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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 October 5, 2008

2๐Ÿ‘ 6๐Ÿ‘Ž


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

1๐Ÿ‘ 2๐Ÿ‘Ž


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

16๐Ÿ‘ 7๐Ÿ‘Ž


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

26๐Ÿ‘ 19๐Ÿ‘Ž


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

21๐Ÿ‘ 19๐Ÿ‘Ž


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

14๐Ÿ‘ 16๐Ÿ‘Ž


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

11๐Ÿ‘ 13๐Ÿ‘Ž