Diaper For Teacher

by Naptime

Rating: teen
Tags: My Little Pony: Friendship is Magic, Fetish, Cheerilee, Big Macintosh, Slice of Life
Length: 15084

With Cheerliee acting as his pretend teacher for the day, Macintosh is roped into playing a number of childish games at school involving silly tests, arts, and diapers.

With Cheerilee acting as his pretend teacher for the day, Big Macintosh is roped into playing a number of childish games at school involving silly tests, drawing, and diapers.

Contains diapers, diaper usage, adults wearing diapers, and teacher/student role playing. Please don't keep reading if you disapprove of any of these themes.

Published 2018-10-29 18:20:01 UTC
Last updated 2023-01-29 17:23:40 UTC

Chapter One

The classroom was sufficiently decorated with educational decor. Charts of math tables and storybook illustrations dotted the pale green walls with the occasional poster about being prepared for class or how to tell time placed in between. A large chalkboard dominated the north facing wall, designating it as the front of the room. Single hung windows provided a fair bit of natural light into the room, brightening up the already vibrant learning space.

Rows of school desks took up most of the room with enough to comfortably seat at least twelve students. They were all neatly organized into rows and columns for optimum paper passing efficiency. Across the room sat a teacher’s desk, a sturdy, wooden thing with plenty of drawers to store pencils, papers and test packets. In one of the back corners of the room was an activity area with shelves of supplies and a round table to gather at. A small kitchenette, consisting of a sink, fridge, counter space, and cupboards sat close by as well. The room was dead quiet this Saturday afternoon.

Macintosh and Cheerliee stood in the center of the room to take it all in. They both wore thick white diapers as large as pillows around their waists, the perfect outfit for what was to come. By the spontaneous and giddy request from Cheerliee, Macintosh had come to visit the school on an off day to partake in, what Cheerliee like to call, “foalish school games”. And he was quick to accept. An afternoon with the cute teacher, it was hardly something he could pass up!

Cheerilee diverted Big Mac’s attention to the cluster of desks. “Please have a seat at any desk you like,” she said while pointing with her hoof, “I have a few things I need to get out of my desk.”

Big Macintosh nodded and scurried off to a nearby desk. He opted for the front row, hardly wanting to seem like a trouble student to his temporary teacher. The small wooden seat took some getting use to, but he found the plushness of his diaper aided in its comfort. The small desk, built for school aged foals, was lower to the ground than what Macintosh was used to, forcing him to slouch forward. He felt silly sitting at such a small desk. He felt like the new kid on his first day of school. These feelings were only amplified by the bulging diaper that crinkled with each tiny shift he made trying to cope with the child sized seat. The diaper made him feel like he should be in nursery school instead.

By the time he looked up, Cheerilee was already walking up to his desk with supplies in hand. With a diaper just as thick as his, the purple pony coped with the bulk by widening her gait into a toddlerish waddle. In front of him she dropped a stapled packet of paper as well as a freshly sharpened pencil. She wore a very happy smile as she spoke. This was something she had been looking forward to for quite awhile. “I want you to take a little test for me. This one I had drawn up special for you.” She took her time explaining, enjoying the scene she was playing out with the overgrown student, “it won’t be anything difficult. My students would have no trouble answering these questions.” Big Macintosh gave the test a quick glance over as Cheerliee waddled back to her desk. “I’ll be here when you’re done,” she added as she opened a book and leaned back in her seat. That left Macintosh with the task in hand, diaper or not, it seemed that Cheerliee had her plans.

Macintosh gave the test packet another look over. On the surface it seemed pretty standard. The first page started a long list of numbered questions with a big space at the top for the test taker’s name. Without reading anything else, he went ahead and filled his name in with a pencil.

The cute little test Cheerilee had written up for him was in no way difficult, hardly going beyond a second grader skill level. Most of it consisted of easy questions ranging from science to history. Easy facts that any kid could recall from their school careers.

Big Macintosh was a bit older than the children expected to do tests like these, but if he searched the deep recesses of his mind he could recall all he needed. It was tough to forget things like how many sides a triangle had or that a yard was longer than an inch. Most of these questions were rather insulting really. Of course, that might have been the point. He was wearing a diaper after all.

Despite the low skill level of the questions, it still took Macintosh time to read them, fill in the little circle next to the right answer, or to write out his answer. Sometimes he struggled to even figure out how to explain his logic. Stuff like what time the little pictures of clocks read or how many cups were in a gallon were difficult to explain because of how second nature the information was. His adult life never asked to explain anything so simple, it was just universally understood that they just were.

And so, whether he liked it or not, the test took at least an hour to complete. An hour that he didn’t quite know he could withstand. About half way through the stapled packet of papers, his bladder began telling him that it was full. Apparently the tall glass of milk he had during breakfast to wash down a rather hefty meal was catching up to him. He had hoped he could just hold it for now and put it off, but crossing his legs only did so much, especially when the diaper’s bulk kept his thighs slightly apart.

He just needed to let a little bit out. Just enough to relieve the pressure, than he’d be able to focus. He inched his thighs apart and shifted in his tiny seat to find a more comfortable posture to piddle into his diapers. Just a little bit, he was sure to constantly remind himself. He found that leaning forward a bit helped things along. But just a little bit, that’s all he needed and then he’d be able to finish the test.

It started with a little spurt which, after using every ounce of self control, quickly ceased, allowing the little splash of urine to soak into the waiting diaper. That seemed to help a tiny bit. Painful at first, but soon the pain faded away and left behind a slightly relieved bladder. He dared another spurt, garnering another brief wave of relief. He was so focused on his tiny, controlled urination that the test fell to the wayside. Another quick spurt was quickly released, followed by yet another brief wave of relief. He sighed at the successful release. Before long his bladder no longer felt so achingly full. All it took was a little bit of control and he was able to get his focus back.

Suddenly a big fluffy diaper plopped itself onto the corner of his desk, nearly surprising the diapered stallion right out of his seat. He looked up startled to find Cheerilee standing at his side with a knowing smirk. He knew she must have been watching him carefully relieve the pressure in his bladder, but couldn’t quite tell how long she had been watching.

“I’ll change you after you turn in your test,” the purple pony simple said before turning away and returning to her own desk. Her thick diapered rump wagged behind her, catching the eye of the big stallion.

Still dry, Big Macintosh quickly concluded. Even after all this time, Cheerilee’s diaper was still dry! He stole a quick glance between his own legs to find a sizable yellow stain on the front of his diaper, the collective moisture of his numerous controlled spurts into his diaper. So much for ‘a little bit’, Big Macintosh mentally grumbled.

Rather peeved by it all, he returned to the test. It was hard to focus with the dry diaper sitting there like a constant reminder of what was to come. It reminded him of the moist diaper that was between his legs and was sure to hint at the futile attempts he made to avoid soaking his diaper which was, ironically, to wet it a little bit. Or it would have been a little bit if he hadn’t gotten carried away.

Looking down between his legs again confirmed that it was, in fact, not a little bit. Why the sum of all his little spurts had amounted to a rather large spot on his diaper, something resembling a little accident. Nothing to merit a diaper change by any means, but large enough to be noticed. He could have very easily achieved such results by peeing into the diaper without holding back for a few seconds rather than the good ten minutes he had killed carefully relieving pressure.

So why would it matter? Cheeriliee was expecting to change him after the test regardless of how wet it was. So why would it matter how wet or sort of wet his diaper was when he reached that point? He still needed to go anyway.

For the numerinth time that day, Big Mac’s attention turned away from the test and focused back on his diaper. Now he had to willingly wet himself with whatever he was holding back not minutes ago. After stopping and going so many times early, his bladder was more than happy to oblige. He only needed to give the final approval before a powerful stream began spraying into the diaper.

He sat there as casually as one could while diapered and sitting at a children’s school desk, which in reality meant he sat stiffly and unnaturally hunched forward. He could feel the urine trickle all around his crotch as the warmth soaked and swelled every inch of the diaper it touched. He blushed as the urine found its way to his butt, tickling it ever so slightly before swelling up the seat. The pillowy soft seat of the diaper now had the consistency of mush as the gels quickly snatched any amount of urine that had come their way.

When his bladder ran empty, Macintosh could only think to sigh, taking in a steady breath of relief. Finally he was able to focus completely on the test, no longer impeded by the aching strains of his bladder. Filling out the test was a breeze after that. With a relaxed bladder and a relaxed mind, he was able to answer the questions easily once he had the mental energy to commit to it.

By the third completed page, he stole another glance down between his legs. The once tiny spot now evolved into an all encompassing yellow that covered the entirety of his crotch. The material had swollen quite a bit, dwarfing whatever the diaper might have looked like when he put it on. He instantly regretted looking. It just made him more nervous. But at the very least, the only real silver lining he could find in this predicament, was that he had enough brain power to finally finish this blasted test, even if that meant he was to spend it wallowing in the heavy, warm diaper the entire time.

In a flash two more test pages were finished. Or at least it felt like a flash to Macintosh. He had stopped looking up at the clock ages ago, too involved in the test to even pay it mind. It didn’t matter what time it was. What mattered was getting this test finished and turned in.

