Doing Business, Part 19 (Patreon)

[Hello, readers. Welcome to Season 2 of Doing Business. It is, very much, a continuation of the story you've come to love so far - and its own little tale. As always, thank you for reading!]

Nineteen

From: Human Resources <hr-services@xxxxxxxxx>

Date: Monday, March 28 at 9:00 AM

To: All Employees

Cc:

Subject: Promotions

Hi Team,

Happy Monday, everyone! Please help me in extending congratulations to some of your teammates, whose exemplary work has earned them promotions.

• Clark Ashburn has been promoted from his internship to Executive Assistant, reporting directly to CEO Gabrielle Heller.
• Lyndie Brown has been promoted from her internship to Special Projects Coordinator, reporting to the executive team.

Clark and Lyndie, congratulations! We are very excited to see what great things lie ahead for you on our team.

***

Every once in a while I’d pinch myself or stomp on my own foot–just to see if I’d jostle myself from a deep slumber. I sometimes wondered if I’d wake up back in a world where I was still a lowly intern and I had never met the CEO. In fact, when I asked about Gabrielle Heller, I’d be told that nobody by that name ever existed.

It wasn’t that I wanted it to be a dream. But things had become so extreme–so quickly–that it sometimes seemed like the only explanation.

Alas, the crinkling in my pants seemed real. The chastity device secured around my cock most certainly felt real.

This was reality now.

The last few days–the weekend that followed my initiation into the office’s strange kink-cult–had been a bit of a blur for me. I had spent most of the time cooped up in my apartment, cycling through every emotion possible. Shame and regret. Then humiliation. Then excitement and pleasure. Followed soon after by worry and concern. And somewhere around that point, the cycle would start all over again.

I was exhausted.

I read HR’s company-wide memo on my phone as I stepped off the elevator and walked back towards The Closet. This was it. My new position was official.

The door to The Closet wasn’t budging.

“Did you forget already?” a voice asked from behind me. Ava.

“Good morning,” I said, bashfully waving. It was still hard to look her in the eyes–we shared a secret shame, and I still had no idea how to just candidly talk about it at the office.

“I think this room has gone back to just being a closet,” she said. “You have a new desk now.”

“Oh, right,” I said, scratching my head.

Ms. Heller–Mommy, as I was to call her when it made sense to–had mentioned my new desk to me before we broke for the weekend, but somewhere in my emotional cycle I seemed to have forgotten about that.

“Come on,” Ava said. “I’ll show you.”

I didn’t actually need Ava to show me where my new desk was. Ms. Heller had been rather clear that it would be directly in front of her office, and I was sure that the plan hadn’t changed any. Still, I followed Ava anyway, finding myself staring at her bottom as we walked. Her plaid skirt reminded me of the uniforms the Catholic school girls used to wear in my neighborhood when I was younger. It was cute–by design, no doubt. Was this how Ms. Beaufort preferred that she dressed, or was this Ava’s choice? There was so little between her diaper and the eyes of everyone else in the office.

I glanced at some of the employees that we walked past. So many people. So many cubicles. So many faces that looked completely unfamiliar to me. It only served to reiterate the stakes of the game that we were playing. All these people, and they were somehow oblivious to what was going on? It seemed unsustainable. Someday, if it hadn’t happened already, someone was going to find out something they shouldn’t have. And then what?

The very thought almost gave me a panic attack. I took some deep breaths and trudged forward. Whatever Ms. Heller and her friends were doing to keep this under wraps must’ve been working enough so that they could keep doing it.

“You alright?” Ava asked, perhaps hearing my heavy breathing.

“Overwhelmed,” I said, being a little more honest than I had intended to be.

She laughed. “You’ll be okay.”

“Do you know where Lyndie is?” I asked. “I assume she has a new desk too.”

“I assume so too,” she said. “I’m not completely sure where it would be though. But I can find out for you.”

