Mistress Jessica wanted this guy to learn a lesson that she had never taught him before and that is why she chose to use her rubber boots to do it. The mistress used them to trample him all over and she laughed at him as he cried and tried to distract her so that she would forget that she was humiliating him and punishing him. She did it while he was naked.
Mistress Jenny is not the kind of person to mess with and hope that she will forget about it. She does not forget easily and when she is wronged, she likes to revenge because she believes that getting even is the best policy and not forgiving people. So the mistress today used her rubber boots to trample and torture this guy because of what he had done to her earlier.