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Kinky Playground from patreon

Kinky Playground

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Kinky Playground posts

CHASTITY CHALLENGE [MINI GAME] 🔒 [RUBY+ PATREON EXCLUSIVE] [ADDITIONAL SCENARIO]

Kinky Playground post CHASTITY CHALLENGE [MINI GAME] 🔒 [RUBY+ PATREON EXCLUSIVE] [ADDITIONAL SCENARIO] from patreon

🔒 BONUS SCENARIO: Mistress Lindsey 🔒
A addition to the Chastity Challenge [MINI GAME] series! Lindsey joins the game with her own twisted rules and obsession with size.

This bonus scenario is available now - exclusively for Ruby+ supporters 💖
Thank you all so much for your continued support. You make these filthy little games possible 💋

Now cage up and see if you're big enough to impress Mistress Lindsey!

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CHASTITY CHALLENGE [MINI GAME] 🔒

Kinky Playground post CHASTITY CHALLENGE [MINI GAME] 🔒 from patreon

Don’t have time for a full-length faproulette? This one's for you!

  • 5 seductive Mistresses

  • 5 unique chastity rules

  • Multiple daily tasks that will tease, humiliate or control you
    And if you're brave enough… most of them offer an optional early release challenge, but trust me, those won’t be easy!

This is the first in a brand new Chastity Challenge series - short, intense games designed for those of you who want to submit without committing t...

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ODD JOBS FOR THE NEIGHBOR [RUBY+ PATREON EXCLUSIVE]

Kinky Playground post ODD JOBS FOR THE NEIGHBOR [RUBY+ PATREON EXCLUSIVE] from patreon

This idea was suggested by my lovely sissy, who's been dying to hear about your own fantasies involving people or places tied to your sissy journey. For him, since he struggles a lot with bi-related barriers, it was all about being pegged by a hot, older neighbor from his apartment block, and one very strict teacher who left quite the impression 😏

We’re super curious if any of you have different fantasies in this realm - maybe a seductive shopkeeper lady? Or a doctor who got a little too close during your checkup?

Of course,...

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FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE] [SAPPHIRE+ EXCLUSIVE]

Kinky Playground post FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE] [SAPPHIRE+ EXCLUSIVE] from patreon

Unlocked version of “FAP TO A NEW KINK (36 Categories)" exclusive to Sapphire Tier+.

Thank you for your support! 💖

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FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE] [EMERALD+ EXCLUSIVE]

Kinky Playground post FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE] [EMERALD+ EXCLUSIVE] from patreon

Unlocked version of “FAP TO A NEW KINK (36 Categories)" exclusive to Emerald Tier+.

Thank you for your support! 💖

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FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE] [RUBY+ EXCLUSIVE]

Kinky Playground post FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE] [RUBY+ EXCLUSIVE] from patreon

Unlocked version of “FAP TO A NEW KINK (36 Categories)" exclusive to Ruby Tier+.

Thank you for your support! 💖

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FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE]

Kinky Playground post FAP TO A NEW KINK (36 CATEGORIES) [FAP ROULETTE] from patreon

And we’re back! Everyone who’s been waiting for new Faproulettes - you’re about to be very happy. This time, the theme strays a bit from the usual sissy focus (though that section is still included, don’t worry!)

For me, discovering and exploring new fetishes is an essential part of life. I honestly couldn’t be with a guy who responds with a hard “no” every time I ask to try something new. You can’t really judge until you’ve tried - sure, everyone has their limits, but let’s not be overly dramatic. That’s exactly ...

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WHY YOU SHOULD TELL YOUR WIFE ABOUT YOUR SISSY FETISH 💍🐔 [RUBY+ PATREON EXCLUSIVE] [SHORT STORY]

Kinky Playground post WHY YOU SHOULD TELL YOUR WIFE ABOUT YOUR SISSY FETISH 💍🐔 [RUBY+ PATREON EXCLUSIVE] [SHORT STORY]  from patreon

It’s evening. Just another boring night of watching some show together, right?
Wrong.

