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8.
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
7 14
 
1.
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
20 10
 
2.
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
18 11
 
3.
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
9 5
 
4.
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
4 0
 
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
10 13
 
7.
an uncircumcised penis
He was thinking about getting circumcised as he had heard headless horsemen were unsanitary.
by zemotg November 05, 2007
2 6