Goddess Anita was due a wardrobe change and she felt that the best way to handle it was to use her findom fetish. She used her sexy charm to dominate the guy and have him do what she wanted. In this case, that was to shower her with money and it was this money that she used to change her wardrobe as she had planned to do. It was long overdue.
Sometimes it has to cost you something when you need to satisfy a craving and that's exactly the position that Jack finds himself in with the young Lexi. This girl is more than happy to let him jerk off to her pretty little feet but she expects to be compensated for it. She'll use his face as a foot stool but he's getting kicked out the second he decides that he wants to keep his money from her.
When mistress Monika realized that this guy was stalking her, she decided to make him useful to her since he already had an interest in her. So the mistress turned the guy into a financial slave and she had fun dominating him for her own fun and she got money from him in the process. He regretted why he had stalked her as it was not going well for him.
Mistress Dita and mistress Wendy did not like how this loser did things. He was supposed to be punished and the mistresses punished him but their motivation was not to change him but to financially dominate him. They used the way he did things as a scapegoat. They humiliated him physically before they humiliated him financially and they got what they wanted from him. He was happy they let him go but he went home broke.