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  • Shrinking You Into Panties (Humilfication Day Episode 4)

    Shrinking You Into Panties (Humilfication Day Episode 4)

    Chastity Crossdressing Feminization Latex Dress Orgasm Denial Panty Fetish Sissy Training Small Penis Humiliation SPH Tease And Denial

    See the full 2 hour video here: Humilification Day (Full Season 1) … Perfect if you're already t**** in a chastity cage! This is the fourth day on this parody of Groundhog Day. You were stupid enough to leave your laptop open and I took the liberty of checkin' out all your “loser porn”. Awe, it’s what you wanted, right? Your biggest fantasy is apStep-Parently for a hot girl to put your inferior cock in chastity and shrink it down to a sissy clit, hahahaha. Well, I could definitely make it funnier by constantly getting you smaller and smaller cages til you got nothin but a one inch sissy clitty, hahahaha. Aiden Ashley

    Duration: 15 min | Price: $17.99

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  • Tell Me What You Did To Him (Episode 7 of Sissy Cuckold Contest)

    Tell Me What You Did To Him (Episode 7 of Sissy Cuckold Contest)

    Crossdressing Cuckolding Domestic Servitude Encouraged Bi Feminization Humiliation Latex Corset Make Me Bi Masturbation Porn Star

    How’s it going girl. I’ve been busy working on our little project, hahahaha. How’s your boyfriend doing with the cuckolding on your end. Oh my god really???? That so funny… oh girl, I’m gonna have to start playing with myself as you give me all the details. He’s there now… cleaning… in a French maid outfit??? Hahahaha! Mmmm, um gonna have MY EX send My Slave home with sore balls after cleaning. I’ll have a super ridiculous maid outfit here waiting for him, mmmm. It’s gonna be all he wears from now on! Mmmm, fuck this is gonna make me cum… keep laughing… keep laughing… I'm gonna cum! Astrid Star

    Duration: 5 min | Price: $17.99

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  • CS, Cum Eating Life – The Charlotte Show (Episode 2)

    CS, Cum Eating Life – The Charlotte Show (Episode 2)

    Cuckold Cum Eating Femdom POV Humiliation Sissy Training

    I’m gonna define your cum eating sex life exactly. No more acting normal the next day, haha! Cum Eating shame is your sexual preference. I want you to be mortified. Admit you want to be my cum eating cuckold servant! Goddess Charlotte Stokely …

    Duration: 6 min | Price: $17.99

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  • Paycheck Pounding Party (Humilfication Day Episode 6)

    Paycheck Pounding Party (Humilfication Day Episode 6)

    Anal Bully CBT Chastity Cuckolding Financial Domination Findom Humiliation Latex Leggings Orgasm Denial Pegging Strap-on Tease And Denial

    See the full 2 hour video here: Humilification Day (Full Season 1) … Perfect if you're already t**** in a chastity cage! This is the sixth day on this parody of Groundhog Day. I found a folder called “pay pig poundings”! Yea… I found it quite interesting. It seems some deranged loser made a ton of image captions and they all have sexy girls that are pegging a wimp in chastity… and then it dawned on me… you wrote them! You did, didn't you? I'll either let you keep your pants on and let you beg for mercy… or I'll let you take your pants off and stroke your beta boy cock while you beg to be my “pegging party pay pig”! So what's it gonna be, loser? This is about your financial destruction, your asshole destruction and the destruction of any hope you might have had of stroking your cock like a “real man” again. The most you'll ever get, is the chance to jiggle your cage while my strap-on pounds your girly asshole. Oh and that's after you hand me your full paycheck on your knees! No check… no poundings! And you will need poundings, beta boy. You'll crave them… you'll beg for me to pound your fag hole just to drip a few precious drop of precum out of your blue balls. Their almost here, cuckie. Time to apply the ice and shrink you down size and get this steel chastity cage on you. I want all my hot girl friends to come in and see you caged and standing in the corner with your back arched and ass presented for destruction. Hahahaha. Aiden Ashley

