This guy thought that lady Naomi was a coward and that she could not do what she had told him she would. The mistress forced the guy to lick her ass and do it according to her instructions. The guy wished that he had never messed with her but it was too late and all he could do was agree to do what she ordered him to do. That is all he did.
Lady Naomi and her friend were interested in some cruel and painful slave humiliation. That is why they settled on caging this guy's cock and he could not believe what he was made to do. He was tricked to disregard the obvious and that is why he had to eat his own cum. She told him that he was lucky not to be eating other people's cum. The slave understood.
Lady Naomi wanted to get some money from this loser and she knew the best way to get it was to make sure that the guy was scared and he knew he did not have an alternative other than to meet her demands. That is why the mistress teased the guy and had him wear a chastity device. He thought they were having fun but as soon as he had worn it, she blackmailed him and made him pay her to unlock it.
Lady Naomi knew that this slave had a weakness for sexy asses like hers. And since she wanted to punish and torture him, she had him wear a dick lock and then she took off her clothes and she teased him. He was turned on but he could not get the cock lock off. And it hurt him as his dick had nowhere to expand to as he got an erection.
Lady Naomi despised this guy and she felt that the best thing to do to him was to humiliate him. So she did not hesitate to do it and she made sure that he was as humiliated and as degraded as she could manage to. She did it by using her chastity femdom. He was made to wear a chastity device and then she teased him and watched as his expanding dick hurt him as it squeezed again the dick lock.
Lady Naomi could tell this debtor was not about to pay her back as he had overstayed with her debt. She had to find alternative means to get the guy to pay his debt and she used chastity femdom to do it. She made him wear a cock lock and since his dick was caged, he could not do anything. He had to beg her to open it and she did it after he had paid her and she had messed with him a little bit.