Today is the last time you will orgasm as a man as Mistress Annie is about to transform you into her perfect little sissy slut. It’s a good thing you are already on your knees as you will be spending most of your time right there sucking lots and lots of cock. German Mistress Annie will not take no for an answer even if you are hesitant about becoming the slutty girl of your fantasies. She is a young, strict Mistress who knows your life will be much happier kept as a sissy girl for her entertainment. Time to burn every last one of your ugly boy clothes as she has just the right sissy outfit that perfectly fits a bitch like you. Now stay on your knees where a good sissy belongs and show her that sissy clit stick. Mistress Annie will instruct you on just how to stroke and play with it one last time before it’s locked up for good.
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To become a real sissy whore, it is vital this slut focusses fully on the pleasure of others. I have explained her that today she will receive her last orgasm, after that no more and the chastity cage will come on. Bound and helpless she won’t stand a chance, with my soft hands and long nails I will force this sissy to cum. She tries to resist my magical touch but starts oozing spunk, much to her own desperation. I stop the bit of pleasure she might have straight away and fully ruin it by instructing the slut to eat her own cum.
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Mistress Isabelle just loves her slave in pink and has decided he will be much better kept as a girl than a boy. The sissy is so eager to please and become the prissy little doormat that his Mistress desire. She unlocks her new sissy bitch out from his cage to give the attention that her bare naked soles deserve. First she demands her heels to be properly licked to show how much the sissy adores the lowest part of her body. The sissy is such a good girl for his Mistress as he obeys her orders without question and worships every inch of her feet like a well-trainedsissy doormat does.
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The feminization process continues as my sissy gets her frilly clothes and layers put on. She can only be called sissy once the transformation is complete.
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Mistress Naomi Swann knows how to treat her sissy sluts when they have done all their chores to the utmost perfection. Just because the sissy rubber maid has deserved a reward though doesn’t mean Mistress Naomi won’t get her fun out of it. With her sissy restrained to the bench a milking machine is strapped to it’s cock for her to edge with the controls. Keeping a sissy thoroughly drained when they have been a good girl is only one of the perks to being owned by Mistress Naomi.
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After 3 months of no orgasms and locked in chastity Mistress Kendra’s sissy slave is being allowed one glorious orgasm. This will be the final milking her sissy will receive to finish milking out every last ounce of testosterone that’s left in his balls. Sissies are only allowed to cum in the name of science or by being fucked in their sissy hole so today is a special day for the slut. Once every drop of testosterone has been yanked out of the sissy’s balls the transformation from man to bitch will be complete. Mistress Kendra attaches her full proof milking machine to the sissy’s horny clit making it impossible to hold anything back. The final step of the sissy’s transformation will be completed whether the bitch wants it or not. It’s officially too late to turn back to his old life as a real man now that the machine is turned on sucking every drop of cum from it’s balls. The sissy’s fate is set….
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How do I create the perfect sissy? Watch me dress up Jenna from nude to fully transformed prissy sissy. Her new life as my slut can begin. Every layer of clothing will change her from male to female. Her cock locked and giving her huge boobs will be the first part of the feminization.
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Wearing a very short latex maid dress and a tiny little pink chastity cage, I work hard on completing my chores, mopping the floor like a good girl while my Master relaxes on the couch watching TV. Inevitably, he gets distracted by me prancing around and bending over in front of him and orders me to my knees with a snap of his fingers. I immediately comply and start sucking his cock as I’ve been trained to do – my own dripping precum in it’s cage. He starts to finger my ass and I know what that means – he’s going to fuck me. He bends me over the arm of the couch and pounds my asshole long and hard, making me moan and gape. At one point I try to play with myself, but he pulls my hand away – I know better. Once he’s had enough he puts me on my knees and drains his balls into my open mouth, plastering my tongue and face with his cum. With cum still on my face, he orders me back to my chores.
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Mistress Naomi has rented a vacation home for the summer and her very own sissy rubber maid comes attached to the deal. The sissy maid is trained in most areas of servitude but just in case it needs to be put into its place a shock collar is locked around its neck. Mistress Naomi has had a long day of traveling and just wants to rest her feet up and relax. She calls upon her new personal rubber sissy maid to do just as he was trained to do and worship every inch of her beautiful soles. The sissy bitch isn’t as perfect as the flyer made it seem and Mistress Naomi shocks the hell out of the slut to whip his service into shape. By the end of her stay, he will be a well-trained sissy maid and Mistress Naomi’s feet worshipped to perfection.
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A sissy maid should keep my shoes and her heels in perfect condition. Failing to meet my standards will result in a good OTK spanking until the naughty ass cheeks are red and painful.
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Mistress Isabelle allows her newly trained sissy bitch one final milking before his transformation is complete and his clitty stick is locked away forever. His balls are tied, tucked and pulled as far back as they can possibly go. Isabelle strokes his horny clit stick edging it until he is ready to burst. She makes the sissy throw his legs over his head and shoot a huge, nasty load all over his face and into his gaping mouth. He is going to be a very well-trained sissy cum dump but needs to learn how to take and swallow gigantic loads like a good whore.
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Oh, now it’s no good crying about it sissy – that’s not going to change my mind and besides, you can’t expect to stay in the hotel room with me and my real man surely? No – you’re going to be locked out all night! and that’s an end to it! As soon as I’ve secured the padlocks to the collar of your pink frilly maids’ uniform and snapped the locks closed on your pink platform heels, you’ll be ready to go. You’re completely feminized and locked into every humiliating piece of girly clothing. Your dress and heels – padlocked to your body, your tight corset – locked in place – even your panties cannot be removed. You have no way of removing any of your effeminate sissy outfit which is going to make your night of public humiliation one you’ll NEVER forget.

Your pretty blonde wig, long eyelashes and perfect makeup might just fool some people but the over-the-top pink uniform with layers and layers of ruffled lace are going to totally give you away as a complete sissy! My real man will be staying with me in the hotel tonight and your services won’t be needed so when he gets here – you’ll be locked out. You’re going to have no money, no phone and nowhere to go! Every second you’re locked out will be excruciatingly humiliating for you. Starting with the elevator ride from the 23rd floor to the lobby – can you imagine the giggles you’re going to attract sissy? Then where are you going to go? You can’t stay in the hotel bar dressed like that. Where on earth can you hide in your bright pink sissy uniform huh? I can’t wait for you to tell me and my real man all about your humiliating adventure in the morning.
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If it’s one thing all sissies need it’s to be constantly filled with cock. Mistress Naomi’s sissy rubber maid has proven to be very useful and deserves a reward of a thick, strap-on dick fucking his slutty holes.
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Mistress Kendra’s male slave has failed as a man in life and in sexual slavery. He is no longer of any use to her as a man but she has better plans in store for the bitch. Instead of throwing him to the wolves she decides he would be much better suited as a sissy slut for her business ventures. His cock is worthless and will now be permanently caged shut so the only sex life her sissy will be having is with his holes. Mistress Kendra orders him to strip the last of his manhood away as she begins transforming him from boy to sissy whore. Big, extra thick and gigantic anal balls will do just the trick to start stretching out the sissy’s holes so dicks can just slip right in. Kendra’s sissies must be stretched, hollowed out and constantly filled if they are going to impress her big stud cocks she has lined up.
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