Cruel Intentions (1999)

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Cruel Intentions
Directed by: Roger Kumble
Year: 1999 | Duration: 97 min
Genre: Drama, Thriller
Starring: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon
Country: USA
Languages: English, Vietnamese, French
Kathryn makes a bet that her step-brother, Sebastian, won't be able to bed Annette (a virgin, who wants to wait until love). If he loses, Kathryn gets his Jaguar, if he wins, he gets Kathryn.