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Doing Business [Season 4] [Part 79 posted on 4/26/2024]


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I just found this story and I think the writing is very good. I agree with Babypants that some additional character development showing how they developed their “adult” personalities. On the other hand I think taking the spin of having this happen in a corporate executive suite is an interesting spin. Keep up the great work.

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Twenty-Five

You have [ONE] new voice mail:

“Hey Clark, it’s Ava. About last night…maybe we can talk about it sometime soon? Whenever you’re ready. You know where to find me.”

***

The haze of the rapidly-approaching trip with Ms. Heller had consumed almost all of my thoughts. There were other things that I should’ve been thinking about, but they had been pushed to the backburners of my mind. The burners way in the back.

I had listened to Ava’s voicemail that morning in my apartment before going to work. I was not only surprised that she reached out so soon, but that she reached out at all. I was kind of hoping the moment she was referring to–an all-too brief blip at the very end of her visit to my place–would’ve just been forgotten or disregarded.

I did want to talk to her. I just didn’t know what I was going to say yet. And there were just so many things on my mind…

“As much as I’d love to take you aboard a flight in your current state,” Ms. Heller said, her hand reaching between my legs to squeeze the bloated diaper that held her piss, “perhaps it’s time to get you into a fresh diaper.”

I had been shadowing her most of the morning, watching her every move and taking notes. She took calls and meetings. Sent emails. Consulted charts and graphs, all while pointing out the key details for an assistant like myself. Most of that time had been spent behind her desk with her, without pants–just marinating in the soggy padding of Mommy’s doing. Even when Ms. Beaufort came to visit.

“If you think that’s for the best,” I said.

She laughed, shaking her head. “You’re almost too much of a pushover sometimes, Baby. Which isn’t a complaint–to be clear. But eventually you’ll need to use a diaper for yourself. And this one feels about a drop away from being the Exxon Valdez. For your sake, and my sake–and the sake of everyone else on our plane later–I think a new diaper is in order.”

She was right, of course. I simply wasn’t ready to take off this diaper yet. I didn’t have a choice in the matter, however, and she once again changed me on the floor of her office. I was tempted to ask her if I could keep the old diaper. I had no idea what I’d do with such a thing…maybe just hold it in my hands. Maybe I’d sniff at it. It just felt like a crime to throw away something so steeped in her pee.

I said nothing, of course. There was no shortage of things for her to humiliate me with. I’d be doing myself no favors by adding another to the list.

“We’ll have to leave soon,” she said. “You brought your bag with you?”

“Yes, Mommy,” I said, nodding. “It’s at my desk.”

“And what all did you bring?”

“Not much…”

“Perfect,” she said, smiling.

Soon, my pants were finally back on, I was shutting down my work computer, and I was grabbing my bookbag.

This was it. Into the great unknown, led by the hand by my boss-turned-Mommy.

I suddenly remembered Ava’s voicemail. I quickly typed out a text to her:

“Hey. I’m not ignoring you. Just been busy this morning. And about to go to the airport with Ms. Heller soon. I don’t know when I’ll have a chance to chat. But I don’t want you to think you’re being ignored.”

Send.

Her response came swiftly:

“Don’t worry about it. Everything’s good. Have a safe trip, and I’ll see you when you come back.”

I didn’t believe her, nor did I want that to be the end of the conversation. Sadly, I’d just have to come back to this later and hope that she’d be willing to revisit this.

“How are you feeling?” Ms. Heller asked me as her Range Rover rolled out of the parking garage and onto the highway. We still had a 45 minute drive ahead of us to get to the airport.

That was a complicated question, but I took my best shot at summing up the answer: “Anxious. But, tentatively, excited.”

“For as good at being a baby as you are, you’re still too adult sometimes too.”

“H-how so?”

“Anxieties? Babies don’t have those.”

“Maybe they do,” I said. “That’s why they’re crying all the time.”

She laughed–a genuine and hearty chuckle. “Are you usually funny? I don’t know if I’ve ever thought of you as a particularly funny baby.”

“I have my moments,” I said. “But I don’t think I’m known for being particularly funny all the time.”

“What are you known for?” she asked.

“As of late? Uh…messing my diaper.”

