What is Chicago Workboot?
1.
While she's asleep, shit in her shoes. Hide in the closet in the morning, and masturbate almost to the point of ejactulating. When she puts on her shoes, she'll slip and fall and when she is on the ground, spooge on her face.
I totally gave that skank a Chicago Workboot this morning
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House guests that are a nightmare to house, tolerate or entertain. Someone visiting from out of town soon to be an "ex" friend..
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Something that is dull, but tries to appear significant or original.
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