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1.
1.) verb. 'To cash out.' to exploit a situation to such an extent that you gain financial, sexual or food-based rewards for your efforts

2.)verb. 'To cash out on.'
to cash out on. to beat another man so comprehensively at any competition that the beating is equivalent to ejaculating on their face. e.g. "I cashed out all over his face."
1.) "I cashed out on some sexy pre-teens"
2.) "I cashed out all over his face."
3.) "I'm cashing out this weekend"
3.) "You just cashed the boys out in a big way."
by a.bond May 07, 2008
 
2.
The Act of removing ones penis from a partner’s ass and placing it in their mouth. You must ejaculate in order to "cash out"
Last Thursday some chick let me go A.T.M so i ended up cashing out
by H the black guy April 09, 2011