Headless Horseman

The extremely rare occurance of a penis with no head.

What? Do you have a hydra?
No..its headless horseman.

by Scotsburn July 28, 2009

Headless horseman

An alcoholic mixed drink invented in San Francisco which combines one part straight Jameson and one part straight Jack Daniels. "Headless" because you have to be stupid to order it and "horseman" because you need to be able to have the tolerance of a horse to drink it.

"Bartender, I'd like one headless horseman please"
"You seriously want me to mix jack Daniels and Jameson?"

by Halbert9000 September 8, 2017

The Horseless Headless Horsemann's Headtaker

Its a Giant af sword used by the horseless headless horsemann who has too many h's.
It is given by craft with 2 refined metal, 1 haunted scrap, and 1 scotman's skull cutter i think.

Demoman: I have crafted the The Horseless Headless Horsemann's Headtaker!
Scout: cool

by anonymous March 1, 2021

Headless Horseman

While driving a car, the driver gives the passenger oral pleasure.

I gave that bitch a headless horseman while driving to her parents house.

by Matt McL. Helped by Eric January 16, 2009

Headless Horseman

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 19, 2006

Headless horseman

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 January 2, 2009

headless horseman

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