The seventh, and to Macintosh’s relief, final page at long last was turned to. The end was near! He breezed through the last set of questions without issue. At least, most of them.

Things were fine until he reached the final question. ‘Is Macintosh a big boy? Explain your answer.’ The final question on the test made Big Macintosh’s cheeks flare up a bright red.

He gulped, looked up at Cheerilee with blushing cheeks, and then looked back down at his paper. Thankfully Cheerliee was too involved in her book to really notice the stallion’s sudden discomfort. Was he a big boy? His wet diaper made that question easy to answer. He picked up his pencil and reluctantly answered as truthfully as he could manage.

Big Macintosh is not a big boy, not any more, He wrote in the space provided, He’s not a big boy because he couldn’t hold it and chose to wet his diaper during the test. A big boy would have held it till the end or even asked nicely to use the potty. An idea that came to his mind as he wrote it. He kicked himself for not even considering such a simple solution. He was just so focused on completing his test. Big boy’s don’t wear diapers. He added that last part with a tingling blush in his ears. Surely he wasn’t a big boy anymore.

He closed the packet of paper with a satisfied nod. He was done. After quickly reviewing his test, he stood up from his tiny desk and waddled over to Cheerliee. He was immediately reminded of his soaked diaper as its swollen weight pulled at his waist. The diaper’s happy crinkles were now replaced by hefty, soggy sways as he made his way over to his teacher. Cheerliee was ready for him when he arrived, long since putting down her reading book after hearing the loud sloshing of Macintosh’s diaper draw near.

“A-all done,” the stallion blushed, plopping the stapled packet of papers on the mare’s desk before quickly twisting around to retrieve the diaper off his desk.

“Hold on, eager beaver,” Cheerilee quickly interjected before Macintosh could take a single step away, ”I gotta see how well you did!”

Big Macintosh’s cheeks flared up and slowly turned back around to face his stand-in teacher. Cheerliee meanwhile took her time retrieving a red pen from her desk and scooting her seat up close to the desk in preparation. Macintosh uncomfortably rocked from hoof to hoof. He had no choice but to stand beside the desk as Cheerliee gave his test a thorough review.

Silence fell over the classroom as Cheerliee switched to grading mode. It was a silence almost like the one that hung over the room during the test, but this one had a hint of embarrassing subtext added to it. She uncapped her red pen, retrieved the answer key from a drawer, and positioned Macintosh’s test dead center of her desk.

Standing here, Macintosh was completely exposed with his diaper out in the open for anypony to see. At least during the test he had the desk to hide behind. During the test he could have probably slipped in close to the desk and completely hide his diaper away from any prying eyes. It wouldn't have looked very natural, but he’d be hidden sort of. But now he stood there, hardly daring to move an inch out of fear his diaper would draw more attention to himself. He silently begged Cheerliee to finish her work as fast as possible.

Cheerliee took her sweet time grading the test. It was fun to keep the big diapered stallion in suspense, but she also had her professionalism to uphold. Even if the test didn’t hold any academic weight, she couldn’t even think to rush through it. Beside the open test packet sat the well organized answer key. Of course knowing whether answers were right or wrong was easy to determine without referring to any answer key considering their low skill levels, but for some of the harder ones, she made sure to glance back to the reference material two or three times ‘just to make sure’.

Finally Cheerliee got to the last page, making Big Macintosh tense up. She glanced over his answers while occasionally looking at her answer key to double check his work. Anything to stall and keep the big stallion in wait. During the whole thing she kept the same expression on her face: focused but thoughtful.

Her expression then suddenly changed to an inquisitive smirk and a raised eyebrow. She looked up at Macintosh and her smile grew with a knowing grin. Macintosh felt red flood his face. She was reading his answer for the big boy question, he just knew it. She seemed to like it quite a bit. She didn’t say anything though and simply wrote her final notes and made her final mark on the front page.

“Well I must say Macintosh, I am very proud of you,” Cheerliee smiled, “you passed the test with flying colors!” To further drive her point home, she decorated the test paper with a smiling star sticker. “I can see you’ve been studying! Well done!”

“Th-thank you...Miss Cheerliee...” Macintosh responded with a bashful blush.

“Thank you for answering your questions truthfully,” Cheerliee winked with a smile.

She paused for a moment to keep Macintosh waiting. She enjoyed the sight of the blushing stallion standing in front of her desk like a little child. She could have spent all day staring at that saggy diaper butt, but instead she sighed peacefully and set out to cleaning off her desk. Papers and pencils and little tabletop knick knacks were taken off the desk and redeposited into their designated drawers.

“Alright, hop on up,” Cheerliee said as she gave the wooden surface a tap.

Macintosh was surprised, “wh-what? Why?”

“This desk isn’t just for grading papers,” Cheerliee answered, “it’s also good for changing diapers. And YOURS will be the biggest of them all!”

Author's Note

Here's the first chapter of my first story. It's diaper fetish related, but that's the kind of stuff I wanted to write. I'll likely be doing more diaper stuff in the future and might dip deeper into other related fetishes with other stories. For now I decided to just stick with a simple diaper story involving Cheerliee and Big Macintosh. It will probably not get sexual (although if you were to imagine they had those urges bubbling in the background it might actually improve the story), but I have a couple more chapters planned out for this one.

Thanks for giving it a read through.

Chapter Two

The big stallion shuffled from hoof to hoof as Cheerliee cleared off the last of the desk debris. His newly graded test was the last thing to go, temporarily placed on her chair. The desk was now completely cleaned off with only a few flecks of dust to quickly brush off as she waited for him to climb up. She eventually looked up to the stallion with an expectant expression.

Macintosh recognized that expression right away. He wouldn’t be able to talk his way out of this. Cheerliee was determined. His cheeks flared up once again as he lowered his head and slowly waddled closer to the sturdy desk. Cheerliee retrieved the fresh diaper from Macintosh’s desk, wagging her diapered rump in the air as she moved. Macintosh caught a quick glance of her pronounced diaper bottom. Still bone dry.

A loud rustling and sloshing could be heard as Macintosh finally swallowed his modesty and pulled his body up onto the wooden desk. The well built furnishing hardly buckled or creaked under his weight. A very wet smacking sound could be heard when his diaper made contact with the hard surface, squishing the soggy thing deep into Macintosh’s backside. It was tough for the stallion to think of any other time he felt so small than how he felt now.

From a bottom desk drawer Cheerliee retrieved the necessary supplies for the impending diaper change. Like the grading, she took her time with the task, rationalizing that she didn’t want to forget anything before she began. “I had a feeling you’d need a change first,” she tsked as she placed all the needed changing supplies on the desk, one by one.

It was funny now that Cheerilee thought about it. She had gathered plenty of experience in the past changing foal diapers, but now she was changing a fully grown stallion. She could fondly remember all those times as a teenager where she earned a living babysitting the neighbor kids on a regular basis. Those kids, especially the younger ones, always needed her full attention and care. Couldn’t let them get into trouble.

But now she was changing Big Macintosh’s diapers, a diaper that was noticeably bigger than the children from her past. It looked even fuller than them too! With the urine having enough time to fully absorb into the diaper, the absorbent garment was noticeably swollen, bulging out in all directions with its fullness. Not an inch of it was left dry after such a fill up. There was definitely no doubt about it, he needed a diaper change.

“Whoof! That diaper is SOAKED!” Cheerliee mused, poking and prodding at the diaper that bulged before her. She had a little giggle at the heavy mass, a solid mound of over saturated gels. “Well don’t worry,” she started again, reaching for the diaper’s tapes, “once we get you into a nice dry one, we can start activity time and you can have some snacks!”

Despite his burly appearance, Big Macintosh couldn’t help but bashfully look away from the intimate ordeal. He could hardly look down once he heard the sound of the diaper tapes being pulled away. A nervous blush covered his face when he felt a cool breeze brush over his crotch as the diaper was opened and pulled out from under him.

Cheerliee huffed with exaggerated strain as she heaved the hefty diaper about. She knew all to well that it couldn’t have gotten this soaked by accident. And by the feel of this first one, the stallion was more than willing to soak them for her.

The diaper was tossed into the nearby waste bin, immediately overfilling the small plastic container with its swollen mass. Built for discarded papers and broken pencils, the bin now hardly had any room left in it for anything else. Now whenever Macintosh might have glanced down in that corner of the room, the urine soaked reminder of his large fill up would be clearly seen.

With the diaper gone, wipes were brought down on the area to mop up the lingering stink of urine. Cheerliee handled the task delicately, humming a tuneless tune as she did so. Wipe after wipe, Macintosh was cleaned up before the dirty wipes were tossed into the waste bin, barely balancing on top of the large diaper inside.

For a moment between diapers, Macintosh’s lower half had time to cool in the open air, bringing with it a spine tingling chill. He stole another glance at Cheerliee’s diaper. Why was she so dry? Was she teasing him? Did she just have a stronger bladder than him? It was like that dry diaper was toying with him, reminding him that he was a bigger baby than her. Whatever the reason for it though, it made Macintosh huff in displeasure.