    Duration: 14 min | Price: $17.99

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  • CS, Eat Cum, Piggy – The Charlotte Show (Episode 4)

    CS, Eat Cum, Piggy – The Charlotte Show (Episode 4)

    Brat Girls CEI Cum Eating Instructions Humiliation Masturbation Instruction Orgasm Control

    You wanna see my pussy at the end of this clip right? Well are you gonna be a good little piggy for me? Are you gonna eat up all your cum like a devoted loser? I'll tell you exactly how I want you to stroke it and when to stop! I want you to obey all the humiliation in this video so that it just proves that you would do anything for a glimpse of my perfect pussy! Goddess Charlotte Stokely

    Duration: 12 min | Price: $17.99

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  • Permanent Chastity Ass Tease (Humilfication Day Episode 7)

    Permanent Chastity Ass Tease (Humilfication Day Episode 7)

    Ass Fetish CBT Chastity Humiliation JOI Masturbation Humiliation Orgasm Denial Tease And Denial

    See the full 2 hour video here: Humilification Day (Full Season 1) … Perfect if you're already t**** in a chastity cage! This is the seventh day on this parody of Groundhog Day. Yea, I saw all your humiliation porn on your computer… all those denial photo captions… I really do think wimps like you are funny. In fact, I took the opportunity to dress up in this bunny outfit to SERVE up some super funny and cruel humiliation for ya! So stroke it, loser! Start stroking your beta boy cock while you still can. Cuz one of these sick fantasies is comin' true for you. Stroke… stroke it… awe… are ya feelin nice and stupid??? Yea??? I bet you're feelin stupid enough to tell me that you want the most cruel “Bunny Chasity” photo caption to come true for ya, huh??? I told all my hot friends all about you. I bet you'de like to kneel and kiss our asses in these outfits, huh??? Well that's good cuz you will be! I'm gonna have a permanent chastity cage attached to your cock while my ass is in your face and my hot friends all laugh at you! Isn't that the idea from that chastity caption on your computer??? I thought it would be perfect for you! And as much fun as this little party is gonna be, the best part comes later. Over the next couple months, you're gonna be trained as my new cuckold servant! Isn't that hot??? Now thank each one of my ass cheeks for rejecting you. Aiden Ashley

    Duration: 16 min | Price: $17.99

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  • Oops, I Broke Another Peasant (Full Season 1)

    Oops, I Broke Another Peasant (Full Season 1)

    Chastity Domestic Servitude Female Led Relationship Female Supremacy Feminization FLR Foot Fetish Head Shaving Humiliation Legs Fetish Lipstick Fetish Pantyhose / Stocking Fetish Shoe And Boot Fetish Submissive Training Wet And Messy

    A 2 hour movie / series… Binge watch all 8 episodes early and save $. Plus, this video file adds bonus features including walking in latex bonus footage and a (behind the scenes) picture slideshow. 1. Wanted, Personal Assistant 2. Locked Shoe Licker 3. The Ground I Walked On 4. Careless Kisses 5. Soaked Pantyhose 6. We Call It Clowning 7. Pie the Sissy Maid 8. Truly Broken For My Boots Plus 2 bonus walking in latex scenes and a BTS slide show Description: You're an unlucky guy that just wanted to apply for the "personal assistant job" for a beautiful woman… and out turns out your now an enslaved servant in chastity to a spoiled and rich Step-Step-Daddy's girl that has a way of breaking her new peasant servants. Heather Highborne actually enjoys her status as a superior in society and she loves showing her friends at the polo club her destructive power over you.

