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Midoriya's Elementary Re-Education (Commission)
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EmperorCharm
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Cheerleader of the MAX Gym (Commission + STORY)

Gaomon V. Gatomon - Catch These Claws (Commission)

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Commission #179
For VS21

---

“Go! Go! Max!” Ash shouted out to his boss from off to the side. He had been practicing his chants and cheering for a long while now and he figured he had one that was going to please the boy.

Still, he was reluctant to go all out as far as cheering for the one who put him in this humiliating position. Unfortunately for him, Max was aware of this and smart enough to see through Ash’s pathetic attempts to somehow spare his dignity if such a thing still existed for him.

As the leader of the MAX Gym, Max had a vision of his own to upkeep and Ash needed to follow it to the letter. If he didn’t, he’d be in serious trouble. He already was for seriously believing he’d get away with that limp wristed chant.

“Ahem,” Max called out to Ash, turning away from the Gym Battle he was currently engaged with in front of a small crowd of onlookers to the side. “You can do better than that and we both know it. Raise your voice! Put some excitement behind your yell and say it proudly!”

Even if he wasn’t proud, he needed to say it proudly.

Ash gulped, sweating a bit more and blushing a bit deeper as he danced from foot to foot like he had to go potty. He was on orders to do what he was avoiding so what other choice did he have but to go do it?

“GO! GO! MAX! YOU’RE THE BEST AND YOU FIGHT STRAIGHT FROM THE GUT! YOU DIDN’T NEED SKILLS TO KICK MY BUTT! GOOOOO~! MAX!”

Laughter ensued. The emphasis that Ash put on the fact that his defeat was so incredibly decisive and easy that it happened when Max was barely skillful at this just showed how delusional Ash had been up to the point of their fight.

As if he could have ever become a Pokemon Master with skills like his. Somewhere, deep inside, he yearned for that dream to be viable again but he knew it just wasn’t possible anymore.

He didn’t even have time to pretend he was still able to train to be a Pokemon Trainer anymore. His daily routine was very clearly outlined for him by this point.

It always seemed to go the same way.



Ash woke up in his nursery every day at 7 AM. Today, his eyes shot open when he had a dream that he was at the Alolan Championships and managed to win. Each time he went to sleep, he’d get a reprieve from the actual life he lived by experiencing a wondrous dream like that.

Of course, the instant he was always about to be handed the trophy would be when he’d open his eyes to the cutesy voice from his baby alarm going “TIME FOR BABY TO WAKIE WAKIE!”

Every morning. “TIME FOR BABY TO WAKIE WAKIE!”

Over and over again. Every. Single. Day.

He sat up in his crib, in a pair of baby footed pajamas with a butt flap on the bottom. There was also an obvious diaper bulge around his waist, signaling that even while sleeping he was to be a baby. Then again, you already knew that thanks to his unsubtle alarm.

He would jolt with surprise at the face of whatever mascot from a baby show was there on the television beside him. It would either be Barney, Sesame Street, PJ Masks, Paw Patrol, or Blues Clues. Sometimes it was Dora the Explorer if Max felt really cruel.

Today it was Barney. Ash grumbled. He hated the sound of his stupid voice.

Ash was about to say “Screw this” and lay back down in his crib but, of course, that’s when Max would walk in.

As leader of his own Gym and owner of him, he had final say in when he woke up. Those were the rules and Ash knew the consequences of disobeying them.

“Up!” Max said, clapping his hands once. Ash sat up, a grumble under his breath and his lower lip quivering.

Max reached into the crib and grabbed him by the armpits. He always had to lower the bars a bit in order to do this correctly but he always managed to lift him out and take a gander at his diaper.

Sometimes it would even be wet. Yeah. Ash was feeling himself getting more and more lazy when it came to exercising his desires to find a bathroom nowadays. With his dream gone, his potty training seemed like an afterthought. Max wasn’t even doing much to enforce diaper usage which was extra pathetic.