“What’s with the grumbles, fussy britches?” Cheerliee spoke up as she opened up the new diaper.

“Its n-nuthin,” Macintosh quickly stammered out, looking away once again as he raised his rump up to allow the new diaper to be slipped underneath. “Ah just...It’s just that your...diaper’s still dry...”

“My diaper’s still dry?” Cheerliee parroted as she gave the new diaper a few minute adjustments before lowering Macintosh’s rump onto its pillowy soft fluff. “I didn’t know it was a contest.”

Macintosh just crossed his forehooves in a bit of a pout, “Ah’ve already soaked mine, but yers is completely dry...”

“Guess I’ve just done a good job watching my fluids,” Cheerliee shrugged as she pulled Macintosh’s diaper up and taped it up snuggly around his waist. She gave his fuzzy belly a couple pats to signal the end of the diaper change. Belly pats usually solicited a giggle or even a shy smile from the stallion, but his fussy pout hardly budged from its spot on his face. She concluded that a compromise would be in order. “Would it make the baby more comfortable if he wasn’t the only one waddling around in wet pants?”

Macintosh just pouted at the question. Answering it would just make him look silly, especially with Cheerilee referring to him as “baby”. Obviously, it would make him feel better if she did wet it, but he wasn’t going to admit that anytime soon. Denying it wouldn’t be much better, considering that he wouldn’t be able to say so without sounding flustered.

“Well?” Cheerliee asked again, lowering herself to give the stallion a playful tickle on the chin, “would it make little Macky happy if his Cheercheer wet her diapee?”

The tickle on the chin made Macintosh squirm a tiny bit. Even his most pouty of pouts couldn’t resist the lighthearted teasing. A tiny, shy smile grew on his face as he nodded with a blush. It felt silly to think it, but he would feel better if she wet her diaper as well.

“Hmmm, maybe later than!” Cheerliee answered, giving Macintosh’s nose a playful tap, “maybe if Macky’s extra good, he’ll have a soaked diapee to change too!” Macintosh frowned, but reluctantly accepted the offer. It seemed like it was the best he could get. “But now, its activity time for the diaper butt!” Cheerliee chirped nudging the stallion off her desk.

With a chorus of crinkles, the two waddled off to the activity area of the classroom. A low, round table big enough for six kids dominated the area with shelves of colorful plastic tubs lining the wall behind it. The tubs were marked with big sticker labels that spelled out things like “Flashcards”, “Arts and Crafts”, and “Theater Supplies” on them in big, thick writing.

Cheerliee went straight for the blue tub marked “Arts and Crafts”, carrying it over to the round table. She dumped the plastic tub out, spreading the art supplies across the wooden surface. Preschool safety scissors, glue sticks, pads of construction paper, popsicle sticks, loose crayons, a treasure trove of supplies for any artistic student to let their imagination run wild.

“Now you go ahead and make something fun while I go get us some snacks!” Cheerliee sang as she guided Macintosh over to one of the child sized chairs that surrounded the table. When he was comfortably seated, as comfortably seated as one could be in a chair half their size, she trotted off to the kitchenette to get things ready.

That left Macintosh alone with his thoughts and the piles of school art supplies that laid out in front of him. He sat there silently for a few minutes as he took it all in. Scrap cuts of paper lied skewed across the table as pipe cleaners and crayons scattered in every direction. Creatively, he was drawing a blank. All these colorful pieces of stuff and he hardly knew what to do with it.

For Cheerliee’s sake, he decided to at least make an attempt. Some crayons were gathered and scribbled across a sheet of red construction paper he found. A glue stick was used to stick random pieces of scrap paper onto the scribbling, changing the rectangular-ish shape of the paper into something else. When that was all done, he scribbled some more on the pieces of paper, adding silly little clouds and flowers and trees to the design. Stickers were stuck onto random parts of the art piece, adding to the mess of doodles and glued on pieces of paper. He wasn’t really thinking about the ending result at this point, he just focused on looking busy.

“Wow! What a great job you’re doing with that, Macky!” Cheerliee appeared out of nowhere behind Big Macintosh, making him jump a bit in his seat.

“U-uhm, thanks,” the diapered stallion answered with a blush. It was only now that he took a mental step back and examined what he had created. Sitting before him, among the cuts of craft fabric and glitter sticks was a mosaic of construction paper filled with a number of little drawings. The chaotic nature of it all made the art project appear to be made from a five year old.

“Well you can take a little break from your little art show and have a much deserved snack to recharge!” Cheerliee chirped as she placed the treats in the center of the table.

It was a variety of schoolyard treats all neatly arranged on top of a wooden tray. Apple slices and celery sticks dominated the selection, but Cheerliee also included a small stack of cookies for each of them. Little cups of peanut butter for dipping and orange slices gave the two quite the selection to choose from. Two tall glasses of fruit punch were also provided to wash down the tasty treats.

“Dig in,” Cheerliee chirped, grabbing an apple slice off of the tray.

Macintosh was happy to oblige, eyeing those delicious looking cookies above all things. He grabbed a couple of the chocolate chipped treats and chowed down. It almost felt like he was getting away with something, going straight for the sweets before finishing the healthy stuff. He felt a little tingling in his chest from the silly thing.

All art projects were put on hold for snack time as the two diapered ponies merrily muched away at the delicious selection. Both took healthy gulps of juice between bites, enjoying the sugary red drink immensely.

For a moment, Big Mack found himself lost in it all. The schoolhouse treats tapped into a long forgotten part of his childhood where he would eat these sort of things all the time. He found himself eating a healthy amount of apple slices and peanut butter, a childhood favorite of his, all the while swaying a bit in his seat in a sort of euphoric bliss. For a moment there, he felt like he was back in school. A happy rhythm of crinkles rustled from his seat in the process.

Suddenly Macintosh’s stomach began gurgle as he lurched forward in pain. He was snapped out of his blissful daze as the pain began to burn. The sensation was so sudden he almost spilled his drink in the process. A distraught look fell on the stallion’s face as a twisting pressure grew deep in his belly.

Loud stomach churns grabbed Cheerliee’s attention as she looked up across the table. “What’s the matter, Macky?” she asked with perked up ears as she took a bite out of a celery stick, “got a tummy ache?”

Author's Note

Second chapter delves deeper into this unique make-believe student/teacher thing brewing between Big Macintosh and Cheerliee. Still no sexual stuff planned for the future, but they'll certainly be changing enough diapers for the day.

Thank you for reading.

Chapter Three

The pressure in Macintosh’s gut quickly intensified, causing him to groan and grab at his stomach. He did his best to respond, but could only muster a pained glance over across the table. He noticed Cheerliee hadn’t touched her cookies yet.

Finally, in a moment of weakness, the pain in Macintosh’s stomach was too great. He hopped up off his seat and leaned forward as his eyes slammed shut. Already he could feel the burning humiliation on his face begin to build as he prepared himself to do the unthinkable. He began to push at his bowels, desperately wanting to rid his body of this surging pain.

His bowels, much like his aching bladder not too long ago, was more than willing to listen to his brain’s commands if that meant relief. His diaper abruptly inflated in the back, puffing out as a semi-solid material began oozing into it. The surging muck plopped loudly into the waiting diaper, staining the once pristinely white material a murky brown.

He was stuck that way for what felt like hours, eyes slammed shut, forehooves balanced on the table, and his diapered rump sticking outward behind him as it inflated and sagged more and more. Rude sounds of passing gas mixed with the stench that was emanating from the diaper as he continued to relentlessly soil himself. It felt like every time he managed a good push, there was always so much more waiting to be squeezed out. Eventually though, he found himself reaching the end. He could feel his bowels emptying the last of the sizable load, leaving him with the satisfaction and relief of emptiness. That sweet relief was instantly overpowered by humiliating embarrassment as the red color in his ears and cheeks returned with a vengeance.

Finally able to open his eyes, Macintosh looked across the table with shock in his eyes. He was frozen with bashful shame. Cheerliee had been watching the entire thing, pausing midbite to enjoy the show.

The silence that loomed heavily on the scene was broken by the sound of Cheerliee tsking at the sight. She shook her head in playful disappointment as she spoke, “looks like I’m going to have to write home about your little accident.”

“Y-you-!...The cookies!” Big Macintosh could hardly form complete sentences. The post-soil exhaustion coupled with the aching frustration of soiling himself without warning tuckered the stallion out, making him appear like a fussing toddler. “You made me-!”

“Did you like the cookies? I made them special for our little playdate,” Cheerliee smirked, “you can even have mine if you want.”

“I-I couldn’t...help it,” Macintosh scowled, weakly stomping at the ground with a huff.

“Oh there’s no need to pout. It’s just a stinky diaper,” Cheerliee rolled her eyes, “everypony has accidents. Why I could tell you a dozen times I’ve had a student...” Only her words trailed off to silence.

