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Category: Feminization

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)

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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
I Share My Maid

Ass Fetish Bisexual Encouragement Cross Dressing Feminization Humiliation Latex Fetish Middle Finger Sissification Sissy Maid Sissy Training

So like everyone was amazed by how good of a maid you were last night at the party. I let them know that you’re really good at obeying commands and that you’ll do anything that’s asked of you even if it’s super humiliating and super pathetic. Oh and did I mention that they’re gonna be paying me for you by the hour? Of course you won’t be getting any profit. Start stroking faster and show me how eager you are to work LOL! There’s like a bunch of hot guys following me so I’m sure one of them is gonna see my ad and want to hire you just to give you a good pounding LOL. Heather Highborne Categories: Ass Fetish, Bisexual Encouragement, Cross Dressing, Feminization, Humiliation, Latex Fetish, Middle Finger, Sissification, Sissy Maid, Sissy Training

Duration: 9 min | Price: $$16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 7, 2026
Denied And Sissified

Bisexual Encouragement Brat Girls Encouraged Crossdressing Female Domination Feminization Humiliation Latex Dress Lip Stick Loser Porn Make Up Sexual Rejection Sissification Sissy Training

I could never date you. I’m into more manly guys ya know? You’re more of a little sissy pants don't ya think haha… Would you let me dress you up as a girl? Let me put this lipstick on you… Now come sissy! Let’s go get you pierced and tatted we have no time to waste… Heather Highborne Categories: Bisexual Encouragement, Brat Girls, Encouraged Crossdressing, Female Domination, Feminization, Humiliation, Latex Dress, Lip Stick, Loser Porn, Make Up, Sexual Rejection, Sissification, Sissy Training

Duration: 8 min | Price: $$16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 7, 2026
Blackmail Birthday Party

Ass Fetish Bisexual Encouragement Blackmail Cross Dressing Feminization French Maid Humiliation Sissy Maid Sissy Training Taboo

Oh, don’t act like you didn’t want a “Blackmail-Fantasy Birthday Party”… your step-sisters and I have gone thru your computer and “blackmail-fantasy fetish porn “ is apparently your favorite thing. How long did it take you to get dressed up this morning ??? I see… your makeup is flawless by the way. How are French maid outfit and the heels fitting? Hmmm, your lips do look a little swollen… how's your tailpipe? Oh, well allow me to fill you in, ass boy… since you think it’s appropriate to cum in your pants for my ass… I thought I’d add some daily ass kissing to your duties. That’s right… start kissing the ass that u exploded for.

Duration: 7 min | Price: $18.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 7, 2026
Million Or Makeover Episode 2

Bisexual Encouragement Bisexual Gay Humiliation Cross Dressing Cross Dressing Encouragement Crossdresser Crossdressing Crossdressing Made To Crossdress Cuckolding Encouraged Feminization Feminization Sissification Sissy Fetish Sissy Training Sock Fetish Socks

Zara gets praise and a warning from the Spacebabe Generals to be more hands on with her Sissy recruitment. Doja and Harley suggest the latest wanna-be influencer as the next contestant on Million or Makeover! Zara arranges a set-up with Ryder to see how weak he can be for a bit of humiliation and destruction. All goes well when Ryder gets a boner for the Sock and Cuck humiliation she shows him. Now Ryders putty in Zara's hands as she books him for total Sissification on her Galactic gameshow! Starring: AI Zara, AI Doja, AI Harley Categories: Sissy Training, Sissification, Feminization, Socks, Sock Fetish, Cuckolding, Latex, Cheerleaders, Bisexual Encouragement, Encouraged Bi, Make Me Bi, Shaving Fetish, Humiliation, Special Effects, Cosplay, AI

Duration: 10 min | Price: $9.99

Starring: Zara Valentine AI, Doja, Harley Tip Zara Valentine AI Directly

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October 6, 2026
Sissy Poses Become Permanent

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It’s called pansy posing… yea… there’s poses that you do until you start to self identify as a total pansy. I mean, have you really given yourself “permission” to be a total tart? Muscle memory is an important part of your destruction. You might find it easier to just jerk off to the idea… but why live a conflicted life? And I deserve the glory for doing this to you, LOL.

Duration: 6 min | Price: $17.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Downward Spiral Of Denial

Bisexual Encouragement Costumes Female Supremacy Feminization Sexual Rejection Sissification Sissy Training Uniform Virgin Humiliation

I must say I am surprised someone actually had the balls to come here and claim to be the chosen one. You will be required to publicly state that you are a virgin, plus my phone has a lie detector app so I'll just record it on my phone and see the truth. I'm happy to tell you that you're now our slave. Yup slave. Too late to back out now, we take finding the chosen one very seriously. Also we've arranged for you to have a lifetime supply of sissy frilly panties, bras and pantyhose plus super sexy high heels. Your ass is a permanent cock hole, a depository for cum.

Duration: 7 min | Price: $15.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Absorb My Hyper Femininity

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I’ll be giving u my femininity… sharing my smooth skin… letting you feel my wet pussy… letting u hear the way I breathe and moan as u pleasure me… mmm yea… you’ll absorb the femininity I’ll be putting out… kinda like helping a charity case. You'll be hyper feminine in no time! LOL.

Duration: 8 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026
Taunting Sissy Wardrobe

Bisexual Encouragement Cross Dressing Feminization Humiliation Lipstick Fetish Makeup Pantyhose Stockings Nylons Sissy Training

I mean I didn’t throw away all your boy clothes just for you to get lazy about all this. I got you some cute pink plugs with sparkles on them… now back that ass up on the suction cup dildo on the wall while I tell you all about your new wardrobe. Heather Higborne

Duration: 11 min | Price: $16.99

Starring: Heather Highborne Tip Heather Highborne Directly

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October 6, 2026

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