I scored another laugh from her. “Fair enough.”

Truth was, this was what I had been looking forward to the most–these moments where it was just her and I, talking. No elaborately humiliating scheme. No other people. Just the two of us, talking.

“I’m going to be taking care of you,” she said. “Did I not say that enough? What else can I do to ease your anxieties?”

“I’m good,” I said. “Really. I just had a long night and…”

“Ava and Lyndie came over to your place, is that right?”

“Y-you know about that?”

She laughed, her gaze still set on the road ahead of her. “Is that really all that surprising, Baby? I know everything. It’s my job to know. I’m Mommy.”

“I didn’t realize that…”

“Ava tells Neve every little thing she does. Ava farts into her diaper, and Neve probably gets a three-paragraph report about it in her email within 10 minutes. So, of course, she told Neve yesterday that she was invited over to your apartment yesterday. And, in turn, Neve told me.”

“I…I’m sorry that I didn’t tell you myself. I didn’t think that you’d want to know…”

“You’ve been under no obligation to tell me what you do in your life outside of work,” she said. “Did you have a good time?”

I sighed. “I had a good time…”

“I feel a ‘but’ coming.”

“I-it’s nothing…”

“Oh come now, Baby. That’s what mommies are for, yes? To listen? Comfort? No matter how trivial you think your little problem is.”

I took a deep breath. I did want to talk about it with someone. In a perfect world, maybe I’d have shared this sort of thing with Lyndie. Sure, she’d probably tease me a little. But she’d eventually listen. Such ‘big sister’ energy. In her absence, though, maybe Mommy really was who I should be sharing this sort of thing with.

“Ava kissed me last night.”

I watched her eyes widen as she continued to stare out the windshield. “Oh?”

“Well…she tried. I guess…she actually did kiss me–I just didn’t reciprocate?”

“No? Don’t you find her to be quite adorable?”

“Y-yes, of course I do. I think she’s very cute. And very nice. I-I just wasn’t expecting it and…I was afraid.”

“Afraid?” She laughed again, shaking her head. “Afraid of what? Ava might be the only person with a chance of being a bigger baby than you.”

“No, not afraid of her,” I said. I swallowed hard, not sure if I wanted to admit this aloud or not. But, here went nothing: “Afraid of you.”

“Hmm.” Ms. Heller took a beat or two to think about that as she drove. “I suppose we should unpack that, yes?”

I shrugged.

“Why on earth would you be afraid of me?”

“Because…I’m your…baby?”

“And that means you can’t be kissed by other girls?”

“I don’t know,” I said, shaking my head. “I just…I’m yours. You know?”

“Mm,” she moaned. “Well, fuck. That just melts me a little, if I’m being honest. Such dedication. You might have earned yourself a few minutes out of your cage tonight.”

That certainly got my attention. Just the thought of release made my cock attempt to expand, straining against the warm steel of the cage.

“Do you think that I’d forbid you from kissing someone else?”

I shrugged. “We never talked about it. And, given my track record with romance, I didn’t think that it was ever going to come up.”

“Do you have feelings for Ava?”

“She’s really nice,” I said. “I like her. But…it’s hard for me to have feelings for anyone right now when I’m so enamored by you, Mommy.”

“Sometimes I wonder if you’re a robot.”

“A…robot? Do you think that I sound…fake?”

“No, no, Baby. I simply mean that you say all the right things, all the time. It’s too good to be true.”

“I feel the same way about you,” I said. “For all the humiliation and embarrassment…it all still feels, surreally, too good to be true.”

She took a hand off of the steering wheel and reached over into my lap, squeezing the thick padding between my legs through my pants. Goddamn, I wanted release from this cage so badly.

“I’m glad you talked to me about Ava, Baby.”

“P-please don’t be mad at her. Or get her in trouble with Ms. Beaufort.”

“I could never be mad at Ava,” she said. “I’ll likely tell Neve. But only because we tell each other these sorts of things. Nobody’s going to be upset about it.”

I nodded.

“I have no opinion on you and Ava making little kissy-faces at each other, if that’s what you choose,” she said, squeezing my diaper again. “I understand that it’s not something you want right now. But maybe someday you will.”

“M-maybe.”

Do I regret not kissing Ava back? Absolutely.

