Princess Serena did not like how this guy was comfortable wanking in public. That was perverted behavior and the mistress did not like it. She did not want to report him to the authorities and she did not want to let him go scot-free. She had to do something so she dragged his ass to her house nearby where she used her high heels to trample his hands and warn him against doing so again.
This guy had perverted tendencies and mistress Jane and queen Hanna did not like it. He lived near them and they did not want anything to happen to them or to anyone else as a result of his perversion. So the mistresses used their high heels to make him do his perverted things within the walls of his house and not try to do any of it out in public.
This mistress likes to take people at their word. And she did that to this girl. She trusted that the girl would keep her word as well as keep her end of the bargain. But she was pissed to learn that the loser did not meet her end of the bargain. She could not stand it and she punished the loser painfully by trampling her using her high heel shoes.
This does not trample or punish slaves at home. That is because she can get visitors who will distract her from the task at hand. She also knows that her slave can also scream or make a lot of noise and alert the neighbors. That is why she likes to do it in the woods where she knows that no one will go to his rescue even if he screams.
Mistress Gloria discovered her slave had lied to her about his sickness and made some good money from her. She did not want the money back because she knew he did not have it. But for lying to her, she used her high heels to trample and crush his back as painfully as she was able to. She punished him to send a message that she would not tolerate such behavior again.
Princess Serena was feeling naughty so she teased this guy. She did not have a boyfriend but she did not have a shortage of men who could do anything a boyfriend can do for his girlfriend. She teased the guy and she turned him on. She then took advantage of him and trampled him for fun. She made it all look naughty and fun and the guy endured fun and humiliation from her.
These mistresses had hired this guy to make drinks for them at their party. He had told them he was a world class mixologist but he turned out not to be. The mistresses were angry as they had paid him. Instead of demanding for their money back, they resorted to trample and humiliate him for fun so they sat on him and they trampled him for fun using their high heels.
Lady Milana felt that kicking this guy in the balls would quicken getting answers from him. He was the only one she knew who could help her with her problem but he was not cooperating. She was pissed about it and to make sure he learned his lesson, she used her high heels to kick him in the nuts and to trample him. He was naked as she did this.
Goddess Chanel likes people who keep their promises. She hates disappointment and that is what this guy did to her. He did not keep his end of the bargain and she was not going to let him go scot-free. She' used her high heels to dominate him. She trampled his dick using her heels and he experienced excruciating pain like he had never experienced before. It was a learning moment for him.
Mistress Daniela promised this guy that she would ride him the way he wanted but only if he endured what she wanted to do to him. He had always wanted to nail her and the temptation was too much for him. He agreed and she used her high heels to trample him. He had never endured anything the way he endured the pain he felt. But it paid off as he nailed her good.