She could have very well regaled Macintosh of stories about the number of times students wet themselves a tiny bit during tests or couldn’t quite make it to the bathroom when they needed to pee. But as she quickly realized, none of these stories involved a student openly soiling themselves in a big baby diaper. Instead, she changed strategy.

“What if I wet my diaper a little? Would that cheer little Macky up?” she asked with a smirk.

Macintosh just nodded, not even bothering to look up from his scowling staring contest with the ground.

With a sip of her drink, Cheerliee stood up and stepped off to the side. From here, Mac’s view of her diapered behind was unobscured, the perfect view for what was to come. She positioned her four hooves out far apart from each other, closing her eyes to steady her breath. She wiggled her butt a tiny bit as her body began to tense up.

As she let out a long, drawn out breath of air, a stream of urine began to spray into the diaper. It started as a thin dribble, but quickly gained its full strength once the message to release fully took hold of her body. The hissing could be clearly heard as it loudly gurgled and warmed the insides of the diaper. Unlike Macintosh’s careful diaper wetting, Cheerliee was more than willing to pee into her diaper at full force.

She didn’t just wet it, she practically soaked right through the thing. Her once pristinely white diaper was now completely tinted yellow. From front to back, the absorbent padding had swollen immensely right before their eyes.

Macintosh stared at the soaked thing with wide open eyes. His mouth hung open in disbelief as he could hardly fathom the amount of liquid that poured into Cheerliee’s diaper. Looks like she had a stronger bladder than him after all.

Cheerliee finished the soak with a sigh, smiling at the warming glow that now encompassed her entire lower half. And not a single drop on the floor! That also was worth celebrating. She noticed Macintosh staring and when she was done fully recovering she let out a little bashful giggle. “Oops,” she couldn’t help but smile, “I think I had a little accident.”

“Little?” Macintosh answered in disbelief, “yer absolutely SOAKED!”

“I guess so,” Cheerliee answered with a wag of her heavy diaper. The sodden bulk sagged and swayed with and exaggerated heft, nearly pulling her off her feet by its weight alone. “And I was doing such a good job at holding it in,” she sweetened the comment with a fake pouty lip.

“Well ah think you need a change more than ah do,” Macintosh concluded.

Cheerliee’s ears perked up at this. It was a suggestion she wasn’t quite expecting. “But your diaper...”

“It’s just a stinky diaper,” Macintosh quoted as he retrieved a fresh diaper from Cheerliee’s desk, “‘sides, ma diaper can hold. Yours might leak all over the place if we leave it alone.”

“Oh very well...Mister Macintosh,” she smirked, plopping down to the floor where she stood, “you win!” Her legs splayed out as she made herself comfortable, completely fine with having her diaper changed wherever she ended up.

Macintosh smirked at the nickname as he gathered the remaining supplies needed for their schoolhouse diaper change. He had planned on using Cheerliee’s desk as a changing table, help drive the whole ‘Mister Macintosh’ angle she was teasing him with, but by the sound of that loud slosh he heard as her diaper plopped noisily on the ground, she wasn’t gonna want to move. Instead he carried everything he needed back to the play area, where Cheerliee idled by on the floor.

Despite not having the prestigious background of being a babysitter like Cheerliee, Big Macintosh had plenty of diaper changing experience from changing his little sisters. It had been years since he tapped into such experience, but he knew the basics well enough to get by.

Cheerliee took delight in being as unhelpful in the task as possible. While Macintosh stayed still during his earlier diaper change because of some deeply ingrained sense of good manners, Cheerliee saw it as a game. She felt silly laying there on the school room floor, but the good kind of silly. The freshly soaked diaper made her squirm as the warmth sloshed around with every move she made. She even kicked her legs about in the air, coming dangerously close several times to hitting Macintosh.

Macintosh tried to keep the mare settled by holding one of her back legs steady with a hoof. This forced him to do the entire diaper change with only one hoof, but at least it sort of settled his charge. Despite this handicap, Cheerliee gladly continued to fidgeted and wiggle on her back.

It all felt rather silly to Big Mack to be changing somepony else’s diaper while wearing a messy one himself. Every time he moved, the sticky muck inside the diaper would press and smear against his backside, giving him a subtle embarrassing reminder of what he did. The infantile act of soiling himself still burned in his cheeks, but at least he was able to distract himself somewhat with the diaper change. Paying too much attention to his own diaper would lead to him catching a whiff of the stink that emanated from the mess, which he didn’t enjoy one bit.

“Don’t forget the baby powder, Mister Macintosh,” Cheerliee called out, shivering a bit as the warmth of her soaked and heavy diaper was pulled away.

“I won’t,” Macintosh answered, doing his best at rolling up the soggy diaper with one hoof. He noticed how unphased Cheerliee was about the obvious stink that was coming off of his diaper.

“And make sure you wrap the old diaper up tightly when you’re done with it,” Cheerliee gladly added, wiggling her legs in the air even more, “ that way it doesn’t make a mess.”

“Am I going to have to spank you?” Macintosh asked plainly.

Cheerliee’s squirming stopped right away with her staring up with genuine surprise. She couldn’t quite figure out whether Macintosh was being serious or not.

“That’s what I thought,” Macintosh nodded as he opened up the new diaper, “now lift up yer rump so we can get this on ya.”

The mare was much easier to deal with after that little scare. She dared not squirm anymore out of a creeping fear that Macintosh would actually uphold his threat. Macintosh easily manipulated her legs about once he had full access to both of his hooves now. He breezed through the diaper change smoothly after that.

Plenty of baby powder was used, giving Cheerliee’s lower half a powerful, infantile stench that completely replaced that intoxicating urine smell. The fluffy scent of the lavender scented powder even helped ward off the heavy stink coming from Macintosh’s diaper. The new diaper was taped on shortly after, with Macintosh making only a few minor adjustments to the tapes before the fit was snug.

The soaked diaper was dropped off into the trash bin at the front of the classroom, delicately balanced on top of the soggy diaper that already filled it to the brim. Macintosh made a mental note to properly dispose of those diapers later when he had the chance. For now though, he busied himself with cleaning up and ensuring Cheerliee was satisfied with his diaper changing skills. It seemed a little silly tidying up the place while wearing a messy diaper, but he hoped that he wouldn’t have to deal with that for long.

Now that he had everything cleaned up in front, Macintosh returned to the back of the room where he found Cheerliee already back at the crafts table. A pile of crayons laid before her with a sheet of white paper already filled with cute scribbly drawings. She made sure to use every color she could get her hooves on, creating quite the whirlwind of color on paper. Her baby powder scented diaper bottom occasionally floated inches over her seat as she leaned forward, deeply involved in her drawing, even humming a little happy song as she wiggled her crinkle butt.

Macintosh waddled over to the busy mare. “Aren’t we forgetting somethin’?” He was sure to call attention to his messy diaper with a hoof.

Cheerliee looked up at the stallion, doing her best to hide a mischievous giggle. She leaned back to stare at his messy diaper for a moment or two, only to sit up straight and answer with an innocent, “nope!” She quickly returned to her drawing, taking hold of a blue crayon and scribbling large strokes across the paper.

“No? Then ah guess ya wouldn’t mind if ah sat next to you,” Macintosh answered, dragging a plastic chair over to Cheerliee’s side of the table.

“Nope!” Cheerliee chirped.

“Ya sure?” Macintosh asked, wiggling his heavy diaper bottom, ”ahm awfully stinky.”

“I babysat tons of kids when I was young,” Cheerliee answered with a shrug, continuing with her drawing, “poopy diapers don’t bug me at all.” She looked up at the stallion one final time, this time with an almost challenging smirk on her face. A sort of ‘and what are YOU gonna do about it?’ sort of expression. ”I think it just makes you look even more like a baby!”

“Hmph!” was all Macintosh responded with as he stubbornly plopped down in his seat. Immediately he was met with the jarring sensation of the filthy muck oozing around his butt accompanied by an audible squelch. He froze for a moment or two, doing his best not to completely lose it on the spot. He quickly recovered and grabbed for a handful of art supplies. This was a contest now. Messy diaper or not, the two were now locked in a friendly competition to see who broke first.

Big Macintosh turned to his arts and crafts to give off the impression that the stink didn’t bother him. He tried his best to appear as laid back as possible, gluing random pieces of paper together and then scribbling some random shapes onto the finished results. It was tough to appear like he knew what he was doing when, in reality, he honestly had no idea what he was doing.

Cheerliee responded in kind by picking up another bunch of crayons to add to her collection of scribbles. The piece of paper was more crayon than paper at this point. She stubbornly ignored the foul stench that Macintosh brought with him. Baby boys were supposed to be stinky, she rationalized. She wasn’t gonna let some little boy win this little test.

Fresh air was a little hard to come by, especially with a messy diaper sitting not ten inches away. In a matter of minutes, even Macintosh struggled to find a smell around him that didn’t smell faintly of his own stinky diaper. It was beginning to smell like a real nursery in here. Or an old outhouse. Or like a bunch of old apples left out in the sun, next to an old outhouse with a bunch of diaper pails dumped into it.

Macintosh had to stop himself before he made himself sicker.

