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.
Mistress Madison was bored in the house so she went online and searched for interesting things to watch. She came across blowjob sissy training videos and she loved them. She was so into them that she chose to try them out. She did not have a slave but she had a dildo so she pretended that she had a slave and she used her dildo to dominate and humiliate the imaginary loser while preparing to do the same to a real one.
Goddess Lilith is a cruel girl and she knows it. She was fed up with her slave and she chose to make him do the one thing she had never made him do. She made him wear female clothing and she turned him into a sissy. She whipped him hard and when she was done, she trained him how to suck a dick. He was in pain and he was degraded but she did not care.
Mistress X wanted to humiliate this guy without him realizing it. She was having fun at his expense as well as trying out her new skills. She used her seductive charm to turn him on. She then used her hypnosis skills to take control of him and then she got him to suck a dildo as she trained him how to suck a dick. She made him believe that he was having fun with her and he did it all.
Goddess Jordan had a new recruit and she wanted to sissy train him. She used her dildo to do it. She got him to learn how to give a good blowjob. She did not care how he felt. All she wanted was to humiliate him and she managed to do it. By the time she was through with him, he had learned how to do it like a pro. She warned him not to mess with her as she would make him suck a real one.
Mistress Ginger is turned on by guys who are easily sissy trained. She wanted to fuck this guy but without sissy training, she did not find him attractive. So she sat him down and she explained to him the things she wanted him to do for her. She sat back and she enjoyed how he learned blowjob skills, dolled up and did all manner of humiliating things to please her.
When this mistress found out that this guy was dying to fuck her, she took advantage of it and she humiliated him for fun. She pretended that she was a kinky girl and she got him to do all the kinky sissy things she wanted to try. She made him doll up and she got him to try blowjobs as well as other kinds of sissy training. He did it all thinking it was turning her on.
Lady Stefanie felt that this guy was behaving like a girl and he had to be treated like one. She made him wear stockings, female shoes, a bra, a blouse, and a weave. She was forced to do what the mistresses asked him to do. She was tied up and humiliated him using sissy training. The sissy was not only in pain, but he was also humiliated like never before.
Mistress Coco is not the kind of person to mess with and get away with it. She is the kind of person who will punish you and forget about it. She was bored today so she used a different type of punishment for the loser. She turned him into a sissy and she got him to do sissy things. She sissy trained him and enjoyed as he did what she ordered.
Mistress Amberleigh loves to get money from her paypigs. She was broke and she needed some money so she used her high heels to get money from her paypigs. She made this loser watch as she described what she could do to him with her high heels. She told him she could make him blow it and then use it to trample him on the nuts. He gave her the money.