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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 October 30, 2007
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2
When the driver, preferably girl, gives a blowjob to the passenger. Often confused with road dome. Except this gives off the appearance no one driving the car, like the headless horseman.
Heard he got road dome!!-Jeff
Nah bitch he got dat headless horseman shit, she was driving!!!-Grizzy
by HGrizzy July 01, 2011
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3
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!! February 26, 2011
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4
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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5
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 October 03, 2008
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6
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 March 12, 2006
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The vengeful act of crapping on a lover's chest while they sleep.

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7
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
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