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.
This takes place several years before Cruel Intentions, back to when Kathryn first meets Sebastian, their sexual attraction to each other and their enjoyment in destroying the lives of their peers.
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.