skitty on wailord 

When your erect dick is so big it splits her vagina during sex;
also, when in pokemon, a huge sperm whale inserts its dick into a common house cats ass

Oh man, last night my boyfriend and I had sex. It was totally Skitty on Wailord!

Skitty: "Skiiiiiiitty!!!!" (Realizes it's too tight)
Wailord: "Wail Wail!!"

skitty on wailord by Wailord69 May 29, 2016

HOT SKITTY ON WAILORD ACTION 

When a skitty (a 2 ft. tall cat-like pokemon) and a wailord (a 47 ft. tall whale pokemon) breed in a Pokemon Day-Care center and make a egg

Origins from the Gamefaqs's Ruby/Sapphire Board

also known as HSOWA

Joe: Did you just breed a wailord and a skitty?
Frank: HELL YEAH!!!!!
Joe:...I wonder how that works.............
Frank: WHO CARES, IT'S HOT SKITTY ON WAILORD ACTION
Joe: your a fag frank

HOT SKITTY ON WAILORD ACTION by Concarious April 14, 2010

HOT SKITTY ON WAILORD ACTION 

A joke on Gamefaq's Pokemon Ruby/Sapphire Board.

It originated when one of the local trolls realized that one of the largest Pokemon (Wailord) could breed with one of the smallest (Skitty).

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HOT SKITTY ON WAILORD ACTION by Fats McRobot September 2, 2004