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
Get the headless horsemanmug. 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.
Bob: Make me your pony slut.
by Boner Jones!! March 13, 2011
Get the headless horsemanmug. by The Return of Light Joker May 12, 2010
Get the headless chickenmug. A hot dog, sausage, weiner, or other cylindrically-shaped meat based food product.  So named for its resemblance in size and shape to the male penis, minus the mushroom "head" or glans-like bulbous anatomical feature at one end. Also can be abbreviated to "H.D." or "HD's" (plural) for added trendiness & urban hotness, or when uttered in public places or among mixed company.
"Are you hungry? 'Cause I'm gonna fry up some headless dicks here for us." Or, "Chet's gonna make his famous Headless Dick Fricassee for dinner tonight!"  And "Can we go to Albertson's? I need to get some milk, butter, and HDs!"
by SJ Pablo April 3, 2006
Get the headless dickmug. 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
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
person 2:hes a headless horseman...hes trying to find some head so his soul can rest
by Bigeast 34 April 16, 2006
Get the headless horsemanmug. by Scotsburn July 28, 2009
Get the Headless Horsemanmug. 'I made a project reboot software-based headless server.' 'We finally made the most powerful physical headless server.'
by BlueNeva October 25, 2022
Get the Headless Servermug.