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headless horseman

I coudln't believe it when that Jewish guy whipped out his headless horseman, I thought those guys had some kind of foreskin trimming part or something.
by Schuhdaddy November 19, 2007
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Bojack Horseman

The most, depressed, traumatized, alcoholic, drug addict, idiotic, stupid, selfish, bad person (or horse) to ever exist.

If you are a BoJack horseman kinnie, consider yourself sick, kinning bojack horseman is an illness. (I myself am a BoJack Horseman kinnie don't come at me)
"Dude! have you heard of BoJack Horseman?"
"The worst person-horse to ever exist who traumatized a lot of people, killed and hook up with the girl that viewd her as a father figure who uses his trauma as an exuse for everything who is a mess and doesn't know how to deal with themselves?"
"Yeah, that one!"
"Cool! I hope he dies!"
by xxxx_is_al1v3 January 3, 2022
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headless horseman

an excruciatingly pleasureful yet taxing homosexual act in which both participants are simultaneously gagged and resemble the headless horseman mounted on his bucking bronco
Neil: Great headless horseman last night. You make one hell of a stallion.

Bob: Make me your pony slut.
by Boner Jones!! March 13, 2011
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headless horseman

a guy who is doomed to roam the earth looking for some head which he has sadly never gotten

a close but slightly more sad cuzin of a perma-virgin
person1:why is he talking to them fat chix...
person 2:hes a headless horseman...hes trying to find some head so his soul can rest
by Bigeast 34 April 16, 2006
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Headless Horseman

The extremely rare occurance of a penis with no head.
What? Do you have a hydra?
No..its headless horseman.
by Scotsburn July 28, 2009
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Headless horseman

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?"
by Halbert9000 September 8, 2017
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Headless Horseman

While driving a car, the driver gives the passenger oral pleasure.
I gave that bitch a headless horseman while driving to her parents house.
by Matt McL. Helped by Eric January 16, 2009
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