Wealthy and manipulative stepsiblings Kathryn Merteuil and Sebastian Valmont make a bet in the high stakes game of seduction and deceit. Kathryn challenges Sebastian to seduce Annette Hargrove, the headmaster's virgin daughter who has published an essay about saving herself for love. If Sebastian fails, Kathryn gets his prized vintage Jaguar; if he succeeds, Kathryn offers him a night of passion with her, as he has long desired.

Kathryn has her own vendetta—revenge on her ex-boyfriend, who left her for the innocent Cecile Caldwell. Kathryn enlists Sebastian’s skills to deflower Cecile, thus ruining her for her ex. Along the way, Sebastian meets with resistance as he pursues Annette, only to find that his usual charm and calculated maneuvers are ineffective against her genuine goodness and strong will, leading to unexpected consequences for the cold-hearted step-siblings.