Lady Stefanie wanted some money from this guy. She knew he had some money and she wanted a piece of it. She did not hide that fact so she humiliated him financially without hiding it. She asked him for the money and when he hesitated, she told him what she was capable of doing to him and he got afraid and gave lady Stefanie the money she had asked him for.
Madame Marissa knows that her pay slaves are not good without her teasing them a bit in order to get them to have good motivation to bankroll her. She likes to tease them and to flirt with them. Once in a while, she gives them jerk off instructions and she makes them have fun before she gets to humiliate them financially. She does not lose focus from the fact that it is all about financial domination.
This mistress is cunning. To make sure her pay slaves never grew tired of spending on her, she made them believe she was their personal project. And she subdivided the roles for them. Everyone was in charge of something. And she created a little competition between them and since everyone wanted to please her and to win, she was always awash with money. But she also ensured she spent quality time with them and entertained them.