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2.
1)
When you know you have a bad hooker.

If you can fit all five fingers in, its gonna be a bad night, so you get a discount.
2)
When you jack some shit from a store, or see someone else jackin shit from a store. ( because you pick it up with five fingers and run like hell)
(guy 1 )Damn i had the worst sex ever, i got the 5 finger discount.
(guy 2 ) *laughing* hahahaa well i fucked your mother, and got it too.
(guy 3) thats fucking disgusting

Look at that stupid mother fucker! He just got a 5 finger discount, and ran right into a cop.
Yo nigga, im workin as a stock boy so i can get the 5 finger discount when ever i want.
by Gangsta Stoner January 30, 2008
 
1.
To steal something. When you steal, you grab the item with your hand - five fingers.
I got this hat at a 5 finger discount at the store!
by Shauna Buchheit March 18, 2006