Doing Business, Part 24 (Patreon)

Twenty-Four

Baby,

Things you’ll need to pack for our trip to Seattle:

• Toiletries and any health needs (medications, eyeglasses, etc)

There’s nothing you’ll need to bring, as I will be taking care of everything else.

-Mommy

***

It’s funny how quickly we adapt. What seems like a critical interruption of a daily process one day can seem like the new normal just two days later.

Just a few short weeks ago, I was using the bathrooms at work.

Then, suddenly, I was entering the office in a diaper. And exiting in another diaper. Sometimes there would even be another diaper in between the two. My morning routine now involved me bypassing my desk to directly report to Ms. Heller, who was always waiting for me–fresh diaper in hand. This, of course, meant wearing my morning piss from the moment I woke up until I got to work.

Wet diapers were sometimes handled in her office. Messy diapers–still not an everyday occurrence, thankfully–were handled at the Nursery. Trips to The Nursery seemed reserved for especially heavy diapers. Or when Ms. Heller just couldn’t make the time to change me herself. Or, probably, when she just wanted to see me squirm at having Lyndie change me.

It was all pretty weird when I thought about it, but I had adapted.

This–the trip to Seattle–didn’t feel like something I’d adapt to. It lacked that feeling of permanence. This wouldn’t be a part of the new normal in a week or two–this was a deliberate exception from the norm. This was far outside of even my newest comfort zones, and it didn’t help that the entire trip was an unknown to me. Where were we staying? What were her plans for our time together? Did anyone else know?

“You’ve got a look to you, sweetie,” Ms. Heller said as she changed my morning diaper on the floor of her office. I was on my back, my pants tossed aside, and she was between my legs, tending to wiping up the remnants of the puddle I had been sitting in for the last hour. “Stress, I bet.”

I didn’t respond. There was a pacifier in my mouth, but even if there wasn’t, I had nothing ready to say.

But she was right. This was the day we departed for Seattle. Work half-a-day and then we were headed to the airport. And after that? A giant question mark, and it scared the piss–quite literally–out of me and into my diaper.

“Nervous about Mommy and Baby’s big trip?” she cooed?

I nodded. Though, my stress was more than just travel.

I really should talk to Ava about what happened last night…

“I’m sure that it does feel overwhelming,” she continued. “But you do trust me, right?”

I was so prepared to offer an affirmative answer that I had to stop myself to really think about her question. It seemed obvious to a degree where iI wondered if it was a trick question.

Yes, I trusted her. Or, rather, I wanted to trust her. In a short time, she had brought a lot of chaos and humiliation into my life. I still didn’t know where her limits were–or if she had any at all. And while she had been doing a good job, thus far, of dancing on the line between professional office culture and kinky shenanigans, I still found myself bracing for the day she pushed our game a little too far.

Sick of not being responded to, she plucked the pacifier from my mouth. “You trust me, yes?”

“I do,” I said. The rest just sort of tumbled out, not completely processed: “And I want to trust you. But it feels like there’s so much at stake. And I never know what’s coming next. So…it’s pretty easy for me to be scared about it.”

She laughed, bending down to kiss me on the head. “Silly boy. I’ve said this before to you, and I’ll say it again: You’re not the only one with a reputation at stake. And, don’t forget, I’ve been doing things like this long before you ever stepped foot in my office.”

She was right. And I did know that–but it was sometimes easy to forget it.

“I’m going to humiliate you,” she said. “I’m going to make you into a tiny whimpering baby–the most pathetic you’ve ever felt. I promise you that. And I can do that because I trust you. I trust the other executives. I trust their assistants. I trust the infrastructure we’ve built here in this company. I just need your trust too.”

My cock strained against my cage–her promise of patheticness overloading my senses.

“I trust you,” I said. Any lingering doubts or hesitations were, at least temporarily, overridden by my ever-increasing need for the sexual release I couldn’t have.

“That’s a good boy,” she said, slipping a new diaper underneath me. “Seattle is going to be a lot of fun, you know?”

“I-is it?”

“Oh yes. New fun things for you to wear. Things to try. Diapers to ruin. I’d say more, but… Well, my panties are already getting a little damp just thinking about it all.”

Horny Clark–the frustrated bit of my subconscious who struggled the most with chastity–was now piloting my body. “Maybe I can help?”

“Help?” she asked, giggling. “With my wet panties?”

“I…I could…pleasure you. Mommy. Please?”

She smiled. “You are such a delight, baby boy.”

I was blushing. More importantly, I was beaming.

“I’m starting to think you might be a more advanced student.”

That certainty sounded good, but I was unsure what that meant. I tilted my head, feeling like a curious puppy dog–eager to hear my master elaborate.

“There’s this point in the career of an assistant–a baby, or whatever role an assistant around here is actually serving–where they no longer need to be told to do things. They just do them, because they already know it's expected. Or, even better, because they want to. And I sense you’re already well on that path. Sooner than it usually takes.”

I was flattered–but also a little concerned. Was I that submissive? Pathetic?

