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Chicago goatse

To make monkey noises while spreading your buttcheeks all while forcing all blood pressure to your rectum.
Hey man, did you see TheDooo when we drove by? I think he was doing the “Chicago Goatse” on the sidewalk…”
by JvstSayin178 January 16, 2025
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Chicago goatse

The Chicago goatse is when a man and woman engage in funky time and the lady sticks 8 of her fingers in your ass and stretches your hole as far as it will go the Chicago part comes into the equation when the lady uses au jus as the lubricant
“I was with Melissa the other night she gave me a Chicago goatse!”
Damn dude rip your ass
by Zanderguy January 16, 2025
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Chicago flicker gooning

When you get a BD to edge a GD which causes a universal blue and red nut to flood the streets of Chicago
God damn those Chicago flicker gooning gooners there gonna flood the streets
by Not south side February 8, 2025
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Chicacheeks

a women with a nice set of buns.
Wow that women’s got chicacheeks” “hey chicacheeks”
by Thatonemech April 10, 2025
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Chicago Freestyle Bandit

When a male urinates inside his partner.
Bro, I had like six liters of beer before we got to it. I had to go so bad, I accidentally became the Chicago Freestyle Bandit. I wonder if she'll want to see me again.
by Curtis Claymore April 15, 2025
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Chicago Hair

A term used to describe a young man who is balding or trying to hide his bald spot—often by wearing a hat. The name “Chicago Hair” comes from the windy reputation of Chicago, where a strong gust could easily blow off a hat and reveal a hidden bald patch.
Man: “Let’s go swimming on the first date—so you cant catfish me with your makeup or filters.”

Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
by yunggravy4 April 22, 2025
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Chicago Hair

A term used to describe a young man who is balding or trying to hide his bald spot—often by wearing a hat. The name “Chicago Hair” comes from the windy reputation of Chicago, where a strong gust could easily blow off a hat and reveal a hidden bald patch.
Man: “Let’s go swimming on the first date—so you cant catfish me with your makeup or filters.”

Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
by yunggravy4 April 22, 2025
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