Cruel Intentions (1999) – Kathryn teases Sebastian to the max
Plot Summary: Kathryn (Sarah Michelle Gellar) makes a bet that her step-brother, Sebastian (Ryan Phillippe), won’t be able to bed Annette (Reese Witherspoon) (a virgin, who wants to wait until love). If he loses, Kathryn gets his Jaguar, if he wins, he gets Kathryn. Here Kathryn takes Sebastian to the absolute point of no return, before holding back and frustrating him off totally.