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1.
Old sailor slang for a giant squid, kraken, or really, anything large with tentacles.
'Don't be goin over there, them's chooley waters.'

by Kilen September 16, 2008
 
2.
The area of skin between the scrotum and the anus.
Boy, does my chooley really itch right now.
by Senor Chooley September 21, 2008