Oh, probably. There seemed to be little point in pretending that I wasn’t either of those things, or that it was wrong to be that way. Those were likely the qualities that Ms. Heller had identified in me in the first place.

It seemed best, for both of us, to just lean into it.

“Please?” I asked again–a juvenile tone unconsciously working its way into my speech. “C-can I taste you?”

“Of course,” she cooed. “You stay right there.”

She hiked her skirt up to her hips, but she left her panties on. Her body crawled over top of mine, until her bottom was positioned above my face. Slowly, carefully, she lowered herself and her damp panties onto my face. Had I been able to, I might’ve asked what she expected me to do. Was I to shift the panties aside? But my tongue was already reaching up, pushing into the bottom of the silky underpants.

I was tasting her. More specifically, I was tasting her panties, soaked through. She was finding her own rhythm, gently grinding over my nose and mouth. I did what I could, licking and stroking the cloth with my tongue. I was worried that it wouldn’t be enough–but her moans seemed to suggest the opposite.

Fuck. I wanted to be out of my cage so badly. If I didn’t explode out of the metal cage now, then the chastity artisan who crafted this unit deserved a raise. And if the cage itself didn’t burst into pieces, perhaps it would be my cock. How much strain was too much?

“Does that taste good?” she asked. “Is that what you wanted to taste?”

I couldn’t answer her. Surely she understood.

“If you are so desperate for a taste,” she said, sneaking her words in between deep breaths and groans, “perhaps I should let you take my panties with you. Carry them around in your pocket for whenever you need a taste.”

That sounded like the best idea I had ever heard.

“Or,” she continued, “at that point I might as well just have you walk around with my panties in your mouth for the rest of the day. That sounds nice, doesn’t it?”

Completely infeasible in an office. But I wished such a thing could happen.

“Keep going, Baby. You’re doing a very good job.”

She had a way of taking me out of space and time. I had no clue how long I was under her, cycling between massaging her with my tongue and suckling on the soaked panties, but if it had turned out to be either 30 seconds or an entire week, I’d have believed it. My own helpless desperation had been channeled into pure adrenaline, which I freely gave back to Ms. Heller.

And then she came, coating my face with a final burst of hot wetness that was forced through the panties.

“Now, where was I?” she finally said, after taking a few beats to recompose herself and slide off of my moist face. “Let’s finish getting you into this new diaper.”

Moments later, it was like nothing had happened. She was taping the new diaper on me, looking just as she did when I first laid on my back for her. It’d have been easy to convince myself that I had just imagined her brief residency on my face.

Except, a damp bit of cloth was suddenly forced into my hand while I was daydreaming. I quickly looked to see that I was, in fact, holding her wet panties.

“I won’t make you keep them in your mouth,” she said. “As fun as that would be. But consider that my reward to you for a job well done this morning. Do with them as you please, they’re yours now.”

Had I ever been given a better gift? I certainly couldn’t think of one.

“Thank you, Mommy.”

“Now then. As fun as playing with you is, Mommy should try and get a few things done before we head out on our trip.”

“Of course,” I said, nodding. “But…”

“Yes?”

“What shall I do in the meantime?”

No sooner than the words had left my mouth, I found myself worrying that I was opening myself up for some stinky, diaper-filling, task.

“Seeing as how you’re on track to mastering your role as ‘baby,’ perhaps it’s time you start working on the role of ‘assistant.’”

“I’m ready,” I said.

“We’ll start small this morning. Stay here with me in the office. Let’s start getting you acclimated to a normal day for me. You should take notes.”

I nodded, already exhilarated by the idea of shadowing her for the morning. “Let me just grab my notebook.”

“I should probably visit the restroom myself,” Ms. Heller said with a sly smile. “Since, you know, I can. One of the perks of being a Mommy and not a baby.”

I felt this pang in my gut–this overwhelming, but mostly undefined, feeling of lust. The very thought of her using a toilet caused my cock to strain itself in its cage again.

“Uhm.” Am I actually going to say this? “I…want that,” I said.

She laughed, raising her eyebrows. “I’m sorry? Baby, you’ll have to be more clear. I’m not sure what you mean.”

I wasn’t completely sure what I was saying myself. I wanted–that’s all I knew. I wanted…something?

“I just…”

I tried to shut off my brain so that I didn’t overthink it. What was it that I wanted her to do? Was I hoping she’d let me follow her into the bathroom so that I could watch her piss? I supposed that would be nice, but I was sure that there was something I wanted more than that.

A naughty smile spread across her face. I didn’t think she knew what it was I wanted either, but she still took delight in seeing me trying to figure it out.

“Yes?” she asked. “Go on. Tell Mommy what you want.”

“I want…you to use me,” I finally said. It was a half-formed thought, at best.

“I think we’re already there, sweetheart.”

“N-no, I mean…use me. My diaper.”

She slowly shook her head, as if unable to believe that I actually asked such a thing.

