Derrick's Awakening - Chapter 11 (Patreon)

He had been waiting to hear those words, dreaming about it, for what felt like his entire life, even though, in reality, he knew it hadn't been nearly that long. If it had happened before he'd taken that first diaper, before he'd tried it on, he would have assumed it was a weird joke, one that he didn't get. Maybe he would have laughed it off so he wouldn't seem dumb for not understanding... Now, it sent a shiver down his spine, made his knees weak.

"Y-Yes, Nanny," he mumbled, head swimming. "I-If you say so..."

"I do," Mrs. Holland smiled. "What a sweet boy... Come along." She held out her hand, Derrick grabbing at it greedily, like a swimmer about to drown if not for the assistance he'd just been offered, shuffling beside her through the house he'd been in a thousand times, if not more, that somehow felt brand new now, as if he were walking into it for the first time.

He was used to diapering himself by now, for the most part, and he thought he'd gotten decent at it, anyway. There was something different about the idea of having someone else do it, especially someone he called Nanny, someone whose 'job' it was to look after him. It was so very hard to think of himself as a grown-up, knowing that was what was about to happen, and, as much as he knew that should be a bad thing, he couldn't help being ecstatic, excited, to experience it at last.

Except... Obviously, if this was going to happen, he was going to have to get naked. She was going to see him, all of him - or, at least, the lower half of him, which was kind of the important part in this situation. That was going to be weird... Anybody who had seen him like that since he was actually a little boy had been on accident in the locker room, or someone walking in on him when he was in the bathroom. And there was no way to avoid it... That was an essential part of the process.

His cheeks began to heat up even more, in a less pleasant manner. He had known, intellectually, that this would be required; there was a difference between knowing it in the abstract, and being faced with it in his immediate future. Was Mrs. Holland really going to be the first woman he let see him pantsless? There was something about that that felt wrong, almost incestuous, given how long he'd known her daughter, how often he was over here...

"Umm..." he managed to speak up, after quite a few more steps, only the sight of the guest room approaching spurring him into action, telling him that he was running out of time. "N-Nanny, maybe... I-I mean, I'm a big boy, right?"

"Derrick," Mrs. Holland chuckled, "you're not changing my mind, young man. You are wearing a diaper today, and that is that!"

His knees came close to giving out on him again, the words once more making him melt a bit inside. "I-I know," he couldn't help giggling at the prospect, no matter how serious his concern seemed. "B-But... I-I could put it on myself?"

He hadn't meant it as a question, though that was undeniably how it came out, completely lacking the confidence of an actual offer. He could do it, yes, and maybe he should... That wasn't what he wanted, wasn't how his fantasies played out in his head... In those, however, the thought of being naked had somehow not even crossed his mind, everything so innocent and sweet that it had never occurred to him that it would be a part of this.

"Don't be silly," she brushed him off without a second thought, as she reached out to the guest room's doorknob, turning it and pushing it open. "You're way too little for that, Derrick."

That was what he wanted to hear, deep down, what pushed his buttons, despite the concerns, what got him stumbling through the doorway, feeling like he had to agree, that there was no way his Nanny could be wrong about that. He was too little, wasn't he? He was too little for a lot of things...

"That's why you have a Nanny," she reminded him. "If you could just do it all yourself, your Mommy would never have left you with me. But you can't, can you, Derrick?"

Derrick gulped, looking around the room. He'd been in there before, but not in a long time. They weren't forbidden from it by any means, but he and Malory tended to avoid it. There was nothing in there for them, and it was where Mrs. Holland ran her business from, basically, so they didn't want to mess anything up. He would have expected everything to look smaller now, like he was going back to his elementary school after graduating high school, yet, instead, it all felt bigger, more imposing. That crib he'd been so uncertain whether he could fit in or not looked more than big enough now, seeing it in person.

And, more importantly at the moment, there was something else there that he didn't recall seeing the last time he'd been in the room, something that felt incredibly relevant right now. "Y-You have a changing table?" he asked, staring at it, at the rows and rows of diapers stacking up on its shelves, the many bottles of lotions and creams and powders alongside them. And on top, open and waiting, was a diaper. His diaper.

