Category Archives: sissy training

Miss Kendra Will Free You from Chastity to Give You a Slut Facial

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Kendra James from www.humiliatrix.com
“I will release you from your 21 days of chastity cage agony, ONLY if you agree to be tarted up like a tramp, in full makeup, acrylic nails and a skimpy sissy outfit. So that I can command you to arch your hips, hike up your skirt, pull down your panties and spunk all that cum all over your slut face for Kendra. Well, sissy?…” 7 minutes. 
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Princess Tiffani Transforms You into a Sissy Ballerina

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Princess Tiffani from www.humiliatrix.com
“I decided to expose your secret sissy side to my girlfriends – by signing you up for ballet class! The instructor is sooo mean. She spanks her students and makes them wear these disciplinary heels. But don’t tinkle your panties. I’m gonna prepare you. First we need to insert this sissy plug to help you with your posture…” 6 minutes. 
Now showing at Humiliatrix.com

Goddess Stephanie Gives You a High Heel Humiliation Assignment

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Princess Stephanie from www.humiliatrix.com
“When I sent you into my shoe closet, I told you to clean and organize – not drool and dribble. Since you have such an uncontrollable fetish for my high heels, I’m going to take the pair of spike heels that you ruined and use them to punish and humiliate you. Crawl back into my shoe closet and strip. NOW… ” 4 minutes. 

Sissy Trainer Stephanie Pimps You out on a Gay Date

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“Since you’re a total failure as a man, I got the password to your dating site and changed your profile from Man Seeking Women to Sissy Seeking Cock. I’m making you a date with hunky guy who wants his massive dick sucked. Don’t worry, sissy. Stephanie is gonna teach you how to take care of your man…” 5 minutes.
Princess Stephanie from www.humiliatrix.com
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Small Penis Panty Humiliation at the Sorority

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Snarky Princess Harley decides to humiliate you in front of her sorority sister Robin by making you strip and show off your tiny penis. After the sorority sisters have a huge laff at your tiny winkie, they decide to put you into panties and make you do sissy sorority chores. 12 minutes of small penis panty humiliation.
Princess Robin and Princess Harley from www.humiliatrix.com
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Princess Liz Tricks You into Sissy Servitude

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Princess Liz puts you thru a cruel tease and denial session to weaken you into wearing panties for her. One Liz gets you into panties? It won’t be long before she can coax you into a sissy maid dress and turn you into her helpless, fully-feminized sissy servant. Think you can resist you bitchy-bratty owner? 7 minutes.
Princess Liz from www.humiliatrix.com
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Make a Worship Shrine to Cougar Akira

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You are going to stay up all night tonite and prove to Goddess Akira that she owns your sputtering little cock – by making her a worship shrine. First you’re going to plaster your walls with photos and screen caps of sexy Akira. Then you’re going to plaster your sissy panties with worship cum for Akira. 7 minutes.
Princess Akira from www.humiliatrix.com
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Jenny Turns You into Her Sissy Servant

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Bikini Goddess Jenny set you up. She knew you’d get weak if she left you to launder her dirty lingerie. Now she’s caught you red-handed, pervert. Now you have no choice to but to put on the sissy maid uniform and become Jenny’s full time sissy attendant. Perfect for a weakling and idiot like you. 3 minutes. 
Princess Jenny from www.humiliatrix.com
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Miss Kendra Commands U out of the Closet

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You simpering little liar. You prissy-prance around in real-man clothes trying to fool the women in your life – but Miss Kendra knows the shameful sissy truth about you. It’s time for you to get real with your sissy self. Miss Kendra assigns you a humiliating task designed to make you reveal the real you. Like it or not, naughty miss sassy panties. 6 minutes. 
Kendra James from www.humiliatrix.com
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Amazon Princess Jasmine Pops Yer Cherry

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Princess Jasmine has no doubt that she can overpower you, pin you down and strip you of your sissy virginity. Do you doubt it? Because you are getting the strap-on tonight, bitch boy, one way or the other. You can lift your legs and take it like a good fuckbrat. Or you can try to resist Jasmine – and really get humiliated. 3 minutes. 
Princess Jasmine from www.humiliatrix.com
Now showing at Humiliatrix.com