Rick_JL

Now extended to 85 weeks

As promised, this is my diaper chastity post. It will be up for four weeks. Once its done there will be nothing I can do while I listen to my hypno in my diapers and chastity

If you have suggestions feel free to message me.

Note goals

100 notes - plastic panties at all times

150 notes - must carry pacifier with me at all tomes

200 notes - must wear locking plastic panties with time lock

400 notes - must start wearing plug full time

450 notes - every 25 notes I must change out plug for bigger size (hollow plugs)

500 notes - locking sissy dress with timer lock

525 notes - must go shopping for one hour minimum in locking dress

550 notes - must buy locking spreader panties

700 notes - must wear locking dress and spreader panties out in public for half an hour minimum

800 notes - must go swimming once a week in diapers and one piece bathing suit

900 notes - estrogen cream to be used during diaper changes around sissy cage

1,000 notes - bottles only

1,200 notes - talk with doctor about hrt

1,500 notes - double diapers from now on

1,600 notes - new sissy baby outfit ever 50 notes from now on and throw out male outfits for each replacement

2,000 notes - babyfood for breakfast and dinner everyday

2,500 notes - laxatives and water pills mixed with formula everyday

10,000 notes - create a discord showing my sissy baby humiliation

14,000 notes - glue the lock shut on my chastity

20,000 notes - make an only fans sharing any profits with @sissybabyskye

Well after being logged out of this tumblr for a good minute.... it's time to get her back active again

This is exactly why Emma is still in diapers. This happened in the book section right before we checked out with her new toys!

Personal Update

“You still haven’t showered?” April asked. “They’ll be here in half an hour!”

I never understood why she felt the need to throw an ‘Easter’ party. That’s something done for families, not a bunch of her girlfriends. I refused to ask her about it, though. After all, it was she who made the rules around here.

“I’m sorry,” I said, hanging my head. “Got a little distracted.”

“Just hurry,” she sighed, frustrated, but still managing a smile. “How’s your diaper?”

“A little wet,” I shrugged, “seems a shame to waste…”

“It’s okay,” April giggled, “I got you some more yesterday. Pants down.”

There was a stirring in my crotch as I swiftly obeyed. I loved it when she’s firm like that. It makes me…well, firm. 

She squeezed the front of my soggy diaper, laughing a bit. “A ‘little’ wet,” she scoffed mockingly, quickly pulling the tapes off one by one until the diaper plopped to the floor with a dull, crinkly thump!

Her nails wrapped around my purple, swollen balls, jiggling my cage back and forth so that it clanked and rattled. “D’aww!! Poor wittle purple pee pee!” she cooed. 

My legs clenched together and I couldn’t help but let out a needy whimper. I know I asked to be caged, but I didn’t think April would have quite so much fun with it. Getting her to be more dominant towards me was a slow, and sometimes arduous process. It took a lot of communication for her to feel comfortable with the diaper thing. She always felt a little uneasy, like she was doing something wrong, or not enough. But once I brought up chastity play, everything sort of clicked–no pun intended. Suddenly she had motivation. She had stakes. Things she could use to both torment me and get me to do things I otherwise wouldn’t want. 

She picked the yellowy pink diaper up off the floor, balling it up and taping it into a compact orb.

“Shower. Now.” She told me in her stern voice, “No funny business. I need you in and out pronto!” She gave me a sharp smack on the ass to get me moving. I yelped, scampering down the hallway. But she didn’t give me the diaper. She usually always makes me handle the diaper. Come to think of it, she hadn’t made me throw my own diaper away in quite some time. 

As I made my way down the hall, a wall of stench practically smacked me in the face. The laundry room just so happened to be where we kept my used, soiled diapers. A quick glance inside showed the diaper bin absolutely overflowing. No wonder it stunk so bad. My little creations were starting to become quite ripe outside of the plastic of the diaper genie. I pinched my nose, leaning over to get them back in the bag so they could stop smelling up the house, I didn’t exactly want April’s friends getting a whiff of my–

“I’ll handle that.” April said, scaring the bejeezus out of me. I jumped, startled. She stood behind me in the doorway, arms crossed. “Let it get a bit full, did we?”

