chicago whitesock 

taking your used condom and putting it on the girl's foot then telling her to take her walk of shame like that.

I totally gave her a chicago whitesock last night. The walk home must have been brutal.

chicago whitesock by jinjabread_man February 24, 2011

Chicago homeless 

the classiest people you will ever meet, they would never involve them self in any sort of trouble or nonsense. they are a higher class of homeless than the homeless anywhere else in the world! they don't touch any illegal paraphernalia and are considered to be at a higher social class level than the wealthy citizens of Chicago.

Indian girl "Homeless people carry guns and rob people wherever you go in Chicago it's not safe anywhere. i can't even walk to my dads house which is 5 steps away without getting robbed by a hobo that's strapped up!"

Smart socially cultured person "No they don't, they have principles and are good people, they help you in times of need and will watch your kids and raise them like their own. The only better suited creature to raise your children better then a Chicago homeless person would be an alpha wolf or lion with wings. they are majestic and beautiful people and they can only be found in Chicago."

Indian girl "idiot no, i make eggs so i know everything"

SMCP "you'll never understand i give up..."

Chicago homeless by Dom988 February 7, 2014

chicago steampump 

The Chicago Steampump is a unique act. This is the fetish in which two lovers have sex and one lover has a large penis. The man with the large penis furiously gives anal to the other lover till they rip the lovers stomach open. Causing the acid to pour out on the large penis.

Man I wanna give that girl a Chicago Steampump.

chicago steampump by daleppard August 7, 2014

Chicago Pizza 

Exclamation. This is a statement indicating the highest approval of something. It can be shouted or whispered or spoken at any volume in between.

The studly porn star, after having sex with a new partner, was so impressed that, he forever after, referred to her as Chicago Pizza.

Chicago Pizza by Frank Le April 3, 2015

Chicago Style Surprise 

This is the Chicago Style Blowjob, Surprise variant.
This time, instead of ya girl giving you a blowjob with you dick in a hot-dog bun with mustard, relish, onion, pickle, tomato, and celery salt, in that order. (But never ketchup, ketchup never belongs on a Chicago Style Hotdog), you put your ween in said bun and surprise her (or him, we don't judge) by sticking the Chicago Style Ween in her puss or Bunghole.

I was feeling a little spicy last night, and you know my girl likes surprises, so I gave her the Chicago Style Surprise.

Michael was being a real d*ck, so I gave him a Chicago Style Surprise he would never forget.

Chicago Style Surprise by NateTheOriginal June 2, 2017

Chicago Deep dish

A Chicago Deep dish is when an uncircumcised man pulls his dick skin up and over head of his penis creating a small well and then another man ejaculates into that well.

It took some goading but my buddy Carl finally gave me the Chicago deep dish I have been begging for.

Chicago Deep dish by mighkey November 4, 2022

lilGOTH of chicago

me

i'm the lilGOTH of chicago

lilGOTH of chicago by lilGOTH of chicago January 22, 2009