An alcoholic mixed drink invented in San Francisco which combines one part straight Jameson and one part straight Jack Daniels. "Headless" because you have to be stupid to order it and "horseman" because you need to be able to have the tolerance of a horse to drink it.
"Bartender, I'd like one headless horseman please"
"You seriously want me to mix jack Daniels and Jameson?"
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!
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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.
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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.
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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
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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.
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