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 team people are thought to be insane if they root for after over a hundred years of no titles or championships, and people still root for them anyway, because winning is not the point of everything in life.
Not many other sports teams would keep people rooting for them after not winning for so many years, a lot of people would abandon a different team than the Chicago Cubs.
by The Original Agahnim July 1, 2021
Get the Chicago Cubsmug. Eddie “hey homie, where’s my house at?”
Chicago Housing Authority (the Governor) “hey, here’s a multi million dollar penthouse cuz you’re black”
Chicago Housing Authority (the Governor) “hey, here’s a multi million dollar penthouse cuz you’re black”
by Hood rat chiraq bud December 17, 2023
Get the Chicago housing authoritymug. The act of sticking your glock up your loved ones ass ...letting her shit on it then sticking the glock down her throat
by Randomshit34 February 9, 2017
Get the Chicago penetrationmug. 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.
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
Get the Chicago White Sockmug. by Ecrotex March 14, 2021
Get the Chicago sausage shufflemug.