Dear Diary - Chapter 5 (Patreon)

It was hard to tell, for sure, in the morning, if anything had happened or not. It was already strange enough to see him as much smaller as he already was... She wasn't positive if he'd gotten shorter, or if she'd forgotten how much he'd already shrank before then. Of course, with Ryan standing there, tears in his eyes, in wet pajamas, he probably looked littler than he truly was anyway.

"I-I'm sorry!" he sniffled. "I-I don't know what's wrong with me!"

"The doctor said nothing," Morgan pointed out. "Honestly... I don't know what I'm going to do with you..."

He hung his head, definitely looking the part of a chastised little boy. Morgan debated, for a moment, what she should do, whether she ought to fetch the Pull-Up now or not, and send him to work in it. It would be fun... But so would waiting, letting him think it was over, and springing it on him. And, if the Pull-Up didn't fit, they could go on a little shopping trip, since the first one had gone so well, and the diary would make sure what she bought did work.

That gave her something to look forward to, as well. "Well, go get changed," she ordered, at last, making up her mind. "I'll get these sheets in the washer." He nodded, started to scurry off to the bathroom. "Do you not want your jammies clean, too?" she stopped him, making him blush and strip out of them, adding them to the pile of wet things.

"I guess we should have gotten you two pairs after all," she teased, as he shimmied out of the pink panties. Again, she felt the temptation to break out the Pull-Up, had to talk herself down, into letting him think the worst was over. "I suppose one more day out of them won't hurt too bad. And, since they're going to be washed, we can put off buying more until tomorrow. Unless you want to do it tonight?"

"N-No!" he shook his head.

"I didn't think so," she smirked. "Well, go ahead... I'm not going to go in there and clean you up, too. Unless you need me to?" He shook his head again, leaving her alone to gather up the laundry and carry it to the machine. She could already tell this was going to be a good day.

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

She wasn't quite correct. She'd expected the higher-ups to call her in, give her a promotion to take over Diana's spot, but that didn't wind up happening. She started feeling a little antsy about it, and nearly ran home on lunch to grab her diary, make sure it happened that day, whether she considered it 'cheating' or not, although she managed to stop herself. She was taking a break, after all... And, seeing as she was basically filling Diana's spot already, with the woman fired, spending her days sitting around at home, filling her Pampers, they had to eventually realize she was capable.

It was probably nerves over that which caused what happened next... That, or maybe her daydreams, replaying what had happened to Diana in the boardroom, as she pooped her pants in front of everyone, her training pants bulging beneath her tights, the shocked look on her face as she realized what was happening, and that she could do nothing to stop it... It had been so utterly delicious... 

That almost made it worse when Morgan snapped out of her fantasy, only to notice her own stomach was begging for relief. She hadn't taken time to eat breakfast, after throwing the bedding into the washer and getting ready, and she'd had a light lunch, so she wasn't sure where the sudden urge came from, but it was undeniably there... And far more powerful than it ought to have been.

She got up from her chair and started to head for the bathroom, getting only a couple steps before her calm, steady pace was forced to turn into a mad dash, with no regard for how ridiculous she must look. Even so, she barely made it to the bathroom on time, slamming the stall door shut and ripping down her clothes to plant herself on the toilet, gasping in relief.

Except... She didn't quite make it, not entirely. As she glanced down, feeling her body relieve itself, she saw a large, brown smear in her underwear, one that made her turn bright pink as she stared at it. It was nowhere near as big as the one her former boss had, certainly, yet she'd still had an accident... She grabbed some toilet paper, wiping her underwear out as much as she could, getting them mostly clean, then, after wiping herself, taking them off and peeking out the stall door before rushing to the sink to give them a bit better of a wash, drying them off with the hand dryer for as long as she could bare to stand there, heart pounding, constantly terrified someone else would walk in and catch her.

So, the rest of her work day was less than stellar, as she squirmed in her slightly damp underwear, terrified someone would smell what she'd done on her, despite how long she'd taken to clean up, and also afraid someone would have noticed how long she'd been away from her post, which wouldn't speak well towards her suitability to take Diana's place.

Maybe it was all just one, big coincidence... Maybe it had nothing to do with what she'd been doing lately, and something in her salad had simply disagreed with her. She had a bad feeling it wasn't that simple, however. In stories, when it came to things like the diary, there was always a cost... Was this hers? Compared to what Diana had been through, it could have been far worse... But she was glad she'd had the restraint to take a break.

