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make his pockets hurt

it basically means to make a dude go broke cause he spent all his money on you. Lil Kayla made the term become popular in her hit song, “Make His Pockets Hurt.”
Girl 1: I seen you was with that cute dude, what y’all do?
Girl 2: you already know, Imma make his pockets hurt

Pockets on My Panties

I have so much dough in my jeans pockets i need pantie pockets so fit the rest.
Bitches can stand me i got pockets on my panties.
Pockets on My Panties by leelee1234 November 30, 2010

No Pockets

When you’re trying to flex on someone but really you broke as shit.

To have no blue faces to your name.
“Damn dude brought his girls buggy to work again instead of his Maro’?”

“He’s trying to save gas he gots No Pockets!”
“Let’s go to lunch?, nah I brought my lunch today.” -“No pockets!”
No Pockets by NeetzBeatzCheekz January 17, 2019

I got 2 pockets full of sunshine 

To have something that is better than what someone else has, to have something really cool/interesting.
Guy 1: You ain't got shit!
Guy 2: Mother fucker I got 2 pockets full of sunshine!!

Thigh Pockets 

The act of wearing loose pants, usually worn by a nigga or white trash, loosely around the buttocks and below the waist. Usually, a belt is put in place and the boxers pulled up to prevent the pants from falling off completely.
Thigh pockets are most commonly used to conceal guns, drugs, and stolen items from your local convenience store.
"Yo, nigga, put yo hands on da cah, and let me seen wut's in dem thigh pockets"
Thigh Pockets by BAKR, Abdul December 19, 2008

Cum Pockets

Two indentions located on the small of a woman's lower back, located on both sides of her backbone. These indentations can be used to temporarily contain ejaculation in a pocket like fashion. This is found quite useful during "doggie style" sexual intercourse as a place to hold semen.
Last night I was nailing that broad doggie style, when I pulled out and I shot my load right into her cum pockets on her back! It was awesome! Not even one drop spilt!
Cum Pockets by Kelley M. January 11, 2009