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 Chicken

A complex sexual act involving five men and 1 woman. The woman takes one cock in her mouth, one in the pussy and one in her ass, whilst the remaining lucky two guys fuck her armpits. This results in the woman gagging and flapping like a headless chicken.

"Dude I'm glad that girl shaved her armpits before last night!"
"Yeah me too, we totally headless chickened that bitch!"

by KFHC September 17, 2008

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 Moe Beer August 23, 2007

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 Kyle June 15, 2004

Headless oscar

When one cuts tip of penis off, plugs into sex partners asshole, then put the headless shaft into the vag.

I rode over to my girls house slap her in the mouth then gave her the best headless oscar she ever got.!

by irish cockfoot August 04, 2010

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 05, 2008

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