I knew she was talking about me letting it become overflowing. It is my job to take it out when it gets bad, but I honestly didn’t realize it had gotten this far.

“I’m sorry!” I apologized again. Usually this kind of thing led to a firm spanking, which I wasn’t exactly in the mood for right now, but she just shrugged nonchalantly.

“It’s okay, silly babies can’t always remember their responsibilities. I’ll take care of it. Now. Get. In. The. Shower!”

I bustled off before she could change her mind. What has gotten into her? I could hear her fussing with the crinkles of the diapers and plastic before I flicked on the water. I kept it cold to ease my aching balls, but soon turned it back to hot to relax my nerves. I always get a little anxious when April’s friends are coming over. All of them are so bright and beautiful. It’s hard to be in their presence without getting a little…flustered. April knows it too, that’s why she invites them over as much as she can.

I found myself getting a little worked up again. This fucking itch throbbing inside my cage that was impossible to scratch. I squirted a little body soap into my hand, making sure to keep the water from washing it away. I reached behind me and coated my crack with it, gently pressing my finger into my little button. Putting something up my ass would not have been my first choice at the moment, but since I didn’t have another option, I figured this had to be the next best thing. The soap made it burn a bit, but I didn’t care, this was the only way I could get a bit of relief...or maybe it was just working me up more. I quickly worked a second finger in and was pumping them in and out of my ass when the shower curtain ripped back.

“Whatcha doin?” April grinned. I quickly straightened and popped my fingers out, but it was obvious I was caught in the act. “I told you: no funny business!”

I stuttered as I grasped for an excuse, but none came. I was in big trouble.

But once again, she didn’t seem to mind. “Get out and dry off.” she said, tossing me a towel. “Your clothes are on the bed.”

She left without another word. 

I was waiting for her to reappear around the corner with her hairbrush or a paddle. Perhaps this was a late April Fool’s joke (again, no pun intended). She was lulling me into a false sense of security only to really bring it on later. But nope, nothing. I tiptoed through the house with trepidation. Turning into the bedroom, I immediately stopped in my tracks.

Laid across the bedspread was a frilly little dress. It was canary yellow with accents of pink and white fringe. 

Next to it was a diaper I’d never seen. It was, admittedly, quite cute, with pink and purple accents and stars around a little bunny on the front.

“Do you like it?” April asked, startling me once again.

“I…yes.” I confessed. I really did. “But not for today.”

“Why not? It’s Easter!” she proclaimed.

“But your friends are coming over.”

“So what? They know you wear diapers and dresses.”

I gulped at that, flushing in shame. I wasn’t particularly proud of the fact that her friends were in on my little secret, but it was one of the stipulations for April to agree to the whole ‘diaper’ thing. 

“Ok, fine.” I sighed, changing tactics, “But they’ve never seen me in diapers and dresses.”

“Sure they have.” April said simply.

My stomach dropped again. “What??”

April laughed and rubbed my naked shoulder affectionately. “Honey…you don’t think I could tell them something like that and not show them a few pictures, do you?”

I shivered in shame, or was that just a very violent cringe? I decided not to ask her which ones she showed them. I was better off not knowing.

“They thought the video of you twirling in your sundress was adorable!” she told me with a smile. “They also think you’re cuter than Ella.”

Oh god. 

Ella was what April liked to call my sissy ‘gurlfriend’. We have gotten together for quite a few…playdates. Oh fuck! I hope she didn’t show them videos of me and Ella–

“On the bed, sweetheart.” April said, patting the mattress and picking up the diaper. “We need to get you ready!”

******

“Aren’t you the cutest!!” Daisy cooed, pinching my cheeks.

“The pigtails are just adorbs!!” Brooke admired, curling them in her fingers.

Lily laughed, “Is his diaper wet? I wanna see his diaper!!”

They all turned to April expectantly, who just smiled like a proud mother. “Show them, sweetheart.”

