Mistress Masha was cheated on by her ex boyfriend and it hurt her to the core and led to their breakup. She was pissed at him and she had to torture him and she felt that the best thing to do to him was to humiliate him and do the kind of things that she wanted to do. She knew that doing that would lead to her having fun at his expense and she did it.
This mistress needed to sissy train her slave and she did so using her strapon. She wore it and used it to fuck him in the ass. It was painful but she did not care what he felt. He had to obey all of her instructions and he had to put up with everything that she wanted to do to him. He felt pain and he was even more degraded but she did not care.
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.
Mistress Gaia was tired of asking for her money back from this guy. She felt that for her to get back the money, she had to do something she had never done before. And that is how she turned to sissy girl training. She used it on the guy and in no time, the guy was doing things that he had never imagined were possible. He regretted why he had not paid her.
Lady Rockabella wanted this guy to learn his lesson and so she used her sissy girl training to dominate him. He was turned into a sissy and he had no choice or say in the matter. He had to follow her instructions to the letter and the mistress made sure that he did things her way. As a result, she not only dominated him, but she also had fun seeing him do what she asked him to do.
Mistress Isabella noticed that her slave had sissy tendencies and she knew it was time to turn him into one and she did no hesitate to change him into one. He was forced to wear like one, to wear make up like one and she even threatened to use her strapon on her. She cried and begged her not to do that so instead she had him lick the soles of her heels.
Princess Serena does not like this sissy and she knew the best way to torture him and scare him not to mess with her or approach her or be seen anywhere near her was to do something he did not expect. And so she teased him a little and when he was turned on, she punished him for being turned on and she threatened to ass fuck him with a strapon.
Goddess Yasemin did not like this slave's attitude and she had to do something she had never done before which was to turn the guy into a sissy. The guy had to learn his lesson and learn it in a way he had never done before. So she took a dildo and a strapon and she used them to torture him. The sissy also had to lick her high heels.
Mistress Sofi and her friend mistress Kira did not like what this sissy had done to them. He had tried to mess with them thinking that they would either like what he did or they would be scared and he was good with either reaction. But they did not like any of what he did and they were not scared of him. Instead, they used strapons to fuck him in the ass as punishment.