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.
Princess Serena wanted her slave to know the kind of person she was. He did not understand her at all and he assumed that she was someone he could control however he wanted. So she did the best she could and used riding boots to dominate the guy. The slave was in pain and she used that pain to send a message to him as well as to control him.
Lady Scarlet needed to jerk off her slave and she did it with her boots because she did not care what the guy felt. She was doing it for her fun and so she recorded it all. She was at her study working while she did it. It was a challenge to also see if she could multitask and she managed to do so. He was humiliated but at least he came.
Goddess Vivienne was fed up with this slave. She had caged him thinking that he would change but he did not and she was confronted with either letting go or punishing him. She decided to punish him and she had to use another tactic as caging him did not work. So the mistress used her riding boots to trample his hands and fingers to make him learn from the pain he felt.
Mistress Gaia does not care what one feels or thinks when they have pissed her off. Her response is always to get back at them and do it in a way that they would never forget. That is why today, with the help of her friend, she kicked this guy in the balls using her riding boots before she gave her friend a chance to also kick him in the nuts. He was naked.
Madame Marissa and her friend did not want to be lied to anymore. This guy had done more than enough lying and it was now time for them to get the truth from him. That is why the mistresses chose to teach him a lesson so that he would appreciate that fact. He was cruelly trampled and crushed with their riding boots to the extent that he begged them to stop and he agreed to never lie again.
Madame Marissa did not want to tolerate her lazy slave. She felt that he needed to be humiliated and she did so using her riding boots. At first, she had him lick the soles of her riding boots but then she felt that it was not enough and that is why she opted to trample him with the same boots. That was painful and she felt it had given him something to think about.
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.