“Will you come to me if you change your mind?” she asked. “Will you come tell Mommy when you feel a special way about another little girl–whether it’s Ava or someone else?”

“W-would you like me to, Mommy?”

“Yes.”

The very thought of such a conversation sent a shudder right through me. I could barely even imagine what that conversation would look like. “Mommy, may I please fuck Ava?

“You’re such a good boy.”

“I’m trying.”

“I showed another man the key to your cage the other day,” she said, apropos of nothing.

“Y-you did? Who?”

“Oh, you wouldn’t know him. Unless, of course, you’re up to date on all the hot-shot hedge fund managers in the city.”

“No…”

“To be honest, he’s not really my type,” she said, shrugging. “He’s handsome and well-mannered and such. I’m sure he’s husband material. But I think I’m broken, because I just have little-to-no interest in a man who I don’t have to take care of.”

I turned back to face her again. I liked hearing her talk about herself.

“He’s a regular at my gym, though,” she continued. “So we see each other often. We do a fair amount of flirting. Which, you know, is whatever–I flirt with a lot of men. I’m good at it, and it gets me what I want quite often. But this guy–Rick–he’s probably the closest thing there is to a nice, normal, man who I’d actually entertain the idea of going on a date with. He’s vanilla, of course. Not even, like, french vanilla–whatever that is.”

“With french vanilla,” I said, “the ice cream is made with an egg custard.”

She laughed, and gave my diaper another playful squeeze. “What a smart little baby.”

I shrugged.

“We met up at the juice bar the other day,” she continued. “He bought me some sort of dragonfruit thing. Honestly, I don’t really get those healthy juices. No matter what you order, it always comes out looking green and tasting like bananas.”

“I…wouldn’t know.”

“Anyway, he sees this chain hanging around my neck, right? He asks if it has any special meaning for me.”

“D-did you tell him?”

“Even at my most flirtatious, Baby, I’m not one to lie. I hoisted your key right out of my cleavage and I showed it to him. I said that this key was for something very important to me.”

“What did he say?”

“Well, obviously, he wanted to know what was so important that it was locked up, with the key remaining in my position, and around my neck, at all times. And I told him the truth: I had locked up my new assistant’s little cock in a cage. I didn’t mention the diapers. Not this time.”

My heart was pounding. I felt humiliated, and I wasn’t even present for that conversation. It was with a man that I would, likely, never even meet.

“W-what did he say to that?”

She shrugged. “He laughed. He thought I was joking. He did admit that he didn’t quite get the joke, but I think he just assumed that I had some weird sense of humor. I didn’t correct him. I didn’t really care to. I could’ve shown him some pictures, I guess. But it didn’t seem all that important in the moment.”

A little sigh of relief from me.

“I may keep him around yet,” she admitted. “I doubt I’ll actually ever come around on having romantic feelings for him. But maybe I’ll have a use for him someday.”

“A use?” I asked.

“Sure. Maybe it’d be fun to fuck with him a little one night. Invite him over for a nightcap, and let him play with my pussy a little. Then, maybe, we hear a sound on the baby monitor. I tell him we should check on the baby. He, of course, would be confused–I’ve never mentioned having a baby before, you know? He follows me to the nursery. And there you are, lying on your back in your big diaper. All fussy because you’ve filled it to the brim.”

“I…I don’t know…” My face felt like it was melting off of my skull. I couldn’t breathe. Was it possible to feel both incredibly hot and incredibly cold at the same time?

She laughed. “I’m teasing you, Baby. I swear, it’s too easy.”

I took a few deep breaths and attempted to center myself again. The problem continued to be my locked up cock. I had never gone this long without being able to touch myself before, and the lack of relief seemed only to heighten every emotion and thought of mine.

Per the sign on the side of the highway, the airport was only a few miles away now.

“How’s your diaper holding up?” she asked.

“It’s dry, Mommy.”

“I’ll change you again at the airport, if you need it. Otherwise, you’ll be flying in the diaper you’re wearing now. Do with that information what you will.”

Sound advice. If I wanted to spare myself the potential humiliation of being stuck in a dirty diaper for the entire flight, my best bet was to use the diaper now.

