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Anal Shoehorn 

The act of prying open a womans anus with ones fingers to allow for a larger opening to insert an erect penis. Once the penis is inserted the fingers are slowly withdrawn in a similar manner to a regular shoehorn to allow for intercourse to begin
My cock wouldn't fit in that chicks ass so I had to give her an anal shoehorn
Anal Shoehorn by seedy old man August 4, 2012

Shorthorned dribbler 

A person who's swagger is MUCH bigger than their junk..
He played her like a fiddle, got her in bed and she laughed at his shorthorned dribbler. He was hung like an angry gerbil.

Spokane Shoehorn

A sexual maneuver involving the insertion of a gentleman's testes and scrotum into a lady's vagina during coitus. The maneuver can be accomplished manually or with the aid of a shoehorn, giving rise to the maneuver's name as well as the oft-quoted saying "sometimes you just have to shoehorn them in there."
Steve: "I gave her the ole Spokane Shoehorn last night!"
Ryan: "Ladies love a man with flexible balls. Have you tried the anal Spokane Shoehorn?"
Steve: "The Spokane Valley Shoehorn?! I thought that was a myth."
Ryan: "No, it's real. My brother's friend's dad performed the first one in 1974."
To force something, usually an idea or concept, into a field in which it doesn't belong
"I really wish they wouldn't shoehorn microtransactions into these adventure games."
shoehorn by Angry Groceries June 14, 2015

Chicago Shoehorn

A driving term for an offensive lane change where a driver puts their car into a space where it doesn’t fit but their coming over anyway.
I was just in Chicago last weekend and three drivers pulled a Chicago Shoehorn on me. I had to yield or get in a wreck.
Chicago Shoehorn by R-Dickulous August 28, 2019

scranton shoehorn 

The act of inserting your penis flaccid into a rectum using your thumb as a shoehorn and then tickeling your nuts until you become erect at which point urinating is optional but preferred.
The midgets ass was too tight so I had to scranton shoehorn that slut.
scranton shoehorn by b00stinsc00by November 18, 2009