Doing Business, Part 40 (Patreon)

Holy crap. Has it been 40 chapters already? Well, if you need a recap...here are links to all previous chapters: https://www.patreon.com/posts/78092358

Forty

“Are you much of a drinker, Clarky?”

“I mean…I like beer, I guess.”

“You guess?”

I laughed. “I mean, it’s not my favorite, but…”

“There’s a social expectation for a man of your age to drink that sort of thing, and so you drink it out of obligation?”

“Uh…probably.”

I was sitting on the floor of the suite in just my diaper. Mommy had been kind enough to remove the remote-controlled plug from my ass, but had insisted I remain in my soggy and sticky diaper until it was ‘completely full.’ She was pouring herself a glass of wine, and I almost wondered if she’d be offering me a glass. She did not.

“Could I, uhm, ask you something?”

She carried her wine glass over to the sofa and took a seat, crossing her legs. “Of course, Baby. Anything.”

“How did…this start?”

“This? Be more specific.”

“Like…the diapers. Baby things. This whole corporate…kink…thing.”

“Ah,” she said, sitting back tapping the edge of the wine glass against her lip as she considered my question. “Asking the hard questions.”

“If you don’t want to talk about it, that’s okay. I was just curious.”

“It was my idea,” she said. “I suppose that shouldn’t come as any sort of surprise to you.”

“No,” I replied. “Not especially.”

“Well, here’s something that might surprise you: It all started because someone once put me in a diaper.”

She was right about that being surprising. I stared at her, eyes wide and mouth agape.

“I suppose you’d like to hear that story?”

“Uhm…” Yes, with every fiber of my being. “If…you wouldn’t mind?”

She settled into the couch a little further and uncrossed her legs. “Come up here. On my lap, baby. Mommy will tell you a little story.”

===

“I’d be embarrassed to tell you how long ago it was that this happened. So, we’ll keep it vague. Once, some time ago…”

Everyone has to start somewhere. Some people are lucky enough that they get to start at a slightly better place than everyone else–but I wasn’t that lucky. I started at the bottom.

Honestly, I think I preferred it that way. Considering where I am now, it seems that much more impressive that I started at the very bottom of the totem pole. I was in my mid-twenties and it was my first ‘big’ job, having just earned my masters degree a few months earlier. My ego had been a little inflated by the collegiate experience, admittedly–having earned the respect and praise of my teachers and peers. This translated into absolutely nothing when it came to the corporate world. I was given a cubicle and a few hours of training before being expected to figure the rest out for myself.

Within a week, supervisors and managers who had never properly introduced themselves to me were suddenly asking to see the progress I made, and minced few words when they were disappointed in my productivity.

My ego, suffice to say, was squashed almost immediately. I became a pathetic little shell of a woman, channeling more energy than I thought I had in me towards satisfying my superiors. I was coming into the office early, skipping meals, and staying late. I wasn’t taking care of myself.

Yet, all this sacrifice seemed to yield results. I was finally getting recognition for my contributions and the same superiors who criticized me before were finally getting off my back. I couldn’t take this opportunity to relax, of course. In my eyes, I thought this meant that I needed to work even harder to continue building my reputation.

But, wouldn’t you know it? All that additional work seemed to mean very little to the company as a whole. Around me, people were getting promoted. Men, mostly. People who knew people, if you know what I mean. Former frat bros with drinking problems who were probably present for the right game of golf, or something. Because they sure as hell weren’t being recognized for their hard work. I knew that because I was the one doing all their work.

For a while–probably longer than it should’ve been–I let it go. Eventually, I thought, my hard work and dedication would be recognized and I, too, would have earned my promotion.

But no. And perhaps you can imagine the reasons. Why would you relocate your best performing worker bee?

And so it became rather clear that if I felt I was due any sort of elevation in status, I’d need to be the one to initiate that conversation. I wasn’t about to go to my direct supervisor, though. Todd was a player in the office ‘boy’s club’ and had little time for me when I asked for something as simple as new office supplies. There was no chance that he’d offer me any more than an eye roll if I took my wants to him.

So I went above his head, our department director, Mr. Alexander. We had interacted only a handful of times, and I suspected he didn’t even know my name. I was worried that by even approaching him in the first place, I was putting my neck on the chopping block. But, at that point, I didn’t care much.

So be it, right? If the conversation went poorly, I’d probably want to be looking for a better job anyway. I scheduled a meeting with Mr. Alexander.

Nothing in my life had ever made me more nervous. I was terrified of the man. Terrified of the corporate ladder. Terrified of losing my job. Worse, my psyche might have been at its absolute lowest point–the months of overworking and not taking care of myself causing immeasurable damage to my well-being.

At first, I found him to be rather refreshing. He seemed warm and chatty–a welcome change from the cool and distant co-workers I was used to interacting with. He asked questions about my position and humored my suggestions on how we could improve efficiency within our department. Finally, he asked the big question: What did I actually want?

