Lady Scarlet felt that this guy was not ready and was not willing to learn so she had to make sure he was. And she did so using her riding boots which she used to trample him. He also had to lick her dirty soles and do other crazy things for her entertainment. It got to a point she forgot she was punishing him and she just did it for fun as it was enjoyable.
Mistress Michelle and mistress Betty had beef with this guy and they felt that it needed to end as it had gone on for too long. So the mistresses chose to dominate as well as humiliate the guy and the did so with their riding boots. The guy was not only trampled and kicked, but they also made him eat horse shit. He tried to beg them not to make him do it but they did.
Mistress Nica was not amused with the way her colleague behaved and she had to tame him. That is why she chose to use her boot fetish to do it. He was not in the best of shapes and she knew that if she used her boots to trample him, he would not manage to do anything about it. So she kicked and trampled him before she peed on him.
This mistress was out to teach her slave a cruel lesson and she did it with her riding boots. The mistress was so pissed at the slave that she stomped and jumped on him without caring what he felt. He cried and begged her for mercy but she did not show him any. The mistress did not bother to speak to him. She just punished him and then went away.