Finally Cheerliee exhaled a burst of air, her shoulders slumping in defeat. “Alright, you win!” she grumbled, “let’s get the big, stinky baby changed.”

Chapter Four

“Hurray,” Macintosh chuckled, putting down his glue stick and standing up from the table. His well used diaper, now stained a dark brown in the back, peeled off his backside as he moved, sagging low to the ground. “Ahm sure ya know where to find the supplies,” he stuck out his tongue before waddling off to the front of the room.

Cheerliee stuck her own tongue at the departing stallion. She had to giggle at the brown tinted backside of Macintosh’s diaper though. She may have been the one doing the diaper change, but the sight of the big stallion waddling up to the front of the classroom with a huge load in his pants made it worth it. Although...she did feel a twinge of envy looking at the hefty diaper.

Earlier that day Macintosh was incredibly embarrassed by it all but now it seemed like he was holding all the cards. If he didn’t know any better, he’d say he was actually beginning to enjoy himself. Maybe a bit at Cheerliee’s expense, however. He didn’t even mind the squishy sensation against his backside so much when he rolled onto the desk. After sitting at the crafts table in it for so long, he was starting to get use to it which was weird in its own way.

When he finally got himself comfortable, he turned to see Cheerliee heading up with the supplies in hand. A hint of displeasure was seen on her face, clearly not looking forward to changing such a messy diaper. He could only imagine how daunting of a task it was to change a full grown stallion.

After the teasing and bratty behavior Macintosh put up with all afternoon, he had the idea to tease back. “And don’t forget the baby powder, Miss Leakybottoms,” Macintosh grinned with a cocky smirk.

“Oh don’t worry,” Cheerliee answered, plugging her nose with an exaggerated scrunch. “I’ll be using plenty of that! Gonna need a bunch of wipes too!”

Satisfied with the answer, Macintosh rolled his head back and stared up at the ceiling, even going as far as to spreading his thighs apart to make Cheerliee’s job slightly easier. He didn’t squirm about like she did, even when the idea seemed oh so tantalizing. He figured a hefty, messy diaper that he had been stewing in for the past twenty minutes was bad enough.

Taking in careful breaths, Cheerliee opened Big Mack’s diaper. True to her word she used plenty of wipes, managing quite well with the small cuts of moist, scented cloth. It was obvious that she had done this before. Many times before.

“Peeeee-yew! What a stinky stinky diaper!” Cheerliee exclaimed, rolling the diaper up tight and keeping it at arm's length at all times. The diaper was plopped down beside Macintosh’s head, close enough for him to get a good whiff of his dirty deed. “An actual foal couldn’t have made a bigger stink!”

“Wouldn’t be a problem if somepony didn’t spike the cookies,” Macintosh retorted. That seemed to curb any other snarky comments the mare might have had.

A new diaper was promptly placed under Macintosh’s rump. He found solace in that soft, cushy feeling of a nice dry diaper. It felt so gentle against his crotch, immensely different from that cold, sticky thing he had been wearing this whole time. This must have been what babies felt when they got their diapers changed. For a moment, he felt relaxed, content in his fresh, powder filled diaper.

Cheerliee seemed to pick up on this calm state, because moments after the fresh diaper was taped on, she was quick to speak up. “Okay, diaper boy, you’re on trash duty,” she chirped, lifting a small garbage bag filled with their diapers. “Take all this to the dumpster outside.”

“U-uhm...Cheer, come on...” Macintosh blushed, shrinking half his size on the desk, “don’t make me do that.” Gone was the cocky confidence and suddenly he found himself back where he started this whole diaper thing, embarrassed and bashful.

“You’re responsible for most of this mess anyway,” Cheerliee shrugged, even going as far as to grabbing the messy diaper off the desk and tossing it into the bag.

“Somepony might see!” Big Mack’s voice squeaked, making the scene all the more embarrassing.

“Oh nopony’s gonna see ya,” Cheerliee dismissed, “the dumpster’s just outside. You hardly have to leave school grounds. Now come on,” she rolled him off the desk with a push of her head, “off you go.”

Cheerliee handed off the heavy garbage bag to the dazed stallion, giving him a few encouraging nudges for good measure. Macintosh was still trying to find the courage to even move. His hoof tightly gripped the loosely tied up bag as he gulped a nervous bunch of butterflies down. Cheerliee left him to it, happily abandoning the nervous colt to go back to her drawing.

Eventually Big Mack gathered enough nerve to budge from his spot at the front of the classroom. He had to take a couple deep breaths to get that far, but soon he found the strength to lift his feet off the ground. With the old diapers in hand he turned towards the exit, a single solitary door that was the only barrier standing between him and, as he could only assume, a thousand cameras and ponies waiting for him outside. His body language had become stiff and cautious as he mentally prepared himself to make a mad dash if he saw anypony.

Much to his relief, however, there were no cameras when he peeked his head outside. There was nopony passing by the schoolhouse or school children ready to laugh at the big diapered pony. He realized he was letting his fears and worries get the better of him. Still, he kept the garbage bag of diapers as well as his own diapered behind hidden from view until he was absolutely, super duper sure nopony was around.

His eyes then locked onto the school dumpster. It was a large metal container painted a deep green. The dumpster showed its age through the various paint chips and scrapes as years of being filled and emptied had taken its toll. Located on the far side of the building opposite of the playground, the metal bin proved to be quite the trek for him to waddle through.

Macintosh took in a deep breath and gripped the garbage bag tight. He closed his eyes for a moment to center himself. Then in one mad burst of energy he ran out the door. He ran as fast as his legs could carry him. Everything around him fell away as he focused solely on the dumpster that laid ahead. The diapers were chucked into the open dumpster the split second he was close enough and he was running back inside a split second later. A task that may have taken a few short minutes was done in half the time by the hasty stallion.

He returned to the safety of the schoolhouse out of breath and ready to collapse from the panicked dash. A wave of relief rushed over him as he returned to the safe indoors unscathed and unlaughed at. When he finally recovered from that brief panic attack, which in all fairness only took a couple seconds, he found Cheerliee had moved away from her arts and crafts and was now standing over in the kitchen area munching away at the tray of treats left over from their snack time. In particular, she was focusing on her share of the special cookies.

“Cheer? What are you doing?” Macintosh exclaimed, hardly allowing himself time to fully catch his breath.

Cheerliee’s head shot up with surprise with a mouthful of cookie. She paused for a moment or two before swallowing the sugary treat.

“Th-that was quick,” she said to Macintosh, hiding the half eaten cookie behind her back. She resembled a startled child caught with her hooves in the cookie jar.

Catching his breath some more, Macintosh looked at the mare. Even if he didn’t notice the cookie behind her back or her very guilty expression, the crumbs on her muzzle were a dead giveaway. “Are you being naughty?” the stallion finally asked.

“Noooooo,” Cheerliee answered, bashfully avoiding eye contact. She swayed in place all cutely, thinking that playing it cute would distract Big Mack enough to get away with the deed. “I just saw how much fun you had with your cookies...I kinda got a little jealous.”

“Jealous that you weren’t being as stinky as me?”

Now it was Cheerlie’s turn to blush. She answered after a small pause. “...Kiiiinda.”

There was another long pause. Macintosh’s surprised expression melted into a smirk as he spoke, “well you certainly won’t get very far if you just eat one cookie. Now will you?”

Cheerliee blushed deeply, “yeah, I guess you’re right...” And with that she picked up another cookie and munched it down. With Macintosh’s nod of approval, that cookie was followed by another and then two more after that. She would giggle between cookies as the taste of the delicious treats coupled with the thought of what was to come made her wiggle like a child.

“Alright then,” Macintosh exclaimed, nudging Cheerliee away from the snack tray. “Now that we’ve had our little snack time. We can go back to our lessons.”

Cheerliee, surprised at first, happily allowed Big Macintosh to take the lead. The two returned to the group of desks in the middle of the room.

“Here, you kin sit in my seat,” Macintosh smiled, presenting the desk with a theatrical wave of his hoof.

Cheerliee had a good laugh as she settled into the small wooden seat. She thoroughly enjoyed the new direction their game was taking. The roles had been reversed and now she could enjoy all the wonderful benefits of being the student for a change.

It was certainly a change of perspective to sit in one of her student’s chairs. The tiny desks made her teachers desk look enormous and made Macintosh look all the more commanding. Such a position made her feel little, young again, and all the while her diaper crinkled up a storm as she giddily wiggled in her seat.

Big Mack took up the role of teacher quite well. Even with the diaper, he carried himself with such confidence and wisdom, marks of a good teacher ready to teach. Picking up the white chalk and standing in front of the clean blackboard, he was in a rare position of power. He could teach his little student anything he pleased. Anything that popped in his head he could teach her. Because he knew for every cute little thing he pretended to lecture Cheerliee on, the longer the mare would have to sit there at the small student desk. And the longer she sat there, the more time her special cookies had time to bubble and stew inside her belly.

