A few weeks back I invited readers to share their most horrifying true stories of desperate and/or depressing holiday sex. As promised, the author of the best horrifying true story–as determined by me–wins a $75 Toys in Babeland gift certificate. See if you can spot the winner before you get to the end of the column…

I moved away from my friends and family last year to Seattle. As I left work on Christmas Eve, some homeless people were having a trash-can-fire, plastic-bottle-liquor hoedown on University Ave. I figured what the hell and decided to join in. I wound up sharing a bottle of cheap vodka with one particularly attractive homeless girl. My judgment eroded, I invited her back to my apartment. Before I could protest, she invited two of her friends to join us. My Christmas Eves until this point in my life had been Norman Rockwellian cliches. This particular year, I had an all-night drunken orgy with three homeless girls. We fucked our brains out, baked cookies naked, and fucked some more. When I woke up in the early afternoon, the girls were gone. So were my wallet, most of my food, my toiletries, and my CDs.

Best of Chicago voting is live now. Vote for your favorites »

–Freaked Out Then, Freaked Out Still

My ex-girlfriend was in town from college and called to ask if we could meet up for a beer. Eventually the Coronas became tequilas. After we staggered out to my freezing car, she pulled my face down to her crotch. After I had gone down on her for five minutes, she lifted my head up and, sobbing, told me that she couldn’t do this, that she had a boyfriend she loved. She begged me to take her to a pay phone so she could call him and apologize. I drove around for a while, hoping she would calm down and not make the call. But when we drove past a gas station she demanded that I stop. After she was on the phone for a few minutes, she motioned for me to get out of the car. “He wants to talk to you,” she sobbed. Here’s how our conversation went:

“Went to a bar. Ate your girlfriend out. She started crying. That’s about it.”