Mistress Anastasia had to find out what this guy's pain threshold was because she felt that he was too proud for her and she was not going to let him continue down that road. He also bragged of how tough he was and how he could not feel pain. But he regretted it when she used her high heels to trample him and made him regret bragging about being macho.
Goddess Nika was not happy at the way in which this slave was doing things. She felt that he needed to do better and that is why she forced him to endure the pain of her high heel trampling. She even showed off her hot ass in a thong as she trampled him and he had never seen an ass so fine before and he was turned on despite being trampled. He was chased away shortly thereafter and it was double humiliation for him.
Goddess Harley does not like boring people and this guy was the poster child for boring. She had never been bored with anyone the way she was with her so she trampled him as a way to make sure she had fun at his expense. And it was brutal as she did it to his naked body. But he was lucky she did not use her high heels to do it.
This mistress had tried her best to warn this guy not to piss her off by stalking her but he did not listen to her. She felt like he was doing it on purpose and so she had to punish him which she did using her boots. The mistress brutally trampled and crushed him until he cried and peed himself. That was when she let him go as she felt he had learned his lesson.
This mistress did not want to have an unruly slave. She felt that it was up to her to deal with him as he did not seem to have a moral compass to guide him. She went ahead to trample him with her high heels and she dominated him like never before. He tried to get her to forgive him but she did not. She even slapped and kneed him.
This guy was so annoying to the point that this mistress had to punish him and do it in a manner he had never experienced before. The mistress knew that for her to do so, she had to trample him and do it with her high heels so that it would be as painful as she wanted. He wished he had never messed with her as the consequences were too painful for him.
This guy procrastinated like crazy and this mistress was not happy about it. She felt that she had given him enough time to do something about it and since he was not making any positive steps to deal with the issue, she had to get involved and change him. So she trampled him and made sure to trample his balls as well and that is when he learned his lesson and changed.
Lady Phoenix does not respond well to disobedience and when this guy was not obedient to her, she knew immediately that he was a good candidate for punishment. And she did not hesitate to punish him. She used her martial arts skills to throw him down and she followed it up with her trampling. And she trampled his head and made sure to go all the way to his balls.
This guy thought that he had such mad game that he could hit on all of them at the same time and yet they were together. The mistresses lured him to their house where he was humiliated and tortured by being trampled by the mistresses at the same time. He was shocked at the turn of events but he took it like a man and he did not cry further impressing them.
Mistress Tiffany was angry at her slave for not doing the dishes. She had instructed him to wash the dishes and then prepare dinner thereafter. But he ignored her instructions and did not do it. She was so pissed at him that she trampled him with her boots while he was naked. He cried but she ignored his cries and went on punishing him as cruelly as she was able to.