Mistress Evgenia was pissed by this sissy and she wanted him to get humiliated. She felt that that was what he deserved. So she used her strapon to ass fuck him. He had to feel the pain and beg her for mercy. So she made him remove the lingerie he had worn and she went to town on his ass. He felt pain he had not felt before in his life.
This investment banker's advice had backfired so badly that these mistresses lost a lot of money. They were so angered at what he had done and they had to punish him so that he would be careful with his advice next time. That is why the mistresses had to make sure that the punishment would be the kind that he would never forget. So they used strapons to ass fuck him and turn him into a sissy.
This mistress had a landlord who was into all kinds of fetishes and he wanted to explore them with her. She found it weird and she told him off a couple of times. But he kept asking her for it and she got tired and she turned him into a sissy and she did it so that he would never have to ask her about any kinky or naughty thing.
Princess Nikki and princess Smiley did not want this guy to go on cheating on people and being a player. That is why they had to punish him and they did so using their sissy girl training fetish. The mistresses turned the guy into a sissy and ass fucked him in the ass. He felt untold pain and wished that he had never been a player. But he had no choice other than to take the punishment.
Goddess Kiffa and mistress Victoria had no use for this guy because he was disobedient. The mistresses had to punish him and they used their strapons to do it. They turned him into a sissy and they had a great time torturing him for fun. He could not understand why all that was happening to him but he had no choice but to do what they asked him to do which included deepthroating him.
When mistress Alexandra realized that she was dealing with a spy, she had to make sure he would never do so again and that he told her all he had gathered as well as who had sent him and what he had reported. She turned him into a sissy to get him to talk and as he got fisted in the ass by her, he told her all she wanted to know.
Mistress Antonella needed this sissy to be put in his place and she did so by giving him the sissy training. She made him undress, then she had him wear female underwear. In addition, she had him kneel down for a few lashes of her whip before she got him ready to do all that she wanted him to do including sucking on her dildo and strapon. He knew obedience to her was paramount.
This sissy needed to be dominated and mistress Nica did not hesitate to do so. She had to go out of her way to dominate as well as humiliate him and she did it with her strapon. She wore it and she used it to deepthroat him and make him get used to it. She told him if he did not obey her at all times, she would use it on his ass.
Mistress Nica did not like this sissy and she had to express her feelings towards her. She did so using her high heel boots which the sissy had to lick. The mistress told him she would not ask twice and he feared what she would do to him if he did not obey her so he licked her soles and also swallowed her saliva out of fear of mistress Nica.
Mistress Harley felt that she needed to sissify this slave as she had seen his behavior and it was that of a sissy. So she used her hot body and especially her big tits and her big ass to dominate him. He was turned on and the mistress went ahead to sissify him and to make him endure a lot of humiliation as well as degradation before she let him go.