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Chicago sausage shuffle

When you jerk off 2 people while also taking it in every hole including eye and ear hole
Jack wanted to do a Chicago sausage shuffle but I said no
by Ecrotex March 14, 2021
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Chicago penetration

The act of sticking your glock up your loved ones ass ...letting her shit on it then sticking the glock down her throat
I have my girl a Chicago penetration last night
by Randomshit34 February 9, 2017
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Chicago White Sock

A good luck pre-game ritual for Chicago White Sox fans where your girlfriend slips on a black sock (normally used for feet) on your cock and jacks you off until you cum into the sock while you sit back, relax, and strap it down with a beer, preferably a Miller lite (or modelo if your girl is Latina)

This is similar to the Clark Street Cock Sock, which is performed exclusively among men within the gay community and into a blue sock before Cubs games instead.
My girl surprised me with the ole Chicago White Sock before the game that was so good I nutted through the sock and Giolito threw a no-hitter!
by DamnGoodCockSock April 1, 2021
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Chicago French Toast

Chicago toast is fast becoming one of the most famous breakfast foods in America— with its meteoric rise in popularity being credited with Barack Obama famously ordering a whole loaf on his first day in office as POTUS.

Chicago toast is similar to classic butter toast in every way, except in that it’s only ever served in odd numbers (one slice, three slices, five slices etc). The origins of Chicago French toast is currently unknown.
Is that toast? No. It’s Chicago french toast.
by Walters Brew October 28, 2022
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outside chicago

You see, it’s not that we Chicagoans are extremely particular people; we just don’t consider it correct for someone from Naperville, Elgin, or Deerfield, Illinois, to say they’re from Chicago when they truly aren’t. You don’t hear people from some little town in California saying they live in L.A. or people from a small city in New York saying they live in New York City. You are not from Chicago; rather, you live near Chicago
"I'm from outside Chicago" " BRUH...you're from Evanston..."
by HustleSTL February 2, 2017
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bo from chicago

hes bo and hes from chicago, has some d1 prospects but dropped them for a monk. hes bo from chicago tbh.
Bo from chicago. Wow thats bo from chicago
by bdustdadawg March 6, 2023
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chicago bob

defined: the primal act of taking a woman from behind whilst her head is in a toilet
Girl he took me from behind while my head was in the toilet, he gave me a real Chicago bob!
by Doris Pringle Brule June 17, 2024
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