And that was the thing about exclusively wearing and using diapers for the last few weeks–it seemed that I was just always on the verge of having another accident. My bladder was on call now. I could probably even summon something from my bowels if I really wanted to.

This was all her doing. She was making me into the perfect baby–the one who could fill their pants on demand. I liked that. I was proud of it, even. And when I began to pee in my diaper, feeling the warm pee get soaked up into the padding, I could barely contain my excitement for telling her what I had done.

But Mommy, per usual, was a step ahead of me.

“Does that feel good, Baby?”

“Y-yes, Mommy.”

“That’s a good boy. Don’t stop there. If we’re going to change your diaper anyway, you might as well get it all out of your system. What do you think, little boy? Can you push a stinky little mess into that diaper too? For me?”

“Yes, Mommy.”

“Good Baby.”

Two miles to go until the airport. Without a single thought as to where, or how, or when she’d change my diaper, I did the only thing I could think to do: filling my diaper because I wanted to make Mommy happy with me.

 

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  • quietlyhumiliated changed the title to Doing Business [Season Two: Business Trip] [Part 25 posted on 12/23/2022]

It's good to read that you have some 15 chapters already in the bank.  Margaret Mitchell famously remarked that she wrote the last chapter of Gone With the Wind first, and the first chapter last.  Particularly when writing ad seriatim, it is important not to put a chapter into the public domain until the following five chapters are in the bank.  This allows an author to avoid being painted into the proverbial corner from which there is no escape.

It will be interesting to see what happens to Clark at the TSA checkpoint.  A steel cage is going to trigger the alarm, and he will be denied entry unless he removes it.  Normally, I would suggest that he take the bull by the horns and request a private screening (I do this routinely), but he doesn't have the key, and "Mommy" would not be allowed in the room with him.  This is why I expected their trip to be on a private jet.  

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On 12/23/2022 at 4:37 PM, Babypants said:

It will be interesting to see what happens to Clark at the TSA checkpoint.  A steel cage is going to trigger the alarm, and he will be denied entry unless he removes it.  Normally, I would suggest that he take the bull by the horns and request a private screening (I do this routinely), but he doesn't have the key, and "Mommy" would not be allowed in the room with him.  This is why I expected their trip to be on a private jet.  

I'll be upfront with you (and anyone else this matters to), I didn't really want to address TSA all that much. There's a scene that takes place there, but admittedly, I breeze through it in a manner that might come off as a tad unrealistic, considering what Clark is packing in his pants.

At the end of the day, I found the logistics of TSA, air travel, and security in general to be unfun to write about. In hindsight, I could've gone with a private jet to alleviate some of this, but...we're well past the point where I can make that adjustment. I was more interested in writing what came before and after the airport than I was in breaking down the scrutiny and regulations of air travel. I have some regret about some of the details in these chapters but, y'know, lessons learned. Such is the nature of serializing a story that is unfinished while it gets posted here.

Thanks for reading!

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2 hours ago, quietlyhumiliated said:

I'll be upfront with you (and anyone else this matters to), I didn't really want to address TSA all that much. There's a scene that takes place there, but admittedly, I breeze through it in a manner that might come off as a tad unrealistic, considering what Clark is packing in his pants.

At the end of the day, I found the logistics of TSA, air travel, and security in general to be unfun to write about. In hindsight, I could've gone with a private jet to alleviate some of this, but...we're well past the point where I can make that adjustment. I was more interested in writing what came before and after the airport than I was in breaking down the scrutiny and regulations of air travel. I have some regret about some of the details in these chapters but, y'know, lessons learned. Such is the nature of serializing a story that is unfinished while it gets posted here.

This is from the first page of the Acknowledgments in Nelson De Mille's recently released The Maze: "Writing is a solitary occupation, but no writer knows everything about everything, so as with all my novels, I've reached out to friends and acquaintances in various professions to assist me with facts, details, and inside information that a writer needs but can't find in books or on the internet."  If you read as well as write fiction, then you may well have seen variations on this in a great many prefaces or afterwords.  Editors push writers hard to get the background right because as the errors mount the entertainment value of the product declines exponentially-- and so do the sales.

