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

The Horseless Headless Horsemann's Headtaker 

Its a Giant af sword used by the horseless headless horsemann who has too many h's.
It is given by craft with 2 refined metal, 1 haunted scrap, and 1 scotman's skull cutter i think.

Demoman: I have crafted the The Horseless Headless Horsemann's Headtaker!
Scout: cool

The Horseless Headless Horsemann's Headtaker by anonymous March 1, 2021