So the next twenty minutes or so went on that way. Macintosh seemed like a natural teacher and Cheerliee was a good little student for him. As Big Macintosh taught her about the water cycle, the diapered mare stayed at attention. As Big Macintosh taught her about the difference between numerators and denominators, the diapered mare kept quiet to not interrupt her teacher’s lecture.

Although, Cheerliee’s quiet behavior might have been less about good behavior and more about controlling the churning gut pains that steadily made themselves more known to her as time went on. As time went on, the special ingredients laced into the delicious cookies were beginning to take their toll. She would occasionally wince at the cramps in her belly as Macintosh seemed to endlessly drone on about whatever he pleased.

In the middle of he lecture about the difference between a neutron and a proton, Macintosh seemed to pick up on Cheerliee’s faltering attention. “Cheer, why don’t you come up to the board and write some lines,” he called to the mare, holding up a fresh stick of chalk.

Cheerliee felt the color drain from her face as dread tingled the fur on her back. She would have loved it more than anything to just sit there at her desk. At least that way she could stave off the intense pressure in her belly for just a little longer. But Macintosh was insistent, she had to stand up.

She made her way to the front of the classroom as she gripped her gut hard, struggling to keep things together. Her forehead grew cold as it took every ounce of control not to lose it right then and there. She took hold of the chalk and stood in front of the blackboard like a good student. “Wh-what do you want me to write...Mister Macintosh?”

“Oh let’s see,” Macintosh smiled, leaning back in his seat as he pondered. Every second he stalled brought Cheerliee that much closer to having her accident. “How about...’Little Cheerliee wears diapers because she’s a foal.’” Cheerliee’s cheeks flared up a bright red. As if to add to the embarrassment, Macintosh smirked and added a smug, “and you’ll write until you fill up the board.”

With a loud gurgle from her gut, Cheerliee had no choice, but to agree to her teacher’s terms. With chalk in hoof, she started from the top corner of the board and began writing out her lines. Word after word she slowly made progress through her silly, schoolhouse punishment. Line by line her gut continue to churn away, becoming more and more unstable as time went on.

Macintosh simply leaned back in his seat, watching with glee as the diapered mare completed line after line. He was impressed by Cheerliee’s speed as well with her chalk writing being quick and efficient. He also enjoyed that little butt wiggle she’d make every time a cramp hit her belly and her desperately trying to shake off the pain as she continued.

Suddenly Cheerliee dropped her chalk in surprise as a surging cramp sent a shock through her system. The pain locked her entire body up, freezing her in a rather compromising slouched position. Color drained from her face as a hard truth became known to her. There was no more holding it back. She needed to poop.

The reality of the situation materialized into a humiliating squat in front of the chalkboard. She closed her eyes as her focus now centered around relieving herself and hopefully putting an end to the burning embarrassment that loomed overhead. By the time she squatted and gave her gut one tiny push, a large mess was already dumping into her diaper, loading it up with its loose, brown muck.

There was hardly anything she could do to stem the tide once it started nor could she silence the rude sounds muffled by her diaper. The back of her diaper immediately darkened as the messy load inside seeped into the soft padding, crinkling loudly as it shifted the material downwards.

She groaned lowly as a burning blush filled her cheeks as the diaper continued to get heavier with each good push. She dared not look up the entire time, finding the chalkboard to be a much more manageable thing to stare at as she made a mess of things.

“Oh noooo,” Big Macintosh was heard behind Cheerliee as she recovered from the rather humiliating diaper fill up. “Did we have an accident?”

With a heavy sigh, Cheerliee turned around to face her teacher. She didn’t have to look at the diaper. The hefty weight that pulled at her lower half was all she needed. “Will you change me now? Please?”

“Now hold on there, missy, you still have some lines to finish,” Macintosh answered as he leaned back in his seat, “you can getcher diaper change once you’re done.”

Cheerliee gave him a pout, but surrendered to his authority and returned to her work. The messy diaper was a bother, but Macintosh was the teacher here and he was the one running the show right now. With the pain subsided, she reluctantly picked up her stick of chalk and returned to the chalkboard. Her cheeks never stopped burning as she was forced to stand there in front of the chalkboard with her messy diaper hanging heavily behind her. Every step she took solicited a series of crinkles as the lump in her diaper swayed between her thighs.

Finally, after what seemed like hours of standing there, Cheerliee reached the end of the chalkboard, finishing up the last of her lines. She let out a sigh of relief when it was finally over, dropping the chalk once she was finished.

“D-done,” she called out, slouching in front of the board. She turned to face her stand-in teacher, finding the stallion peacefully lounging in her chair.

Macintosh smirked at the bashful mare, taking his sweet time standing up from her desk chair to inspect her work. “Not bad, not bad,” he chortled, “neat lettering, straight lines, no extra space.”

He took an extra long while inspecting the chalkboard. It was really something else to see the words ’Little Cheerliee wears diapers because she’s a foal.’ written in white chalk over and over again. He had himself a little chuckle at how cute it made Cheerliee look. Even as she stood next to him silently hoping he’d hurry up, she looked cute in her messy diaper.

“Alright, ah think I let you stew in that stinky thing long enough,” Big Macintosh said as trotted over to the teacher’s desk, “come on up and hop onto the desk.”

Cheerliee let out another sigh of relief as she was more than happy to climb up on to the desk for a diaper change. She didn’t even mind the mountain of muck she had to lay on top of in order to do so.

Macintosh did what he could to help the diapered mare up, but most of his attention was drawn towards her desk which seemed ripe for the snooping. All those desks drawers and cubbies were tantalizing to the curious stallion. Instead of beginning the diaper change right away, he decided to stall just a little bit longer and take his time perusing the contents of Cheerliee’s desk.

Most of the stuff inside the desk drawers were pretty standard. Extra pencils, answer keys, printouts for this week’s spelling pop quiz. None of it really grabbed Macintosh’s attention. He did however get very interested when he stumbled across a neat stack of papers found in the lower right side drawer.

“Ou! What do we have here?” Big Mack smiled, pulling out a paper off the stack, “peer evaluations?”

Cheerliee looked up from her spot on the desk to see the stallion smuggly holding the sheet of paper with a mischievous grin. It looked like she wasn’t going to be changed right this minute afterall.

The peer evaluations were a tool Cheerliee used to encourage better teamwork in group projects. They were handed out to students so that they could evaluate each other with a number of questions. Choosing from a range of answers from ‘strongly agree’ to ‘strongly disagree’, these evaluations helped pick out the hardworking individuals and keep the students better behaved in groups.

For their diaper play, however, this was just another tool for Macintosh to tease her with.

“Let’s see, ’helped others with their work when needed’,” Macintosh read off the first item on the list, hovering a pencil over the answers. “Less say that was an ‘agree’. If ah remember correctly somepony had to wait a little bit for his diaper change.” He wiggled his diapered rump in Cheerliee’s face for added measure.

Cheerliee crossed her hooves and pouted. It appeared that Macintosh was deliberately taking as long as he could with this evaluation, forcing Cheerliee to lay there in her messy diaper for just a little longer.

“‘Remained focused on the assignment’,” Macintosh read out the next question, taking a good long while to think the question over, “yeah, ah guess that’s a ‘strongly agree’. Ya can be ah pretty focused student...even if you’re in a big baby diaper.”

Cheerliee had half a mind to argue the big baby comment, but the ever present scent of her muck filed diaper reminded her to hold her tongue. She didn’t want to dig a bigger hole than she was already in.

“‘Did work accurately and completely’? ‘Agree’. ‘Completed work on time’? Hmm, ‘disagree’,” Big Mack breezed through the next couple of questions. “‘Worked well with other group members’,” he paused, tapping his chin in thought, “well I guess you did do that, huh, Cheercheer. ‘Strongly agree’.”

“I should get to do one too,” Cheerliee finally grumbled.

Big Mack looked up from his paper and smirked at the diapered mare, “what’s that, Miss Pouty?”

“I should get to do a peer review for you too!” Cheerliee exclaimed, coming dangerously close to making it sound like a whine, “it’s not-!...It’s...not fair if just you do it...”

“Well alright, you can have one too,” Macintosh said, handing over a new evaluation and a freshly sharpened pencil, “here, you kin fill it out while ah get you changed out of tha’ stinky stinky diaper!”

Cheerliee happily snatched the paper out of the air and went right to work with the evaluation. She was sure to give Macintosh a seething review, free of mercy and leniency. She read every question carefully and carefully thought about Macintosh’s performance. Did he work well with others? Sort of. Did he remain focused? Not likely.

She was so involved in filling out the assessment that she barely took notice of the entire diaper change. As Macintosh undid her diaper and cleaned her up, the mare was hard at work filling out her assignment, aimed to finishing it before the diaper change was over.

Near the end of the change however, she couldn’t help but notice Macintosh pulling out a second diaper to add to the mix.

“Another one?” she fussed.

“Oh I just thought since we’ve been going through so many diapers,” Macintosh answered, tapping at the rolled up stinky mass that was Cheerliee’s old diaper, “little Cheercheer needed to be DOUBLE diapered!”

Cheerliee pouted at this, even scowled at Macintosh, but could only let out a sigh of resignation. He was the teacher. He was calling the shots.