The easiest way to minimize the damage is to anticipate it and do workarounds.  Two big-time errors that crop up too often in stories on this site are ignoring the realities of criminal law with regard to indecent exposure, and having doctors intervene with prescriptions and/or treatments for individuals who are not in their care.  Contract law also takes a beating in these pages, and I do wish that authors would take the time to learn just how age specific formula and baby food really are.

You are one of the authors here whose work is consistently worth reading.  Where this story can be improved is by providing Clark with enough background to make his choices understandable.  This far into the story, the standard form technique is a series of reveals in answer to questions broached by other characters. The plot is really good, the dialogue consistently well crafted, but the character with narrative POV remains a mystery.    

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Twenty-Six

My mother–my biological mother–was an oversharer. She’d tell anyone anything. A favorite topic of hers was embarrassing stories from my childhood. No party, gathering, or Sunday dinner was complete without a quick dip into the annals of ‘silly things that little Clark did.’

Was this the actual origin of my recently-realized penchant for humiliation?

A favorite story of hers was an incident at the wedding reception for my Aunt Becky and Uncle Tony. I don’t know, exactly, how old I was at the time–retellings of the story usually had me between a year and two years old. But I was in diapers at the time, that’s the important part.

Supposedly, I had become incredibly bored with the wedding celebrations and was getting fussy. Understandable–I think I’d still be rather fussy if dragged to a wedding now. For a while, my mother did her best to soothe me, but I was getting in the way of her being able to enjoy her sister’s wedding–an event she had been pretty excited about. And so, I was passed off to my cousin Heather.

Twelve years old at the time, Heather loved the idea of babies. Until she actually held one and decided the responsibility wasn’t for her. Then I was passed off to Aunt Louise. Who, supposedly, didn’t even care for her own babies. I was then passed off to Grandma, who at this point was a little too deep into the wedding-day libations. She opted to just let me roam free, and set me down on the ground to scamper about as I wished.

And so I did, wriggling my way out of my tiny baby tuxedo pants as I crawled around. In a few short minutes, I had not only made my way onto the dance floor, but I had deposited a sizable wedding gift of my own into the back of the diaper–seemingly oblivious to the party that was taking place around me. This would prompt the wedding DJ to stop the music for a second and announce: “Would someone please come collect, and change, your baby? He’s stinking up the place.”

Now, my Aunt Louise would later question the final detail of that story, claiming that no such announcement was made. But my mother stuck by it, and continued to include it in all future tellings.

But the actual takeaway from this story–besides the fact that I was apparently born to make a fool of myself while in diapers–was one that I wouldn’t realize until much more recently: What makes a baby a baby is more than just a diaper. It’s also a lack of consideration for consequence.

A baby doesn’t care where he is when he uses his diaper. He just does it, and it’ll be someone else’s problem. Case in point: my current diaper, stinking up my boss’s car as we enter the airport.

If my mother could accept the fact that her now-adult son was still wearing diapers, maybe she’d find this predicament as amusing as her beloved wedding story.

“It seems like you had to go more than you thought you did,” she said, smirking.

“It smells like a bigger mess than it is,” I said, bashfully looking down at my lap. “I think.”

“I have to leave the car in Extended Parking,” she said. “And it’s not a short walk to the airport from there.”

“Oh…” The thought of an extended walk while my diaper was in this state was less than favorable.

“There is a transport though,” she said, pointing to a tram that seemed to connect the parking lot to the airport.

“B-but…we’d be around other people. And they’d smell me for sure.”

“True,” she said. “I suppose the only alternative is…to be changed in the car?”

“The car? But…”

“It’s not perfect,” she said. “But these are your options: a long walk; a ride on the tram; or you get changed in the car now.”

I didn’t really care for any of those options. Again, I’m reminded of the one or two year-old Clark, filling his diaper on the dance floor with no consideration for what the aftermath would be–for either him or whoever had to take care of him.

I probably shouldn’t have done everything in my diaper a few minutes earlier. I could’ve held it until after the flight, I thought.

Or, perhaps, in an alternate universe, I didn’t poop my pants in Mommy’s car. Instead, mid-flight while I’m stuck in my seat, the pressure in my bowels become so strong that I have no choice but to mess myself right there. And every other passenger on the plane is forced to breathe in the toxic fallout of my diaper. At some point, Mommy is given no choice but to drag me back to drag me out into the aisle and…

No, you’ve got to stop that right now. My cock aches.

