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Derived from the trend of planking, bating, and owling. Originated in Chicago, IL; it involves the opening of ones mouth, a surprised facial expression, and the deliverance of a guttural utterance while standing perfectly still. The sound that is made resembles that of a vocally challenged person moaning aggressively with a closed throat.
Bob: "Hey Jim, what are you doing?"

Jim: "Well, I'm just about to go to the store to get some milk and *wailing* AHHHHUUUUGHHHHAHHHHH!"
Wailing by TheJanitorialBatman April 30, 2012
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Wailing underpants

Activities in the underwear that demand immediate attention either sexual or toilet related.
Palmer had to go to the toilet quickly due to his wailing underpants!
Wailing underpants by I, Wreckerrr October 30, 2016

wailing wall 

noun. A Facebook wall with an emotional complaint, desperate cry for help, or call for attention that draws numerous sympathetic and sentimental comments from Facebook friends.

verb. Making such a post.
She was really close with her pet goldfish, and after it died, her wailing wall had fifty comments! I was impressed that so many people had so much love!

After he got fired, he wailing walled on Facebook and got so much pity that he felt OK being unemployed for a couple of months.
wailing wall by Doctor Science November 28, 2010

wailing fisherman 

A wailing fisherman is when a guy literally gets sick and hurls while going down on a girl, usually from drinking too much, but occasionally the vagina itself can be faulted. (Not to be confused with the "whaling fisherman," which is a guy who only likes going down on really huge chicks.)
After he finished those last three shots, Johnny went home and pulled a wailing fisherman on his girl. She left him passed out in his own pile, and he spent the whole next day smelling like stale vag and vom.
wailing fisherman by cx99 December 28, 2009

wailing dick 

(N) Any douche or chode guy who's yelling and/or pissing the hell out of people by drawing a lot of unnecessary attention to himself.
***Steelers vs Ravens game*****

Guy 1: YEEEAAAHHH GO PATRIOTS!

Guy 2: Fucking wailing dick...

wailing woods 

a place where no one goes unless they are building a sky base
lets go wailing woods and hide from everybody.

wailing on guitars 

1. Makeing the gutiar sing like the woman you just had sex with
2. Totally rocking out
Dude you sounded awesome in that set you were really wailing on guitars.
wailing on guitars by penguin7 June 29, 2006