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Farting while getting a blowjob or rimjob. Named because Chicago is the Windy City.
What went wrong? I gave her a Chicago Surprise.
12👍 4👎
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.
2👍 2👎
The act of leaving ass pennies around town for unsuspecting pedestrians to find.
I was walking by the Willis tower when I bent down to pick up something shiny. "Wow," I thought, "a lucky penny. My luck is surely changing!" I couldn't have been more wrong. As I drew the penny near my face for a closer look, I could tell that I was being punked. The smell of copper laced with rotting feces left no doubt. I'd just found a Chicago Surprise.