To beat up someone using a flurry of punches and kicks thrown quickly one after another and landing so fast that the victim has no time to avoid or block any of them.
yo that big nigga's gonna wail on that lil nigga and fuck him up!
To fuck a woman so hard that it doesn't become sex anymore. It is now the act of wailing on her, dominating her. It is emphasized best when it is pronounced "Hawailed on." Typically slampieces are whaled on the hardest and the most often.
"No, no, no. You don't even know what it means to wail on someone, Moss. Did you hear that Josephina from Sierra Madre got wailed on like Jake was her padre."