Ash was stood up and his arm was grabbed by the much younger and much smaller boy with a look of excitement on his face. It was as if every day Max couldn’t believe this was his reality.

“Come on. Time to feed you,” Max snickered, yanking Ash along. Ash stumbled, the size difference making being pulled along by him all the more awkward.

They did eventually reach the kitchen where Max gestured towards the high chair set up by the table. Ash was all but pushed into his seat and locked into place.

Of course, Max’s first priority was himself so he went to go pour himself some cereal and milk, delighting in a bowl of Fruit Loops in front of Ash while setting down an open jar of mushed carrots for his diapered cheerleader.

“Here we are,” Max said as he scooped a tiny bit into the baby spoon and hovered it towards Ash’s mouth. “Open wide!”

Ash winced, already turning a bit green in the face. These jars of baby food were horrendous and always seemed to get worse with each sitting.

So, of course, Max would just double down on feeding him this gunk right?

He shoveled the spoon into Ash’s mouth, making his eyes widen and pupils cross. Ash’s eyes fluttered as the taste almost made him pass out with disgust.

Max wouldn’t let that happen though. “Nuh-uh. No more nap time. You’ve got stuff to do,” He said, shoving more of the goop into his unwilling maw.

Each spoonful felt like a stab to the gut for him. He wanted the jars, plural, he was being fed to be empty. Soon, they were. Mercifully so.

That’s when Max finally unlocked the seat of the high chair and yanked him out by his arm again. Ash stumbled but managed to steady himself a bit so that Max could lead him over to the table proper.

Max sat down and patted his lap, signaling for Ash to make his way over. Ash sighed but did as he was being pushed to do.

It was beyond embarrassing and he felt the puffiness of his diaper smoosh against Max’s legs in a manner that made him blush heavily. Max just giggled, sensing his embarrassment. It just never got old to him.

Next came the bottle of baby formula, which was even worse. When you eat something gross and wash it down with an even grosser thing it just makes you want to hurl.

The bottle feeding took such a long time, always. When the bottle was empty, Ash’s puffed out cheeks and rolling eyes made him look doofy as hell. He swallowed the lump in his throat and then sighed, feeling exhausted despite having just woken up.

“Good baby. Now then,” Max leaned Ash over his shoulder and began patting his back restlessly. Ash moaned a bit in delirium before he belted out a loud belch. Getting burped by Max was just as humiliating as ever too.

After this, Max got to changing Ash out of baby blue pajamas with Thomas the Tank Engine prints on them. Yeah, they were little boy pajamas he had on. They were a reward for good behavior or a good performance during Max’s gym matches.

Normally, they’d be sissy girl pajamas but hey, he could be nice sometimes.

Ash found himself yelping as he was flung back onto the carpet. He grunted and laid there, looking at the ceiling and shutting his mouth to keep from letting out an embarrassed whimper.

His legs were raised and his diaper would be removed. It was wet today.

“Not even trying to use the potty properly anymore eh?” Max asked. “Don’t blame ya.”

Ash put his hands to his face, feeling the shiver of being cleaned, powdered, and then re-diapered. This time he got put into a rather extravagant pink diaper before he had a nice canary yellow cheerleaders uniform thrust onto him.

It looked really good. You could tell this was something that a loud and proud cheerleader would definitely wear and that’s what Max needed Ash to be for him today.

He’d been challenged by a newbie to this whole Pokemon Trainer thing and he wanted Ash to show him what could happen if you dare to aim too high.

When Ash was dressed, Max patted his back and opened the door, gesturing for him to leave first.

“Ladies first,” Max chuckled, doing a nice eyebrow spasm.

Ash growled. He wanted to protest. He wanted to say something but he knew any word out of his mouth, unsolicited, would just go badly for him.

So instead he clenched his teeth and his fists and marched outside. The angry face turned into an embarrassed frown while his pupils dilated from the realization that he was out in public, dressed in the most ridiculous manner imaginable.

