Derrick's Awakening - Chapter 10 (Patreon)

Derrick would have thought that, now that everything was out in the open, it would have been easier. Somehow, he felt even more nervous now, with his first appointment looming. He'd been so excited about it, he could barely sleep the night before, tossing and turning in his customary night-time diaper, fretting about what the next day would bring... But, also, at the same time, practically vibrating with the possibilities.

He returned home after work, not wanting to show up in his work clothes, though that left him with a decision he didn't know how to make. What should he wear instead? Nothing felt nearly cute enough for what he was about to do... He was going to need a whole new wardrobe for this, if he wanted to feel the part he was getting to play, and he simply didn't have it yet.

And, when he did settle on a pair of shorts and a plain, light blue t-shirt - the best he could do for now - he was left with another decision. Did he show up in a diaper? He still hadn't worn outside the apartment yet, which was definitely about to change... So, should he start it off now? He'd definitely feel like a little kid, showing up to 'daycare' already in a diaper, and he didn't plan on doing anything except going straight to his car after he stepped out the door...

What if he ran into one of his neighbors? That was probably the scariest part... Going to the store, or to the park, or whatever, might be tough, but there was a decent chance that, if anyone saw him there, they'd be someone he didn't know, who he might not ever see again, or who at least wouldn't be likely to recognize him if he did. The other people in the apartment building, however, did know him, had seen him many times, even if they hadn't spoken, would almost certainly remember him, if they spotted him running around in diapers...

So, maybe it would be better to wear his regular underwear, for now. He knew Mrs. Holland was going to put him in a diaper anyway, when he arrived... Perhaps it would be more special to let her handle it. The idea of her immediately having to undress him, to take away his undies, brought an intense warmth to his face, yet... It was going to happen eventually. If he was going to wear diapers - and that was why he was doing this in the first place, wasn't it? - he was going to have to be changed at some point, and, since she was his Nanny now, she was going to be the one doing it.

Should he rip the band-aid off right away, to hopefully help him get used to that thought? Or risk a neighbor recognizing his diaper bulge as he dashed to his car? Neither seemed appealing, in the moment, but he had to pick one, or he'd never leave, never get started in the first place.

He was already in underwear, having slipped into some instinctively after his quick post-work shower, so he might as well stick with those, right? He didn't know if Branden would be home when he returned or not, so he was going to have to go back to underwear after the session, to avoid any chance of him seeing him in diapers... This way, he wouldn't have to figure out what to bring them along with him in. He didn't have any need for his backpack, now that Mrs. Holland had promised him more diapers whenever he wanted them... Although, he could have worn it anyway, he supposed, to help him look more childish. He didn't really have anything to put in there other than underwear, however, and if he was going to wear those...

He could have stood there and second guessed himself all day, and he might have if he hadn't heard a chime from his phone. He picked it up, looked at it, smiling softly to see a text there from Mrs. Holland. 'Can't wait to see you!' she'd written. It was nice and vague, which he appreciated, in case, for some reason, anyone else looked at his phone, but he, and she, knew exactly what it meant.

And he couldn't wait either... He was going to have to make a call, once and for all, so he could actually arrive at her place at some point today. He sighed, nodded, pulling on his outfit, sans diaper. He didn't really feel like a baby yet; he hadn't gotten to daycare yet, either, to be fair, and it might have been for the best if he didn't get too into his little space when he was about to get behind the wheel of his car. 

It wasn't a long drive to Malory's house, normally; today, it seemed like he hit every stop light, and they all stayed red for an extra minute or two, as if they were all conspiring to keep him away, to prevent him from making it there, and finally getting to live out this fantasy for real. Eventually, however, he did make it, pulling into the driveway and turning off his car, sitting there for a few moments to let it sink in.

He had made it. He was here, and all he had to do now was walk inside. Barring a meteor crashing into the house, or his car exploding, there was nothing that could stop him now. Ever since she'd made the offer, it had been almost all he could think about, and, really, ever since he'd taken his first diaper, he'd fantasized about some version of it, though not specifically with her, never having dared even imagine that could happen. 

