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."