Mr. Smith Gets a Hustler(2002)

A banker, husband, and father, Mr. Smith must leave it behind him. He's made a mistake and he's trying to pay for it but he doesn't know if there is enough money in the world. Or so he tells Bobby, the eighteen-year-old male hustler Smith employs for company. Bobby quickly learns however, that Smith is no regular John, and their meeting has unintended consequences that neither of them is prepared to afford.