The townsfolk he walked by as the two of them were on their way to the Gym proper were keenly unsympathetic to Ash.

“Whoa! There he goes! It’s the Baby Cheerleader of the Max Gym!”

“He’s got on such a tiny skirt. I guess he likes freeballing it?”

“I doubt he’s got any balls but he must have a thing for humping pillows or something. There’s one stuck between his legs.”
Ash would hear laughter follow soon after and he’d shrivel up with anger while his face would turn red from embarrassment.

Then they would finally arrive at the Gym. Whenever these situations went down, it was always a show for Max.

Ash was led towards a little play area that had been set up just for him. It was weird that it was set up right off the side of the area where the Pokemon battles were to happen but it was also the most open and visible spot in the Gym. Max needed to make sure everyone could see him.

There, Ash would be forced to play with dolls and little kid toys as he waited around for the proper festivities to begin.

Trainers just like him would come all over to greet Max at his Gym for the badge that wasn’t the M-Badge on Ash’s chest.

The Max Badge that Ash had on was a special badge that, when worn, made it explicitly clear that he was Max’s property. He just belonged to him now.

This all started so long ago when Ash came here to challenge Max for the normal badge. He lost badly and a bet gone sour saw him leaving in a short pink dress and a diaper back then.

His rematch saw it happening again but he didn’t end up leaving. He was given the Max Badge while all his other, legitimate, badges were taken from him. His Pokemon were set free and his Pikachu was sent back home to his mom.

Reflecting on this saw the time pass rather fast. When Ash looked up while making the Barbie dolls he had crash into each other, he noticed the trainer, around his age, was finally there.

The trainer was staring right at him, looking shocked and a bit put off. However, Max made it clear to him that Ash was a special case. It would be less humiliating for Ash if someone could share in his treatment after all.

That caused the new trainer to laugh, as well as the small crowd that came to witness the fight. Ash forced a smile on his face and grabbed his pom poms.

This got us back to the position he was in now. He threw out that cheer that recanted how Max barely needed to try in order to defeat him and delighted in seeing Max’s delight.

A smile and a laugh from Max as a result of Ash doing a good cheer was a good thing. He might get another chance to have some big boy pajamas privileges tonight if he keeps this up. Maybe even a bottle of real milk?

Whatever he had to do, he’d do it. He was only granted the privileges that Max chose for him and that’s the way things were.

God. He was so stupid to ever think he could beat him. What on Earth was he thinking?

---

Support me on Patreon or Pixiv FANBOX and get images and bi-weekly stories. Even more colored images await you for 10 dollar patrons and above too. Check it out at http://www.patreon.com/SDCharm or http://sdcharm.fanbox.cc/


Keywords
male 1,179,453, pokemon 188,434, human 107,029, diaper 76,410, diapers 21,659, anime 16,727, embarrassed 14,589, humiliation 12,522, sissy 8,489, diapered 7,175, nappy 5,880, embarrassment 4,465, diaperboy 2,316, cheerleader 2,036, public humiliation 1,957, embarrassing 1,757, max 1,686, humiliated 1,483, crib 1,301, humiliating 974, ash 869, nappies 765, sissification 741, sissyboy 562, loser 533, ash ketchum 306, sissy boy 210, sissified 158, gym leader 138, bottle feeding 131, cheerleading 126, satoshi 50
Details
Type: Picture/Pinup
Published: 11 months, 2 weeks ago
Rating: General

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Asa12
11 months, 2 weeks ago
Great story
VS21
11 months, 2 weeks ago
Once again I have to say it, Fantastic work here Charmy, thank you for taking up another one of my commissions!
GoldenFlowerBoy
11 months, 2 weeks ago
It's nice to see a sequel to that one pic from long ago! I loved this Max's sissy diaper wearing cheerleader series~
joelfeila
11 months, 2 weeks ago
Ash should be glad he gets a skirt to wear.  
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