She walks up to you without a word. In her hand? That pink, humiliating little chastity cage. She drops it in your lap and just stares. No questions. No teasing. Just one silent command:

Put it on.

And you do. She locks it shut with a satisfying click. Your cock is gone. Caged. You're already hard… well, trying to be.

Then she tosses you a pair of her old thong panties - the ones that used to dig deep...

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TAROT CARDS FUTURE [CAPTION WITH A CHOICE] Choose what you want to happen to you this year! 🃏🍀

Kinky Playground post TAROT CARDS FUTURE [CAPTION WITH A CHOICE] Choose what you want to happen to you this year! 🃏🍀 from patreon

What Will Happen in Your Near Future? ✨🔮

Time to find out. Pick one tarot card and discover your next sissy life event!

Will it be:
🍆 Getting used by your BBC landlord?
📸 Becoming a cute sissy influencer?
💋 Or serving a dominant trans baddie?

[Explain your choice in a comment!]

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LICK THOSE PRETTY FEET AND DON’T TURN YOUR FACE AWAY LITTLE BOY [500 PIECES] [PATREON EMERALD+ EXCLUSIVE]

Kinky Playground post LICK THOSE PRETTY FEET AND DON’T TURN YOUR FACE AWAY LITTLE BOY [500 PIECES] [PATREON EMERALD+ EXCLUSIVE] from patreon

I’ve got a fun little Monday puzzle treatment for you - plus a quick question about foot fetish.

Is there a point where feet become too filthy to still be enjoyable for you? (For those who are into feet, of course)
Let’s set a few levels to explore:

  • sweaty after the gym

  • dirty from walking barefoot outside

  • peed on

  • and something even worse (feel free to suggest your own!)

I’m just curious where your personal limit is - where does the pleasure sto...

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💖 HOW TO MAKE SISSY SELFIES SEXY & SEDUCTIVE - FEMINIZATION GUIDE #5 [GUIDES] [PATREON EMERALD+ EXCLUSIVE]

Kinky Playground post 💖 HOW TO MAKE SISSY SELFIES SEXY & SEDUCTIVE - FEMINIZATION GUIDE #5 [GUIDES] [PATREON EMERALD+ EXCLUSIVE] from patreon

1. Prep Your Body Like a Goddess
Real men notice the little things - so become their obsession. Start by shaving your entire body thoroughly: legs, arms, underarms, intimate areas - everything should be silky smooth.
After shaving, use a good body lotion to make your skin glow. Style your hair (or wig) nicely, apply makeup that suits your vibe, and don’t forget about details like lips, lashes, and brows. When you look soft, clean, and delicious - you feel that way too.

2. Set the Scene Right View Post

FEMBONDER | FEMBOY DATING APP - SO WHO WOULD YOU TAKE ON A DATE? [CAPTION WITH CHOICE] [CREATIVE ART]

Kinky Playground post FEMBONDER | FEMBOY DATING APP - SO WHO WOULD YOU TAKE ON A DATE? [CAPTION WITH CHOICE] [CREATIVE ART] from patreon

Our long-term love is back - Captions With a Choice return! A little game, short and sweet… but oh, so fun!

This time it’s FEMBONDER, the dating app made exclusively for ultra-feminine beauties with a little something extra between their legs 💋

Meet 5 stunning candidates, each with her own photo and personal bio. Every one of them is unique - and tempting in her own way.

The rules?
Pick the one you’d take on a date.
Just one.
And tell me what made...

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MOM, I BECAME AN INFLUENCER! (but not the kind you were hoping for...) [CREATIVE ART]

Kinky Playground post MOM, I BECAME AN INFLUENCER! (but not the kind you were hoping for...) [CREATIVE ART]  from patreon

They thought I'd end up reviewing skincare and iced lattes. Instead, I found something far more addictive - being used by BBC.

This post is all about my filthy rise to influencer stardom: not through hashtags or reels… but by spreading my legs for powerful men with bigger needs - and even bigger cocks 📸💦

In front of cameras. Behind closed doors. On streaming platforms and whispered chats.
The likes? The comments? Oh, I get plenty - especially when they see me stretch for another deep, dominant, inter-...

