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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 January 17, 2009
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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
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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
by omgwhatiswhy November 17, 2023
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