A difficult or awkward situation with no obvious correct course of action, literally something which fucks with you head.
"I slept with my girlfriend's identical twin sister without realizing and don't know whether to tell her or not, it's a complete headfuck"
by Henners17 May 06, 2008
by trace45 16 April 28, 2009
V. When a male sits on the females shoulders and thrusts the erect penis very hard against the back of the females head and also when the male slides the erect penis all over the top of the girls head.
"He sat on her shoulders, and got to Headfuck her with his erect penis against the back of her head very hard and fast till he came all over the top of her head."
by Headfucker July 11, 2009
A person who is dumb, not cool, fat, gay, bi sexual, sketch asexual, Adam Lambert, Clay Aiken, Knickelback, Thomas Swartz, Every Member of Hinder and Buckcherry, Ben Rothlesberger, Etc.. Etc..
If you're in traffic yell out your window "Move it HEADFUCK!!!" with a slightly German accent people will most likely move or try to fight you. Or you could be just walking down the road and scream "HEADFUCK HEADFUCK HEADFUCK" and people will believe you have tourettes.
by 330ch16 December 01, 2009
To mess up someone's thinking with illogical or distorted arguments, sometimes with a deliberate malicious intent, sometimes just out of misguided ignorance.
by CyberCrone January 31, 2018
by Car-lie October 21, 2007