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.
To have submitted and been approved for publication by slangdefine
Tom: "Yo shitface, I just thought of a great word for slangdefi..
1.
Inspired by the gay faggot on American Idol 6.
A person that cannot sing at all
Also used for a person with no talent.
An ugly fucki..