Define The Headless Horseman Meaning

Headless Horseman
When the driver, preferably girl, gives a blowjob to the passenger. Often confused with road dome. Except this gives off the appearance no one driving the car, like the headless horseman.

Heard he got road dome!!-Jeff
Nah bitch he got dat headless horseman shit, she was driving!!!-Grizzy
By Amabelle
Headless Horseman

I coudln't believe it when that Jewish guy whipped out his headless horseman, I thought those guys had some kind of foreskin trimming part or something.
By Kalinda
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 Sibby
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 Caprice
Headless Horseman
The extremely rare occurance of a penis with no head.

What? Do you have a hydra?
No..its headless horseman.
By Brena
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 Emmi
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 Cordy
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 Rena
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 Molli
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 Bobinette