and it’s getting hot and heavy. There’s biting and licking and heavy breathing. I say to her, “You like that?” “Yeah, yeah, I like that,” she says in a loud rasp in my ear, which I’m digging. “Hey, talk dirty to me,” I tell her. “What?” “Yeah, come on,” I say. “Anything, just try it.” We continue to make out, and I can hear her breath in my ear, but she’s just not comfortable with it. At the same time she’s getting all excited. “Come onnnn,” I whisper in her ear one more time. She leans in close to my ear, in rapture, and not thinking too clearly: “You’re an asshole…a dirty asshole.” —male reader, Wrigleyville

Fang bang
My ex-boyfriend had a thing about vampires well before Twilight was inflicted upon pop culture. Books, movies, music, decor—if it said “goth” or “undead,” he was into it. Unfortunately, this appreciation managed to find its way into our foreplay, to the extent that my normally sweet and good-natured boyfriend liked to savagely attack my neck with his teeth. It wasn’t that he was trying to draw blood—he just really liked to bite. —female reader, Ukrainian Village

Safe but unsound
I asked what her safe word was. She insisted it be mom. Ick, ick, ick. —male reader, Oak Park

Digital broadcast
This is an all-points bulletin to the hetero guys out there, from the ladies: Please stop with the fingerbanging. What’s that? Only giddy, inexperienced high-school boys would think that’s erotic? Not so. I can’t tell you how many men in my adult life have tried to jab me repeatedly in the vag, sometimes without clipping their nails first. Ouch. You may think it’s an appetizer before the main course, but I for one, would like to skip right to the sausage. —female TOC staffer

Undead in bed
To say that the guy I dated a few years back was “socially awkward” would be an understatement—and an upgrade. But all was well for us in the bedroom until one night when he decided to get his dirty talk on. While on top of me, he bored holes into my head with his eyeballs and asked in the flattest of monotones: “Do you like it when I penetrate you?” I think he was going for intense, but the effect was more dead-eyed serial killer.—female reader, Uptown

Double trouble
My best friend from high school and I went to college together, returning home most weekends to visit our boyfriends, who also happened to be BFFs. On one visit, as my guy and I were in the throes of passion, he suddenly tried to sneak in the back door! The poke was a complete surprise! I was mortified and told my friend the next day. She could not believe it—turns out her guy had made the same backfired attempt. On the same night. We were disgusted by the surprise, but even more grossed out that they’d conferenced about it before ambushing us from behind. Not cool! —female reader, South Suburbs

P.S. I love spew
A few years ago, this guy I had gone out with a few times came over to my place and made dinner. Nice enough, especially considering he had been complaining of nausea. After dinner, he disappeared into the bathroom and what sounded like some serious puking ensued. When he reappeared, he started whining that he really wanted to make out with me. Needless to say, the combo of barf breath and the prospect of him upchucking again made this is a less than appealing proposition. When he pleaded that he could just run home—an hour away—to grab his weed stash to quell his queasiness, I had to lock the door behind him and declare the night officially over. —female reader, Avondale

Our hot make-out sessions were damped by her need to set the mood by playing Yanni CDs. That’s right, Yanni—pretty much the soundtrack for erectile dysfunction. —male reader, Oak Park

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