Cruel Intentions (1999)

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.

• addiction
• bet
• cocaine
• cynic
• drug abuse
• innocence
• love
• love letter
• manipulation
• private school
• psychotherapy
• sadistic
• seduction
• sex
• sexual obsession
• sibling relationship
• upper class
• virgin