Once she got home, she changed out of her underwear and into a fresh pair, and prepared for the night's festivities. She could have fun without the diary... She'd give it some time to do whatever it needed to do, and then she could move on to the next big step. For now, she cooked up some supper, and made sure the Pull-Up was ready to go.

As soon as Ryan came back into the house, it was easy to forget about what she'd gone through that day. Almost without thinking, she fixed his plate of food for him, then kept it, cutting the chicken into bite-sized pieces before handing it over to him. "Y-You didn't have to do that," he pointed out, blushing, but too timid after what had happened that morning to get too annoyed about it, at least outwardly.

"Oh, yeah," she nodded. "I guess you're right. Sorry, I guess I'm just used to doing that for Barbara."

She watched his blush deepen, as he was compared to her babysitting charge, then continued to eye him as he munched away on his food for a moment, feet swinging below him, not quite reaching the floor. "So," she spoke up after a few minutes, "I think we ought to talk about last night."

"Yes, we do," he nodded. "I don't think those... underwear... are going to do me any good, and..."

"I'm glad we're on the same page," she smiled, cutting him off. "I thought you'd be more upset about it."

"Huh?" he frowned, confused. "I-I guess we did go through all that for nothing, but... Y-You thought it was for the best... I-I think that doctor was just messing with us, though..."

She tilted her head, pretending not to understand him, that what she was going to do next was so obvious he ought to have already figured it out. "I think you're a little mixed up," she smiled down at him condescendingly. "Finish your supper... We'll talk about it once you're done."

"But..." he looked even more uncertain now, which was exactly what she'd wanted.

"Eat, eat," she urged. "There's no rush."

She refused to elaborate further until he'd cleaned his plate, barely stopping herself from telling him a growing boy like him needed the food. That might be too on the nose, she decided... He knew he wasn't growing, since he was too old for that by far; she didn't want him to guess he truly was shrinking, however, or that she'd known he was all along.

Once he was finished, she led him back to the bedroom, giving him a kiss, starting to undo his pants, letting him think, for a moment or two, they were going to have sex, before pulling away and grabbing the pink Pull-Up, and watching his eyes widen. "What the hell is that for?!" he demanded, stepping away, stumbling over his half-removed clothes.

"You, of course," she chuckled, as if it was obvious. "As we agreed, the panties we got you aren't going to do you any good... But these ought to. They're pink, like the doctor ordered, and definitely for women... Well, girls, I suppose, but that's close enough. And, after your little accident last night, at the store, and again in bed... They're better than a repeat of those, aren't they?"

"No!" he shook his head, disgusted. "Those are diapers! I don't need diapers!"

"No, they aren't," she told him gently, in the same tone she used with Barbara, when the girl insisted she'd gotten over her bedwetting, and didn't want to wear them anymore. "They're Pull-Ups, and they're for big kids, not babies."

"They aren't even gonna fit!" he stomped his foot.

"We can try," she shrugged. "There's a bigger size, so if we need to go get them..."

"No!" he whined. "We don't need them at all! This is insane, you can't... Hey!" He gasped as she grabbed him, sitting down on their bed and yanking him over her lap, his rear exposed, since he'd so eagerly begun to strip. "What are you doing?!"

"Well, you're acting like Barbara," she said. "I guess I can treat you like her."

She wouldn't have spanked Barbara, of course... Ryan, on the other hand, was a different story. She felt a grin forming on her face, remembering how Barb had suggested that as a punishment, the day Morgan had first learned he was cheating on her... Was she going to make that come true now? Staring down at his wiggling bottom, it was certainly tempting...

"I'm sorry!" he squealed. "W-We can give them a try!"

It was almost disappointing... Perhaps finding himself over her knees reminded him how great their size difference was, how much it would likely hurt, if she'd gone through with it. Or maybe he'd decided going along with her would be less emasculating than getting spanked, then doing it anyway, probably. His ego was surely still bruised from the shopping trip the night before.

"That's better," she told him, letting him slide off her lap and wiggle the rest of the way out of his pants. She held out the Pull-Up for him, stretching it out, slipping it up his legs, wondering how it was going to go. It fit, but she could tell it was tight, certainly not comfortable for him.