It seemed like a pointless endeavor, the bottom of my diaper could easily be seen beneath my dress, but the girls–including April–relished in my humiliation. So I obliged them, lifting the hem of my skirt and exposing my diaper to their ooo’s and aaahhh’s.

“Is he wet?”

“I think so!!”

“Already?” April asked, aghast, “I just changed him!”

Like 30 minutes ago. I thought, as if that would save my dignity. I had plenty of room left though, there was no need to change me. 

“There’s no need to change him right now,” April said to my relief. Having my diaper open and exposed in front of four beautiful women would be quite humiliating. If only I knew what was to come…

“Is it time for the Egg Hunt yet?” Daisy asked impatiently. 

April’s smile looked a little too mischievous for my taste. “It sure is!”

They made me get down on my hands and knees, shepherding me along until I made it to the backdoor. The light burned my eyes as the sunlight peeked through the open door. If it weren’t for my thigh-high stockings, the concrete of the patio would have scraped up my knees. 

“Today is a special day for you, sweetheart!” April said, “You get the chance to have your cage unlocked!!”

My ears perked up, suddenly I became much more attentive. 

Lily brandished a woven Easter basket—a rather large Easter basket—setting it down in front of me. 

“I have hidden the key in one of your used diapers.” April explained, “and have hidden those diapers around the yard.”

Scanning the landscape, I started to notice hints of white, colorful, taped-up diapers scattered around. I didn’t have long to look though, my attention was quickly drawn to Brooke and Daisy pulling my arms behind my back. There was a clinking of chains, and soon my wrists were cuffed together. To make matters worse, I felt my hands being stuffed inside of what I recognized to be locking mittens. 

“You have 10 minutes to gather as many ‘eggs’ as you can.” April explained. “Any eggs you fail to retrieve after the allotted time will be forfeited.”

I wanted to protest, to say something clever or ask questions that would get me an advantage, but before I could even utter a word, April had her phone out. 

“Your time starts…now!”

There was no time to argue. I knew April was very particular when it came to time. There were several instances of her unlocking me and only giving me 30 seconds to achieve orgasm. Even when I was incredibly close, she would stop me as soon as the alarm went off, leaving me whining and crying while she readministered the chastity device. 

I quickly bent over and grabbed the handle of the basket with my teeth. Climbing awkwardly to my feet, only to stumble and fall flat on my face, much to the girls’ delight. I spit the grass from my mouth with a pffft and replaced it with the reeds of the basket handle again. I surveyed the area for any glimpse of pink, white, or blue padding. Though, admittedly, there weren’t very many blue ones.

Some were obvious, resting right beneath the tree or scattered on the grass. A part of me thought she wouldn’t put the ones containing the key in such an easy location, but the other part told me to just grab as many as I could in the allotted time. 

“Grabbing” proved to be difficult though, hands being tied behind my back and all, so I was forced to drop to my knees, bend over, and sort of use my chin to nestle the dirty diaper into my neck, lift it, and drop it into the basket. If that doesn’t sound easy in theory, it was even harder in practice. It took me several attempts just to get the warm, squishy padding in the right position, followed by me dropping it right back to the ground as soon as I began raising my torso into the air. What really set me off though was when I finally managed to drop one into the basket–only for it to hit the edge and knock the whole thing over, causing the diaper to roll out and putting me back at square one. 

I tried to nudge the diaper back into the rolled over bin, but my head kept bumping the handle, scooting it away before I could get the diaper any closer. Switching tactics, I tried biting the handle and pulling it along the ground in an attempt to scoop it up, but this just scooted the poopy diaper along and caused the same problem in an opposite direction. Grunting in frustration, I bent down and clamped the diaper between my chin as tightly as I could. I was more delicate before, but I was wasting too much time, I had to be more zealous. The forceful smushing of the diaper must have caused the already sun-ripened diaper to release an even more pungent smell. I was choking and gagging as I finally managed to drop it into the basket. One down. I thought, relieved.

“7 minutes, baby!” April called. 

