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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Random Words:
1.
Highschool/College slang meaning you didn't do an assignment/essay before the due date and something happens that pushes back the d..
1.
N.
1.Highest Texan Ranking.
2.Extremely Heterosexual, to the point of all men's jealousy.
"Can it get cooler than The Thom..