chicago deep dick

When you put a frozen cube of lube into someone and then provide the deep dick

I gave her a Chicago deep dick last night, it took forever for the KY to freeze

by Not Young Honey February 21, 2021

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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 Paycheck

When someone gets shot.

JFK cashed in his Chicago Paycheck.

by YourSexyDad March 25, 2021

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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

Where queers who's parents don't love them and live in Elmwood park think they are from

"I heard he claims Chicago"
"It dont matter, hes from Elmwood park"

by HueyLouisAndTheNewey May 30, 2021

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Chicago Snowblower

A sexual act where, at the conclusion of sex, a male ejaculates violently and excessively somewhere in the room, recreating a snowblower blowing snow. The semen is left in place for several weeks until it starts to smell and stinks up the entire room, much like how the entire city of Chicago smells awful.

"I gave Becky the good ol' Chicago Snowblower a few weeks ago and man, does my bedroom smell like shit!"

by femboydestroyer4960 September 12, 2024

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