This guy was hired by mistress Gaia and her friend to do some work for them but he did not meet the terms of their agreement. He did not impress them and he had to be punished. The mistresses did so by trampling him with their riding boots. He was in pain as the mistresses crushed and trampled him from head to toe. But he learned his lesson the hard way.
When this guy missed his targets, mistress Gaia and her friend had to deal with him. They had to do it in a cruel manner so that he learned never to piss them off. They considered him lazy and lacking seriousness so they had to punish him as painfully as possible. That is why the mistresses used riding boots to trample the shit out of him. It worked and he never missed his targets gain.
This equestrian was disappointing as mistress Amrita, mistress Patricia and mistress Youko had bet on him. He lost them money and they had to humiliate him so that he performed better in the next round. The mistresses used their riding boots to ball crush him and have him feel pain. He remembered what they had in store for him and he performed well and they loved that as they got their money back.
Mistress Nica did not want her stable boy to learn the hard way. So she made him learn before he made a mistake. She had him know what she was capable of doing to him if he did not care for her horses as well as she expected. The mistress explained in detail and he was scared to the point that he did not want to disappoint her. He ensured his grooming was perfect.
Mistress Nica felt that her slave needed to be tamed. She did not want to take a lot of time to get that done and so she used her riding boots to trample him while he was naked. She did not spare his dick and his balls as she trampled him. He cried and she knew that her punishment was achieving the desired effects and this was confirmed when he changed.
Madame Marissa felt that this guy needed to be punished so that he stopped bothering him. So she lied to him that she wanted to massage his balls and suck them and he bought the lie. She instead used her riding boots to trample them instead of massaging them and he was in pain and he begged her to stop but she did not until she felt that he had gotten the message.
Mistress Betty could tell that this slave was not well trained and she did not want to take a long time training him. So she did what she does best and she trampled him with her riding boots. The poor slave was naked in a lot of pain. This in turn made him more attentive and that is how she got him trained in a relatively short period of time.
Madame Marissa does not like slaves and losers who piss her off the way this one had. He had to be punished for his mistakes and the mistress used her riding boots to do it. She shocked him at the kind of kicks he received and he cried and begged her not to do it again. From his cries, she knew that he had learned his lesson and would not repeat his mistakes.
Mistress Nica is a woman of few words and she wanted to make sure that this loser did what she asked him without asking a lot of unnecessary questions. So the mistress used her riding boots to send the message. He had to lick the boots and to endure her trampling and he learned the lesson that she wanted him to learn. The two of them never had any issue after that.
Mistress Gaia and her friend had boyfriends who were also good friends and they were hanging out all the time. But they had started misbehaving and going on drinking sprees and parties without telling them or lying to them about their whereabouts. The angry mistresses put a stop to that nonsense when they turned their boyfriends into human ponies and rode their backs and used their riding boots to trample them.