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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What the hell is going on?!
Joe: I'm leaving my girlfriend and starting a new life in Bulgaria with my new boyfriend Fredrico!
Am..