"I do," Mrs. Holland replied. "I used a changing mat on top of the bed for a while, but it's so nice to have a dedicated spot for it. I still use the bathroom down here for some of my bigger kids who are trying to train, and who get embarrassed about having to lie on the table... I don't think that's going to be the case with you, now, is it?"

Derrick shook his head, almost in a trance. "N-No, Nanny," he answered. A real changing table... He was about to be diapered by someone else for the first time since his toddlerhood, and it was going to happen on a real changing table. "Y-You're right," he bobbed his head, going back to her previous question. "I-I can't do it on my own, Nanny."

"Of course you can't," Mrs. Holland patted his bottom, before kneeling down in front of him. "Now, let's get started, shall we?" He let her untie his shoes, obediently stepping out of them at her command, and then...

Derrick squirmed, seeing her hands reach out, grabbing for his belt, a flash of his old concerns passing through his mind, and quickly vanishing. She loosened his belt, unzipped his pants, yanking them down, not saying a word, not acting like it was anything unusual for her to be doing. She did this every day for other little boys, and that was what he was, wasn't it?

It was all so natural, so calm, despite his panic earlier. His hand did twitch towards his underwear when he saw her fingers curl around the waistband, but all it took was a small shake of her head, and he let it go, taking one deep breath to prepare himself before those, too, were whisked away. She still didn't stare, didn't laugh, didn't react at all to seeing him that way. In her eyes, he really was just a kid... And that was what he wanted, right?

No, even that wasn't quite right. It wasn't about what he wanted... Here, now, under Mrs. Holland's care, it wasn't that he wanted to be a little boy again... He was one. He was a tiny little toddler, and if a grown-up told him he needed to wear a diaper, then that was what he was going to do. And the sight of the diaper spread open on the changing table told him that his Nanny did, indeed want him in one... And that his Mommy had no doubt agreed to it.

"Up you go!" Mrs. Holland exclaimed, taking his hand again, helping him step onto the stool beside the changing table, going up the few steps it had so he could sit down smack dab in the middle of the waiting diaper.

It was the same kind he had at home, that he'd stolen from here, yet it felt completely different now. Whether that was the knowledge that he wasn't going to be the one taping it up, or taking it off, or the feeling of the changing table under that, soft and gently crinkling as he moved, he wasn't sure, but he could have sworn it was bigger, bulkier, more babyish.

"I know you're a big boy, and you probably won't have any accidents," Mrs. Holland gave him a knowing wink, "but we're going to use lots of baby powder anyway. It doesn't hurt, and it smells so nice, don't you think?"

He blushed, nodded, with another, "Y-Yes, Nanny." He did like baby powder... He liked it a lot, in fact. He was always careful with it, not wanting his room to smell too much like it afterwards, or the living room of the apartment, or anywhere else he might dare to go. Seeing it snowing down over his crotch, the scent overwhelming his nose, informing him that this was now what he smelled like, his cologne, was exactly what he needed, the final step to helping him push away his big boy worries.

"Here we go!" Mrs. Holland announced, adjusting the diaper beneath Derrick's bottom slightly, then grabbing the front, pulling it up between his legs, folding it over him. 

This was it, Derrick thought. In a matter of seconds, the tapes would be fastened, and his first diapering would be over. Malory's mother would have put him into a diaper, and there would be no going back from that, no pretending this had all been a joke of some kind... Not that he expected she would believe that, after their conversation. There was no turning back...

He heard the first tape being opened up, his heart thumping loudly in his chest at the sensation of the side of the diaper being raised, wrapping around his body carefully, lovingly, Mrs. Holland's fingers pushing it softly into the landing strip with a small rub to guarantee the adhesive stuck, that it wasn't going to get loose, or fall off, that he wasn't getting out of it until she decided to let him out of it.

"We'll get it nice and snug," she told him cheerfully, moving on to the other side. "There aren't going to be any leaks today!" He shook his head dreamily, his own diapering jobs feeling so inadequate now, so amateur, even before she'd adhered the second tape, securing the bulky padding around Derrick's bottom like an inescapable, crinkly hug. "There... That wasn't so bad, was it?" she asked, helping him sit up.

He shook his head, glancing down at himself, unable to stop grinning as he saw the diaper bulging between his legs, looking, and feeling, so natural there, especially with the scent of baby powder surrounding him. "N-No, Nanny," he managed to reply after a moment. "Not at all..."