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The act of using a finger to slide a penis into a tight vagina, normally a vagina, imitating the act of using a shoehorn to slide your foot into a shoe.
Guy: Dude did you hear about Jac?
Fag:No, What?
Guy:She got shoehorned by that dirty redneck.
Shoehorn by Jacky got shoehorned January 29, 2008
To "Shoehorn" is the ability and occasional obligation to assist a friend in charming and seducing a girl of their choosing.

A "Shoehorn" is the exact opposite of a "Cock Block". Rather than steal or discourage his/her girl you do your fucking best to get him/her a piece of that ass.
Seriously man I need this. Can you please shoehorn me this time?
Shoehorn by Martles the Great February 12, 2009
A move used on a virgin. You stick a finger or thumb into the vagina, so it makes it easier to get that big ass dick into that slut, bitch, or cunt.
My cousin Kyle once used the shoehorn to fuck dat bitch Jacqueline.
1. (noun) a young woman, usually under thirty, with the implication that her vagina is excessively small(tight) so that one may "need a shoehorn" to insert anything into it, i.e. a penis, finger, dildo, squash or coke bottle
"Nice...look at that shoehorn sitting over there."
"Laura was a shoehorn; I had to work it for 45 minutes until I could hit it."
shoehorn by schlitznola May 31, 2009

Long Island Shoehorn

When a man is about to cum, he pulls out and ejaculates into the heel of a particularly tight pair of dress shoes in order to ease the passage of his foot into said shoes.
I never thought I'd fit into my size 9's for the wedding until a Long Island Shoehorn provided the lube to fulfill this impossible dream.

Alaskan shoehorn 

there is a girl and a guy in the mountainman position. Under the girl is another girl eating her out. As she is eating her out, the guy puts his dick is the girl getting eaten out. Before he cums, he pushes the girls off the rockwall then sprays the cum down on their stomacks. He jumps down and rubs his belly in it
I totally got 2 girls in the Alaskan shoehorn last nights
Alaskan shoehorn by brankle June 28, 2009