The act of vigorously fucking the empty sleeve of one's winter coat, often leather. In the act of Armless Horsemaning the person usually ejaculates into the sleeve of said winter coat.
My roommate just did The Armless Horseman into my new leather jacket!
by PerkinsHadSexWithFiala December 15, 2010
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The disappearance of the head due to the act of shoving it up a vagina.
I dove my head in vertical and performed the Headless Horseman.
by Goods and Wares May 11, 2006
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A spasticated, autistic horse called Tyler Cornelius and he has the same hair style as sonic the hedgehog because Tyler is a smelly nonce and a pedo
Tyler is a dumbass horse thst has mentally stupid autism this defines the word Bojack Horseman
by BenKeenan03 May 28, 2019
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The result of someone getting their dick severed in the door of a Ford Mustang.
Watch out Jimmy! You almost shut your dick in the door and gave yourself a headless horseman!
by Moe Beer August 22, 2007
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Fucking a girl while she's on top with a bag on her head.
I had to give these beat girl the ol' headless horseman cuz she was a butterface.
by Kyle June 15, 2004
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When a man cuts a jackolantern face in a pumpkin and jacks off into it
I heard Chris had fun on Halloween. He totally did the headless horseman to Mrs. Grossman's jackolantern.
by Dirrrrrrty Frrrrrreaks October 05, 2008
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