The act of defecating on the back of your one night stands head before leaving their house in the middle of the night.
Mark: Did you hear what happened to Steve Last night?
Jenny: No....Is he OK??
Mark: Yeah, just got The Chicago Woodsman from his one night stand
Jenny: No....Is he OK??
Mark: Yeah, just got The Chicago Woodsman from his one night stand
by The Real Woodsman September 13, 2023
Get the The Chicago Woodsmanmug. 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?”
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
Get the Chicago Hairmug. the act of a male ejaculating through a Red Vine, followed by the female sucking all of the semen out. Consumption of the candy afterwards is optional.
by bigdog4448 June 13, 2020
Get the the chicago red shoot-n-suckmug. When you nut on your girlfriends back while your upstairs neighbor floods their condo soaking your entire bedroom
"I can't escape living in a place where it rains indoors. This is the third Chicago Wetback I've had in a row. I'm so over this curse"
by anonymous August 4, 2025
Get the Chicago Wetbackmug. A Chicago Truffle Power Couple (known as gooning squared) is when a man edges himself for hours, sometimes in multiple spurts, to achieve something of a trance state of being. His dick and body are aligned, and he has lost control of most motor skills, cognitive ability and communication ability. His body reverts to shaky, jerky motions, tounge sticking out, dull expression in his eyes, face. All communication is done with grunts and moans, and all thinking ability is removed. He is white as a sheet and embodies a walking, living erection. The woman he is with (the squared part) also edges herself into this same state, sometimes using the man’s dick to edge herself, and becomes a “goonette” or “truffle”. Together they make the Chicago Truffle Power Couple, being many of headlines in newspapers thanks to their deregulated motor skills and antisocial behavior. These couples usually manifest themselves in low income areas or low iq areas (more if these overlap) and are very entertaining to watch. They exit this state when they ejaculate, and revert back to their normal, much less fun state.
Look at those people over there, they are completely whacked out!
Yeah, that’s the local Chicago Truffle Power Couple, they are at the peak of the gooning cycle. They’ll be arrested for public indecency here before too long, get a bag of popcorn.
Yeah, that’s the local Chicago Truffle Power Couple, they are at the peak of the gooning cycle. They’ll be arrested for public indecency here before too long, get a bag of popcorn.
by Lostnationmudflap July 19, 2025
Get the Chicago truffle power couplemug. Safe not dangerous town full of Mexicans boring really boring nothing to do also known as west cheesy n idk what else yall good luck if you come🙏🏽🙏🏽
by Alicruz May 26, 2024
Get the West chicagomug. Person 1: "Dude that chick last night was crazy!"
Person 2: "how come?"
Person 1: "she had her cats in the room while we were having sex!"
Person 2: "Oh like a Chicago Cat Mom."
Person 2: "how come?"
Person 1: "she had her cats in the room while we were having sex!"
Person 2: "Oh like a Chicago Cat Mom."
by SpankyHanky69 August 23, 2020
Get the Chicago Cat Mommug.