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 HGrizzy July 1, 2011

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 29, 2009

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 October 3, 2008

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 11, 2006

headless horseman

An uncircumcised penis.

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 Schuhdaddy October 31, 2007

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!! February 27, 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 March 13, 2006