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2.
During the act of anal sex, a man will pull his penis out of another mans anus and insert the poop covered wiener into the armpit of the reciver. He will then continue to make love to the armpit untill an ejaculation is achieved. At this point the man will ejaculate into his hand and rub it onto his penis. To complete the Chicago Dog the man will insert his poopy, armpit, sperm covered wiener into the mouth of the reciever.
Jesus, your breath smells terrible! Did you just eat a Chicago Dog?
by Joey Bagel October 16, 2011
 
1.
When you take your penis and have sex with only a person's butt cheeks. Sliding back and forth like a hotdog in a bun. Eventually climaxing and releasing the spicy mustard.
That lady has such a wonderfully round ass, I would love to give her a chicago dog.
by PlumpFrankfurter March 05, 2010
 
3.
while fucking a person in the anus, you punch them in the kidneys untill the shit or deficate on your cock
I was drilling the bitch and gave her a chicago dog and she gave me all the fixin's
by MlLF Hunter April 26, 2006