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Penny (Nicole Doshi) is estranged from her family and down on her luck. That's why she's so surprised one day to discover that her chauvinistic grandparent left her his entire estate in his will. It was no secret that he hated Penny, especially her boldness in the face of men, so she can't imagine what would have prompted the change of heart before his passing. But when she talks to Jack (Tommy Pistol), the lawyer overseeing his estate, it becomes clear that this wasn't so much a change of heart as one final reckoning. Penny shockingly learns that in order to get her inheritance, her grandfather left one perverted condition: Penny must submit to a man's sexual desires, doing everything he wants, no matter how humiliating. Penny is disgusted, and even more so when Jack insists she must have sex with HIM that very instant. When Penny argues, Jack even goes so far as to enlarge the requirements, insisting that she must now have anal sex with him to boot. Penny is still shocked, but her desire for a better life wins out, prompting her to accept the terms. She has anal sex with the lawyer right in his office, all while his paralegal (Kasey Warner) watches from the sidelines while chatting nonchalantly with Jack.