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2. Jackson Five
A term used to describe a hundred dollars; because the twenty has a picture of Andrew Jackson on the front, five of them would equal a hundred dollars. Thus, The Jackson Five. Similar to calling a hundred dollar bill a Benjamin.
Bouncer: I'm sorry, I can't let you in.
Man: But I have some friends who can vouch for me. The Jackson Five, perhaps you've heard of them? (Hands the man 5 twenties)
1. Jackson Five
The ultimate disrespect
When you ejaculate into your palm during sex and then slap the female in the face while shouting "SLAP!".
by Andrew Jul 16, 2004 add a video
3. Jackson five
jackson pollock Euphemism for masturbation. Amalgamation of 'jacking it' and 'five knuckle shuffle'. Abb. 'jackson'
What'd you do last night?
Stayed in for a Jackson Five.

Just goin' for a Jackson
4. Jackson Five
In poker (namely Hold 'em poker), when your hole cards are a Jack and a 5, especially when the cards are clubs and/or spades.
Johnny's got Jackson Five, and folds quickly.
5. Jackson Five
When you poop on someone when they're are fisting you. See Action Jackson
It's hard not to give him a Jackson Five, when he's got his fist up your butt all the time.
6. Jackson five
jackson pollock Euphemism for masturbation. Amalgamation of 'jacking it' and 'five knuckle shuffle'. Abb. 'jackson'
What'd you do last night?
Stayed in for a Jackson Five.

Just goin' for a Jackson
7. Jackson Five
Sticking 4 fingers and your thumb up a girls pussy.
After giving her a teaser, a pleaser and a shocker, he finally put them all in her pussy, the jackson five
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