“Now then,” Macintosh exclaimed once Cheerliee was properly padded up in her double thick diaper, “let’s take a look at how I did.” He snatched the evaluation out of Cheerliee’s grip, plopping back in her seat before reading over the paper. “‘Worked well with other group members’ ‘strongly disagree’?” Macintosh read out, “is it because I was mean and made Miss Stinkybritches sit in her diaper for so long?”

Cheerliee huffed, “that was part of it.”

Macintosh only glanced at the rest of the evaluation. Most of it was marked as ‘strongly disagree’ or ‘disgree’, but this was likely Cheerilee getting back at him for making her sit in her diaper for so long.

“Well you can stop pouting now,” he finally said, slipping the two peer evaluations back into the desk, “mean ol’ Mister Macintosh changed you. So you don’t stink anymore.”

“...I guess it feels nice to be in a fresh diaper,” Cheerliee reluctantly answered with a roll of her eyes. “Thanks.”

Chapter Five

The first thing Cheerliee noticed as she rolled off the desk and back onto her feet was how much bulk the second diaper added to her lower half. The second thing she noticed was how goofy her waddle was now that she had twice as much padding to deal with. It was funny, she had spent the whole afternoon playing and using diapers when the need struck her, but only now did she feel truly infantile wobbling from hoof to hoof as she attempted to cope with the mound of white that bulged off her rump. She was actually starting to enjoy the waddle.

“Ah think it’s ‘bout time fer recess,” ‘Mister’ Mcintosh then said behind her.

“Recess?!”

“Mhmm, can’t keep cooped up in here all day, can we?”

Cheerliee looked outside through the row of windows on the classroom’s back wall. A vacant playground could be seen out there, cloaked in the orange light of the setting evening sun.

“No, no I’m fine in here,” she said with a shrinking voice.

“Awww come on Cheercheer, you know ya gotta get out and stretch yer legs a bit!” Mcintosh insisted.

“B-but somepony might...see...” Cheerlee found herself repeating the same excuse Mcintosh tried to use not too long ago. And judging by the smirk on the stallion’s face, she wasn’t the only one who was aware of the irony.

“Nopony’s gonna see ya,” parroted Big Mack, “we’re far ‘nuff from town n’ it's pretty late in th’ day.” He took a glance outside where precious sunlight was slowly fading. “Plus,” he started again with a knowing look, “don’t seem real fair that you’d send a student out on his lonesome without doing it yerself.”

“Alright, alright,” Cheerliee conceded. “I’ll go.”

The second she agreed, a plastic sippy cup was thrusted into her hooves. By the looks of things, Big Mcintosh had already gone ahead and filled the thing up with juice, screwing the lid on nice and tight to avoid any leaks, of course. “And don’t forget to take yer sippy cup!”

“Where did you...”

“Gotta stay well hydrated when playin’ outside,” Mcintosh interjected, patting the purple pony on the head.

Dug out from the bottom of a utensils drawer, the sippy cup was a rare item Cheerliee had to hardly ever pull out during class. When a student was particularly accident prone and liable for spilling their drinks, the sippy cup was there as a helpful reminder. No student actually used the sippy cup. It was just a deterrent. Just the idea of being stuck with it for the day was embarrassing enough to keep any student from getting too clumsy or reckless with their drinks. So it didn’t see much use in her classroom, until now. She just never imagined she’d be the one to use it.

“Ah want ta make sure yer keepin’ yer fluids up, so ah want to see this cup empty when ya come back in, alright?” Mcintosh said, “and no cheatin’. Good students don’t cheat.”

“Yeah sure...” Cheerliee grumbled. She was still not too keen on playing outside.

Still, it was kind of exciting the more she thought about it. She always fantasized about being caught outside in public. wearing a big diaper. She had to admit it was fun to think about even if the reality of being seen in such a vulnerable state would leave her reputation in shambles. But at the same time, even THAT was exciting to think about. To be found waddling around in a big diaper, sucking on her hoof, and babbling like a foal. She could only imagine what her students would think.

And she did already kind of make Mcintosh go outside earlier. It should have been expected that he’d make her do it as well. It was only out to the playground anyway. Plus, it really was late so the chances of anypony coming this far out of town was highly unlikely.

So, whether it was because of ‘mean ol’ Mister Mcintosh’ or her own thrill seeking, Cheerliee found herself waddling outside onto the playground with sippy cup in hoof.

Taking her first steps outside, she quickly found that Mcintosh was right: no one was around to see her padded predicament. There were no students waiting outside to laugh at the diapered mare or a horde of hungry paparazzi ready to snap pictures of her humiliation. All that was there was playground equipment and grass.

The school yard was a small area of open field and playground equipment that sat adjacent to the schoolhouse. It consisted of a slide, swing set, jungle gym, as well as a sandbox. All of which was surrounded by some spacious grass that was perfect for running around on. Everything looked like so much fun and it was often difficult for any student to make the hard decision of what to play on first.

Cheelriee was understandably not looking for whatever looked the most fun. Although she had to admit the slide was always her favorite. Considering her current situation, her mind focused not on fun, but privacy. She instead looked around the play area for the best place to hide. The best place to lay low until she was allowed back in. Because even though it was late and even though she seemed to be alone, she still felt she needed to hide. The only question was: where?

The slide? No, too high up and exposed. Even in the dim evening light, her white diapered behind would be a beacon on top of the metal structure. Plus she couldn’t imagine being able to climb the ladder with such a bulky diaper so easily.

The swings? Still no. No place to hide when you’re on a swing. Especially when you’re high up. And even still, she wasn't even sure if her butt would fit in the swing's seat.

Now the sandbox. There was a good spot. The wooden box filled with sand was low to the ground and she could quickly dig a hole to hide in if she started working at it now. Plus it was a clear creative outlet for the diapered mare. Yeah, the sandbox was a good idea. So with sippy cup in hand, she plopped her padded butt among the light tan sand that filled the area.

The first of her building projects was a crude wall around her to use as cover. At their stout height they hardly gave her complete cover, but it made her feel a little better knowing there was something around her. With their hasty construction, her first set of walls were simply a means to an end. They were formless blobs of sand that were simply there to obscure the pillowy silhouette of her padded bottom.

Soon, however, she grew tired of that uninspired design and started adding crude bastions and towers to the perimeter. When the wall was well established, she started sculpting out sandcastles as well. And the trenches she dug sand out of, well those only needed a little touching up to be rivers and lakes albeit dry and water-less. Later on she started utilizing little stones in her builds, using them to decorate her towers and paths.

All the while, she would take sips of juice out of her sippy cup. Partly because she was thirsty, but also partly because that’s what ‘Mister’ Mcintosh told her to do. And all that juice eventually started to work through her system which is when the diaper came in handy.

She had to admit, the diaper was convenient to have. The extra padding shielded her sensitive bottom from the abrasive and coarse sand. The comfort and security that came with wearing the bulk spoke for itself as well. Plus, she didn’t have to get up to pee as she worked on her sandy magnus opus. All in all, despite her initial worries, she was having a pretty fun time.

“Hey Cheercheer?!” Big Mac’s voice rang over at some point later in the evening, “why don’t you come on in now. It’s getting late!”

Looking up from her sandy city planning, Cheerliee found the evening sky was almost gone overhead. The light purples of night were closing in over the scene, bringing with them a cool chill. The chill in the air reminded her of the chill that was growing around in her diaper as the outside air slowly sapped the squishy garment of its heated warmth.

“Oh...okay!” she cheerfully replied as she finished off the last of her juice and climbed back to her feet.

She dusted the sand off her backside and waddled off. The diaper had swollen immensely under her, giving her a bulky, sloshy thing to waddle with as she made her way back into the safety of the schoolhouse. Although the outside layer was only just barely starting to show signs of being used, the cool, clammy insides was unmistakably wet.

“Hope ya had lots of fun playin’ outside!” Mcintosh said, taking the sippy cup and giving it a little shake, “and ya drank ALL yer juice while ya played too! How's your diaper?” he asked this while already reaching for the mare's padded posterior. An apparent weight could be felt. The kind of heft that a diaper could only get from being quite wet. "Feels like little Cheercheer couldn't hold it like a big pony."

But he wasn't the only one checking diapers. While he was distracted by Cheerliee's padding, an invasive hoof suddenly appeared pressing the sides of his diaper. Mcintosh didn't have the luxury of a second layer to cover up his yellowing shame.

“Looks like I wasn’t the only one who couldn’t hold it!” Cheerliee called out, prodding the diaper some more.

“A-ah was too busy keepin' an eye on you!” the stallion stammered out. And that was partly true.

“But yeah, I have to admit. It was fun playing around in the sand for a bit,” Cheerliee sighed, “didn’t realize how late it got.”

“Might have ta wrap things up fer the night soon...”

“I think we have enough time for oooone last activity,” Cheerilee said before tapping her chin in thought, “it’s gotta be special though,”

“Well, do ya have anythin' special in that cabinet of yers?” Mcintosh asked, motioning towards a far corner of the room.