I liked Ava, and I could see what Ms. Beaufort saw in her–she was dedicated and trustworthy. A loyal puppy.

“I could probably just ask Ms. Heller too,” I said.

I found myself missing Lyndie almost as much as I was missing Mommy. She had become a close friend, and quite possibly the only person I could talk to about these things candidly. But I hadn’t been all that great of a friend the past weekend–ignoring a number of her text messages checking in on me.

I hoped to see her today, if for no other reason so that I could apologize.

“Here you are,” Ava said, pointing to the desk. It was exactly where I thought it’d be–directly in front of Ms. Heller’s office.

“Thank you,” I said.

“Of course.”

“Do you, uh, want to go get some breakfast with me?” I asked, suddenly feeling a little desperate for some sort of companionship.

“I wish I could,” she said. “Mommy…er…Ms. Beaufort is, uhm, feeding me this morning.”

Oh right. I recalled the taste of Ms. Beaufort’s breastmilk on my tongue. If Ava gets to experience that everyday, she’s a very lucky girl.

“Enjoy that,” I say.

She giggles a little behind her hand. “I always do. I’ll talk to you later.”

“Later.”

“Oh, Clark?”

“Yeah?”

“I’m really happy you’ve joined us,” Ava said. She doesn’t specify who ‘us’ is, but she doesn’t have to.

“I am too.”

I’m pretty sure I mean that.

My new cubicle disappoints me a little. While I do like where it’s located, it feels far too exposed for someone in…my position. I’m used to The Closet. Secrecy and a locking door. Instead, I feel like I’m on display.

I sat down in my new chair for the first time, finding it to be much firmer than my old one. My diaper crinkles loudly as I lower myself into it, suggesting that this was a chair was picked out by Ms. Heller herself.

Of course, to be reminded of my diaper is to be reminded of my chastity. Its presence still feels alien to me.Not only haven’t I gotten used to it, but it feels like I’ll never truly adjust. I just feel it at all times. The way it constricts. The weight of it, hanging between my legs. The awkward discomfort I feel when my cock even attempts to grow a little stiffer.

I can recall entire weeks where I didn’t masturbate. It wasn’t even something I planned for–I would just get busy with life and suddenly I’d realize that it’s been a while since I last touched myself. But now, starting just my fourth day in the cage, all I can think about is masturbating.

What’s that song? You don’t know what you got ‘til it’s gone.

Lyndie would have loved to hear me say that. She’d get a good laugh out of it.

“Settling in, I see,” a new voice said.

It’s Ms. Heller herself. Mommy.

“Y-yes,” I said, standing up suddenly like I had to salute her. “Good morning.”

“Did you have a good weekend?” she asked.

That’s certainly a tricky question. “Yes…”

“Come join me in my office. We should go over a few things. Your new responsibilities, for one. But also, the current state of your d–”

“Yes,” I said quickly. “Let’s go talk about that, uh, in your office.”

I follow her inside so that she can close, and lock, the door.

“First thing’s first,” she said. “I assume that you got the shipment of diapers I sent to your house without incident?”

“Uh, y-yes, Mommy,” I replied. Evan had been the one to receive them, of course. Just as he had wasted little time in texting me that my new diapers had arrived–throwing in a few humiliating infantile-themed emojis for good measure.

“And you were a good boy who wore his diapers all weekend?”

“Yes, Mommy.”

“And what about this morning’s diaper?” she asked. “Is it ready to be changed?”

“I…I haven’t…”

But she was already checking for herself. My belt was suddenly unbuckled and my pants were falling to the ground–as tended to happen when I was around her.

“Still dry,” she mused aloud. “I’m a little disappointed, if I’m being honest. I was hoping you’d come back to work today with a real disaster of a diaper for me.”

“I changed before I came to work,” I said.

I already knew this was going to be an issue. I had even told myself the night before that I’d leave my diaper on in the morning until I got to work. And what was the first thing I had done this morning? Changed my diaper. Without a second thought–like it was a completely normal part of my morning routine.