Still, I told him what I wanted, as calmly and coolly as I could. I told him that I wanted to be paid more. I wanted a promotion. I wanted to lead, and train new associates to do the good work that I knew I was doing.

And he said: “No.”

He fed me some lines about needing me to keep doing the good work I’ve been doing, and that maybe there was a chance–down the road–to discuss advancement opportunities. But for now, there wouldn’t be any changes.

I’m not proud to say that I lost my shit.

I stood up and berated the man for a solid ten minutes, going into detail about the amount of work I had done, the sacrifices I had made, and the nonchalant buffoonery of my co-workers that had been rewarded with promotions that I wasn’t getting. If I hadn’t actually said the words ‘I quit,’ in my little diatribe, I felt it was at least implied.

The man, to his credit, had maintained his calm and cool demeanor. He finally asked: “Are you done?”

“Yes,” I told him.

And I’ll never forget what he said to me next: “Did you really think you’d get what you wanted by coming in here and throwing a temper tantrum?”

To you, maybe it doesn’t sound like the worst thing he could’ve said to me. True, I suppose he could’ve said far worse. But at that moment, I found his words absolutely devastating. I was obliterated under the weight of that implication–that I had thrown a temper tantrum like I was just an angry toddler who needed her nap.

I made my way towards the door to his office, my head hung in shame. I was ready to just gather my belongings and leave the building. I assumed I’d just spend a few weeks sulking and crying before finally working up the courage to put myself out in the workforce again.

But he stopped me, calling me back to him. “Come here,” he said.

I was so defeated, so empty, that I just pivoted and walked back towards him. I braced myself, thinking that it was his turn, now, to berate me.

Instead, he beckoned for me to walk around his desk to where he was sitting. I couldn’t make any sense of the request, but I did it anyway.

“Not even my ten year-old daughter speaks to me like that,” he said to me. “And if she did, you better believe that I’d make her regret that. So you’re not going to just yell at me like that and be allowed to walk out of my office without consequences.”

“What are you going to do?” I asked. “Fire me? Because I think I already quit.”

“Nobody’s firing you, little girl,” he said. That ‘little girl’ further crushed my spirits. “Quit if you want, but I still need you to do your job.”

I had a brief glimpse of reality at that moment. I needed this job. I didn’t have the resources to live on my own without a job. I’d have to compose myself, calm down, and go back to work.

I told him: “Yes, sir.”

“Now, “ he said, “get over my knees.”

It still seems kind of surreal, when I think about it. I had tried to argue for my right to a promotion, and ended up getting pulled over my director’s lap and spanked in his office. Like a child.

And, believe it or not, it gets worse.

I hadn’t been taking care of myself–I told you that. Not only had I been skipping meals, but I had been putting off bathroom breaks for as long as possible every day. By the time Mr. Alexander had pulled up my skirt and began striking my ass with his flattened palm, my bladder was just about bursting at the seams.

I pissed myself on his lap as he spanked me. An absolute mess. He got it worse than I did, I think. My black panties and skirt would do a good enough job of concealing what I had done to myself until I got cleaned up. But Mr. Alexander’s pants weren’t so lucky–the beige pants had dark splotches all over them.

“Get out,” he said to me. “I’ll deal with you later.”

I couldn’t have ever predicted what being ‘dealt’ with looked like. He had already said he wasn’t going to fire me. What else could he do then? Tell everyone else I pissed my pants while he slapped my ass? It seemed unlikely–it’s never been exactly smiled upon to spank your employees.

All I could do was wait. And I waited for an entire week. After a few days, I had assumed that he had just forgotten about me. It didn’t change much for me. I was still working too much. Too hard. More than ever, I felt like I had to push myself because I needed to assure Mr. Alexander that I at least deserved the job I had.

And then, one day, he calls me to his office. You can probably imagine that my heart is just pounding in my chest. What is he going to say? What is he going to do, right?

I get there, and he immediately closes the door behind me. And I see it sitting there on the desk–a diaper. I knew what it was immediately. It was an adult diaper–which I don’t think I had ever seen before at that point, but I still knew what I was looking at.

He gave me an option that day. He said that if I laid down on the floor of his office, and allowed him to put that diaper on me–since I was nothing more than a ‘whiny, pissy, little toddler’–I’d be given a promotion. And, honestly, it wasn’t that hard of a decision. I wanted a promotion–that was all I had ever wanted. I wanted more money, and I wanted a little more authority–even if it meant sacrificing a little of my dignity.

That was that. Every morning, from that point on, I’d report to his office first thing in the morning. He’d do a thorough inspection of the panties I wore to work, making sure that I didn’t leave any stains in them. When he was satisfied with what he saw, he’d make me strip them off, and I’d lie down on the ground so that he could put a new diaper on me for the day.

