Cassandra is relaxing naked in her suite and does not wish to be disturbed so she leaves a note for the delivery guy to leave her dry cleaning hanging on the door. When she sees a little twerp sneaking around her room a few hours later she is furious and immediately calls him out as peeping tom perv. The little sneak knows he is busted and his weak excuses are just ignored by Cassandra as she easily spins him around to get a better angle for some punishment wedgies. She yanks the wuss up on his tippy toes to reveal his tighty-whities which make her burst out laughing when she sees them.

Instead of getting to sneak a peak at a hot woman in the shower the dirty trespasser gets his butt crack burned and balls crushed while being mocked and humiliated for his underwear choice and cock size. Cassandra eventually makes him strip down to just the tighty-whities and even intimidates him into jerking off for her just so she can make fun of his little boner. She has a blast making him dance around with a tight-whitey wedgie leash but she finally gets bored enough to let him go free. But not until after she makes him submit to butt smothering and some apology ass kisses of course!