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.
Mistress Liliana and mistress Sonya found out that they were being played by the same guy. They did not take it kindly and they had to make sure the guy learned his lesson and he would not do that again. The mistresses both dumped his sorry ass when they were done trampling him and the punishment was to make sure he did not cheat on anyone he dated after them.
This mistress paid this guy to do some creative work for her but he did not do it the way she had asked him to. The result was poor and she was not going to use it for anything. To make sure he learned his lesson and that he redid the work, the mistress turned to him and she trampled him with her high heel boots. He redid the work to her expectations.
Mistress Gaia and her friend chose to make this guy cry. The mistresses did it for fun and not because of what the guy had done. He just happened to be at the wrong place and at the wrong time and he met the mistresses who used their stilettos to torture him. He was trampled and crushed using the heels and he cried and peed himself out of the pain he felt.
This little slave loves feet - he's addicted to them and the pain they cause on him. He was searching for some new trampling goddess and gets into a nice session with Stacey, who's already experienced in this. She needs her bare feet only to make men suffer. So she stands on his head first and lingers there, crushing it with her full weight and squeezing his bones and skin until the maximum of his pain level.
Madame Marissa invited her friend to give her slave some nice double-torturing and spend some funny quality time. They put on their most beautiful high heels for him and let him suffer under their sharp high heels until he cries and screams, but the more fun the two ladies receive by looking in his afflicted facial expression. They even stomp him with their barefeet on him and give his chest some nice, painful jumps!
The slave films his own demise and suffers from harsh pain in this clip. His mistress Aga tries out her winter boots which all have very sharp heels. She's trampling all over his naked chest and his face, and it's obvious that this plagues him a lot. The deep treads of the new pairs of shoes scratch his skin completely, and Aga runs-in every single pair of them on him.