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FEMINIZATION UNIVERSITY [CAPTION WITH A CHOICE] [WATERCOLOR STYLE] CHOOSE WHICH GROUP YOU WOULD BELONG TO?

Kinky Playground post FEMINIZATION UNIVERSITY [CAPTION WITH A CHOICE] [WATERCOLOR STYLE] CHOOSE WHICH GROUP YOU WOULD BELONG TO? from patreon

Hey sweeties 💋 It’s time to choose your crew at Feminization University! 🎀💄

Every gurl needs a group to belong to - and on this campus, the options are as deliciously dramatic as you'd expect. Will you end up with the hyper-obedient beauty nerds? The rich, spoiled bratpack in YSL heels? Or maybe the sissy sadists who run nightly “discipline sessions”? 😈💅

Take a peek at each group and decide:
Who would you join…

[You can only join one of the groups, justify your c...

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MY BEAUTY STANDARD - PERFECT DOMINATRIX [ONE OF THE HARDEST PUZZLES I’VE EVER MADE] [900 PIECES] [SMALL REWARD FOR THOSE WHO COMPLETE IT] [PATREON EXCLUSIVE]

Kinky Playground post MY BEAUTY STANDARD - PERFECT DOMINATRIX [ONE OF THE HARDEST PUZZLES I’VE EVER MADE] [900 PIECES] [SMALL REWARD FOR THOSE WHO COMPLETE IT] [PATREON EXCLUSIVE] from patreon

A gift, or perhaps a punishment, for the most persistent puzzle solvers... I wish you perseverance and good luck!

🧩 Puzzle Info
✨ Style: Pose, Femdom
💥 The image shown is just a mosaic - complete the full version to uncover the secret!
🧩 Pieces: 900
⏱ Estimated Time: ~(8-30) hours

🔗 LINK

P.S. Finishing my puzzles earns you XP on Discord and that can unlock real-world prizes, spicy extras, and exclus...

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HUMAN SERVING TABLE JOB OFFER [RP] [PATREON EXCLUSIVE] [FANTASY]

Kinky Playground post HUMAN SERVING TABLE JOB OFFER [RP] [PATREON EXCLUSIVE] [FANTASY] from patreon

A lot of you asked for it - with comments saying you had a very imaginative night after the last offer (I honestly didn’t know someone could get so deep into a role and spend the whole evening fantasizing about it, but I absolutely love that!).

This time, it’s something more casual, occasional, and exclusively for my lovely Patrons.

Kisses! 💋
Hope you end up fantasizing about it for a long time… 💭💦

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SOMETIMES THINGS ESCALATE QUICKLY 😅💦

Kinky Playground post SOMETIMES THINGS ESCALATE QUICKLY 😅💦 from patreon

One innocent post… a random pic of a submissive guy in chastity… a growing fascination with cute girly clothes - and suddenly bang, you're deep into the sissy spiral!

There are a million ways to fall into it, but let’s be honest - it’s rarely a slow, gentle journey. Once you slip, you tend to dive in all the way, right?

I’m super curious - how did it all start for you? Let’s have a little discussion in the comments! 💕

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REWARD SET FOR A OBEDIENT SISSY [CAPTION WITH CHOICE] [PATREON EXCLUSIVE] 🌟🏅

Kinky Playground post REWARD SET FOR A OBEDIENT SISSY [CAPTION WITH CHOICE] [PATREON EXCLUSIVE] 🌟🏅 from patreon

We’ve already explored the punishments and correction methods - now it’s time for the rewards. Some of them are quite fantastical, others purely physical, but all meant to bring a little pleasure to your obedient sissy soul 💕

Let’s see which ones suit you best! Rank them in order, and don’t forget to explain in the comments why you picked them that way 😘

P.S. Thank you so much for your financial support - this content exists because of You!
None of this would ...

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WORKING EXTRA HARD ON NEW FAP ROULETTES [INFO POST] [TEASER]

Kinky Playground post WORKING EXTRA HARD ON NEW FAP ROULETTES [INFO POST] [TEASER] from patreon

Lately, thanks to a much more relaxed schedule and dropping a few time-wasting distractions, I’ve fully dived back into working on new FapRoulettes. And I mean really working - I'm now putting in nearly twice as much time as before!