Fuck. That took way too long. 10 minutes seemed like a ton of time before I realized how difficult just picking up the eggs would be. I needed to go faster. I clamped my jaw around the handle and took off for the next one. I let the basket down carefully so as to not make it fall over, and went after the diaper nestled in the bush with the same aggressiveness I did before. The leaves of the bush tickled my face. I had to dodge sticks to avoid them poking me in the eye, one still ended up scratching my neck, but I didn’t let it stop me from getting my prize. This one was more plump, it must have been one of my really wet ones, it dropped into the basket with a thud. 

After spotting a green and white one nestled inside the flowerbed, I moseyed on over, my skirt swishing in the wind. Soil went up my nose as I raked it across the ground. I fought the urge to sneeze and cough, keeping my grip on the stinky diaper until I was able to add it to the pile.

By the time April gave the 2 minute warning, I only had 4 diapers in the basket. There was no telling how many more were left in the yard. The bag from the pail must have had at least a dozen in it, and I’m assuming those were the ones she hid around the lawn.  What if I only get a third of the diapers and it’s not even the one with my key in it? I had to get more to increase my chances.

One of them was actually in the birdbath. It had grown to three times the size of the others. I had to nudge it out of the water so it could crash to the ground with a sodden squelch! I couldn’t help but wring out some of the yellowish fluid as I squeezed it into the basket. The added water weight–combined with the weight of the other diapers–made the basket quite heavy. I felt like my teeth would come out any second as I lugged it across the yard. 

The last one I could easily get to was tucked beneath my barbecue pit. It was blackened a bit by some of the soot, and turned out to be very slick on account of the grease the base had collected from me neglecting to clean it for so long. 

“30 seconds!!” April called. The other girls, who had been hooting and hollering the whole time, turned it up to 11 with renewed vigor. They seemed absolutely elated with every ‘egg’ I collected.

I cursed myself as the diaper slipped from my neck for the second–and then a third–time. My neck was greasy. The soot was covering my chest and dress. That, mixed with my sweat from exerting myself made it damn near impossible to lift the diaper without my stupid hands. I was about to make one last, desperate attempt before a call came from April.

“Time’s up!” she yelled, managing to hide her thoroughly entertained smile. The other girls, however, made no attempt to conceal their own delight. “Bustle on over here!” April said, “Let’s see what the Easter Bunny brought you!”

I couldn’t help but feel defeated as I brought forth my pitiful display of just five used diapers. The front of my dress was probably ruined, which is a shame because I quite liked it despite the circumstances, but I was more distraught about the meager amount of diapers I was able to acquire. There was a less than 50% chance that one of the diapers contained the key to my cage within. When it comes to, well, getting the chance to cum, I’d rather those odds be a bit higher. But I guess my fate was up to the gods at this point.

“Time to open your presents!” Daisy gleamed, as if this was the part she’d been waiting for the whole time.

Brooke thought she would do me a favor by carefully taking out each of the diapers and laying them on the patio before me, or maybe she did it as a way to patronize me, counting them one by one as if I was too dumb to be able to do it on my own. 

“Are we giving him a time limit for this too?” Lily asked.

April considered that for a moment, though I’m sure she’d already had her mind made up long before then. “Hmmm…I think so. Watta we think? 10 minutes again?”

“Psh! I think 5!” Lily scoffed.

“Yea! One for each diaper!” Daisy agreed.

It still seemed like a generous amount of time, so I wasn’t complaining. That is, until April started pulling out her phone again, setting the timer.

“W-wait!” I cried out. “Aren’t you gonna uncuff me first?”

April smiled wickedly again, then shrugged with a now innocent look. “I just figured you did so good at gathering them up without your hands, that you should be able to open them up and search through the contents without them too!”

The other girls laughed mercilessly behind me, as if they knew this would be the outcome all along.

I already felt like gagging as I looked down at the pitiful pile of poopy pampers. The idea of having to pour through the diapers without the use of my hands disgusted me, but the thought of getting that key made me prepared for anything.