It was a little sad; she would have loved to have him not just the same Pull-Ups as Barbara, but one that had originally been intended for the girl. It also meant there were definite limits to the diary's power... She doubted it would consider this 'fitting', so she had to stick to making things happen, rather than setting up scenarios, and having a punishment ready to happen automatically if Ryan didn't do as she wanted.

"It's fine," she said, not knowing herself if it was more directed at her, or at Ryan. "They'll work for now, and we can hit the store to get the next size up... Those will be perfect."

Ryan wasn't happy, but that was okay with her. She had him pull his pants back up, getting rid of his big boy underwear, perhaps for the last time. She hesitated for a moment, then ducked into the guest room to grab the diary. She knew she'd resolved not to use it for a bit... Who knew when an opportunity would present itself, however? Why not be prepared to take advantage of it?

And she was certainly glad she did. She took him to a department store, pretending she couldn't recall where the diapers were so she could walk him around in his Pull-Up, feel the bulk of them, realize that was what he was going to be wearing from then on. As they passed by the girls' clothing section, she saw him staring at one of the mannequins.

She wasn't sure why, at first. It was wearing a pretty typical outfit, after all, a light purple tank top, printed with unicorns, and a black, ruffle miniskirt... Nothing too unusual. After a moment, however, noting his discomfort and stopping to pretend to tie her shoe, to let him soak it in, she realized it was the skirt he was fixated on.

It was short, she had to admit, although she'd seen kids in ones even shorter. She couldn't be certain, yet she had a feeling he was saying a silent 'thank you' to the heavens that he'd been born a man, that he wouldn't be expected to wear anything like that... Or, perhaps, because he was in a girls' Pull-Up, he was imagining wearing that, as well, and how much harder it would be to hide the training panties beneath it than his pants.

In a way, she thought, she almost had to do it... He should know what it was like. He was probably already envisioning it... Why not let him experience it? She reached into her purse, still bent over her shoe, and grabbed the diary, scribbling into it hastily, before he started to question what was taking her so long.

She heard his gasp first, glanced up, afraid she'd missed it, to see his eyes wide, staring at that same mannequin, now wearing his work clothes, what he'd worn in, although, since they fit it perfectly, she had to wonder if they'd shrunk. She had, in fact, looked at him just in time to watch his gaze shift downwards, his face turning almost green when he saw he had on the outfit the mannequin had been wearing, though, like his old outfit on the mannequin, it fit him perfectly, which made her suspect it had grown somewhat. He tugged nervously on the skirt, squirming in place, horrified.

Morgan was a little sad she'd missed it... How had it happened? Had he been so compelled by the outfit that he'd been forced to switch it out? She hadn't noticed it, but perhaps... Or had it been pure magic? This wasn't like with the doctor, where a person had to show up, and couldn't just pop out of nowhere... Part of her was tempted to demand to be let into the security office - and write another entry in the diary to make sure she got her wish - so she could watch the tape, though if she did that, Ryan would know she was aware something was up.

It was far more entertaining to act like nothing had changed. "There we go!" she exclaimed, straightening back up, reaching over to take his hand. "Come on, I think they're this way..."

"B-But..." he frowned, still fiddling with his new skirt, blushing as she dragged him through the most crowded aisles, earning him more than a few confused looks.

Really, though, she had to admit, he didn't look all that out of place in the outfit... If it weren't for the hair on his legs and arms, and his haircut, he might blend in. She hesitated, but much less than she should have, considering her resolution, and stopped again, reaching into her purse, claiming she'd heard her phone go off, instead, writing another quick entry.

She saw it that time, as it was a much slower process. At first, she thought the diary had failed her... Then, she noticed him reaching over, scratching his arm, clearly feeling something. She watched, seeing the hairs there growing smaller, slithering back into his flesh, the hair on his legs doing the same, while, in response, the hair on his head started getting longer, like everything from elsewhere on his body was transferring up there.

His hair was still short, for a girl's, but long enough she was pretty sure she wouldn't know for certain right away. He whimpered, scratching his head, probably not knowing exactly what was going on, just that there was... something. Honestly, he looked cute... Especially when he pointed up at the signs hanging from the ceiling, desperately exclaiming, "There! It says they're over there!", obviously wanting to get out of here, and back home, no matter what it took.