That said, creating a single roulette still takes dozens of hours (my record so far is 68 hours for one!), so catching up on content will take a bit. But the first new set is already almost done - stay tuned!

As always, your support means the world to me - and I promise it will be ...

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MOST FEARED CORRECTIVE METHODS FOR A DISOBEDIENT SISSY [CAPTION WITH CHOICE] ⚖️🚫

Kinky Playground post MOST FEARED CORRECTIVE METHODS FOR A DISOBEDIENT SISSY [CAPTION WITH CHOICE] ⚖️🚫 from patreon

Let’s be honest - every sissy strays from time to time, and that’s completely normal. What matters is finding your way back to the proper path. But once the body and mind fall out of balance, they don’t always return on their own. Sometimes … corrective methods are required.

In this post, we’ll explore 5 different correctional techniques designed for a truly disobedient sissy.

Your task? Rank them from the one you’d fear the most to the one you’d (almost) welcome. Let’s focus prim...

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FEMINIZER APP 🎀 [FANTASY?] [FULL SET] [PART 2] [EXCLUSIVE]

Kinky Playground post FEMINIZER APP 🎀 [FANTASY?] [FULL SET] [PART 2] [EXCLUSIVE] from patreon

💎 Part 2 – The Next Steps for the Feminizer App 💎

This is the continuation of my app presentation… now let’s talk features, upgrades, and ideas. Let’s make this fantasy as perfect as it deserves to be:

  • Surprise Recording Section
    A space for sissies who want to impress their Mommy or Daddy with unexpected progress. Here, you could submit personal training clips or performance videos (yes, even your masturbation sessions - as long as they’re in proper sissy style). If approved,...

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FEMINIZER APP 🎀 [FANTASY?] [FULL SET] [PART 1]

Kinky Playground post FEMINIZER APP 🎀 [FANTASY?] [FULL SET] [PART 1] from patreon

We have blogs, we have sissy universities, and hundreds of guides - but do we have a single dedicated app for full feminization, from A to Z? Probably not. That’s why I’m sharing a little fantasy initiative: the Feminizer App - an app designed to guide sissies through every stage of development until they become absolutely ideal. For now, it’s just a fantasy... but who knows? Many of the locked, feminized boys I talk to are IT specialists - maybe one of them will be willing to start working on it after hours...

H...

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GUY FACE IS PERFECT FOR BEING FEMALE PRIVATE STOOL JIGSAW PUZZLE (400 PIECES) - NSFW PUZZLE [EXCLUSIVE]

Kinky Playground post GUY FACE IS PERFECT FOR BEING FEMALE PRIVATE STOOL JIGSAW PUZZLE (400 PIECES) - NSFW PUZZLE [EXCLUSIVE] from patreon

In a small reference to our last discussion 😜 Dedicated to @MrSmiley @Ren_K 💞

🧩 Puzzle Info
✨ Style: Femdom, facesitting
💥 The image shown is just a mosaic - complete the full version to uncover the secret!
🧩 Pieces: 400
⏱ Estimated Time: ~60 minutes

🔗 LINK

P.S. Finishing my puzzles earns you XP on Discord and that can unlock real-world prizes, spicy extras, and exclusive rewards. If you love...

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CURSED FEMINIZATION RELICS [PART 1] [CAPTION WITH CHOICE] 🗿📜

Kinky Playground post CURSED FEMINIZATION RELICS [PART 1] [CAPTION WITH CHOICE] 🗿📜 from patreon

Hey my darlings! 💕
Here are four more feminization artifacts for you to choose from. I hope you still remember the rules from the last round…

This time, I’m presenting you with four cursed feminization relics.
Each one grants its owner a unique magical ability - but each also carries a heavy curse that makes daily life … complicated.

Your task? Choose one. No skipping, no loopholes. Think carefully!

