Chicago Workboot

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

Chicago Workboot by Jordan L. Gibson October 9, 2008

rusty work boot 

A kick to the vagina while the female is currently having her periord or on the "rag" if you will.

"That bitch was pissing me off so I gave her a rusty work boot."

rusty work boot by Birdo McGee May 2, 2006

work boot tongue 

A vagina so beaten up it looks like an old tongue out of a work boot.

middle aged women suffer from work boot tongue

work boot tongue by work boot tongue June 25, 2008

Workbooked 

Caught using facebook at work

Kyle was workbooked yesterday when my manager walked in

Workbooked by tweedle-dum May 5, 2010

Filipino Work Boot 

The Filipino Work Boot is a lewd act involving the act of ejaculating into a shoe, slipper, or otherwise foot holding device. It is extremely hilarious, and should be performed at least three times a week for good measure.

"Man, Tim was pissed when he put on his moccasins and found out I had given him a Filipino Work Boot"

"Wow, you are awesome and not fat at all!"

Filipino Work Boot by Chunk Knuckle February 27, 2010

workbook 

"Workbook" -- A word formed by combining the two words 'Work' which is defined as "A form of torture which can occur anywhere but is executed mostly in places where it is needed e.g. School" and 'Book' which is defined as "An object containing information or 'Hell' that is used for the purpose of education or 'Torment'. This word is hardly used by students but when heard is like saying 'Voldemort' in Harry Potter and is despised by many.

"Don't ever mention the term WORKBOOK in this house again!"

workbook by Fermin Nasol November 26, 2007

Workbook Monkey

When implementing Workday, and working with consultants that don't actually know anything to help you optimize your processes, all they can do is tell you how to fill out an Excel workbook.

We need to transform this process, but John is just a workbook monkey, he can't help us.

Workbook Monkey by Agamemnon999 October 30, 2025