Top Definition
Chicago Boxing is an act where one person restrains another person from behind by holding the arms of the aforementioned person while a third person punches or slaps the restrained person. Specifically, where the restrained person is a female and her breasts are slapped or lightly boxed.
Stacy thought it was funny when she hit Todd in the balls, but when Todd and Steve started Chicago Boxing her she quit laughing really quickly.
by SuperFrostedButts May 17, 2011

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