Category Archives: sissy training

Princess Harley Turns You into Her Sissy

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Devious Princess Harley uses your weaknesses to lure you into her pink lace spiderweb of a trap – and the only thing you can do about it is beg this bossy 19 year-old to have mercy on you and not humiliate you completely. Do exactly as Harley commands and maybe you’ll only end up emasculated and embarrassed. 7 minutes of sissy abuse. 
Princess Harley from www.humiliatrix.com
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Miss Kendra Sends You on a Sissy Humiliation Assignment

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No one knows your innermost secrets and your vulnerable soft spots like Miss Kendra. When Miss Kendra locks you into her hypnotic gaze you become feeble – and powerless. Miss Kendra wants to push you past your boundaries and take you to those forbidden places you’re afraid to go. You will do exactly as Miss Kendra instructs you.  6 minutes. 

Kendra James from www.humiliatrix.com


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Wimp to Wussy: Miss Kendra Hires a College Cutie to Cuckysit You

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You have proven that you can not be trusted home alone when Miss Kendra is out on her dates. Therefore, she has decided to hire a collegiate cutie to “cuckysit” for you. Are you embarrassed? You should be. Your sitter is going to put you into rhumba panties and make you drink a yicky-sticky sissy protein shake. Better behave! Or you might get spanked!  9 minutes.  

Kendra James from www.humiliatrix.com


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Shave and a Tampon: Miss Kendra Leaves You Smooth & Emasculated

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Miss Kendra shreads you of your last vestiges of manhood. She shaves your legs and pubies sissy smooth – and then impales you with a tampon. You are about to become 100 percent girly from the waist down! Add stockings and a pair of panties and you are all ready to be sent out into the world – as a swooshy-silky sissy beneath your laughable manly exterior.  5 minutes.

Kendra James from www.humiliatrix.com


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Sliding Scale: Dr. Kendra Pimps You out to Pay for Your Therapy Sessions

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Dr. Kendra sympathizes with your economic difficulties. You are making such great progress in therapy that Dr. Kendra is going to allow you to take advantage of her special version of the “sliding scale.” The kind of sliding scale where where you slink into mens’ restrooms, slide to your knees, and slip your mouth over throbbing cocks – as a sissy slut $10 blowjob whore.  9 minutes.

Kendra James from www.humiliatrix.com


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Dr. Kendra Encourages You to Explore Your Repressed Feminine Nature

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The shame you feel as an under-endowed man is a source of concern to your therapist. To alleviate the social pressures thrust upon you as a feeble, sexually-inadequate male, Dr. Kendra wants you to fully embrace your feminine side. Dr. Kendra rids you of your masculine pretensions as she guides your mouth along the phallic symbol strapped around her waist.
 
Kendra James from www.humiliatrix.com
 
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Caitlyn Dumps You for Your Dominant Lesbian Boss: Now You’re Their Bitch

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Your dom boss has always bullied and bested you in the office – and now she’s even won your woman away from you! Caitlyn got seduced and stolen away by your lipstick lesbian boss and they have decided to turn you into their lifestyle slave. Your boss even gave Caitlyn a strap-on cock to put you in your proper sissy place. The tables just got turned on you, wussy!  6 minutes.

Princess Caitlyn from www.humiliatrix.com


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Mocking, Teasing Princess Dorothy Is Your Cuckysitter

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Coochie-cuckie-coo! How humiliating is it when your ex-girlfiend agrees to cuckysit you! Dorothy already knows what a ridiculous little sissywimp you are, so she takes special pleasure in mocking you and putting you in your place. Your place is at Dorothy’s high heels, sucking a penis paci, wriggling around in rhumba panties, with gooey cum-cums all over your face.  8 minutes.

Princess Dorothy from www.humiliatrix.com


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Attitude Adjustment: Selena Turns You into Her Sissy Fuckbrat

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Selena says that only way you’re allowed to cum from now on is when she’s pounding yer ass with her strap-on cock. No jerking, no touching yourself any more. If you want to cum you’re gonna have to beg for the strap-on and cum like a sissy fuckbrat: with your ankles held in the air by Selena, your sissy clitty squirting in your face and her big fat cock up your ass. 
 
Princess Selena from www.humiliatrix.com
 
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Mean Selena Hires a Cruel College Cutie to Cuckysit You

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You passive-aggressive pussy. Every time she goes out on a date, Selena knows that you crawl into her hamper and piddle her dirty stockings and panties with your sorry cuckold cum squirts. No more! Selena hired the meanest college girl in the ‘hood to treat you like the pathetic little wimp you are while she’s getting it on with her real men boyfriends. 
 
Princess Selena from www.humiliatrix.com
 
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