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Category: Crossdressing

French Maid Forever – Dweeb Destruction Episode 5

Brat Girls Crossdressing Domestic Servitude Encouraged Fem Feminization Humiliation School Girl Sissification Sissy Maid Sissy Training Slave Training Step-sister Taboo

.. you were quite convincing… the way you begged mom to do all my chores… the way you explained how badly you needed to practice wearing heels… the way you kept your cock sticking straight out while you arched your back and dusted the whole house… mmmm… yea, that was quite convincing, hahahaha You wanna be my full time French maid, huh??? Hahahaha Oh my god, you fuckin do, don’t cha, hahahaha…. look at your pansy penis growing, eww gross… hahahaha… Maybe if you ask for it for your birthday! Yes!!! That’s it… go downstairs and ask if you can be treated like a sissy maid for your birthday!!! Hahahaha. Wanna kiss your masters shoes before you trot downstairs and ask to be the permanent house maid??? Hahahaha

Starring: Morgan Lux Tip Morgan Lux Directly

October 24, 2026
Prissy Performance – Full Season 1

Crossdressing Foot Fetish Humiliation Legs Fetish Office Domination Pantyhose Stockings Fetish Shoe Fetish Sissification Sissy Training

Click Here for this Forced Feminization Video . Prissy Performance – Full Season 1 Humiliation, Sissification I hate you… Your my rival at work… I’m a hot news anchor with hot legs that could ruin you… Oh, and I’m assigning you a role in the company play… Yes, I’m in charge of it and yes it’s Mandatory! You’ll be playing the role of “The Prissy Prickle Fairy” … Emphasis on the PRICK, haha! Oh and I know the play two weeks away but since my legs are so hot, I think you should beg me to make you into a sissy starting right now! haha. Runtime: 1 Hour and 15 Minutes Episode 1: Rivals Revenge Episode 2: Pink Lingerie Episode 3: Oh, Stockings Too! Episode 4: Fairy Dresses Episode 5: Permanently Nailed Episode 6: 24-7 Makeup Episode 7: Prissy Rehearsals Heather Highborne

Duration: 15 min

October 24, 2026
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
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 Stroke For Stockings

Crossdresser Crossdressing Edging Feminization Foot Fetish Gooning Humiliation Jerk Off Instruction Legs Masturbation Encouragement Nylons Orgasm Control Pantyhose Pantyhose Feet Sissification Sissy Training Stockings

We know all about your little gooning obsession. You always come back for more and now you're getting double. Are these nylons making your Little Step-Sissy dick hard? Why don't you go on and put on a pair? Randy Moore & Heather Highborne Categories: Nylons, Pantyhose, Stockings, Legs, Humiliation, Crossdressing, Crossdresser, Feminization, Sissy Training, Sissification, Edging, Masturbation Encouragement, Gooner, Gooning, Foot Fetish, Pantyhose Feet, JOI, Orgasm Control.

Duration: 11 min | Price: $18.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026
Therapy-Fantasy For Pussies

Big Tits Crossdressing Feminization Humiliation Lipstick Fetish Mind Fuck Shrinking Sissification Sissy Training Striptease Teacher Fantasy Topless

My secretary was telling me that you're upset over, a little break up you had with your girlfriend. Well, I'd be happy to help you. You're just a weak little pussy. I knew that before you even got here. That's why she broke up with you. If you're going to act weak and make you might as well have the body of a girl. Did you just feel that? You did, didn't you? You shrink and so did your cock. It's getting smaller. You're becoming very fem. Randy Moore Categories: Therapy-Fantasy, Topless, Big Tits, Striptease, Shrinking, Humiliation, Mind Fuck, Feminization, Crossdressing, Lipstick Fetish, Sissification, Sissy Training.

Duration: 15 min | Price: $18.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026
Cum Covered Foot Licking Sissy

BDSM Butt Plug Chastity Crossdressing Cuckold Cum Countdown Cum Eating Instructions Edging Foot Fetish Garter and Stockings Gooning Humiliation Jerk Off Instruction Latex Fetish NylonFeet Pantyhose Shoe Fetish Sissy Maid Sissy Training Small Penis Humiliation

You look so darling in your little maid outfit sissy. You're still missing your collar and your butt plug. Go ahead, put it in while I watch. We'll save the ball gag for later… I'm gonna put your mouth to use. You know what won't be useful? That cock of yours. Slip this cage on. I know your deepest darkest desire… You want to lick all of my bulls cum off of my toes, don't you? Cause you're not only my Little Step-Sissy bitch… You're my little fucking cuck. Randy Moore Categories: Foot Fetish, CEI, Cum Eating Instructions, Chastity, BDSM, Garter & Stockings, Pantyhose, Shoe Fetish, Sissy Maid, Sissy Training, Humiliation, Crossdressing, Cuckold, Butt Plug, Nylon Feet, Latex, SPH, Cum Countdown, Edging, JOI, Gooner.

Duration: 18 min | Price: $18.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026
Nylon Bitchs Ruined Orgasm

Ass Fetish Crossdresser Crossdressing Edging Foot Fetish Goddess Worship Gooning Jerk Off Instruction Masturbation Encouragement NylonFeet Nylons Orgasm Control Orgasm Denial Pantyhose Ruined Orgasms Sissy Training Stockings

I love knowing that I was the one who gave you your little nylon fetish. Maybe you love nylons just as much as I do. Yeah… You're going to fucking put on a pair for me right now aren't you? You're going to be my little nylon sissy. And you're going to jerk that cock for me just the way I tell you to. And while you do that, you're going to worship me from my feet all the way up. Got it? Randy Moore Categories: Nylon Fetish, Pantyhose, Stockings, Foot Fetish, Ass Fetish, Nylon Feet, JOI, Jerk Off Instructions, Gooning, Gooner, Masturbation Encouragement, Goddess Worship, Ruined Orgasm, Orgasm Denial, Sissy Training, Crossdressing, Crossdresser, Edging, Orgasm Control.

Duration: 6 min | Price: $18.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026
Pantyhose Pumping Pansy

Ass Fetish Big Tits Crossdressing Cum Countdown Foot Fetish Goddess Worship Gooning Jerk Off Instruction Masturbation Encouragement Nylons Pantyhose Pussy Sissification Stockings Topless

It's hard to believe anyone else would love nylons as much as me. But here you are. You like to wear them too, don't you? My little nylon slut. Put them on for me… Show me what a good little nylon sissy slut you are. Go ahead and stroke your cock through those nylons. You're going to worship my feet, my legs, my ass, even my tits. Stroke that nylon cock. Randy Moore Categories: Foot Fetish, Nylon Fetish, Pantyhose, Stockings, Ass Fetish, Big Tits, Topless, Goddess Worship, Pussy, JOI, Gooning, Gooner, Masturbation Encouragement, Sissy, Crossdressing, Cum Countdown.

Duration: 10 min | Price: $19.99

Starring: Randy Moore Tip Randy Moore Directly

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September 30, 2026

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