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Category: Tasks

It’s Too Late Now, Wimp (Episode 7 of The Big Wimp Theory)

Assignments Crossdressing Encouraged Fem Feminization Foot Fetish Humiliation Leg Fetish Make Me Bi Pantyhose / Stockings Shoe Fetish Sissy Training Slave Training Tasks

.. quite a few drinks together and I’m gonna try something a little more interactive this time. It’s a game called “it’s too late now”! Making you thank me for screwing you over is what makes this game super cruel. I’m gonna have a lovely dinner with you tonight as I think up exactly what humiliating outfits I want you to wear and exactly the humiliating things I want you to say. And then I’m gonna have you pause and email me the video! Hahahaha.

Starring: Heather Highborne Tip Heather Highborne Directly

October 24, 2026
Wimps Want Dirty Shoes For Dinner (Episode 8 of The Big Wimp Theory)

Assignments Crossdressing Encouraged Fem Feminization Foot Fetish Humiliation Leg Fetish Make Me Bi Pantyhose / Stockings Shoe Fetish Shoe Licking Sissy Training Slave Training Tasks

Click Here for this Shoe Crush Fetish Video Now what does a humiliation addict want more… to eat regular food… or to have a pretty girl make you eat dirt off of my shoes? You’d love it if I invited all my friends over and I made you the shoe licker of the party, huh? Have all those drinks made you nice and stupid for me??? Are ya ready to go to my personal Amazon wishlist and fascinate over which pair of high heels you’d like to lick next???

Starring: Heather Highborne Tip Heather Highborne Directly

October 24, 2026
Online Relationships Are Inevitable

Assignments Cuckolding Cum Countdown Humiliation Jerk Off Instruction Latex Fetish Masturbation Humiliation Tasks

So like we’ll have no interaction with each other but you’ll consider me your online girlfriend? Well that’s pretty fucking pathetic. So drop your pants and start stroking while I tell ya about all the humiliating things I’m gonna make you do to make this relationship worth it LOL. Here I’ll even give ya a cum countdown! 6, cum for me!……5, cum to being my online boyfriend

Duration: 10 min | Price: $14.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Utilizing Your Cum Catching Face

Assignments Cum Countdown Cum Eating Instructions Jerk Off Instruction Latex Fetish Masturbation Encouragement Orgasm Control Tasks

You’ll do anything I say. Even if that means shooting your load Onto your face and using it as a cum facial lol! And now I'm gonna give you a little countdown til your cum facial finale LOL

Duration: 9 min | Price: $9.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Controlled Burn – Face Only

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Note: This is twice as long than the effects version because it also has a second version of just one face talking. This may be a true story! LOL I'm gonna make you need this… Crave it! I made a video to pound it into your head, Sissy! Since you like stockings and heels so much, I'm burning all your pants! Yup… On the grill for real! Poof! And you'll be wearing nothing but stockings and heels for me! 24/7, LOL!!!

Duration: 23 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Date Or Dedicated Dummy

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I think you deserve an honest answer to the biggest question of your life… which is, “will I date you”. And you swear you’ll respect my judgement… no matter what! Oh my god, you actually thought I’d want you? Since you loved how ur fuck felt so much when u promised to do anything for me… I’m gonna pile it on! Staring off with a nice cum facial! Haha… right in the fuckin face… mouth wide open.

Duration: 8 min | Price: $15.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Social Humiliation

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Awe, still in the hiding phase? Well part of the fun is risking more. Your orgasms won’t come from what I’ve already done to you… but you’ll need to cum thinking about the next set of your pictures that I’m gonna post! You’re a disposable fuckin joke… I’m literally gonna use you up and toss you aside when the ego boost of destroying you wears down.

Duration: 10 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Bimbo Absorption (Randy Moore)

Assignments Feminization Gooning Humiliation Instructions Masturbation Encouragement Mind Fuck Pantyhose Stockings Tasks

Read these out loud 25 times per day as you're stroking. You should practice sounding more ridiculously girly each time. -Oopsie Daisy -I’m so Dipsey -I’m so Clumsey -I’m such an airhead The next step is prancing around the house in short skirts and heels while saying them. Randy Moore Categories: Feminization, Humiliation, Mind Fuck, ****, Instructions, Assignments, Tasks, Pantyhose, Stockings, Masturbation Encouragement, Gooner, Gooning.

Duration: 5 min | Price: $17.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026
Do What I Say CEI

Assignments CBT Cum Eating Instructions Jerk Off Instruction Public Humiliation Tasks

You're gonna be so humiliated! Spread your ass cheeks, Get some lube and obey my instructions, weakling. Oh yea and you'll probably be slapping your nuts for my amusement too! LOL. Let's not forget desert… I want you to cum between two slices of bread for my amusement too! Enjoy! Randy Moore Categories: CEI, JOI, Cum Eating Instructions, Tasks, Assignments, Public Humiliation, CBBT.

Duration: 14 min | Price: $17.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026
The Application Process

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You wanna be invited to one of our parties… Well, that can be arranged. Just so you know… you gotta leave your dignity at the door… and uh… you’re probably never getting it back. You gotta know that I AM gonna be ruining your fuckin life and using you to show off what I can do to an idiot that begged me for it. I want you edging as I describe each one of the humiliating hurdles I’m gonna need you to navigate before the party. Randy Moore Categories: Humiliation, Tasks, Sissification, Make Me Bi, CEI, Cum Eating Instruction, Pay Pig, Edging, Latex, Pantyhose, Gooning, Gooner, Masturbation Encouragement, JOI.

Duration: 12 min | Price: $18.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026

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