    Duration: 120 min | Price: $69.99

    Starring: Heather Highborne Tip Heather Highborne Directly

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  • Wanted Personal Assistant (Oops, I Broke Another Peasant, Episode1)

    Wanted Personal Assistant (Oops, I Broke Another Peasant, Episode1)

    Brat Girls Chastity Domestic Servitude Executrixxx-fantasy Female Led Relationship Female Supremacy FLR Humiliation Orgasm Denial Shoe And Boot Worship Slave Training

    Yay! Step-Daddy bought me another beta boy slave. I broke my last one, oops. I've had to live a solid week without a slave… I simply don't know how people do this. I've been throwing myself into my work with all the cute little critter rescue charities to keep myself occupied. Huh? You applied for a “Personal Assistant “ job? Awe, that's cute. I heard about dumb dums that apply for the “lifetime of servitude thingie“ by mistake. I actually feel sorry for you. I'll keep it quiet, that you made a mistake. You're kinda cute and I don't want them to send you out back to the wood chipper for disposal. Oh… that brings me to my favorite part… I'll be taking away your erections, slave.. and you'll be doing chores with this painful steel chastity cage on. I'll send Gretchen in to show you the most humiliating way to lick my dirty shoes clean. I can't wait to show off my new slaves shoe licking skills to my friends at the polo club! Be happy that I've graciously decided to let you keep your teeny tiny marbles… for now.

    Duration: 14 min | Price: $17.99

    Starring: Heather Highborne Tip Heather Highborne Directly

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  • Castrated Cuck Conclusion (Humilfication Day Episode 8)

    Castrated Cuck Conclusion (Humilfication Day Episode 8)

    Ass Fetish Ballbusting Bodystocking Castration CBT Chastity Cuckolding Gelding Humiliation JOI Masturbation Humiliation Orgasm Denial Tease And Denial Topless

    See the full 2 hour video here: Humilification Day (Full Season 1) … Perfect if you're already t**** in a chastity cage! This is the eighth day on this parody of Groundhog Day. I'm on your computer where you keep all your chastity porn??? Hahahaha. I have enough information to blackmail the fuck out of you??? Hahahaha. You're fate is clearly up to me. I really find this all very amusing. Stimulating and amusing. Ohhhh and then I found your folder called “Castrated Cucks” ! Now that was hot! I gotta admit, that stuff was dirty. I mean just soooo fuckin wrong, hahahaha. So I called my hottest sadistic friend over. Oh and I told her about your “castration cuckold” folder and she even agreed to bring her boyfriend over to Fuck me while she's destroying your nuts! I wanna see you hump the air desperately to try and get the “last orgasm of your life” out of your beta balls. I bet you've always wanted to be totally rejected like this huh??? With a couple of hot girls laughing at you… making you a eunuch slave. Should I put on a little show for ya while you still have your nuts? Maybe I should pose with the elastrator like this and blow some sarcastic kisses at you … muah… muah. Awe… did she band your nuts with this pink elastrator??? Did it hurt when she kicked your banded nuts??? Aiden Ashley

    Duration: 14 min | Price: $17.99

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  • Locked Shoe Licker (Oops, I Broke Another Peasant, Episode 2)

    Locked Shoe Licker (Oops, I Broke Another Peasant, Episode 2)

    Black Stockings / Pantyhose Chastity Domestic Servitude Female Led Relationship FLR Foot Fetish Latex Skirt Legs Fetish Shoe And Boot Worship Shoe Fetish Slave Training Small Penis Humiliation SPH Tease And Denial

    Oh my, would ya look at all these sexy shoes??? Oh my, they are all a bit dusty… and who knows what I’ve stepped in… be a lamb and clean them for me… or in your case… be a worm and lick the dirt off the bottoms for me, hahahaha. I’m supposed to be getting ready for my trip to the polo tournament right now. Keep in mind that this is a special treat and that you’ll be doing this kind of shoe cleaning all alone for months at a time without getting to see me… so I hope you appreciate the precious time I’m taking to help you, peasant. Oh and since this is your first time… I’m gonna make a super cute video for my friends at the polo club. Huh??? Oh no, I won’t be back tonight but there are cameras everywhere so perhaps I’ll check in on you to see if your licking them properly… and to see if your chastity cage is pinching you while your licking them, hahahaha. Oh, there’s that face… there’s that face you make when your cage is really hurting you, Hahaha. Don't worry, it'll shrink down to one inch soon!

    Duration: 12 min | Price: $17.99

    Starring: Heather Highborne Tip Heather Highborne Directly

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