The cabinet in question was the place where Cheerliee kept shelves of organized school supplies. Primarily made up of reams of paper, quill ink, and three different sizes of paper clips, Cheerliee’s stash of supplies was simply just that: a stash of supplies. Taking up the left half of the middle shelf, however, were a number of wipe mouthed, medium sized plastic tubs with lids firmly attached on their tops. Each one contained a bright colored, opaque liquid in a rainbow of colors.

“Hoof paint?” Macintosh commented, recognizing the plastic containers once he spotted them, “gosh, ah haven’t hoof painted since ah was a colt...” he chuckled at the thought, a glint of nostalgia shining in his eyes.

Cheerilee smiled and grabbed the row of rainbow containers off the shelf, “hoof paint it is then!”

Once again the pair returned to the crafting table where the scraps of previous art projects were pushed aside for later. In their place were set the tubs of hoof paint, arranged by color of course. Beside them were stacked a colorful pile of thick construction paper, the perfect canvas for avid hoof painters. With the end of the evening drawing close, the two sat their squishy bottoms at the table and went right to work.

Dipping his hoof into the first pot of paint sent Big Mac back to a simpler time. The slimy texture of the paint against the frog of his hoof reminded him of the days spent in preschool, creating masterpieces with his classmates. Days that felt closer than they ever felt before. The paint was cool to the touch, and he couldn’t help but smirk as it slipped across his hoof and onto the paper. It was as if he had been transported back in time, to a place where the only thing that mattered was the joy of creating something new.

Beside him, Cheerliee tried her best to recapture her preschool muse and attempted to recreate all those pictures she drew as a filly. Flat fields of green across the bottom of the page, a big yellow sun the size of her hoof in the corner, and a tall tree in the center with as delicate of branches as she could muster with such a wide brush. She even tried drawing a pony or two which ended up being splotchy, shapeless forms made of red and purple paint.

Mcintosh, meanwhile, was meticulously layering different colors of paint onto His paper, his hooves moving quickly and expertly. Splotches of reds and yellows streaked across the pale blue sheet of construction paper only to be counter-streaked with greens and blues going the other way. His creations were chaotic, less focused on the subject and more on the process.

It was fun, to say the very least, to surrender himself to the carefree, looselessness of hoof painting. For both of the diapered ponies, silly things like fine detail and even brush strokes fell to the wayside. He personally found it much more enjoyable to just get the colors on the page rather than worrying about what those colors were going to be or whether the composition was correct.

As time went on, Mcintosh found the floor to be a better staging area for his showy and enthusiastic waves of his hooves. He laid out several sheets of paper on the floor and allowed his emerging, childish inspiration to move more freely across the canvas. The floor provided more freedom for his movements and allowed him to encircle the paper with unmethodical hoofstrokes coming at it from all sorts of directions. Sometimes he sliced across the paper with a paint stripe of orange. Other times he bent down, inches away from the paper to take a closer look and make more precise strokes. All the while his fluffy diapered bottom crinkled behind him every step of the way.

Cheerliee, on the other hand, prided herself in having an idea in mind before she proceeded with painting. As the diapered stallion beside her went through one then two and then in no time at all was working on his tenth creation, she pondered on what to do with her second sheet of paper. Ponies playing on a sandy beach? A windmill on a hill? A rosy field of flowers perhaps?

She continued to ponder this. Meanwhile, Mcintosh hopped around his paper pile, occasionally dipping a hoof into a fresh color of paint that he enthusiastically added to the multi-framed mural. Every now and then a flash of almost-white caught in Cheerliee’s peripheral, momentarily distracting her from her deep and thoughtful hoof-painting. After some more pondering, she realized that the paper in front of her was starting to bore her. Then her eyes moved over toward her playmate who was currently facing away from her. His faintly yellow diapered backside stuck up in the air and pointing in her direction. And just like that, inspiration struck her.

Abandoning her sheet of red construction paper, she instead dipped her hoof into the tub of blue paint and then, with a giggle, reached for another canvas. In one swift motion that resembled a cross between a spank and a swipe, the off-yellow backside of the stallion received a fat blue streak of paint across it.

The spank-swipe struck Mcintosh’s diaper hard enough to interrupt his process. As his fluffy bottom was playfully slapped with paint, he looked up from his painting and did his best to give her a stern-faced look. Which was a challenge all its own since he was also holding back a playful laugh of his own.

“Now hold on there, missy,” Mcintosh said as stern and steady as a house of cards, “that ain’t very nice!”

Cheerliee just giggled, squirming in her seat like a child caught red-handed.

Mcintosh couldn’t stay mad at her for long. Even playfully-mad. Instead, he decided to get even. “‘sides,” he smirked, dipping his hoof into the pot of blue, “ah think you look better in blue anyhow.” With a sly motion, he tapped her on the snout, covering it in paint.

Cheerilee gasped at this discretion and hopped out of her seat. Playfully scowling at the stallion, she reached behind her and dipped her hoof into the closest color she could find. Then she darted around Mcintosh and poked a hoof print of red onto his crinkly diaper.

Mcintosh let out a surprised laugh as he felt the painted hoof prod his soggy diaper. He quickly retaliated by grabbing the yellow paint and smearing it onto Cheerilee's cheek. And with that, the hoof paint fight was on. The yellow was countered with a prod of green. And that was countered with a splash of purple. A flick of red and then a splotch of purple.

Before too long there seemed to be less paint on the paper and more on the pair of playful padded ponies who giggled up a storm. They laughed and dodged each other, spreading paint everywhere and not caring about the mess they were making. It was pure, carefree fun as they let their inner children take over.

As the paint started to run out, the two slowed down, both of them out of breath and covered in paint. They looked at each other, both of them laughing and smiling as a rainbow of colors streaked across their coats and matted their fur. It was tough to say who won that fight.

Big Mac was the first one to speak up, still trying to catch his breath. “Ah think we got a little carried away,” he panted between laughs.

“Yeah, but it was worth it!” Cheerliee exclaimed, equally as out of breath.

“Ah ain’t seen you wear so much color before!” Mcintosh replied, “looks good on ya!”

“I think I’ll stick to just white diapers for now,” Cheerliee said.

“Ya mean yellow,” Mcintosh was quick to say, craning his neck to spy on the padded garment that now sagged heavily between the mare’s legs. Underneath the paint splotches was the distinct form of a swollen and wet diaper. “Yer gonna need a diaper change, missy.”

“Don’t think I’m the only one,” Cheerliee laughed, doing the same, “if it were up to me, I’d put you in double thick diapers.” She smirked as she entertained the idea for a little bit. Watching the stallion waddle bow-legged as she did would have made it all worth it, but a sight for another time she told herself. “But I guess we should clean up for the day.”

The two scanned the room together and took in what was to be the last they’d see the classroom in such a state.

“Means we gotta go diaperless now...” she then said, mostly to herself as she looked down at the crinkly, paint covered thing between her legs.

“Yeah...” Big Mac added, doing the same.

The diapers were unceremoniously untapped and allowed to plop down to the ground where the pair stood. On the outside the diapers were smeared with a rainbow of paint, but on the inside they were just yellow from end to end. Well used diapers to end a well used day. It was funny when Cheerliee gave it some thought. As she balled up the diapers and tossed them into the nearest trash can, she noticed that even with the second diaper adding an extra layer of bulk, they weren’t nearly as swollen or as full as Mcintosh’s. How the stallion managed to drench a diaper so well was remarkable.

"We're gonna need a bath after this..." Big Mcintosh said as he examined his paint splotched legs.

"I'll spray you with the hose before we leave," Cheerilee shrugged off, "Hoof paint isn't a hard thing to clean off."

“‘Course, now that leaves the clean up...” Mcintosh said, “we left a heck of a mess at the crafting table.” He glanced over at the squat round table that was still covered in paper scraps, open glue sticks, scattered crayons, and hoof paint.

“And there’s the desk...” Cheerliee said, glancing over at the pile of diaper changing supplies on her teacher’s desk. A fine layer of baby powder covered its surface. “And papers need to be restacked,”

“And...there’s the chalkboard,” Mcintosh added, directing their eyes to the chalkboard that stood behind them. Several neat lines of 'Little Cheerliee wears diapers because she’s a foal.' covered the board from end to end. He had half a mind to leave it as it was. The lines made him chuckle.

“Kids can be so messy!” Cheerliee laughed, “well then I’ll get to washing down the chalkboard and you can clean up the crafts table.”

“Don’t know why ah gotta clean up the table,” Mcintosh said, “most of the mess was from you.”

“Who’s the teacher here?” the multi-colored mare asked, “don’t make me have to hold you in detention after class.”

The rainbow colored stallion rolled his eyes. “As you wish, Miss Leakybottoms,” he said as he walked off.

Cheerilee rolled her eyes and playfully stuck her tongue out at Mcintosh. Kids can be so messy, but she couldn’t wait to do it again some time.

Author's Note

Well it took some time, but here it is! The conclusion to the story four years in the making! Feels good to complete your circles. I'm happy to have this one all wrapped up and done!