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.
Herrin Amy likes to get easy money. And she does not want to work for it herself. The best way she knows to make money is to give her sissies female clothes like g-strings and lingeries and makes them undergo her special feminization process. She then releases them to the market to make money for her. All she has to do is sit pretty and wait for her sissies to bring her the money.
A drunk spectator makes his way backstage after a burlesque show, and Lady Victoria decides to have a good time. She turns him into her own personal pin up girl, making him a proper sissy slave in make up and purty clothes.
You wake up in a hospital bed to find out your wife doesn't want you anymore, and you're going to be turned into a transexual slave and brainwashed into compliance. You're already being feminized, turning your body into that of a woman, and getting you obsessed with feet.
Mistress is resting in her office and wants to have some fun. So of course she brings you in to humiliate for a while. After making sure you know just how much superior she is, she gets in the mood for a good laugh. That's when she tells you to take out your cock
... for you. Because you are a pathetic loser and she's not going to go out to a date without bringing her friend over to make sure you do as you're told, and humiliate you like a loser sissy body. While your hot wife is out on a date, getting fucked by a well hung dude, you get turned into a little girl.
Mistress drags you outside so she can have a lot of fun putting you in your place. She's wearing a pair of sexy black heels and an even sexier fishnet top. While making sure you are completely humiliated, she gets out her strappon to make you feel like the real sissy boy that you are.
You are not worthy of Mistress Ivy Summers, but she likes to humiliate pathetic losers like you, so she's going to take some time to tell you just what she thinks of you, and your tiny little cock. Then she's going to make you hump a little girly pillow while she makes fun of you.
Auburn Mistress Sarah Black has you sit down while working you into a trance with her hipnotic words and pendulous breasts. She's going to turn you into a right proper sissy boy, and make your mouth water for sucking a fat cock.
You've been following a hot girl for a while, and finally she's decided to notice you. But it turns out she's a cruel and demanding Mistress, just like you'd expect of a woman. She makes you get down on your knees to worship her while telling you what to do, and exactly what to do with your little cock.
Lucky you, Mistress Jasmine Jones is going to take charge of your tiny little cock, because you obviously can't handle it. She shows off the little cock lock device she's going to use on you, and then has you put it on while teasing you with the key. Don't you just want to serve her?
Mistress Amyleen Moore is feeling generous tonight, and she's going to give you something. You've always wanted to try anal, right? Oh, no, you're not getting that dick anywhere near Mistress! She's going to give you anal. Bend over, looser, Mistress is going to have some fun.
This is a tutorial from a smoking hot blonde mistress who is going to show you how to dress as her total complete slut with hooker makeup. She's going to give you instructions while you watch how it's done and learn to be a perfect sissy.
Madame Noir and Miss Ella are going to have some fun watching the TV, and because they are out relaxing, they might enjoy the services of a pathetic foot boy. They like what they are watching and lay back to make out while he's forced to lick their dirty shoes, then sniff their socks and lick their naked feet.
Paige Turnah is a gangster, and she knows how to weild her power. She drags you into her office while she's relaxing in some sexy lingerie. But don't worry, the clothes are for you... to wear. She explains how she wants you to dress like a little girl, because she likes that. And she knows you'll do it, otherwise she'll set her goons on you.