In the afternoon, I’d be called into his office again. He’d inspect the diaper, just as he inspected my panties in the morning. If I was wet, I’d be pulled over his lap again, the diaper would be pulled down, and he’d spank my ass raw.

Would it be so hard to believe that I could be a naughty little girl? Save for, maybe, twice, every single time I got spanked for pissing my diaper, I had wet myself on purpose. I wish I was a little ballsier at that time. I’d have loved to see what he would’ve done if I pooped my pants.

This went on for about a year–and it was a pretty good year. Then, news came down from the top that things were changing. New ownership was coming, and a decent amount of management was being pushed out the door in the name of ‘new blood.’ Mr. Alexander was among that group.

It was surreal then, and even more surreal now, that we had maintained this strange little unethical routine for an entire year without it escalating into anything else. We never saw each other outside of work. We never had sex. We never so much as kissed. In hindsight, the entire year could almost be viewed as just a punishment for that one time I raised my voice to him.

I never really saw it that way. There was something there, albeit something that was hard to put into words. We had built something strange and special, and I was quite depressed at the prospect of having to move on in my life without him, his diapers, or his lap.

But the situation wasn’t all bad. I was chosen to be part of that ‘new blood,’ and I suddenly found myself in the surreal position of having Mr. Alexander’s job. And office. As it turned out, all that hard work and sacrifice had been noticed, and it was finally paying off.

The company, seeing a benefit in keeping me happy, offered me anything I wanted.

And do you know the first thing I thought of? I thought of sitting behind that big desk, as Mr. Alexander once had, and beckoning some naive pissant towards me so that I could check to see if they had wet the diaper I was making them wear.

I asked for an assistant. That was, of course, quite a few assistants ago. A completely different company too. Come to think of it, I don’t even think that company is around anymore.

I suppose there’s a few more stories that take place between when I had my first assistant and where I am today, with you. Another day, perhaps?

===

I had been so lost in her story, trying to imagine a younger Ms. Heller being hoisted over her boss’s lap in a wet diaper for a spanking, that it hadn’t realized that Mommy had been gently massaging the front of my diaper as she was speaking. I couldn’t get hard in my cage, but just her hand’s presence had been enough to keep me docile as I sat on her legs. Additionally, my thumb had, at some point, worked its way into my mouth and I just sat there suckling on myself.

“Does that answer your question?”

I nodded, slowly pulling my wet thumb from my mouth. “I have a few new questions now.”

“I’m sure you do, Baby. You’re a curious one, aren’t you?” She reached forward, playfully booping me on the nose.

It wasn’t exactly an invitation to ask another question or two, but she also hadn’t told me that she wasn’t going to be taking more questions. There were so many things I wanted to know about. The origins of the greater executive team’s proclivities with assistants. Hillary. The long term path for my relationship with Ms. Heller.

Instead, I spit out the first random question that floated to the top. “Do you ever, now, wear diapers?”

She laughed, stroking my cheek gently. “Would you like it if I did, Baby?”

“I…I dunno.” I suspected I would, though I could barely process such a mental image. Not while this cage was on my cock.

“It’s been a while. Back when Hillary still worked for me, I think that was the last time.”

“Did you wear them with her?”

“No,” she said, laughing. “I don’t think she knew about it. It was on a trip like this was one, actually–some sort of conference or convention. She had fallen asleep, and I had a little time to kill. I thought, for old time’s sake, I’d borrow one of hers and slip into it.”

“Did you like it?”

“I think I’m happier being a diaper-er, if I’m being honest. Maybe it comes down to that whole leaders and followers thing, you know? I wish I liked it more, but…maybe I’ve changed too many diapers to appreciate being in one again myself. I wish I liked it more.”

“Maybe it was because you were doing it by yourself,” I suggested. “I’m always happier when you’re taking care of my diapers for me.”

She laughed again. “Are you going to put me in a diaper, mister?”

“I…well…”

“Nobody making dirty diapers of their own should be putting others in diapers,” she said. “That’s just a rule.”

I felt my face warming a little. It was silly for me to have, however briefly, tried to imagine a world where I’d be putting her in a diaper.

“Speaking of which,” she added. “This diaper has been dry for far too long.”

“Oh…”

“Let’s fix that, shall we? Can you wet yourself for me, Baby?”

I didn’t think about it at all. She asked, and my body immediately listened. As her hand clutched the front of my diaper, my bladder emptied into it.

“That’s a good boy. You’re such a good baby, aren’t you?”

“Y-yes, Mommy. I am.”

“What do you think, Baby? Do you think that one day, you’ll grow up and become a big boy who has an assistant of your own? Or do you think you’ll just fill your diapers for me for the rest of your life?”

“If I was allowed to choose?” I said. “I’d…probably be your baby. Forever.”