headless horseman

An uncircumcised penis.



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

Bob: Make me your pony slut.


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
Example:
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


headless horseman
Fucking a girl while she's on top with a bag on her head.
Example:
I had to give these beat girl the ol' headless horseman cuz she was a butterface.


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


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