Mistress Madita needed to trample this lazy bastard and she did it with her high heels because she did not care what he felt. He had to know that she did not appreciate his laziness and if he did not change, he would have himself to blame for what would happen to him. He cried but she did not care about what he felt. She was only interested in his change.
Mistress Nemesis and countess Stella had an issue with their messenger for insubordination. They had to teach him never to mess with them and that is why they went out of their way to torture and humiliate him with their high heels. They felt that pain would do the trick and so they trampled him as painfully as they could. He cried and begged them not to continue with their punishment but he was ignored.