Category Archives: challenges

Princess Tessa Issues You a Small Penis Chastity Release Challenge

“I will agree to unlock you from your chastity cage — just to satisfy my curiosity. Because I’m pretty sure you’re not capable of satisfying anything else. Who knows? Maybe you’ll impress me. Or maybe I’ll end up emasculating you so sadistically that you’ll come crawling back into your cage like a scared little puppy….”

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Princess Tessa Proves You’re Hopelessly Addicted to Her Perfect Ass

“The more I degrade you, the more you keep coming back for more. What if I told you to kiss my ass? You’d do it, of course. You’d french kiss my perfect ass if I let you. But what if I told you that kissing it would disqualify you forever from me taking you seriously as a man? Would you still try to kiss it, hmm, piggy?…”

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Princess Tessa Dares You to Challenge Her Boyfriend to a Fight

“I love it when guys fight over me. It turns me on. The winner gets a real-man reward. And the loser? The loser gets humiliated, of course. So. My boyfriend found out about you. And he’s on his way over. Are you going to try to impress me? Or are you going to crawl into the closet and hide there like a scared little baby?…”

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Goddess Amy Offers You a Humiliating Charity Fuck

“Here’s the deal, geek boy. If you can stretch out this XL condom with your cock? I will let you fuck me for real. If not? I will strip the fuckbag off your feeble pecker and make you fuck my fake pussy as I taunt you into sputtering the most humiliating loser load of your life. And then you’re gonna lick it up as I laugh at you…”

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Tessa Mocks and Teases You for Being a Crybaby in Chastity

“Let’s see if you’re up for a little challenge. I just put on my sexy holiday lingerie. Why don’t you come into my bedroom, take a good look at me, and see if you can wear the ‘man-pants.’ Do you think you can do it? Or will you be intimidated by me — and start whining like a little crybaby in need of punishment?…”

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Sissy Test #2: Brianna Sends You on a Panty Humiliation Assignment

“I’m sending you to that lingerie boutique. The one where all the ice princesses shop. The one with all the sadistic salesgirls. I’m sending you into the panty section with some specific instructions sure to reveal whether you are a man who belongs in boxers, or a sissy who deserves to be stripped and pantied…”

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Butt Kissing Challenge with Perfect Princess Rhianna

Rhianna sees you’ve drenched your pants with precum while staring at her divine derriere. She snaps her thong, cocks her hips and uses her perfect ass to put you in a state of total agony and desperation. Would you like to kiss Rhianna’s ass? Would you like to worship it? Be her brown-noser? Be careful what you wish for, weakling. Evil Rhianna is going to make you cry.

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Miss Kendra Blackmails You into a Panty Humiliation Assignment

Miss Kendra has caught you on Humiliatrix.com. You have no choice but to obey her every command – or risk having your most shameful secrets exposed. You will undertake a risky, real-life panty humiliation assignment at Miss Kendra’s direction: a task that will force you to confront the lacy, frilly, emasculating truth beneath your ridiculous masculine facade.

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Mistress Kendra DARES You to Come to an S/M Club as Her Submissive

Miss Kendra calls you out for being the porn-surfing, cock-squeezing, tissue-squirting, feeble little fist-fucker you are – by challenging you to accompany her to an S/M club… as her slave! To do so, you will have to wear a humiliation outfit that reveals your laughable fetishes and showcases your shameful weaknesses. Ready to be publicly humiliated by Mistress?

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