Mistress Gaia felt that this loser was not deserving of being her slave. She punished him using her boots. She had him lick her boots and when he was done licking them from the sole up, she used them to trample him. He had never felt such pain before and he cried like a baby. She, however, ignored his cries and concentrated on torturing him to make sure he would not forget it.
Mistress Julia and her friend Bertie had to tell this guy to stop following them around. He was a stalker and they did not want him doing what he was doing. He was freaking them out but instead of giving in to fear, the mistresses crushed him using their boots. They also made him lick the boots to their satisfaction before they warned him against ever stalking them if he knew what was best for him.
Lady Betty was interested in humiliating and degrading this guy. She had no other intention and she did not hide it once the guy was in her house. At first, he thought that she was being naughty and kinky but he realized she was serious when she made him lick the soles of her high heels. She threatened to crush his head if he did not do it. Luckily for him, they were not dirty.
Princess Serena showed off her sexy ass to this loser. She wanted to distract him and get him to do some naughty things for her. She wanted to turn him on and when he was vulnerable, she takes advantage to get him to lick her high heels. She teased him and turned him on then made him lick the soles of her high heels. She then pretended he had not done it as well as she wanted and chased him away.
Mistress Jenny caught her slave masturbating to her photos and she was not impressed. She did not care what he did to his body but she did not want to be part of what he did. She did not mind him masturbating, but she definitely minded the fact that he used her photos. To make sure he would not do it again, she made him lick her muddy boots as punishment.
Madame Marissa learned that her slave had been lying to her. She was mad and she used her boots to punish him. She had him lick the soles of her boots so that he would learn never to let his tongue utter falsehoods again. She did not listen to him and neither did she forgive him when he begged for mercy because she was sure he knew what he was doing when he lied to her.