Morgan, on the other hand, wasn't done. "No, they just remodelled," she told him. "That's where it used to be. I'm telling you, I feel like it's over here..."

She turned around, back towards where they'd come from. "Why don't we go look over there, at least?" he whined. "We've already walked through here..."

"I think I know my way around here better than you," she informed him. "Come on."

They went back past the kids' clothes section, and into the juniors'. Just as she'd hoped, there was a gaggle of teenagers hanging around, and she aimed right for them, feeling Ryan's hand growing sweaty the closer they got, noting him trying to tug his hand free... Then, after pushing through the group, she, finally, let him go, bumping into the girl who looked like the leader, hurrying off before he could follow her, ducking behind a clothes rack to watch.

"Excuse you," the girl she'd run into said, stepping closer to Ryan. "What do you think you're doing?"

Ryan blushed, staring down at his feet, clearly at a loss for words. "I-I..." he squeaked nervously.

"Hey, be nice to her," one of the other girls said. "It wasn't her fault..."

"She almost made me spill my Starbucks," the leader rolled her eyes. "If I had, you'd really be sorry, pipsqueak!"

Ryan was right around the average height for women... But, fortunately for Morgan, not all these girls were average, so he was far from the tallest. She could see him gulp, looking around for her, as if she was going to swoop in and save him. He looked even more hesitant to speak now, after hearing himself referring to as 'she'... Would it be better for him, she was sure he was debating, to own up to being a guy - and a grown one, at that - or let them believe he was one of them?

"What are you even doing here?" the leader asked. "You don't look like you're even ready for a training bra, much less these."

Morgan grinned as she spotted the realization wash over Ryan's face, seeing he was standing in front of the bras. His hands grabbed the skirt, squeezing it, willing it to grow longer, to prevent any further humiliation from that, not knowing, by doing so, he was pulling the waistband down... Morgan couldn't have orchestrated it better with the diary.

"Be nice," another girl shook her head. "She's just a late bloomer... And that's all right. Hey... Where do you go to school?"

Ryan shrugged, obviously not wanting to say a school and have it turn out to be the one they went to, and have his lie discovered. "Oh, my God," the leader giggled, pointing. "I think it's one of the preschools! Look at that!"

Ryan's gaze followed her finger, along with all the other girls', his face going pale as he saw what he'd done, letting go of his skirt and tugging it up again, looking around, only to see he was practically surrounded now. "Are you wearing a Pull-Up, you little dweeb?" the leader smirked, stepping closer.

"N-No!" he shook his head.

"Yes, she is," one of the other girls piped up. "Those looked just like my little sister's!"

"Is that why you ran into me?" the leader asked. "Are you just learning to walk, baby?"

"Come on," one of her friends, clearly the nice one, urged. "Be nice... Maybe she's... you know..." She looked embarrassed to suggest Ryan was special needs, although that was certainly the implication.

"No, I'm not!" Ryan insisted. Morgan could tell he was speaking higher now, playing into their assumption that he was one of them.

"Then why are you wearing Pull-Ups?" the leader demanded.

"I-I'm not..." he repeated, a bit weaker.

"Then prove it," the leader told him. "Just give us a quick peek."

"N-No!" his face turned bright red.

"Leave her alone," the nice one pleaded.

"Once she shows me," the leader countered. 

Morgan could see this wasn't going anywhere quick, and she thought Ryan had suffered enough for one night. He was obviously hesitant to lift his skirt, afraid they might realize he was no girl, and, other than nice one, the girls were curious what was up. She didn't go rescue him right away, of course... She slipped away, straight to the diaper aisle - she knew exactly where it was, after all her time babysitting Barbara - and returned to find them still at a stalemate.

"There you are!" Morgan shook her head, speaking up loudly, making the teens scatter before her larger, clearly more adult, form. "I've been looking all over for you. Come on, we need to get you to bed!"

She could see the teenagers spotting the package of Pull-Ups in her hands, heard them giggling and whispering to one another as Ryan hurried to her side, and knew he was aware of all that as well. She took his hand and gave it a squeeze, taking him to the front of the store, having to hide her grin the whole way, in case Ryan managed to look up from his feet towards her, not wanting him to know how thoroughly she'd enjoyed that.