April held up her phone, thumb hovering above the button. “Your time starts in 3…2…1…*click*”

Desperate times call for desperate measures, and I was about to learn just how desperate I was indeed…

THE END

How the Gamer got games

No, no no no no no no, this isn't fair, no!" Ryan shouted. He felt powerless as the game informed him of the obvious. He had died, and for the 4th and likely final time, failed to free himself from the dumbest bet he had ever made.

He and his roommate had only lived together for about 8 months now but in that short time his world had completely shifted. The guy who answered his roommate add, Andrew, had been upfront that he had a kink for dominating men. He also had not hidden his stash of dresses and diapers, not for himself but for his "playmates." While Ryan thought this a bit strange, who was he to judge? Plus Andrew had said he preferred feminine partners, so Ryan thought he would get to see some hot ladies in some strange but somewhat arousing sounding scenarios.

But after the 2nd month, no pretty women had come by. Andrew had been chill, but kept to himself and his room mostly. Things changed one night when Ryan was playing his Xbox, and Andrew made a rare appearance in their living room. Ryan loved playing games but wasn't the best, yet he was clearly in denial.

The two guys talked video games, well Andrew asked and Ryan boasted. It was during this that Andrew asked how good Ryan was, and he foolishly boasted that he "Could beat any game on the hardest difficulty first try, no problem!" Andrew asked if he was willing to bet on that, and Ryan agreed.

The terms were pretty simple. If Ryan beat the game of Andrew's choice, then Andrew would pay Ryan's portion of the rent for the next 2 months. But if Ryan failed to beat the game first try, he had to grow his hair out and style it to how Andrew wanted. Ryan agreed and failed to beat the first Halo game after just 3 levels.

It sucked to lose, and after just 2 months, Ryan's hair had really shot outwards. He was getting annoyed with it, having to put it in ponytails to keep it out of his face, so he asked how long Andrew wanted to keep the humiliation punishment going. Andrew answered he was willing to wager the punishment ending as a reward for beating a game, first try, as he said he could. Failure, however, would result in Andrew getting to choose Ryan's outfits for when they were home on the weekends. Knowing it would likely be humiliating still he agreed, and failing to beat the 2nd level of Gears of War had him very much angry.

He got more angry when Andrew pulled out a dress and told him that this was his Saturday outfit. Ryan was very much angry and told him no way, he was done with all this. But Andrew talked him down from his tantrum by telling him he would make the clothing punishment for only for this weekend, and that Sunday night he'd introduce Ryan to the cutest girl. Ryan agreed, and come Saturday, he found himself in said outfit.

Thankfully they just hung around the house, and after 2 days of sitting around in the dress, Ryan was ready to change and meet this cute girl Andrew promised. When he brought it up, Andrew smiled and told him all he had to do was look in the mirror. The statement stunned and confused Ryan, and he rushed to his room to change.

Ryan avoided eye contact with Andrew for a few days, but finally by Thursday he had settled down, and stopped being as angry. On Friday Ryan let Andrew know that he was going to finally cut his hair, but Andrew shook his head and told him he wasn't doing that. Not if he didn't want this photo to get released.

Ryan was furious. How could he take a photo of him? And now he was blackmailing him? What else did he want? Andrew calmed him down, telling him all he wanted was for the bet to be honored. And that he would permantly delete the photo and all backups he had, as well as let him cut his hair, if he could finally do what he said he could, and beat a game first try. Ryan refused, and Andrew shrugged, and told him that's fine, but no haircuts unless he wants to photo released.

The next week, Andrew kept "almost" losing physical copies of the photo. One was placed near an open window. He had left a copy out when Ryan's family came to visit and thankfully Ryan was able to snag it before it was seen. 3 weeks of close calls wore Ryan down, and he agreed. Though he had second thoughts when he learned of the results of a failure.

Andrew had stocked up 20 packs of diapers, and the new terms were that Ryan had to wear, and USE, all the packs up. He only got a change after 1 messing, or 3 wettings, since they were graded for heavy incontinence. The bathroom would be locked, with Andrew having the only key, and Ryan could wear whatever clothes he wanted over the diapers.

