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.
Bob: Make me your pony slut.
by Boner Jones!! February 27, 2011
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
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
person 2:hes a headless horseman...hes trying to find some head so his soul can rest
by Bigeast 34 March 13, 2006
by Scotsburn July 29, 2009
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?"
"You seriously want me to mix jack Daniels and Jameson?"
by Halbert9000 September 6, 2017
by Matt McL. Helped by Eric October 3, 2008
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.
by PerkinsHadSexWithFiala December 15, 2010
by Goods and Wares May 11, 2006