Mistress Gaia knew that this guy had access to info that she did not have and she had to get her hands on that info. So she used her riding boots to trample him after she had stripped him naked. She did not beg him for the info but rather demanded for it and from what she did to him, he had no choice but to do as she wanted.
Goddess Vivienne had endured humiliation from this guy and she took it bravely. She was waiting for her time to get revenge and when the time came, she did not hesitate to do it. Goddess Vivienne used her riding boots to trample the shit out of him while he was naked and make sure he ate it all. The mistress had fun seeing him in pain and she made sure he felt double the pain she had felt.
This errant slave thought that he could not be punished by these mistresses. He saw them as young, meek and weak. So he felt that he could do anything he wanted and get away with it. But he was wrong as the mistresses whipped and trampled him with their riding boots after tricking him to go with them for a picnic. He was in the pain of his life and he regretted his assumptions and his actions.
This guy had attempted to con mistress Gaia and her friend. But they were smarter than him and they had to punish him for what he had tried to do. He wished he had never done what he did but it was too late and he had to endure his punishment. The preferred punishment was to trample him with their riding boots and that is what they did as he cried and begged for mercy.
These mistresses felt that they wanted to trample this guy and make him feel pain. But they did not have a reason to do it as he had not pissed them off or done anything wrong to them. Mistress Krush suggested to mistress Tiffany that they pay her for it and they agreed. He needed the money so he agreed and the mistresses used their boots to trample him and have fun at his expense.