Cruel Intentions 2 (2000)

This prequel to the hit movie follows the adventures of rakish young Sebastian, who, at age sixteen, is determined to redeem himself for past transgressions and become a one-woman man. His kind intentions are complicated by his recently acquired stepsister, Katherine Mertuil, a viciously manipulative debutante who enjoys toying with the love (and sex) lives of her fellow high school students. Sebastian soon finds himself smitten with the adorably naive Danielle, daughter of his high school headmaster, and sets about winning her heart. But Katherine's duplicity may result in his downfall as she slyly positions herself between Sebastian and his newfound love, offering dual temptations of sex and power. Originally filmed as the prospective pilot for a television series that never materialized.