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.
Mistress Roxi and mistress Pomme had an issue with their slave absconding duty and they punished her for it. She had to know that that would not be tolerated hence why the mistresses used their riding boots to punish her. It was a cruel punishment and through it, she learned his lesson the hard way. And she never failed to do what she was supposed to do and to do it well.
Madame Marissa likes to deal with people she can depend on. This guy was undependable and she did not want him anywhere near her. And that is why she went out of her way to torture him as cruelly as he needed to be punished. The mistress used her boots to kick and trample him in a way he had never been before and he cried like a baby at what she did to him.
When this mistress realized that she was dealing with an unreliable person, she had to do something the girl did not expect her to do. And that is why she went out of her way to make the girl be her human horse. She turned her into a human pony and rode her until she nearly broke her back. And she whipped her when she got tired. Licking the mistress' boots was the last thing she did before she was chased away.
When this mistress realized that she was dealing with a loser who did not respect what she was doing and what she had told him, she knew that she had to find a way to deal with him. So the mistress used her riding boots to dominate him because the punishment had to be worth it. And that is how he found himself licking muddy and dirty soles and he had no choice.
Mistress Jessica has never used riding boots to punish or degrade before but today she was up for the challenge and she made sure it was a successful one. The mistress cruelly turned this guy into her doormat and she crushed him gleefully as he cried and tried to beg her not to continue trampling and dominating him. But she did not listen to him and she went on doing her thing.
This guy made the mistake of spanking madame Marissa and he realized that he had misread her. She was so pissed at him that she had to punish him in a way he had never been punished before. The mistress cruelly tortured the loser with her boots and crushed him from head to toe and she even ballbusted him. And that is how he learned never to spank people he did not know well.
Mistress Gaia loves to trample and her friend wanted to learn how to do it. So she agreed to show her friend how it was done and since it had to be a practical lesson, she came with a loser who they trampled. Mistress Gaia took the lead in doing it then she asked her friend to do what she had seen her do. And it was great fun for them.