Kathryn y su hermanastro Sebastian, todavía estudiantes de bachillerato en un elitista instituto de Nueva York, deciden hacer una maquiavélica apuesta. Se trata de que Sebastian, un consumado Don Juan, se acueste con Annette, una joven que quiere permanecer virgen hasta su matrimonio. Si Sebastian pierde, Kathryn se quedará con su Jaguar, pero si gana... la tendrá a ella.
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