The Headless Horseman

When a man cuts a jackolantern face in a pumpkin and jacks off into it

I heard Chris had fun on Halloween. He totally did the headless horseman to Mrs. Grossman's jackolantern.

by Dirrrrrrty Frrrrrreaks January 17, 2009

The Headless Horseman

The girl pulls shirt over her head with a cock in each hand

Heather decided to celebrate halloween by giving mike and mike the headless horseman

by mcj football sunday October 23, 2011

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 2, 2011

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 November 19, 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!! 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