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The act of masturbating while standing on an overpass or tall building, while attempting to ejaculate onto vehicles passing below.
Rahm Emmanuel left the gay club stoned and alone. Full of self pity, he stood on his balcony slapping his giblet until he Chicago Sunroofed over a passing garbage truck.
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When you fuck your girl in the ass between her buns with your “hot dog “ while squirting ketchup and mustard over her ass. Then shoot your load over her back mixing it all together with your dick between her ass cheeks. A perfect hot dog for her.
My boy Billy’s woman, Sabrina wouldn’t stop complaining how hungry she was. So he decided to give her the ole Chicago Hot Dog Stand to shut her up.
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Doing a girl while on her period. Then, taking your penis out of her vagina, inserting into her mouth. Hopefully, it ends up spicy.
"Wow, Marissa sure does love her East Chicago Hot Wing's super spicy"
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Receiving a hand job in the 300 level of the United Center during a Blackhawks game under a glorious red sweater.
I wasn't paying at attention when Dustin Byfuglien scored his third goal of the game because the girl from Beverly I met at West End before the game was giving me the Ole Chicago Yank job in Section 310
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When 3 people all of different genders insert their feet into each other’s mouths causing throw up then puke is shoved into a conform and swallowed whole. super nutritious
i just watched them do a chicago freight train in the back of the classroom
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Peanut gallery: "Look at that guy sitting in the old rickety lawn chair, wearing a V-neck undershirt, tan chinos, and sunglasses, while reading the newspaper and smoking a stubby cigar. Looks like he takes very good care of his vegetable garden, and his grandkids appear to respect the hell out of him. He's old school Chicago Italian. Oh, damn: His wife just handed him a deli sandwich from Alpine Imports and a can of Old Style! Let's get the hell out of here before he kicks our asses!"
Italian guy: "You steppa on my grass, I breaka you face!"
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The act of butt fucking a woman without penetration, in which the man's penis slides through the woman's butt cheeks, much like a hot dog enters it's buns. Ejaculation must occur on the woman's back, much like the hot dog toppings lie atop the bread. Debuted in Chicago in 2011.
She was so drunk and we didn't have condoms, so I gave her a Chicago style hot dog and got the f outta there.
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