“Well then,” she said. “Let’s put that at the top of the list of things for you to do today. I’m going to need to see a dirty diaper by lunchtime.”

“D-dirty?”

“I’d have accepted just a wet diaper if that’s what you came to work with,” she said. “But coming into my office, first thing in the morning, with a dry diaper? Well, I’m going to need to see more commitment to your new role than that. A better ROI, if you know what I mean.”

“So you want me to…”

“Fill your pampers? Yes, that’s right. You owe me a stinky load in the back of your diaper, young man.”

“And if I don’t?”

“Oh, Clark. You’ve been such a good little boy so far,” she said, giving my diapered ass a firm swat. “I doubt you’d want to let me down. So let’s not even worry about silly things like consequences. You just focus on the task at hand. I’m sure you’ll get this project done.”

“You, uhm, also said that you wanted to go over my duties and responsibilities as your assistant?”

“I did say that,” she said, arms crossed in front of her. “But I worry about giving you too much to do so soon–especially when you’re not even able to do something as simple as not changing your own diaper before coming to work. So, instead, you only have the one task this morning.”

“My diaper?”

She nodded. “Exactly. You work on making a smelly diaper for Mommy, okay? And you come back and see me when you’re all done.”

“By…lunchtime?” I asked.

“Exactly. Now, off you go.”

I slowly began to turn back towards the door to her office, only to be reminded by the awkward tension at my feet that my pants were still pulled down.

Ms. Heller laughed, clearly delighted by my foolishness. “It’s like watching an actual toddler sometimes.”

My pants were pulled back up and buckled into place, once again sealing my diaper.

“Oh, and I almost forgot,” she said, stepping towards me again. Her hand reached between my legs, cupping the front of the diaper. I could feel her gently squeezing on my cage through the diaper. “I’m happy to see this is still in its proper place. I suppose you haven’t forgotten that it’s been there, hmm?”

“No, Mommy.”

“And how do you feel about it so far?”

“It’s…” I was at a loss for words. Did I put on a stoic show and tell her that I was dealing with it just fine thus far? Or did I tell her the truth–that I was already reeling from having been cut off from touching myself? “...a new experience. That’s for sure.”

“I bet,” she said, playfully biting her bottom lip. “Obviously it’s nothing I can experience for myself. But I’ve heard what others have said about being all locked up like that. I understand that it can be quite uncomfortable at times.”

I thought back on my secluded weekend, and how if it weren’t for the cage, I’d likely have masturbated my way through my time alone. Instead, I spent a lot of time trying to adapt to the tightness of the device when I started to get excited again.

“It can be,” I said.

“And, being the excitable little boy that you are, I’m sure it doesn’t take much to get you all riled up.”

“N-no, Mommy.”

For the second time that morning, she unfastened my belt and let my pants tumble to the ground again, leaving me standing before her in my diaper. She rubbed the front of the diaper, focusing on the hard area where my caged cock was helplessly stationed. I wanted to get hard, very badly. I felt myself straining against the metal cage.

“So I’m sure that this isn’t helping at all,” she said.

I shook my head.

“And what if I did this?”

She reached down to her knees, where the hem of her dark gray dress hung. She grabbed the cloth and pulled it straight up, revealing that she was not wearing any panties at all. A clean strip of womanly pubic hair seemed to point right into glistening lips.

“Mm,” a short moan squeezed its way out from my mouth.

As one hand held up her dress, the other slowly slid down her body and between her legs. Her fingers lingered for a moment, seeming to tease the possibility of whether or not she was going to actually touch herself.

And then she did. At first, it was just her middle finger that she eased into herself–summoning a long slow groan from herself. I watched that lone finger slide out of her, clearly wet now, before it was plunged back in. I watched her do this a few times.

“Does that–mmm–help your little cock?” she asked.