He practically jumped out of his skin as he heard a tap on his window, turning to face it, heart pounding, to see Mrs. Holland standing there, smiling at him. "S-Sorry!" he called to her, fumbling to put his keys into his pocket, to check to see if he had everything before he left - or, rather, to give himself time to calm down. He didn't have anything other than the keys to worry about, but he hoped she wouldn't realize that.

"Don't be silly," she told him, opening up the door, bending down to reach over him and undo his seatbelt. "I always come meet my little ones at the car to walk them inside... It's a big world out here, and I wouldn't want them getting lost on the way in!"

He blushed, staring up at her, almost feeling himself shrink as she held out her hand. It was easy to forget that he was in the driver's seat, that he'd brought himself here... A couple little sentences, and she already had him nearly convinced that he was getting dropped off here, like any other little kid. He took her hand, stepping out of the car, letting her close the door behind him.

They were almost to the front door before it hit him what it might look like to the outside world, to her neighbors. He'd been so worried about his own, but, of course, she had some, too, and they could be watching. "A-Are you sure this is all right?" he asked, looking to their hands, joined together. "Wh-What if people think you're having an affair, or...?"

"Where did you hear a word like that?" she teased. "I told you, sweetie, I always walk my little ones in... I see no reason anyone would assume anything else was going on."

He could feel the blush spreading through his body; did she honestly believe that people would think he was one of her clients, did she? He didn't look that tiny, that young... Did he?! He certainly felt like it, after hearing that, leaving him staring bashfully at his feet as he shuffled into the house at her side.

"Well, then," she said, once they were safely inside, all alone, "I think I know what we need to do first, little one."

"Wh-What's that?" he asked, staring up at her, confused.

"Aww, sweetie," she knelt down in front of him, "didn't your Mommy explain to you?" He shook his head, still lost, which, in a way, did make him feel more like a child, dealing with things he knew nothing about, things that the grown-ups had supposedly discussed, but that he hadn't been involved in, despite them being about him... Even knowing that hadn't actually happened - he assumed, and hoped - since there was no way she would have talked to him mother about any of this...

"I have a rule here for kids your age," she said gently. "I know you think you're a big boy, but being in an unfamiliar place can be scary for anyone... So, at least for your first couple days here, I want you to wear diapers. If you can prove to me you don't need them, then maybe you can keep wearing your big boy undies after that... For now, though, you're going to have to go back to Pampers. Okay?"

Had she been prepared for him to show up like this? Was she just that good at rolling with the punches, after realizing he wasn't in diapers already? And how could she know for sure? She hadn't checked him, or touched him down there at all... Was she that used to being around toddlers that she could recognize a diaper bulge, or lack thereof, instantly?

Whatever the case, her explanation was exactly what he needed to hear. "D-Diapers?" he pretended to be shocked. "I-I don't need diapers!"

"I'm sure you don't," she replied, with the faintest hint of condescension in her voice. "So, just keep them dry for today, and maybe next time, and you won't ever have to worry about them again, okay? Can you do that for me?"

He could, almost definitely... He wasn't going to, of course, but he could if he wanted to, which made it all the more embarrassing, knowing he wouldn't. He really must be a baby, making the decision before he was even in his diaper that he was going to use it, that he was going to guarantee that he wasn't allowed any big boy underwear while he was here... She could have just declared that was the case anyway, said that was the rule. He was glad she hadn't, however, that she was making him 'earn' it... That made it feel so much more personal, so much more humiliating, in the best way.

"Yeah!" he nodded, brimming with false confidence, unable to hold back a giggle at how silly it seemed to even tell that lie, when both of them knew that was what it was. "I can do that, Nanny!"

She smiled, eyes twinkling. "Good boy," she patted him on the head. "Well, then, come along, little one... We'd better get you in that diaper."