Jack and his buddy Ben check in at a posh Florida resort, planning to spend every hour in hot pursuit of gorgeous babes. But their plans hit a major detour when they try to bed the wife of a conniving jewel thief. They’ll have to outsmart him, a nasty security guard and an obnoxious jock if they’re ever going to get a moment alone with the girls of their dreams!

High school senior Bobby Chrystal fails his French class, which will block him from entering Yale. His rich, authoritarian father hires an attractive 29-year-old to tutor Bobby over the summer and help him pass a make-up exam. While Bobby’s friends lead him away into strange excursions aimed at losing their virginity, Bobby finds all the extracurricular activities he needs with his new tutor.