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Category: Assignments

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

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.. 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)

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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

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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
Try Being More Pathetic

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Sure you have a sexless life…. A small dick…. And like no alpha bones in your body but I still think you could be even more pathetic. And the only way to do that is by doing super humiliating tasks. The only catch is You’re gonna have to do whatever the fuck I say… got it? Are ya close to cuming? Good now I want you to…

Duration: 9 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Utilizing Your Cum Catching Face

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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
I Dont See A Downside

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I don’t see a downside… no matter how much you could possibly spend on my videos… it’s still less than having a wife or girlfriend… and every cent you send ME, you send while ur rock hard… it’s way better. Enjoy your frozen microwave dinners with my videos… that’s our relationship… that’s us dating now. Let’s celebrate who you are with that fat cart full of my clips right now… and then blow a big fat load all over yourself.

Duration: 9 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Destroyed For The Laugh

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I know how badly you want me to laugh at you… it’s the closest you’ll ever come to giving me an orgasm… you could never turn me on, your disgusting and your only way to please me is to be my disposable little clown… isn’t that right, loser. Show me you’re willing to give up everything for 2 seconds of my laughter … show me that I’ve made you a joke of a human being… show me what cuming to this does to a man… show me that you’ve jerked off to humiliation videos so much that you can’t cum to vanilla porn.

Duration: 6 min | Price: $16.99

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
Loser Load Chugger

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You see I have a life too so I don’t have time for load chugging faags like you haha… Ahhh yea, so I decided to give you a humiliating task just so you’re not bored and lonely while I’m out doing more important things. You’re gonna walk up to the bar to order a drink and ask if they have one called “nut shot” LOL… Oh and you gotta make sure it’s a girl bartender. Don’t worry you’ll get you’re humiliating night soon but for now I need you to keep edging. Heather Higborne

Duration: 10 min | Price: $9.99

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

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