This guy was so into masturbating that he did it all the time. Princess Valerie thought that he did it once in a while but it turned out that he did it all the time. And that freaked her out as he was her neighbor. She had to punish him so that he did not get any funny ideas with her and stopped his perverted tendencies. So she used her high heels to trample him while he jerked off.
Lady Scarlet did not care how old this guy was. He had taken her for a ride and it was now time for her to do something about it. Forgiving him was out of the question and that is why she used her sneakers to trample the shit out of him. The mistress cruelly trampled and crushed his chest as he cried and begged her for forgiveness. She ignored him.
Mistress Rissa had a score to settle with this guy. He was her neighbor and she knew a lot of his habits. She knew he did not lock his house so she went and found him in his bedroom and she crushed his head and his balls. He was drunk so she tied her up before she ballbusted him. And it served him right so that he never messed with her again.
These mistresses knew that beating up this guy would not be as good as they would have wished since none of them could throw a punch or a kick as properly as was needed to inflict some good pain on the guy. So they chose to use plywood to trample and stomp on him at the same time using their combined weight to make it a painful affair for him.
Mistress Nikki and mistress Zazzie conducted their investigations and they found out that it was this guy who had snitched on them. He had to be dealt with and the mistresses did not waste any time in doing so. He was forced to endure being trampled with their boots while he was naked. His cries of pain did nothing to make them stop the painful punishment that he was given.
Mistress Courtney did not like how her colleague was condoning and even encouraging dissent from his students. She knew they would be the ones to deal with the consequences later on and she went and told him to stop it. And she crushed his dick in his class after hours and she told him to make sure he never did it again. He stopped as he did not want such punishment again.
This mistress caught her slave jerking off and she was pissed. She did not want a perverted slave in her house and she gave him one last chance but after she had punished him. The mistress made him jerk off while she crushed his head and that was an almost impossible task for him but he did it and he had to do it the way she wanted before she let him go.
Lady Scarlet knows how to read people and from her reading of this guy, she knew she had to dominate him and do things to him that he had never had done to him before. One of those things was trampling him. She could tell he had never been trampled before and since he was gullible, she teased him before she dominated him and made him think that it was a fun thing for both of them.
This guy thought it would be funny to play a prank on mistress Lana and mistress Joanne. So he did it but they did not find it as funny as he had intended it to be. The mistresses were pissed and they chose to teach him a lesson and it was one that he had never been taught before. He was in pain as they trampled him and did it as cruelly as possible.
This guy trespassed on this mistress' property and she had to teach him never to do it again. The mistress used her boots to do it and it was very painful for him. He had never felt such pain before and he had to learn his lesson the hard way. The mistress did not stop until she was sure he had learned that what he did was wrong and would never do it again.