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Category: Sissy Training

Dress Up Revenge

Bisexual Encouragement Encouraged Crossdressing Encouraged Feminization Encouraged Gay Female Domination Gay Humiliation Humiliation Jerk Off Instruction Loser Porn Prank Sissy Training

A lot of people think my step-brother is pretty hot but what they don’t know is he’s also a jerk… Ya know what would be so funny? If we dressed you up as a girl haha… It’d be really cool to prank him that way, he’d never know he was with a guy because he’d be too busy showing off his big hard boner to you hahah… I’ll make sure to put extra lipstick on you too that way he can tell you how pretty your lips are…

Duration: 13 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Irreversibly Feminized And Rejected

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Oh wow… you actually went through with it haha… Your lips look huge you look ridiculous haha! Do you feel pathetic walking in here like that and getting denied by me once again? you seriously think I’m gonna kiss you now looking like THAT! If I didn’t want to kiss ya then what makes you think I’m gonna kiss you now that you’re a permanent sissy? You’re basically a girl now…

Duration: 9 min | Price: $17.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Sissy Spanking Party

Alpha Brat Girls Bully Encouraged Crossdressing Feminization Humiliation Sissification Sissy Training Slave Training

Just because I know you’re secret about craving humiliation doesn’t mean we can’t have fun. I invited some big masculine men to really help me put you in place. I figured we could also dress you up like a pretty little princess. Now go on wimp, go shower and prepare for your guests….

Duration: 9 min | Price: $17.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Immersive Gay Test

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I think it’s really funny for you to assume you’re not gay. Now I’m gonna ask you a few questions… #1 “do you crave to have an alpha males slap you across the face with a superior piece of meat as they laugh at you?” Yea stroke it faster gay bitch….9…

Duration: 7 min | Price: $18.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
The Perils Of Polish Bets

Encouraged Crossdressing Encouraged Feminization Feminization Nail Polish Sissification Sissy Training Taboo

I’m sure she didn’t really expect you to wear nail polish for a week. Ugh, ok I’ll paint them for you… geez… let’s see if I have a “manly color” for ya… I mean, I guess you did lose the bet so you probably deserve what’s about to happen to you…

Duration: 6 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Tart For A Brat Youtuber

Encouraged Crossdressing Female Domination Humiliation Sissification Sissy Maid Sissy Training Step-Mom Step-sister

You’re step-sister and her friends came home laughing hysterically about the way they suckered into being on their YouTube channel. I also heard she did a number on you at school today. I guess she started her videos early huh? You're going to be used and totally humiliated! Do you really think after a year everyone’s gonna forget how much of a sissy wimp you are?

Duration: 11 min | Price: $17.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Stroke While Squealing

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Why the hell do ya think girl’s laugh when they put lipstick on a guy?? Duh, they’re imagining you stroking urself with your eyes crossed and your tongue hanging out moaning and squealing like a girly girl! Girls aren’t laughing just cuz they made u wear pantyhose… they’re laughing cuz your manhood is OVER! That’s it… play with yourself and moan and moan and moan… twirl your little pigtails and lick your lips for step-daddy.

Duration: 6 min | Price: $18.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
How To Stroke For My Profit

Encouraged Crossdressing Female Domination Financial Domination Ownership Pimp Sissification Sissy Sub Sissy Training

This is what I want u to wear while ur stroking to this video… a poofy feather jacket… a pair of super sexy stockings and heels… Stroking for my profit… humiliation for my profit… And I don’t care if it only brings in $2 … I bet I’d live to be my $2 whore. I own a sissy faggot whore that puts out slutty little videos for me…

Duration: 7 min | Price: $20.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 5, 2026
Shrink My Dingdong

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Hello sir, welcome to “shrink my dingdong… I’ll post the pictures and videos if you stroking and thanking me for destroying ur manhood! This estrogen cream is super strong… I gotta wear gloves cuz this is like the equivalent of 5 years of birth control right here… Did ya think that you’d leave the store with a shred of ur dignity left? You’ll leave here in a VERY small chastity cage with spikes! You might as well enjoy this cuz you’ve already absorbed enough to do permanent damage…

Duration: 8 min | Price: $19.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 5, 2026
Sissy Sausage

Financial Domination Food Gay Humiliation Latex Fetish Shoe Fetish Sissy Maid Sissy Training Slave Training

My Little Step-Sissy fagggot Nadia Valentine deserves the privlige of paying me to allow her to eat a lovely stepped on sausage that I made just for her! Hehe!

Duration: 4 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 5, 2026

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