Doing Business, Part 32 (Patreon)

Thirty-Two

“What. The fuck. Are you wearing?”

It went about as well as I expected it to.

I had taken my time in leaving the bedroom to greet Kylie. I was stuck in one of Mommy’s patented ‘rock and hard places,’ and forced to pick between humiliating myself by walking out of the bedroom–or waiting for Mommy to drag me out herself. The former option was clearly the better of the two, though that didn’t exactly inspire much motivation.

“Hey, Kylie. So…about this…” I started, pointing to my sailor onesie as if she hadn’t seen it yet for herself.

“Are you dressed like a…baby?” she asked. “The fuck is that on your ass? Like a diaper or something?” She snorted and shook her head, as if the very idea that I would be wearing a diaper was simply too ridiculous to be real.

“Well, I mean…”

“Wait. Are you? Are you actually wearing a fucking diaper?”

It felt incredibly unfair to have to answer these reductive questions when there was so much context she needed to know first. She should know about how this started. About the executive leadership team’s little club in my office. She should know about Lyndie and Ava and…

Fuck. I needed to start somewhere.

“Yeah…it’s a diaper.”

“Oh my gaaawd.” She bit her bottom lip and shook her head again as she sat back in the couch, seeming completely baffled by this.

“I know, I know,” I said, hoping to have the chance to start explaining myself. “See, Mom…uh…Ms. Heller and I…”

“I fucking knew you two were doing something weird,” she said. “But this? Diapers? Dressing you up like a baby? That’s some pretty fucked up stuff.”

I instinctively felt myself slipping into self-preservation mode. “You can’t tell anyone. You can’t tell your mother, you know? You have to keep it a…”

She sighed. “Look, Ms. Heller already has me backed into a corner, alright? I’m not telling anyone anything. But don’t think for a second that that means I’m going to be all nice and supportive about you dressing up like some pathetic freak.”

Her words hurt a little, but not as much as they excited me. Mommy must’ve broken me, because I found myself craving this kind of scorn now.

“Well,” I said, shrugging. “Here I am, I guess. I don’t know what else to say. So if you have any questions…”

“Do you piss your pants?”

I was not expecting her to jump right into the questions like that. “Uh, well, this is a real diaper that’s made to be pretty absorbent and…”

“Just answer the question, baby. Do you piss your pants or not?”

“Y-yes.”

“Does she change your diaper like a baby?”

“I mean…”

“Just tell me. I’m supposed to stay here with you all day. If it takes you this long to answer every question, I’m going to go crazy and jump out a window.”

So, that’s one way I could get out of this…

“Yeah.”

“Do you have any idea how badly I want to take photos of you right now and send them to all my friends?”

I could only guess. “Please…don’t?”

She rolled her eyes again. “I know it’d probably end badly for me if I did. But, fuck. What kind of hidden-camera show is this?”

I looked around the suite’s living room. “I’m pretty sure there aren’t any cameras.”

“So, what, rich and powerful people can just make little boys at their company crawl around in diapers for their amusement now?”

I laughed, finding that she summarized the last few weeks of my life surprisingly well. “Yes…it would seem so.”

“My mom is rich,” she said. “And powerful. Am I owed a little baby-man of my own?”

I could only shrug, unsure of which side of the line between honest and sarcastic she was treading on.

Behind me, I could hear activity in the bedroom behind the closed door. Mommy was out of the shower now, and getting herself ready for her day.

“How often do you wear diapers now?” Kylie asked.

“Uh…regularly.”

“What does that mean? Like, everyday?”

“Yeah.”

“At work?”

“Uhm, yeah.”

“Seriously? Like you just walk around an office all day with diapers on under your pants? Everyone has to know, right?”

My heart was racing again, and my cheeks were warming.