The cage had never felt as tight as it did at that moment. I felt as if my manhood was about to expand with such ferocity that it would obliterate the cage. Like the Incredible Hulk’s cock in a chastity device–or at least that’s what I was imagining.

But I wouldn’t be busting out of my cage, no matter how turned on I was.

“Fuck,” she muttered. “Look at me, turning myself on. I just wanted to tease you a little. But now I’ve got it in my head that I need a good fuck. I really wish you could help me with that, Baby.”

I opened my mouth, but I had no idea what response I could possibly offer beyond begging for her to unlock me. Which I was sure she wouldn’t do.

“God, wouldn’t you just love that?” she asked. “If I let you fuck me?”

“Y-yes, Mommy.” I cracked a little, my patheticness showing through as I added: “Please?”

“Oh, I’m afraid I couldn’t allow for that. I mean, for one, that cock is staying in its cage. But could you even imagine me allowing someone in a diaper to fuck me?” She laughed, shaking her head while her fingers–two of them now–continued to slowly slip in and out of her. “That’s just not going to happen.”

My hand grasped the front of my diaper, hopelessly rubbing my contained manhood–as if I had a chance of somehow releasing myself by sheer determination alone.

“But I could give you a little treat,” she said.

“A…treat?”

“Obviously, I can’t let you actually fuck me. But I could give you a little glimpse as to what that might be like.”

I said nothing, simultaneously nervous and uncertain about what she meant.

She turned and walked over to her desk. She leaned forward, placing her palms on the top of it, before bending over so that her perfect ass popped up into the air.

“Come here,” she said.

I did as she asked, stepping out of my slacks and walking behind her.

“Lift up my dress. All the way up.”

I did as she asked, her bare ass just inches from my diaper.

“Come forward,” she instructed. “Press your little cocklette against me.”

I didn’t need to be told twice. Cage or no cage, I had an instinctual need to have her body pressed against mine. I took one step forward, guiding my diapered and caged cock into the moist warmth between her legs.

She did all the work, her body immediately beginning to grind against my diaper. It was amazing to watch her at work–she moved with such grace. I could only imagine what it’d have been like if I was allowed to be out of the cage. Out of the diaper. My cock deep inside of her.

“Put your hands on my hips,” she said. “Go on and try humping my ass like you weren’t just a little baby boy.”

I didn’t need to be told twice. I pathetically rubbed my padded crotch against her, while she simultaneously ground herself against the caged lump within it. It became quite evident that she was managing to get herself off by rubbing herself against my useless manhood.

“That’s…that’s perfect,” she said between moans. “Oh, little boy, you have no idea what you’re missing.”

I was pretty sure I did.

“I want you to–unnnh–think about this later when you’re pushing a stinky mess into your diaper, okay? Think about how close you are to my perfect pussy while you’re filling your pants up.”

Oh, that won’t be a problem.

At last, her body pulled away from mine as she let out a few final moans. I’d heard those specific moans before–when she rode my face like it was a bicycle. She had gotten exactly what she wanted.

“There we go,” she said, laughing to herself. “That’s what I needed. Like a morning cup of coffee, you know?”

She straightened herself out, letting her dress fall back into place, covering up her shapely ass so quickly, its exposure suddenly seemed like a fever dream I had briefly.

She cleared her throat and stretched, a wide smile on her face. “Now then. I’ve got some things to do. As do you. You remember your task, yes?”

“Y-yes, Mommy,” I said, still a little shellshocked as I stood there, looking down at the glistening wetness she left on the front of my diaper.

“And, what was that task?”

“I, uhm, have to…mess my diaper? By lunchtime.”

“Good boy,” she cooed. “Now run along. I look forward to seeing you later.”

I pulled up my pants and slowly shuffled out of her office. One would think that the prospect of coordinating a moment to use my diaper in the office would be at the forefront of my mind, but no. I was still thinking about my hands on her hips, my diaper rubbing against her.

I’d probably be thinking about that for a long time.