Hooker speak for anal sex. A must when banging a hooker because you know your girl won't take it in the ass unless you give her a few mickies and drinks.
Me on the phone at work "...I definately want a trip to the islands."
Boss (who over heard) "Taking a trip to the islands huh? Hawaii, the Caribbean, Greece?"
Me "Um. Yeah. The islands"
Boss "Gotcha. You are just nailing a hooker in the ass tonight. Good. See you on Monday."
Boss "Let me get that number by the way."