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Kathryn makes a bet that her step-brother, Sebastian, won't be able to bed Annette (a virgin, who wants to wait until marriage) before the start of the school year. If he loses, Kathryn gets his Roadster, if he wins, he gets Kathryn .
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This takes place several years before the malicious movie (starring Sarah Michelle Gellar), back to when Kathryn first meets Sebastian, their sexual attraction to each other and their enjoyment in destroying the lives of their peers.
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Two guys at a college prep school make wagers on seducing naive young girls, and then meet their match when they agree to see which one can seduce the most popular and devious girl who has her own agenda to everything.
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