I had been in a bubble the last few weeks. I had a cursory awareness of this fact, but I rarely dwelled on it. But Kylie’s presence, and her questions, had suddenly made very conscious of it. I had somehow found myself in a world where the only people I interacted with during the day were the ones who knew I was a baby. They knew I wore, and used, diapers. They expected me to. And that was normal to them, just as it had become normal for me.

This, standing in a room with Kylie as she stared at me, was a glimpse of the reality outside of my bubble. And I found the humiliation to be absolutely crushing.

“I don’t know,” I finally said. “I don’t think so.”

“Get the hell out of here,” she spat back. “There’s no way that a grown man waddles through an office in a diaper everyday without everyone staring at him.”

Way to shine a light on my biggest fears. “There’s people who know, obviously. But…you know, it’s an office. People are busy. They’re not paying attention to my pants.”

“That’s cute that you tell yourself that,” she said. “I was a lifeguard last summer. Mind you–I was working outside, right?” And I worked with this guy who wore this pair of tennis shoes that squeaked every time he took a step. And it drove me fucking insane because I couldn’t not hear it. Now imagine you’re walking around inside with a ton of people, and your ass is crinkling like a toddler.”

“It’s not that loud,” I said, shifting my hips as I said the words. The crisp swish-swish of the diaper’s friction inside the onesie filled the room. Well, damn. I tried not to think about it too much, lest I have a panic attack and never return to the office again.

“Look, I get that I was asked to be, like, a ‘babysitter’ or whatever,” she said, “but that doesn’t mean that I’m going to coddle you like a baby. I’m not going to change your diaper or burp you over my shoulder.”

I hadn’t ever been burped before. The thought of it was…exciting.

“Nobody’s asking you to change any diapers,” a third voice suddenly said. It was Mommy, exiting the bedroom, dressed in a stunning deep-blue skirt suit. “I mean, if you feel compelled to, you really ought to give it a shot–a future woman-of-power like yourself may one day find herself with a large baby of her own, and having a little experience can’t hurt.”

“I wouldn’t change an actual baby’s diaper,” Kylie responded. “I’m sure as hell not going to change his.”

“Fair enough. Clarky does have a knack for making nasty messes out of his.”

I closed my eyes, hoping to blink myself out of existence. It didn’t seem to work.

“Uh, are you saying that he, like, shits himself too?”

“Afraid so,” Mommy said. “And he’s not allowed to change his own diapers this weekend, so if he has a little accident while I’m out–and you don’t want to take care of it–I’ll be happy to handle it when I get home. Of course, you’ll probably want to open a window or something in the meantime.”

Kylie shot me an annoyed glance. “Don’t even think about shitting your diaper today.”

“I’ll, uh, do my best.”

“Baby hasn’t had a bowel movement yet today,” Mommy said, assembling a few final things to take with her to the conference. “If he hasn’t gone by the time I get home, he’ll probably be ready to just…pop.”

I couldn’t believe Mommy was talking to Kylie about the inevitability of me filling my diaper.

“And while I sincerely mean it when I say that you don’t have to change his diaper,” Mommy continued, “if you think he needs some help getting his bowels moving…I did leave a little treat in the fridge.”

Kylie still seemed plenty disgusted. But also curious. “Oh? What sort of treat?”

“Just a baby bottle,” Mommy said. “Mostly milk. And a little extra ingredient that would get a constipated baby’s bowels moving again. You don’t have to give it to him. But just remember it’s there.”

“Anything else I should know?” Kylie asked, her deadpan tone suggesting sarcasm. “Does he need to be put down for a nap? Am I supposed to read him a bed-time story? Breastfeed him?”

“Young lady, if those tits provided milk, I’d be offering you a full-time position on my staff. No, I’m not asking you to do anything special beyond keeping Baby company. I can count on you for that, yes?”

Kylie’s face lost a little of its defiant confidence, and she even crossed her arms in front of her chest–maybe a little self-conscious of her chest suddenly. “Fine.”

