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.

Headless Horseman by Goods and Wares May 19, 2006

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!

Headless horseman by Moe Beer January 2, 2009

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.

headless horseman by Kyle June 15, 2004

Headless horseman

Something that accidentally went free on November 15 2023

1: yoooo did you hear headless horseman was free?
2: really? I should have gotten it

Headless horseman by omgwhatiswhy November 17, 2023

headless-horseman style 

a method of dismembering in which a part of a whole is separated from its larger body in a manner that is especially clean and quick, leaving no remnant on the larger body except a clean slice.

Amy: Yesterday I drove too close to a construction barrier and ripped my passenger side mirror off.

Gary: Like clean off headless-horseman style or did it hang?

Amy: Clean off.

headless-horseman style by wisler April 22, 2009

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.

The Headless Horseman 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

The Headless Horseman by mcj football sunday October 23, 2011