Mistress BlackDiamoond is wearing a black corset and boots over her red latex outfit. She finds that her blonde crossdressing maid is being lazy and sitting on her throne. He is wearing red panties under his short black dress. She hits her sissy slave down to the ground. The cruel Mistress then puts him deep in the basement. This is only the beginning of his punishment and you have to watch the video to find out what happens next.
Bratty Jamie is wearing a hot pink bikini top in this tell all POV video. She confesses about the weird sissy sluts that she deals with in her life. The spoiled brat tells how she turned a real macho man into a helpless feminine whore that will do anything she tells him to do. She goes into detail about the crossdresser that likes to dress up and go shopping for lingerie with her.
Lady Jessica looks stunning in her black elbow-length gloves and stockings. She studies Freddy and starts training him to be her new sissy. The bizarre blonde puts a black wig on him and dresses him in sexy black lingerie and stockings. She gives the slender crossdresser the new name of Chantal. He makes a pretty good transvestite but he must pass the ultimate test of walking in white high-heeled shoes.
Lady CherieNoir remains fully clothed as she puts on her big black strapon. She wears black gloves as she makes her masked sissy slave suck the dildo. Her hot pink long-sleeved blouse matches the color of his mask. She tells him to be a good sissy and take the sex toy deeper into his mouth like a good little bitch. The blonde Mistress then ass fucks his tight man pussy hard and deep as a reward.
Princess Tori is the new college intern that specializes in humiliation. She has a lot of sexy panties for you to wear when beginning your sissification. The cute redhead also a butt plug for beginners. She will make you her new submissive sissy bitch in this POV video. You are no longer in charge and you better do what she says. Princess Tori may look sweet and innocent but she can be a mean Mistress if you don't put on your sissy panties.
These mistresses are the masters of punishments and humiliation. They made their slave lick their dirty feet and humiliated him in different ways making him be a sissy in the process
Miss Deeane knows how to use her hot and sexy self to mentally manipulate slaves. She wanted to feminise this slave but first of all she had to make him agree that he was a sissy and wanted to be sissified
Mistress BlackDiamoond wanted to humiliate her slave in a different way from the usual. So she decided to have the slave wear make up alongside her. And it was all kinds of make up from lipstick to eyepencils
Miss Tessa wanted to hmiliate her slave and sissify him. So she went and looked for lady panties and then made him wear them. He was humiliated but she had fun watching him walk around in it
This sissy wanted a favour from his master. He promised to do anything he wanted in order to get that favour. So his master decided to test his resolve and sought to humiliate him a little bit. He gave the slave a pipe to put in his mouth and then used a funnel to direct his pee into it and into the slave's mouth. The slave had to drink it to get his favour.