Princess Serena and goddess Sheila had no reason to hard trample this guy other than for fun. And they did not mind the optics of it. As long as they wanted to do it and it was for fun, they were ok with it and they went ahead to do it. The guy was shocked by the treatment but the mistresses told him it was for fun although not his fun. Theirs.
Mistress Gaia wanted respect from this guy and she also wanted him to fear her. So she went with high heel trampling as her method of choice to get both of those things. The mistress forced him to lie down and she hard trampled him to get what she wanted. The pain made the guy fear her and it forced him to respect her but it was more of fear than respect.
This mistress had agreed on a recipe with her chef but he forgot about it and he did his own recipe. She was so pissed at what he did that she had to punish him and do it painfully so that he never forgot again. The mistress chose to force the guy to lie down and she hard trampled him all over. He was in pain but she did not care.
Lady Scarlet was wearing her shoes but that did not stop her from jumping on her naked slave and trampling him. She was doing it because he had angered her and in her opinion, he deserved all that happened to him. She chose to teach him never to piss her off again and he learned his lesson in a painful way. He wished he had listened and heeded her advice earlier.
Goddess Nyx noticed that her boyfriend had grown lazy and that was not a good sign. He had to get his mojo back and she did not believe in letting him work on it on his own. She motivated him and then hard trampled him to show him that he had to get up and drop his laziness. The pain got to him and he did not want it again so he dropped the laziness.
Madame Marissa and lady Nora were not ok with how untrustworthy this guy was. They had given him a few chances to prove himself and he had failed at every turn and so they had to punish him which they did by hard trampling him. He was kicked with their boots before the mistresses hard trampled him and he felt a lot of pain in the process of their punishment.
Madame Jeanne used her high heels to send a message to this guy that she would not tolerate any dissent. The guy had been trying to create dissent within the office and she was not going to allow him. So she placed his hands on the floor and she crushed them and hard trampled them with her high heel boots. He cried in pain and promised never to try it again.
Mistress Olivia was not ok at the way in which this guy had misused her stuff. She felt that it was important for him to change and do things the way she wanted and the way they were supposed to be done. She used her bare feet to hard trample him and she made sure he peed his pants and he cried before she felt that it was ok and she let him go.
This mistress wanted to hard trample this guy and she chose to do it with her high heels. She did not talk much as all she was interested in was the action. So she used her heels to trample the nearly naked guy and she made sure that he was in a lot of pain. When she felt that he was not feeling the sort of pain she wanted, she invited her friends and they all had fun trampling him.
Mistress Gaia wanted to trample this slave and she chose to do it with her hard trampling fetish. She cruelly led her friends to do it on the guy who was stripped naked and was hard trampled. The mistresses ignored his cries of pain and forced him to do what they wanted which was to trample as well as humiliate him. He regretted what he had done and pleaded for mercy.