Top Definition
An uncircumcised penis.
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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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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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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by Scotsburn July 28, 2009

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A guy who goes out with a girl and no-matter what, she won't give him head.
Friend 1: Dat nigga's a headless horsemen forreal.

Friend 2: How long him and his girl been goin out?
Friend 1: 2 or 3....days.
Friend 2: And she still aint givin him head?!

Boyfriend: You know everybody at school has been calling me a headless horsemen, right?
Girlfriend: yeah but I mean, we have such a good relationship. Going on 2 years now I think giving in would mess things up for us.
Boyfriend: Damn shawty!!! Nigga jus' tryna buss a nut...
by Professor Whomper February 04, 2010

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an uncircumcised penis
He was thinking about getting circumcised as he had heard headless horsemen were unsanitary.
by zemotg November 05, 2007

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The Urban Dictionary T-Shirt

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The Urban Dictionary T-Shirt

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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 Urban Dictionary T-Shirt

Soft and offensive. Just like you.

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The Urban Dictionary T-Shirt

Smooth, soft, slim fit American Apparel shirt. Custom printed. 100% fine jersey cotton, except for heather grey (90% cotton).

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