The female social hierarchy was on display before me. Kylie, no doubt a queen bee in her usual circle of bratty and privileged friends, still knew her place when Ms. Heller was in the room. If it was commanded, I wondered if Kylie would throw herself over Mommy’s knees for a paddling too.

Too, I wondered if Kylie had more respect for Ms. Heller than she did for her own mother.

“Baby?” Mommy asked. “I left my good shoes in the bedroom. Could you fetch them for me? They’re the black ones near the bathroom door.”

“Of course.”

Her eyes narrowed a little and her head tilted. She seemed to be looking for a specific response, and I could easily guess what it was.

Flustered, I said what I could safely assume she wanted to hear: “Of course, Mommy.”

“Thank you, darling.”

As soon as I stepped foot in the bedroom, I could hear the women talking again. Unlike before, when I could hear them through the closed door, these were hushed tones that I could barely decipher even with the door opened. I could only imagine what Mommy was saying to Kylie. Requests? Permissions? Apologies, in advance, for stinky diapers?

I sighed, grabbing the shoes from the ground. I made my way back to the living room slowly, figuring I would give Mommy an extra few seconds to wrap up whatever secret conversation she was having with Kylie. Sure enough, by the time I returned, there was silence in the room. Both women wore suspiciously smug smiles.

“Thank you, Baby,” Mommy said, taking the shoes from me. “I suppose I should be on my way.”

My heart sank a little. We had never discussed why I wasn’t going to the conference with her. I could make a few assumptions–if nothing else, she wanted to keep me in my more infantile state for this trip. And I wasn’t exactly complaining either; the thought of strolling around a busy gathering like that in my diaper seemed like a recipe for humiliation.

I just wasn’t as fond of the alternative–being left alone with Kylie.

“You’ll behave yourself, yes?” Mommy asked me.

I nodded sheepishly, unable to even imagine a scenario where I ‘acted out.’

“Miss Kylie has the authority to paddle your bottom, if she so chooses.”

Kylie only offered a single “Heh,” that I couldn’t determine the meaning for. It seemed to land somewhere between ‘I’m not touching him,’ and ‘With pleasure.’

“I’ll be…good,” I said, startled at the deja vu I was experiencing from when I was an actual little boy being handed over to a babysitter.

“I’ll check in on you when I can,” Mommy said. “Otherwise, I’ll see you tonight. Kylie, you have my number.”

“Yes, ma’am.”

Ma’am. Her respect for Mommy worried me a little.

Then, the front door to the suite closed behind her, and Mommy was gone. Now, it was the Kylie and Baby show.

I think I had seen this particular scene before in cartoons and movies from my youth–the one where the child slowly turns around after the mother leaves the house, finding themself looking at the twisted grin of the mean babysitter.

“Looks like it’s just you and me now,” Kylie said.

“Yeah…”

“Look, I probably don’t have to say this, but let me remind you that this wasn’t my first pick for how I spent my day.”

“Nor mine,” I said.

“But,” she said, smiling a little, “being handed a pathetic boy in a diaper isn’t exactly the worst thing that could’ve happened today.”

It almost went without saying at this point–if someone new stumbled into my infantile life, they couldn’t be someone kind and supportive. They, too, wanted to have some laughs at my expense.

The fact that I might have enjoyed that was irrelevant to the point.

Kylie got up and strolled into the kitchen. It was my first time getting a good look at what she was wearing today–a short black skirt and a yellow top, with a cropped black cardigan over that. She literally looked like a queen bee.

“Can I get you something from the fridge?” she asked. It seemed a little too nice of her, until I remembered Mommy’s mention of the ‘special’ bottle she had made me.

“No, I think I’m good.”

Kylie returned, a bottle of hard lemonade in her hand.

“Starting early, aren’t you?” I asked.

She shrugged. “Got a problem with that?”

“N-no…”

She sat back down on the couch, crossing her legs as she took a long sip from her adult beverage. It wasn’t that long ago that I was 18–I could remember the same forbidden pleasure of alcohol that she seemed to be enjoying now.

