Kinky Playground

It's been a little while since the last puzzle, but I thought this would be a really fun way to mildly piss you off in your chastity cages, because instead of spending just a minute staring at it, you'll be stuck there for quite a bit longer... And since smothering came in HARD (3 private commission

[This is totally non-offensive toward the commissioner, just so we're clear] But listen to this. The commission description was soooo detailed and long - the pose, the hair, the exact outfit, everything explained in 2–3 sentences rather than just being mentioned in a single word. But one particular

What was that? Mm-mhm. You want more? Eaymmm-mhm. Harder? Mmm-hmm. Remember, communication and fully understanding each other are the foundation of any relationship. Whether it’s about what we’re having for breakfast tomorrow, how we’re going to spend our vacation, or how we’re going to torment you

It has begun, my dear owners of male genitalia! Time to put your little dick into a piece of plastic or metal tubing and give up your regular jerking off for an entire month! No mercy. 2026 won’t happen again. Locktober 2026 won’t either. Lock it up, put those keys away, and let’s try to survive. To

And something EXTRA for my extra naughty boys who, besides chastity, also have that little fetish demon inside them that makes them wanna jump into girly clothes and moan like a girl! 😈💕 Introducing the SISSY VERSION, with tasks dedicated to dressing up, butt stuff, and similar fun! The rules and

I’m really excited to present an polished for a long time challenge for all Locktober participants! 🔒 Locktober is such a great idea (and I really hope it keeps growing in popularity), but especially when you’re doing it with a partner (waaay easy to stay motivated). Solo Locktober can be harder no

First of all, I want to say a huge thank you again for all the lovely get-well messages! I’m already back on my feet and ready for action - it was just a pretty nasty cold after all, and thankfully I managed to get through it without having to torture myself with antibiotics. And now I’ve got a bran

Oh God, the number of requests for more Maisie was absolutely insane. Two subs even wanted to pay for a commission of her, and I got tons of DMs on Reddit saying Maisie is somehow both insanely hot and insanely cute at the same time and she’s one of the best characters in my universe. I decided ther

Shiit, sorting through Reddit from like 6 – 8 years ago (and that really isn’t that far back, we’re talking 2018), sissy content was really, really niche!! Sure, posts existed, but 5–6 uploads a month was basically nothing. And of course, those posts would still get thousands of likes because the de

Getting your cock sucked, getting spit-roasted, breast augmentation - these are things that are far, far, FAR down the sissyfication journey. Of course, for some people, they’ll happen sooner and all at once, but for others, they’re either still a long way off or the progression is much slower. So I

Highly anticipated and seriously polished 4 picks for Part 2 of the Locktober Edition have arrived! The concept changed quite a few times, especially since 3 out of 4 are based on fantasies described by our subscribers. Some of them needed quite a few nerfs to avoid making them too perfect, hence al

If it’s still hard, there’s no point in calling it quits - keep fucking gurl. God damn @Totti, that teal lingerie with the open crotch and open breasts is a fucking masterpiece idea. [COMMISSION] General concept: @Totti Character design: @Totti Outfit & styling: @Totti Revision & extra horniness: @K

“You know, I have troubles because I’m almost 2 meters tall; Fuck, sometimes I lose immersion because I have really broad shoulders and super narrow hips; You know, I crash out of feminization because I look in the mirror and see a total muscleman who spent 5 years in the military. What can I do?” O

Ohhh, it’s coming... The month when you willingly devote yourself to that beautifully sounding “chastity” and hand over the key to your little cage to your Mistress. From what I’ve seen, some people go through Locktober pretty traditionally - maybe with an extra dose of teasing, but not much beyond

Heyyy my lovelies! I usually write ridiculously long info posts, so this time I’ll try to keep it a little shorter to keep your attention until the end and get the key information across - both for the old members and all the new people who have joined our community, because we’ve gotten VERY, VERY

ROUND TWO 💸 You’ve got $500 in cash, you’re two or three drinks in, and your dick is practically spilling out of your underwear from how turned on you are. The brothel owner hands you a beautiful lineup to choose from, with a little introduction for each lady and the price you’ll have to pay. The r

Ohhh boy, I did it!! One of my biggest projects yet - 20 images across 5 sets - is finally finished! The folder with all the attempts, revisions, discarded variants, and everything else is almost 2 GB 😂 I’ve wanted to start this series for such a loooooong time, because I feel like I have a huuuge

Heeey, my lovelies! What would you say to Part 2 of Feminization Curiosities (Tech & Magic)? Here are another 4 picks for you to choose from, this time designed specifically to help you through your difficult feminization journey. Maybe your voice is what bothers you the most? Maybe the best option

Another commission is coming to light! Requested by @Sneaky Goblin, this chastity challenge was specially designed around AC: Resynced. Pirate vibes, chastity cages, and chill evenings spent gaming - although, considering some of the level requirements and the long-term consequences of being locked

Oh, I love this - I absolutely adore magical or tech equipment designed to help turn you into the ultimate sissy. Such a fantastic series. This time, I focused on making each gadget genuinely helpful rather than something that just creates more problems. Maybe you’re suuuuper deep into sissification

Oh, I think this might be my favorite part of the series. The amount of confusion and the sheer spread in people’s choices was absolutely insane. The number of sweet comments, and especially the ones saying that someone had been thinking for 30 minutes and still couldn’t decide what to pick, was so

The Art of Giving a Blowjob - it’s one of the top-selling erotic ebooks in the reading app I use. Even this tiny example shows just how important a quality blowjob is. And during blowie, so many things can go wrong. Catching dick with your teeth, poor technique, lack of tongue control, an unpleasant

AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA These came out sooo hot. Part 1 was, in my opinion, absolutely fucking amazing in terms of kinkiness, but these are a total masterpiece. I think the lore behind each lady’s release system turned out super unique and interesting, and th

Damn, you know, adulthood is waaay harder part of life. When you’re younger, your parents basically guide you to this school, then that one, then a specific university... and then, suddenly, you’re pretty much running free. You can work here, you can work there, you can move to the other side of the

Like in that meme: what’s the most important thing for a guy locked in chastity? Release. Well releases are generally one of the most important elements of keyholding - the theoretical goal for the locked sub and a tool of power for the keyholder. I’m curious whether you have any preferences when it

Dear sissies (and not only - I’m generally saying kinksters, because the same thing applies in a similar way). Your kink is not a race to the finish line, nor is it about constantly pushing yourself to go further. I’ve been noticing this trend where you watch some skinny trans girls on r/sissychasti

Maybe like this? Or maybe like that? Maybe stick my butt out a little more? Or with the chastity cage? Nah... without the cage. Hmm... maybe in lingerie instead... Ah, the eternal struggle of spicy selfies. We all know how it goes, countless attempts, impossible decisions, while the horny Redditors

We’re continuing to work through the requests! (Sorry @IEK for the 5-month delay - I love you for being this patient and understanding ❤️) Remember that Caption with a Choice version where this time it was all about dominant women with different-sized dicks? Hooot one, right? 👀 This time I’m postin

Read the signs carefully. Ignoring them may have… specific and severe consequences. Honestly? I have no idea what possessed me to make an artwork in such a unique style. I genuinely don’t know what goes on in my brain sometimes - this is completely unhinged hahah. Note after finishing it: I just rem

They say you should try everything at least once in your life. And besides, brothels wouldn’t exist if nobody was supposed to use them. Someone’s gotta keep them in business 😏 Let’s say you have $500 in cash and you’re on a work trip in Nevada, where brothels are legal. The brothel madam hands you

Lovelies, we’re making Kinky Playground 3.0, so I really need to get my shit together! You’re all here, supporting me, showering me with hearts and sweet comments, and unfortunately sometimes I’m not very good at throwing the ball back. KP is basically my little spot to dump all the horny energy tha

Bride: @Sissy_victoria Groom: The guy she's had a crush on for three years from her darts class We wish the newlyweds happiness and the strength to keep the promises they made in their vows!😭❤️ [COMMISSION] (Scene, story and characters based on the description and imagination of @Sissy_victoria)

Let’s think about this deeply. In life, we all have a ton of things that, because of our worldview, we would firmly say “no” to. Personally, one example for me would be doing that (no offense at all to anyone who enjoys it, I just genuinely can’t describe it any other way) completely insane sport wh

My dear ones, I absolutely love moving forward in life and constantly improving instead of standing still. Kinky Playground is an extremely personal and important place for me, and I want it to become the best version of itself - as organized, transparent and harmonious as possible for everyone who

Fuuuuuuuuuuuuuuuuuuuuck... this compilation took me three days to finish. I only managed to make one piece per day because every single time I looked at the final result, I got way too distracted 😭❤️ Latex has always been tricky for me - it rarely turns out the way I want, which is why I haven't do

Play Well or Stay Locked: Chastity Challenge is back - this time with a much bigger selection of games! Just like before, each game features multiple difficulty levels, unique rules and different endings. The biggest change is the much wider variety of titles. Because of that, I haven't personally p

First you gently kiss the thighs starting from the knee, delicately moving upward toward the crotch, then you move to the balls caressing them for a long time. Only after that do you slowly climb up her cock shaft, and finally, with grace, you swallow the tip. VS You immediately throw yourself on th

And here it is - the long-awaited Part 2! This time it's available exclusively for those supporting my work (Emerald+). Thank you all so much for being here and making these projects possible (the recent subscription price increases for some of the tools I use have been absolutely ridiculous 💀). In

I was recently commissioned to create 16 unique fantasy classes/characters for PC game, each somewhere on the femboy spectrum, with their own lore, backstory, abilities, stats and role in the world. Honestly, it was an absolute dream project and I loved working on it. Since I can't share the final d

Sissy porn gooner? Or maybe a sissified slut? Where would you place yourself? (waiting for comments) 👀 P.S. Would you like to see a post about different types of sissy personalities? [Testing short post captions]

Hey everyone! ❤️ I've been keeping up with regular posting for over four months now, but unfortunately, the end of July has absolutely destroyed me thanks to the heat. At this point I'm not really living - I'm just trying to survive. I have plenty of ideas, plans and exciting projects, but I simply

Woah, this board took ages. The Advanced version turned out to be incredibly difficult to balance, so it ended up getting a complete remake. Instead of mostly one-day or a few-hour tasks, it now features multi-day challenges because otherwise it would have been far too easy. This board is designed f

A caged domme? Does that even make sense? 🤔 This question popped into my head after reading some of your comments on one of the Choices posts. For me, chastity is somewhat of a symbol of complete submission and giving up your own pleasure for the enjoyment of another person. Of course, I'm open-min

Bonus 4 picks for our fantasy dating app Chastity Dates (PART 3), available exclusively for Emerald (and higher tier) supporters 💋 WARNING: these picks are even more unhinged than the ones from PART 2. I originally wanted to nerf them a bit, but honestly it just wasn’t possible without ruining the