Penny Barber was not happy when she found out the new boy in her office was the spoiled step-son of the company's CEO. It did not take her long to come up with a plan to get him under her thumb and kissing her ass. She invites him over to her house for a meeting but he has no idea that Penny has already discovered some pretty embarrassing blackmail material. The incriminating video she found of him is only the first move in her game to control him with a combination of fear and sexual obsession. Soon after entering her apartment the over-privileged brat finds himself completely naked and totally at Penny's mercy. Penny is going to make him earn back his clothes one at a time by completing a list of humiliating challenges with penalties for losing his erection. He is going to play Penny’s version of Strip and Dare which will include fun activities like cock spanks, ass worship, ice baths for his dick, taking a vibrating plug up his butt, and constant cock teasing. If he can behave like an obedient office boytoy, Penny might just let him have an itty bitty reward before she throws him out.