headless horseman

an excruciatingly pleasureful yet taxing homosexual act in which both participants are simultaneously gagged and resemble the headless horseman mounted on his bucking bronco

Neil: Great headless horseman last night. You make one hell of a stallion.

Bob: Make me your pony slut.

by Boner Jones!! March 13, 2011

headless horseman

a guy who is doomed to roam the earth looking for some head which he has sadly never gotten

a close but slightly more sad cuzin of a perma-virgin

person1:why is he talking to them fat chix...
person 2:hes a headless horseman...hes trying to find some head so his soul can rest

by Bigeast 34 April 16, 2006

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

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

The Armless Horseman

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 17, 2010

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