Cruel Intentions 1999

Directed by Roger Kumble | Starring: Selma Blair, Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon

Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.