When you are having sex with a girl doggy style, spit on her back, then when she turns around you blow your load in one eye, and kick her in the shin and let her hop around on one leg, holding her eye.
Person 1-"Oh man Sarah's angry at me."
Person 2-"Why's that?"
Person 1-"Ah i did a one eyed, one legged pirate to her, it was funny though, watching her hop around like that!"
Person 2-"Why's that?"
Person 1-"Ah i did a one eyed, one legged pirate to her, it was funny though, watching her hop around like that!"
by JewSlap August 8, 2016

by Pocisme October 21, 2017

Euphemism for masturbation.
by DirtyDan'sBiggestFan July 20, 2017

When your boyfriend is going down on you and your pussy is sensitive but he won't stop. Clock him with the palm of your hand in the eye. He will rise up mouth gaping, and moist, winking one eye gasping.
by Love punch April 19, 2018

This is when a person feels like the have a headache on only one side of the head, particularly felt on top of the eye or on the eyebrow.
person one: whats wrong?
person two: Dude I have this horrible headache, but its only one side!!
person one: oh, you must have a one-eyed headache.
person two: Dude I have this horrible headache, but its only one side!!
person one: oh, you must have a one-eyed headache.
by Carlos Santiago September 26, 2005

by Kyle p Cavanaugh March 19, 2019

When you friend or girlfriend is sleeping on their back and you casually walk up to them and fan or "batwing" your sack bag over their eye just nice making them look like a pirate with a scrotum eye patch.
As my roommate wobbled out of his room, he exclaimed "I must have got a One Eyed Winston last night, and my eye smells like scrote-sack.
by Vince Morgan August 28, 2019
