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1. flags
Word used for stamps in Prison. (i.e. a flag is often pictured on a stamp)
I'll give you 5 flags for the old issue of Buttman.
2. flags
Gang colors. Some people say that if more than 50% of your clothing is red or blue, you're "throwin flags"

Most often people won't think you're in a gang unless you're wearing lots of red or blue along with a red or blue durag and hat.
"Niggas wearin flags cause da colors match their clothes/They get caught in the wrong hood and filled up wit holes muthafucka" - 50 Cent
by rsabowski Dec 4, 2003 add a video
3. Flags
A 'Flag' is a proverbial claim made by a male when he has had sexual interactions in a particular way with a female and that female has not had or experienced that particular act/position before with any other male.
Man, that dude is going to struggle to place flags on El, we boned in every way, shape and form possible.

Man, that guy is going to have to stoop to some borderline degenerate actions to claim flags on that girl.

I feel good man, I have totally flagged that girl. short of cumming in her ear while fingering her ass.. he is gonna struggle to lay flags.
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