Category Archives: sissy training

Miss Kendra Snaps You into a Chastity Cage

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Miss Kendra has discovered the pair of punishment panties she put on you – crumpled, hidden and slimed with sissy goo. Miss Kendra pinches your ear and escorts you into her bedroom for an angry scolding. You just won yourself two weeks in a pink chastity cage … beneath a pair of frilly, lacy panties. Yellow panties. For cowards like you. The better to embarrass and emasculate you with. 9 minutes. 
Kendra James from www.humiliatrix.com
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Sissy Regression Session with Miss Tessa

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Not only have you lost your boyfriend privileges and your bedroom privileges, little man. Miss Tessa has now decided that when you’re being cuckolded, you will wear thickly-padded sissy panties and sleep in the closet! You can wriggle around in your rhumba pants and suck a binky while Tessa brings her real-man boyfriend into the big bed. Better keep quiet or you might get spanked! 6 minutes of sissy-cucky shame. 
Princess Tessa from www.humiliatrix.com
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Your Intern Jasmine Takes Total Control

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Does it humiliate you that your college intern Jasmine towers over you in her high heels? Amazon Jaz knows you are a wuss of a boss and now she’s decided to take control of you. Because she caught you drooling over her massive boobs, Jasmine sends you to your knees and makes you suck a binky. Then Jasmine commands you to spill all your worship snot as she verbally emasculates you. 4 minutes. 
Princess Jasmine from www.humiliatrix.com
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Miss Tessa Punishes You in Sissy Panties

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Tess has decided to send you on a punishment assignment to show you exactly what she thinks of you as a man. Your humiliation begins with a snug pair of pink sissy panties tugged tight around your laughable little package. Strip and put your panties on while Tessa tries to contain her laughter. Once you’re properly attired, Tess is going to send you on a public sissy punishment assigment! 5 minutes.
Princess Tessa from www.humiliatrix.com
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Cocksucking Practice with Princess Hanna

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Princess Hanna thinks you’re pathetic. She let you into her bedroom but you’re too feeble to fuck her. Since you’re such a wussy maybe you need to learn what it’s like to lick, suck and swallow a big bad fuckwad of dick, yourself. Hanna shoves dildos down your throat, spits into your mouth and teases you for being such an eager cocksucker. By the time Hanna finishes you off, you’ll be ready to suck cock for real. 16 minutes. 
Princess Hannah from www.humiliatrix.com
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Cuckold Lessons with Princess Paige

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Princess Paige knows that you are jealous, angry, and nervous about becoming a cuckold. So she’s going to teach you exactly how to accept your new “second place” status in the bedroom. Tonight’s lessons: how to dress like a sissy cuckold. And how to dispose of your alpha male superior’s cum-filled condoms. Princess Paige is going to help you make your wife and her new boyfriend very happy! 6 minutes. 
Princess Paige from www.humiliatrix.com
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Cream Your Sissy Panties for Miss Kendra

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Miss Kendra intends on stripping you of all your masculine pretensions tonite. The first step is for you to prove to Miss Kendra that you truly are her helpless sissy weakling. You will wear the darling sissy emasculation panties Miss Kendra picked out for you. And then? After Miss Kendra teases and shames you into arousal? You are going to spill all your worthless wussy cream into your sissy panties for Kendra. And then your real humiliation begins… 8 minutes. 
Kendra James from www.humiliatrix.com
Now showing at Humiliatrix.com

Harley Trains You to Be Her Sorority’s Sissy

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“On your knees, NOW. Can’t you follow instructions!? Do you need a smack to help you pay attention?!” Princess Harley let you be her sugardaddy. Now she’s giving you the chance to become her sorority’s sissy slut servant! You get to handwash the girls’ panties, shine their stilettos and keep them stocked in tampons and XL condoms for their hook-ups. Don’t fuck up – or you’re gonna be yelled at and humiliated by Harley in front the entire sorority. 9 minutes. 
Princess Harley from www.humiliatrix.com
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Princess Harley Is Your Cuckysitter

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First Harley encouraged your woman to date other men – because you are such a wimp and wussy. HA HA! Then she decided to humiliate you even more by stepping in to ‘cuckysit’ you while you are being cuckolded! Now, tonight, while your woman is getting fucked by her new man, you’re going to get punished and humiliated by bratty Harley. That’s right, little miss wussy panties! Harley’s in charge of you! 7 minutes.
Princess Harley from www.humiliatrix.com
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Ice Princess Jenni Sends U to Your Knees

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The agency sent Jenni to be your housekeeper, but she quickly sized you up and stripped you down, helping herself to an expensive new wardrobe, spike heels, diamond jewels, and an elegant set of French manicured nails. Guess who’s doing the housework? You, wimp. Hands and knees, scrubbing the toilet with your own toothbrush, wearing nothing but a pink lace thong, as Jenni lashes out at you in her native Czech. You’ll figure it out or get beaten, imbecile. 6 minutes.
Princess Jenni from www.humiliatrix.com
Now showing at Humiliatrix.com