“I’m sorry,” I said, sighing. “I shouldn’t have asked that. It was just this ridiculous little thought that I probably should’ve ignored and–”

“Stop,” she said, reaching out to me and putting a finger over my lips. “I think it’s a good idea. A great idea. You just never cease to amaze me, that’s all.”

With my dirty thought having been said aloud–and even with her approval–I felt guilty. Shameful. The pathetic musings of someone in such need for sexual release that I’d say just about anything.

“I’ll just get my notebook,” I said, her finger still planted on my lips.

“Stop,” she said again. “I only wish you had told me before I put this diaper on you. But I’m not going to let that stop me.”

“So…”

“So get down on your back again, Baby.”

I did as I was asked, feeling both anxious and excited about what was to happen next. I thought I knew what was about to happen, though neither of us had explicitly stated it aloud. What if I was wrong?

It didn’t matter. Regardless of what she did, I’d love it.

She began peeling back the tapes of the diaper she had just put me in. “Fuck. These tapes are stronger than I thought–I can’t open the diaper without ripping the plastic.”

Did this mean she would stop? No, she brute-forced her way through the tapes, tearing each up from the diaper regardless of the consequences.

“I hate to waste a diaper,” she said as she returned to her cabinet to fetch a new diaper. “But sometimes, minor sacrifices need to be made.”

I suddenly remembered that my pacifier was still in my hand, and I knew where it belonged. It was back in my mouth by the time she carried the new diaper back to me.

“You’re almost too good at being a baby,” she said, looking down at me. “Though that’s hardly a bad thing.”

I took it as a compliment.

She pulled the diaper I had only briefly worn out from under me with a single firm pull before casting it aside. The brand new diaper was unfolded and once more slid under my bottom.

“There’s multiple ways that we could do this,” she said. “As with most things, repeat experimentation will reveal the most effective method.”

Translation: This wouldn’t be the last time we did something like this.

I glanced towards the closed door on the other side of her office–her private bathroom. A toilet was never far from her. It’d have been so quick and easy for her to just walk a few feet to do her business. But, no, she wanted to do this–just as much as I wanted it. I wondered if that would ever stop feeling so astonishing.

She hiked her skirt up to her waist once more, revealing her bare skin. Her panties were still clutched tightly in my other hand. It was unclear to me if she was just figuring things out as she went, or if she already had a plan in place–but she moved as if this was something she had done a hundred times before. She squatted down over my caged cock, facing me. Looking me directly in the eyes.

And then it happened. I probably could’ve moved my head to get a better view of the action, but my gaze remained fixed on her eyes. Instead, I experienced her pissing in every other way. The sound of her urine cascading over my cage, through my legs, and into the puddle forming in my diaper. The feeling of the hot liquid on my skin. The slightest change in scent of my new diaper. All while we peered into each other's eyes.

“There,” she said, as the final drops splashed down on my crotch. “I think that should do it. May I see my panties?”

I lifted my hand, presenting her with the already damp bundle of cloth she had given me moments ago. She took it, wiping herself with it before depositing it back into my hand again.

Neither of us said anything as she quickly pulled the front of my diaper through my legs and taped it shut–sealing me into the wet diaper of her making. There probably wasn’t anything left to say at that point. From my vantage point, it only seemed to make the moment feel even more forbidden and naughty.

I was back on my feet again, feeling the heavy diaper flumph into a sag between my legs. Even if I had wanted to, I couldn’t have put into words how exhilarated I felt. I was both ‘baby’ and Mommy’s toilet. I wanted more. I wanted everything.

As I slipped back into my pants, it occurred to me how different this wet diaper was from every other wet diaper I had experienced over the last week or three. Aside from the alien feeling of it being someone else’s weirdness, the sagging bulk seemed to come from a different part of the diaper. Just a little bit–but enough to make it feel unique. It made it hard to just let the feeling of the wet diaper fade into the background. Instead, Ms. Heller’s wetness felt everpresent and firmly lodged into the forefront of my mind.

“Now then,” she finally said. “I’m ready to get to work. Did you need to grab your notebook?”

I nodded.

“Go on then, Baby. Fetch it and be back quickly.”

Worse things have happened in my time as an office baby. A few days ago, I had been paraded from Ms. Heller’s office to Lyndie’s nursery with an abhorrently dirty diaper on. But there was something about waddling around in a diaper that was wet with Mommy’s pee that struck nerves that seemed previously unstruck.

I hastily trotted to my desk and grabbed my sketchbook, looking around to see if anyone was watching me. I tried not to let myself succumb to such paranoia, for fear of it becoming all-consuming. But I was feeling especially obvious in this heavy diaper and I couldn’t help myself.

There were eyes. Just a few. Peering up from cubicles and around corners. Quick glances. Skeptical grimaces. Maybe it was nothing–maybe these people just looked at everyone who walked by.

But…maybe not. Should have I been paying more attention? Were gossip and rumors starting to spread? Had anyone figured out–or even speculated–that there was a diaper-filling baby in their midst?

I regretted opening up that door, and I hustled back to Mommy’s office. I was more ready than ever to be whisked away for a few days. To a place where nobody knew who I was.

Or what I was.