Chicago Strawberry

When you stick a strawberry roll into a woman pussy and eat it out of there before fucking her

Last night I gave Taylor a chicago strawberry before I gave her the cream filling.

by Tool1979 February 26, 2021

chicago shoeshine

When you pay $20 to a homeless person to get you off on the side walk. Then they wax your shoes clean with a mixture of their spit and your spooge

Livingston was lost on Ohio St. so he paid a homeless guy for directions and ended up getting a Chicago shoeshine. It was more than he bargained for.

by The Sweens June 19, 2016

oral chicago

a sexual act also referred to as "deep dish" where a woman's sexual partner accepts her juices in his/her mouth and uses them to flavor a deep dish pizza or a hot dog

Andrew enjoyed giving Molly oral sex so much, he asked her if he could perform an oral chicago.

by Big Donkey 16 November 12, 2013

Chicago Slide

Used as another name for the Chicago Sweep.

Rather than stopping at a stop sign, a driver slows to a roll and then immediately accelerates as soon as they can't read the stop sign anymore.

Named for the technique used by the vast majority of Chicago drivers when no one is around.

"Yeah, I just sat there and watched that cop Chicago Slide through that stop sign."

by pressyglue July 7, 2018

judy chicago

a feminist queef

I hooked up with that hairy-armed pink pussy hat wearing FemiNazi after the Antifa rally and she Judy Chicago’d so loud it woke up the dog.

by Salohcin2 October 25, 2019

Chicago Suntan

Getting flayed in the pattern of a farmers tan

Ah man, did you hear what happened to Johnny Two-socks? Earned himself a Chicago suntan

by SuspiciousPelican June 22, 2023

Chicago Mary

Another term by JC in Chicago. This is an affectionate term for all those attractive middle aged women (MILFS) that come to Chicago on business and troll the local bars looking for a one night sexual adventure.

She said she was from Kansas here on business but, turned out to be a Chicago Mary.

by Senior Elstonia May 2, 2015