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1.
When the bottom of a persons ass cheeks are not covered by their bikini because the ass crack gobbles them up or because of the ass is full and can't be contained.
Take a look at that cheek leak. That ass is perfect.
by Bulldog January 29, 2006
 
2.
When a person's shorts are extremely short and the bottom of their butt cheeks hang (leak) a little out of the bottom of their shorts.
Susan definitely has some cheek leak out of those daisy dukes.
by CiBaby June 22, 2013