Category Archives: sissy training

Jasmine Transforms You into Her SissiMaid

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Amazon Princess Jasmine explodes when she finds a pair of her panties slathered with your sissy slime. Jasmine gives you an emasculating dressing down before stripping you and transforming you into her feminized sissy maid, right down to the ruffled white panties beneath your uniform. Now get down on your knees, worship your Mistress’ feet and BEG for her forgiveness you naughty sissy! 4 minutes. 
Princess Jasmine from www.humiliatrix.com
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Admit Your Sissy Secret for Miss Kendra

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Miss Kendra is sending you on a date; a date with an attractive, intelligent, commanding woman – a woman just like Miss Kendra herself. On this date you will wear frilly, lacy panties beneath your ridiculous real man facade. And you will confess to your date the embarrassing truth about yourself: that you are a panty-clad sissy who needs to be spanked, cuckolded and sexually dominated. 9 minutes. 
Kendra James from www.humiliatrix.com
Now showing at Humiliatrix.com

Miss Tessa Models Your Sissy Maid Uniform

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To remind you that you no longer have ‘boyfriend’ status in her life, your ex-girlfriend has gotten you a sissy maid uniform. You’ll wear your unform and a pair of high heels when you come over to clean her condo and wash her new boyfriend’s laundry during their love-making sessions. Now, then. Change into your uniform, give Mistress a curtsey and say, ‘Thank you, Miss Tessa.’ 6 minutes. 
Princess Tessa from www.humiliatrix.com
Now showing at Humiliatrix.com

Suckytime Lessons with Miss Kendra

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Open wide for mistress, sissy! Mean Miss Kendra is about to turn you into her cock-craving sucky slave – in three cruel lessons. First, Miss Kendra makes you nurse on an ‘i luv daddy’ baby pacifier, then she graduates you to a cute penis pacifier. Finally, when Miss Kendra determines that you are ready to give head for real, she cock-trains you to suck a life-size nine-inch dildo. 9 minutes. 
Kendra James from www.humiliatrix.com
Now showing at Humiliatrix.com

Miss Paige Locks You into Chastity

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Miss Paige is a conservative Southern woman who firmly believes that wimp husbands and boyfriends belong in panties and chastity. Paige demonstrates how she uses a locking chastity cage to punish naughty wimp-cucks who defiantly smear their emasculation panties with futility squirts. 5 minutes. 
Princess Paige from www.humiliatrix.com
Now showing at Humiliatrix.com

You Are Miss Tessa’s Substitute Sucker

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Miss Tessa has a big problem on her hands. Her stud boyfriend is drunk in the living room, demanding the blowjob that she promised him. But Tessa doesn’t want to get her pretty face and makeup mussed. So, guess what, weakling? Tessa is going to feed him more drinks and lead him on… and then paint your face and pick out some lingerie for you to wear – so you can do her dirty work. 9 minutes. 
Princess Tessa from www.humiliatrix.com
Now showing at Humiliatrix.com

A Sissy Maid for Princess Harley’s Sorority

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19-year-old Harley’s sorority sisters asked her to train a submissive wimp to serve as the their sissy maid. Harley wants YOU for the job. Harley knows just what she needs to do to slide those lace panties up your legs and cinch that maid uniform tightly around your waist. Your first task is to scrub the girls’ bathroom with your toothbrush. Don’t make Harley have to discipline you in front of all the girls. 7 minutes. 
Princess Harley from www.humiliatrix.com
Now showing at Humiliatrix.com

You Are Dani and Cobi’s Sissy Cuck Maid

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Princesses Danielle and Cobi need someone to shine their high heels, handwash their lingerie and scrape the sticky condoms off the floors of their bedrooms. That someone is YOU, missy. Dani and Cobi describe your duties in emasculating detail as they dress you in a frilly sissy maid uniform and belittle your manhood. Be a good sissy cuck maid and you can kiss Cobi’s toes and worship Dani’s ass! 7 minutes. 
Princess Danielle and Princess Cobi from www.humiliatrix.com
Now showing at Humiliatrix.com

Tessa Demotes You from Boyfriend to Sissy

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You finally got your chance. Stunning Princess Tessa lets you take her on a date. Now you’ve made it all the way back to her bedroom, only to be rejected. Tessa calls her ex-boyfriend right in front of you, tells him what a wimp and dork you are, and invites him over. Then she orders you to wear sissy panties and stand in the closet – so you can see what a real man gets to do to her. What a cuck wussy you are. 9 minutes. 
Princess Tessa from www.humiliatrix.com
Now showing at Humiliatrix.com

You Will Cum Like a Girl for Miss Kendra

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Miss Kendra continues to prepare you for your sissy punishment fucking by teaching you to cum like a girl. Miss Kendra forbids you from touching your silly, worthless “boy parts.” Instead, Mistress makes you use a penis-shaped vibrator to deeply penetrate your sissy-clitty, until you begin to squirm, squeal and beg to make a girlie cummy for Miss Kendra, as she teases and encourages you. 10 minutes.
Kendra James from www.humiliatrix.com
Now showing at Humiliatrix.com