A recently orphaned millionairess, Olivia, really hates her scheming step-father. Olivia finds love with a young yacht racing captain, Tim, who isn’t completely truthful with her. When the two run into a problem the local cop, who happens to be an old friend of Olivia’s, seems to be turning a blind eye to incriminating evidence.
Director Bob Swaim’s R-rated, plot-twisting, psychological sex-filled thriller was about murder, greed, double-crossing deception and betrayal. The film’s title referred to the name of a yacht anchored off the Hamptons. The film’s tagline hinted at the plot:
MASQUERADE – It’s not a game anymore.
The main story centered around the fortune of wealthy Hampton heiress Olivia Lawrence (Meg Tilly), who was forced to live with her scheming and despicable stepfather Gateworth (John Glover), with his companion Anne (Dana Delaney). After graduating from college, Olivia met two possible suitors:
Tim Whalen (Rob Lowe, just before he was involved in a sex tape scandal), a playboyish sailing instructor and yacht skipper with another lover on the side
Mike McGill (Doug Savant), a grown-up children friend, now a police officer
One of the side plots was Tim’s passionate encounter with his other lover:
Brooke Morrison (TV’s Sex and the City’s Kim Cattrall), his wealthy boss’ sex-crazed, bored and lustful wife
After their love-making in the film’s most quoted scene, as he stood there bare-assed, he gave her a birthday present – a pair of black-lace panties, about which she asked: “Do you want me to put these on?” to which he responded: “I can’t bite ’em off if you don’t.”
Olivia didn’t know whether to trust Tim – did he love her truly, or was he marrying her only for her money? The plot was about various conspiratorial plans or plots to murder Olivia, to acquire $3 million of her trust fund. By the film’s conclusion, although Olivia had thought that Tim had betrayed her, she learned otherwise that his love wasn’t a masquerade.