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
See
Random Words:
1.
A phrase from "Family Guy" when peter meets the US Senate to allow smoking for minors. He is greeted by Al Gore and Dick Army..