Derrick's Awakening - Chapter 12 (Patreon)

Nanny smiled down at him, brushing a strand of hair out of his face gently. "I had a feeling you'd say that," she cooed. "Such a good boy, not fighting his diapers..."

Derrick blushed slightly, not sure if it was more at the thought of being praised for that, or the fact that it was true. Even in his mental narrative, he was supposed to be too old for this... That was part of the appeal, really. Being a baby was one thing, but for whatever reason, he preferred the idea of having outgrown them, or so he thought, of being 'too big' for them... Yet, still needing them, which was a fact that only he seemed unable to accept.

"I-I'm just following your rules, Nanny," he told her, surprised at how quiet his voice came out, how high, how childish. 

"I know," she nodded. "And that's how I know you're a big boy, unlike so many of the kids I look after. Now, then, do you want your shorts back?"

"Wh-What?" It was a simple question, one that shouldn't have thrown him, though it definitely had. He ought to say yes... It made the most sense, since she'd asked his opinion, and he couldn't imagine a way, in the fantasy he'd constructed, he could justify the opposite... Thinking back to how exciting it had been being outside his room, however, even if it was only in his kitchen or living room, he hated to let the opportunity pass him by. "Umm..."

Mrs. Holland, as if reading his mind, let out a small chuckle. "You know what?" she said, "I don't know why I asked... I'm not sure these shorts would fit over that diaper anyway!"

"R-Really?" he blinked up at her. He doubted that was true... There would be a bulge, certainly, and perhaps a bit of the plastic waistband would peek out at the top, but the shorts weren't so tight that they couldn't go on at all, were they? It didn't matter now, either way... His Nanny had spoken, and he wasn't going to question it any further. If anything, he was happy to have that decision taken out of his hands, decided by someone bigger and smarter than him. "If you say so."

"I do," she said, holding out her hand, helping him down off the table.

He wasn't sure how it was possible, but the diaper felt so much better than any he'd put on himself, whether it was some special babysitter magic Mrs. Holland knew about, or the plain fact that someone else had done it to him... It just seemed snugger, more comfy, more cushy... And he'd loved all those things already, when he'd been diapering himself. This only amplified them, made him feel so very tiny and babyish as he toddled along beside Nanny, following her blindly.

Walking through her house ought to have been just as nerve-wracking as leaving his room in his apartment... There were plenty of windows there, too, plenty of opportunities for him to be seen from the outside, if they hadn't been properly prepared. And what if Malory came home?!

But... He was with his Nanny, and he trusted her completely, was positive she'd thought of all of that ahead of time, that she wouldn't be taking him anywhere he wasn't safe. Not to mention that, if anyone did catch a peek of him through a pair of curtains not completely closed, they might assume he was one of Mrs. Holland's normal charges, might not give him a second look. It was probably normal, here, to see such a sight... And now, he was just another one of the little boys she looked after. 

She led him to the living room, where, sure enough, the curtains were drawn. "Why don't you sit down here for a minute?" she suggested, gesturing not to the sofa, but the floor in front of the coffee table. Instantly, he thought back to his fantasies, to the mental babysitter he'd created for himself, to being told, "The furniture is for grown-ups!" Mrs. Holland didn't say that, not with words; her actions spoke loud enough on their own.

"Yes, ma'am," he nodded obediently, listening to the diaper crinkle beneath him, feeling its bulky padding compress under his bottom as he settled in. The television clicked on, cartoons instantly starting to play as Nanny pressed the button on the remote, then slid it into her pocket. Derrick didn't get to choose what he watched... He watched what his sitter wanted him to, and she had decided he was only mature enough for cartoons.

He wasn't paying particularly close attention to the TV, but he still barely noticed that Nanny had left until she returned, setting a small, plastic bowl of baby cereal puffs on the table in front of him. Derrick reached for them without hesitation, not stopping until he'd nearly popped one in his mouth.

He froze there for a moment, staring down at them. Suddenly, he was back on that first day, the one where this had all started, riding in the back seat of Mrs. Holland's car, diaper tucked beneath the waistband of his pants, him praying that his shirt would hide it, that Mrs. Holland wouldn't spot it there, or realize, when she got back home, that there was one missing from the stack in the downstairs bathroom. Had she known, even then? Was this her way of telling him?

No, that couldn't be... She'd offered him the snack before he'd gotten to her house, before he'd even seen the diapers. Unless... Had she known about this before him, somehow? Had she been certain that, one day, things would end up this way? That sounded even more insane, and yet, with all her experience, looking after kids... Wasn't it possible she'd recognized something in him that she normally saw in them?

He didn't know, wasn't able to bring himself to ask, so he bashfully popped the cereal into his mouth and began to chew. He'd thought, back on that day, that it wasn't too bad... Now, sitting here, with a babysitter, wearing a diaper, while cartoons played on the screen in front of him, it tasted perfect.

"I don't want you to think that I just let my kids sit around and watch TV all day," Mrs. Holland told him. "Since this is your first day, though, Derrick, I thought it would be best to start small, and calm. Is that all right with you?"

Chewing another handful of puffs, Derrick nodded. This wasn't anything he hadn't done on his own, not really, but he was satisfied with this, with having someone else there for real, instead of only in his imagination.

"I'd love to take you to the park, or the zoo, but before we do that, we need to get you some cute clothes," she continued. "Not that I don't like your shirt there, or your little shorts... I think we can do better, though."

Derrick squirmed, glancing over his shoulder at her, sitting on the couch. "L-Like... Going shopping?" An image popped into his mind of being pushed around in a shopping cart by his Nanny, an image that had come to him before, that, as embarrassing as it was, was also intriguing, exciting.

"Very good!" she praised him. "That's right, that's where we get new clothes!"

"We could order them online," he pointed out.

"We could," she agreed. "Is that what you want to do?"

His cheeks darkened, and he shook his head truthfully. It would be easier, yes... It didn't sound nearly as fun, however. "I didn't think so," she chuckled. "I think it's a good idea anyway, so we can get just the right fit... And we'll have to find out if you're going to need clothes that a diaper will fit under or not."

"R-Right." He'd almost forgotten about that. He was, theoretically, only in this diaper now as a test, to see if he'd need them in the future. He had a feeling Nanny would find a reason to make him wear them in the future regardless of what happened, extending the deadline he had to meet without any accidents to prove he didn't need them, but supposedly, if he stayed dry, he could go back to his big boy undies, or at least Pull-Ups. Or maybe this was a test, a way to see how serious he was about their arrangement.

Either way... He knew he had to do it. He had to use his diaper, and the sooner the better. He'd never wet his pants in front of anyone before, not that he could remember, and there was no way he was going to be able to hide it, to do it without a trained sitter like Mrs. Holland noticing, and knowing exactly what he was doing.

"A big boy like you, though, I'm sure we won't have to worry about that at all, now, will we?" she asked with a knowing wink.

"N-No, ma'am," he blushed deeper, grabbing some more cereal puffs as he fidgeted in his seat. "Not at all..."