“You don’t have to just stand there,” she said. “Sit down. Let’s chat.”

I hadn’t even realized I was still standing there, my infantile get-up still openly on display. I turned and started walking towards one of the other chairs in the room.

“No, dummy, sit on the ground, Like a baby.”

I felt a pang of humiliation. She was quickly finding her babysitter voice. Maybe a little too quickly. I sighed and did as she asked, plopping myself down on the ground, my diapered bottom making a dramatic FUMPH as I landed.

“So, are you, like, incontinent now?” she asked. “Did you forget how to use the potty like a big boy?” The way that her voice sneered as she asked her teasing question implied a history of being the bully.

“I can use a potty…er…toilet. You don’t just lose control.”

“But when’s the last time you used the bathroom?”

“It’s been a while.”

She laughed, clucking with satisfaction. “And you’re fine with this? Everyone else your age is going on dates and enjoying the best years of their lives. And you’re just…pissing yourself?”

I wasn’t sure what answer I could offer besides the truth: “I’m fine with this.”

She took another swig of her bottle, kicking it back like she’d been a bar regular for years. “What then? Is this the rest of your life? Are you going to be in your mid-30s and still crawling around in a diaper with a bonnet on your head?”

That doesn’t sound all that bad. “I don’t know. I think I’m just focusing on…now.”

“I get the appeal,” she said, before quickly adding: “...from Ms. Heller’s perspective. I don’t want someone pooping their pants around me, but I wouldn’t mind having some stupid little love-puppy following me around.”

I shrugged. To each their own.

“You want to be a good boy, right?”

I shrugged again. “Y-yeah…” My heart was already beating faster in anticipation of where this was going.

“I should get some practice in. Are you gonna do what I tell you to do?”

“I-if you want…”

“I do want,” she spat. “But, also, your Mommy put me in charge. So you’re going to do what I say, whether you like it or not.”

Ah, yes. Here she was: the brat. I wondered what ramifications there would be if I didn’t play along. Was she going to whine to Mommy? Would Mommy actually care?

Perhaps. Kylie might not have been Mommy, but she was acting as a representative of Mommy’s. An ambassador. And Mommy had, after all, told me to behave. It was safe to assume that ‘behaving’ meant listening to whatever it was Kylie asked.

I nodded. “Yes.”

“I like the sound of ‘Miss Kylie.’ Can you start calling me that?”

“Y-yes…Miss Kylie.”

“Hm. Yeah, I like that. Now, can you…crawl?”

She wasn’t asking me to do anything I hadn’t done plenty of already, so I was happy to be able to accommodate the request. Sitting on the ground, I was already halfway there–I just allowed myself to lean forward until my hands were on the ground. Then, it was just crawling. Like I always did.

“It’s a little annoying that I find this to be cute,” she said from the couch as she watched me do a little lap around the room. “Now, tell me that you’re a stupid little baby.”

I liked this request a little less than being asked to crawl, but it still wasn’t all that hard to do. If she asked me to say that I was a ‘fat-ass walrus,’ I would’ve said that too.

“I’m a, uh, stupid little baby.”

“Now, let’s put it all together,” she said. “Come crawl over to me. Then look up at me and say: ‘Miss Kylie, I’m a stupid little baby.’”

I could see where this was going. It was no different than the first morning I spent with Mommy. Or the first time I had revealed my diapers to Lyndie. It started small, but they always managed to quickly discover how much power they had. Kylie would be no exception.

I did exactly as she asked. I crawled back across the room again, only stopping when I was at her legs, briefly peering into the darkness between her legs in her skirt before guiding my eyes up to her face. My cock, once more, tried to expand in my cage, only to be thwarted.

“Miss Kylie…I’m a stupid little baby.”

She moaned with delight and clapped her hands together. “I take back what I said before. I think we are going to have a good day together.”