Goddess Lena felt that this guy was a sissy and since there was nothing he was good at, she thought of making him excel at being a sissy. The mistress went ahead to make him deepthroat her strapon and she fucked him in the mouth with it. He was told to do it well or else it would end up in his ass and he did as she told him.
This mistress could not believe what had happened to her boyfriend. He was acting weird and she was pissed because she did not know what it was and he was not telling her. She chose to humiliate him in order to know the truth. She did not want to keep asking and not getting an answer. So she made him lick her feet and threatened to trample him before he told her the truth.
This mistress knew this guy did not get a lot of female attention so she resorted to making some money from him. She gave him her attention and she teased him. She got him to jerk off to her instructions because she could not fuck him. And for fun, she made him eat his own cum. She gave him instructions to that effect and he followed them to the letter. He paid her for her troubles.
Lady Milana did not want a sissy in her house. That is why she punished this one hard. She used her whip to do it and she did it in the woods where no one would come to his aids even if he screamed all he wanted. She stripped him naked and she whipped his naked butt and wore a strapon to fuck him in the ass as well as deepthroat him.
Lady Krasaviza could not accept the fact that he had lost money to this loser. She went to him and asked him to give her back her money. He refused. She had come armed with a wheel of torture. So she rolled it and wherever it stopped, that is what she did to him. Lady Krasaviza did it twice and he gave her the money and she went away happily.
Mistress Harley is an awesome girl with an amazing body. She enjoys luring guys with it and teasing them then denying them. She loves how they beg her to do something for them. She did that to this guy and while he begged her, she gave him jerk off instructions. He was glad and thought he was at least getting something out of it. But she turned to him and gave him cum eating instructions too.
Madame Marissa placed her slave's face in a trampling box. She then got the slave to lick her socks. She also used the same socks to cover his nose so that he could not breathe properly. She had a great time choking him and she made him pee his pants since he was defenseless, scared and was being choked. She let him go after she had had enough of it.
Mistress Ava Black wanted to punish her slave using a different method. She was afraid he would get used to the way she punished him and that would make her punishments less effective. When she was punishing him today, she used a total different punishment and he was shocked. He expected pain but she gave him cum eating instructions which he had to follow to the letter after he had jerked off.
Princess Morgana knows what to do to slaves and losers to get them to do what she wants. She customizes her punishments to fit the individual slave. This slave had not messed up big time so she made him lick her socks and her bare feet. She degraded him slowly and she there was nothing brutal in any of her punishments. It was just slight humiliation because his mistake was small.
Mistress Lindsey Leigh loves to mess with guys. If she likes you, she will get freaky with you. If she does not like you, she will tease and deny you then humiliate you. She did not like this guy so she teased him with her gorgeous ass. She then went ahead to give him jerk off instructions and when he came, she gave him cum eating instructions. The guy was degraded like never before.