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SISSY MAID JOB OFFER 🎀🧹 [ROLEPLAY] [FANTASY]

Kinky Playground post SISSY MAID JOB OFFER 🎀🧹 [ROLEPLAY] [FANTASY]  from patreon

God, I'm a little twisted... I was recently looking for a new job and that's when I had a thematic fantasy. What if, while scrolling through LinkedIn or recruitment sites, you noticed such an offer... Would you submit your CV as a sissy or submit your sissy's application for this position as her mistress / master? (For that kind of money, I would pack her up immediately and let her go, of course 80% of the funds from the paycheck would go for me hahahah). In time, maybe I would start an entire agency that would give work to other sissies. View Post

SISSY EXPOSURE CHALLENGES [CAPTION WITH CHOICE] [EXCLUSIVE] Which ones would you take on? 📸🤯

Kinky Playground post SISSY EXPOSURE CHALLENGES [CAPTION WITH CHOICE] [EXCLUSIVE] Which ones would you take on? 📸🤯 from patreon

I can’t even begin to tell you how much your support means to me. The constant flood of comments about how much you love my caption choice art seriously lights a fire in me. Your words fuel my creativity like never before. And beyond that - thanks to you - I don’t have to stress about graphic software costs or subscriptions. You make this dream possible. Big hugs to all my wonderful supporters! 💖

And now… ready for another juicy round of choice art?
This time: View Post

MONSTER GIRLS ⚔️🏰 [CHOICE] [PATREON COMISSION]

Kinky Playground post MONSTER GIRLS ⚔️🏰 [CHOICE] [PATREON COMISSION] from patreon

Pixel, and also the subject of this work slightly deviates from the subject of my Patreon, but the long term Patreon strongly requested, and I couldn't refuse ... Since it turned out quite nice (in my opinion), I'm also posting the work for you. I'm curious about your opinion (my first time in this field)!

Choice story:

You were thrown into the world of an RPG game, in which the fight between characters takes place on the basis of sexual intercourse - the one who gives the opponent more pleasure wins. Your task is to defeat any o...

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FUTAS & CORNFLOWERS JIGSAW PUZZLE (300 PIECES) - NSFW PUZZLE [EXCLUSIVE]

Kinky Playground post FUTAS & CORNFLOWERS JIGSAW PUZZLE (300 PIECES) - NSFW PUZZLE [EXCLUSIVE] from patreon

I love cornflowers, one of the first bouquets I received, mainly consisted of cornflowers ... here art with them mixed with my kinks. Happy saturday solving ❤️

🧩 Puzzle Info
✨ Style: Futa
💥 The image shown is just a mosaic - complete the full version to uncover the secret!
🧩 Pieces: 300
⏱ Estimated Time: ~30 minutes

🔗 LINK

P.S. Finishing my puzzles earns you XP on Discord and that can unlock rea...

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INTERVIEWS WITH FORMER SISSY INMATES | SISSY PRISON PART 2 [EXCLUSIVE] [ROLEPLAY]

Kinky Playground post INTERVIEWS WITH FORMER SISSY INMATES | SISSY PRISON PART 2 [EXCLUSIVE] [ROLEPLAY] from patreon

🎤 This time, I’m sharing something very special...

Excerpts from real interviews with former Sissy Prison inmates. Each of them has undergone full resexualization - and now, they’re ready to open up about their experiences, desires, and the intense transformations they went through behind locked doors 💋🔐

These stories will help you understand what it really means to serve time as a sissy. And who knows… maybe they’ll inspire you to take that step yourself 😈 View Post

BEING SISSY IS ALWAYS BETTER IN COMPANY - ART SERIES OF MOTIVATIONAL GUIDES ON FEMINIZATION #4

Kinky Playground post BEING SISSY IS ALWAYS BETTER IN COMPANY - ART SERIES OF MOTIVATIONAL GUIDES ON FEMINIZATION #4 from patreon

Most of you probably imagined your adult photos with friends as something spontaneous - a bit blurry, taken quickly by the river with your buddies after catching a big fish, maybe with a few beers in the background.

But in reality, your path will probably lead to something like my art on this post ...

And you know what? That’s a good thing.

Having sissy friends - people who truly get what you're going through - can be one of the biggest sources of support when you’re entering this world. They u...

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