rascarse el bolsillo

1.
SpainLatin Americawidespreadneutral
- To put one's hand in one's pocket to take out money (literal action).
2.
SpainLatin Americawidespreadinformalcolloquial
- To pay or be compelled to pay money, often reluctantly; to shell out or contribute funds.

Examples:

ES: Que los conmueva, les haga rascarse el bolsillo y les arranque lágrimas. Deja de comer ese salami.
EN: Something that'll tug at their heartstrings make them dig down in their jeans and bring tears to their eyes.
ES: Conmigo, todo el que quiera un poco de... tiene que rascarse el bolsillo.
EN: With me, anybody who wants a little "mmmph," he's gotta put up for it.
ES: Vincy habrá tenido que rascarse el bolsillo para este jaleo.
EN: Vincy's had to dig deep in his pockets over this palaver.
ES: Si quiere rascarse el bolsillo, este es francés.
EN: If you're willing to stretch your guineas,this is French.
ES: O sea, mi padre podría rascarse el bolsillo, pero... - Y Gary.
EN: I mean, me dad might stick his hand in his pocket, but... ~ And your Gary.
ES: Vale, pero diles que si quieren que colaboremos y eso, tendrán que rascarse el bolsillo.
EN: Listen up, tell them if they want to become partners, they'll have to dig real deep.