Dark Souls was the game of choice, and minutes after it started, Ryan slumped as he saw "You Died." And for the last 3 months, he had been stuck in diapers. The thickness of them was something he still wasn't used to, and despite trying to work his way through them, he still had 5 packs left. Seems Andrew didn't mention that the packs were 32 sized.

It was today that Ryan asked to once again try and get free of the restrictions. End the diapers early, cut his hair, delete the photos, all of it over and done with. Andrew had agreed, and added into the pot 10 years rent coverage with no more bets ever again like this if he won. And he would let Ryan pick from a selection of 5 games. But failure, and the bets were over, but the punishments as long as Andrew wanted.

Andrew would own Ryan as his sissy diaper slave. There would be no end to the diapers and he would not be allowed in the bathroom at all save for baths from his new master. Clothing wise, Ryan would wear whatever Andrew chose for him and would not back talk him at all. Ryan would be allowed vanilla clothes for work, but the diapers would remain, and he would be locked into plastic panties during said hours to ensure he didn't remove them or use the bathroom there.

Additionally, with the lease up for rent, Andrew would take over as sole listed name on it, meaning that Ryan would only live there so long as he obeyed the rules, and without any recourse if he was evicted. But Ryan still would owe his portion of the rent.

Last, Ryan would be required to learn how to service Andrew however he wanted. Every month he would be given a set of tasks to be completed, and they would need finished to let him stay living in the apartment. They could range from household chores, to photo shoots, to sexual favors and services.

Ryan thought for a solid hour, but realizing that he was no longer in control and unable to guarantee anything, he reluctantly agreed. Andrew offered him 5 choices as promised. Though between Cuphead, Ninja Gaiden, X:Com 2, Nier Automita, and Devil May Cry 5, he never had a chance.

The first month of tasks were almost ironic. He had to play a video game, Stardew Vallye, for 150 hours. Though he could only play with a plug up inside him, while grinding on Andrew's groin, and during the time frame of only 8am-8pm. Ryan had ended up calling off the last few days of the month since despite full weekends spent with an invader hiding inside him under his padding, and forgoing his post-work diaper change to get in some extra hours, he was several short to meet his quota.

Andrew smiled, he was enjoying finally having the sissy of his dreams. He had chosen very carefully, choosing the best looking target he could have. And thankfully he had an ego that was as massive as the plug inside him currently was. Though next month would be more fun, and he was working on deciding what would be more enjoyable to demand first; requiring a set number of orgasms while in a month long chastity cage or Ryan spending all time inside the apartment inside of a dog cage with only pre and post work diaper changes. Either way, his toy would learn that Master Andrew doesn't play games, he wins them.

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Photo is not mine, credit goes to original owner. Contact me if you would like credit for it, and if you would like me to remove it from the page.

Since I like knowing people enjoy my captions, I'll make another bet. I bet this post won't get 200 notes by 5/18/2024. If I'm right I get nothing. But if I'm wrong and there are over 200, then I'll recreate a photo used in one of my captions by the end of May prior to this post. If it's tripled by the date, then I'll let a poll from y'all decide what photo I recreate.

It's silly, really. Just looking at a pair of jeans makes me...jealous. I can't remember the last time I've put on a real pair of pants. Not skirts that do nothing to hide my pink pampers. Not dresses that make me look slutty. Not onesies that make me look infantile.

It's not fair. What I wouldn't give to feel the denim against my skin again, something other than satin and lace and frills. Something other than wet, dirty diapers. I never truly appreciated what it was like to wear men's clothes.

Now I'm sorting and washing the clothes of the man that's fucking my wife. Except his underwear don't have skidmarks and jizz stains in them. Maybe if I was more careful, I wouldn't be in this situation. Maybe if I learned to keep the seat down, to not sprinkle when I tinkle, to wipe my ass better, to control my orgasms instead of ejaculating at her slightest touch, maybe if I learned to keep my dirty clothes off the floor, then maybe she wouldn't have gotten so frustrated with me.