In imageboard culture, nudity.

The opposite of fail; when something of awesomeness happens.

W.I.N stands for Wank Induced Nap

After a wholehearted bit of masturbation rewarding your hard work with a well earned nap

originally used as a normal word in phrases such as "we win the championship" "I will win this trophy" etc. But since the rise of online gaming, it has been used more and more out of context, and has developed into a nerd slang term.

Instead of using proper grammar, these geeks say "win" every time they see something funny or amusing. (See example).

I do not know how this is a "cool" word, but like I previously said, it's nerd lingo.

convincing a girl on webcam to show her vagina

When an action is done that is so mind boggling Win, one must stand off to the side, and give a round of applause. Most common when someone completes a task at over NINE THOOOOOOUUUSSSAAAAND!