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Window Pain 

Pain that comes from watching a loved one leave through the window
X: I lied to her again, now I have to watch her leave through the window

Y: Guess that's why they call it window pain..
Window Pain by IamBeowolf January 9, 2011

Window Pain 

Pain that comes from putting yourself in somebody else's shoes (windowing or looking through a mirror)
I automatically window pain when my mom suffers.
Window Pain by IMJean May 30, 2019

window pain 

Window Pain
To Window Pain is to take LSD by using a eye dropper,
and placing drops into the eye. It is a fast and effective
way to take acid inducing the desired effect almost emediatly.
Mr. Stickey Ickey Window Pained Some Acid today.

Windows pain 

(Not to be confused with window pain.) The protracted and excruciating pain of having to wait for Windows software to work.
Interrogator: Are you going to tell me about the plot, or do I need to take out the Windows PC?
Villain: I'll tell you everything I know.

John Doe: Arghhhhhh! The Windows pain is unbearable!!!
Bill Gates: Why don't you just use Linux? LoLz
Windows pain by SoberDicktionary January 27, 2021

Windowpain 

Whilst in the act of intercourse, the man picks the woman up and stuffs her through an open window; while she supports herself in the window, the man aggressively slams the window shut repeatedly on his penis, which is resting in the windowsill.


Can also be used as a verb, windowpaining.
ex1:

dude1: Dude, did you see that girl hanging out of that window naked? I wonder what she was doing.

dude2: It's just the old windowpain my friend.


ex2:

dude1: oh man dude, my dick hurts so bad right now. I windowpained the shit out of Kelsey last night.

dude2: That's so hot, man, I wish Amanda would let me do it to her.
Windowpain by Bob Winston October 30, 2008

windowpain 

whilst having sex with ones girlfriend, wife, or boyfriend i suppose, the screen in a window is removed, and the receiver is hung out the window. the giver then repeatedly slams the window frame down on the penis, resulting in pain and satisfaction at the same time.
Dude 1: hey man, i totally windowpained with megan last night!
Dude 2: wicked! how was it?
Dude 1: o it hurt so good!
windowpain by oldskoolkid February 21, 2009