“M-maybe you can just change me here?”

“If you think that’s for the best, Baby.”

“Probably.”

“Excellent,” she said, seeming to be excited about this prospect. “It’s been a while since I’ve changed a baby in the back of a car.”

“Hillary?” I asked.

She nodded.

I still wanted to know more about Hillary. Really, I wanted to know more about her dynamic with Mommy. What was that like? How different was it from what I had now? And, of course, how did it end?

All questions that felt like they’d be better asked at another time.

“It’ll be quick,” she said. “We might get a gawker or two walking by. But I suppose that’s better than everyone on the tram knowing that you’re a little poopy-bottom, yes?”

“Y-yes, Mommy.”

She chose one of the parking spots under an awning. I was mildly curious about the cost of a covered parking spot as opposed to an uncovered one, but details like that seemed far too adult for me. That was Mommy’s problem. She’d take care of all that.

But the spot under the awning seemed to afford a little more privacy than some of the others. And, considering that all of the spots around ours were already occupied–the owners of those cars, no doubt, scattered around the world at the moment–I suddenly felt much better about the prospect of getting my diaper changed now, as opposed to in the airport. Or…the airplane itself.

“As much as I’d like to take my time with this,” she said, putting her SUV into park, “we’ll have to be quick. There’ll be plenty of time to relish diaper changes once we’re in Seattle.”

I nodded, preferring a quick procedure myself if it had to be done in a car.

“There’s no elegant way to do this,” she said, sliding out from the driver’s seat. “I’ll put the rear seats down and open the back door. That should be more than enough space for you to lie down.”

Fresh air rushed into the car as our doors opened. I blushed again, realizing how quickly I had acclimated to just breathing in the air that was polluted by my diaper.

“Hurry up,” she said from the rear of her car. “Are you coming over here to get your diaper changed or not?”

Perfect timing, as always, as a pair of middle-aged women strolled past us at about that moment. They both looked in our direction, looking mildly confused. I had no clue if they actually heard Ms. Heller’s question or not, but with my luck being what it was, I’d have guessed so.

“C-coming.”

I scurried back to meet her–every second that I wasn’t at her immediate side felt like a second she could use to further embarrass me–finding that she had already laid out a blanket on the floor of her SUV. I wondered how long that blanket had been back there, and if it had always been used as the changing blanket.

Her diaper changing skills remained, so far as I knew, unrivaled. It didn’t matter where we were, she knew her way around a dirty bottom.

“Aww, you might’ve been right,” she cooed. “It’s not the biggest mess you’ve ever made. Just a potent one. You were right to push that into your diaper now, though. You’d end up getting our plane diverted, if that happened in mid-air. They’d arrest you for unleashing a dangerous weapon.”

She held my caged cock in her hand, gently lifting it and shifting it from side to side as she wiped around it. She treated it so nonchalantly–like it wasn’t anything of importance. It was just an obstacle in her way–no different from pushing a tree branch to the side.

Ugh. I needed to be unlocked so badly.

A rogue finger of hers came close to my asshole in the midst of her wiping me clean. I had to assume this was a purposeful tease. A little, anticipatory, moan escaped my mouth.

“Oh, poor baby,” she said. “You sound absolutely desperate.”

I nodded.

“Not to worry. I’ll be revisiting this little hole of yours later.”

My cock strained in its cage. “Y-yes, Mommy.”

I had no idea what sorts of sinful things she had planned for the next few days, but I knew she had ideas. She had not one, but two large suitcases. Far more than even the heaviest packer would need for just 4 days away. I could only imagine the armory she was bringing along.

She quickly slid a new diaper beneath me, coating me with a liberal amount of baby powder–far more than she had ever used while we were in the office, when she used it at all. The thick infantile scent wafted to my nose immediately, bringing out even more red in my cheeks.

“We’re away from all the familiar faces and noses,” she said. “So I’m going to be a little less concerned about things like how much you smell like a baby.”

I was close to protesting, but I thought better of it. She was right–it wouldn’t matter if an entire airport of strangers thought a grown man smelled like a baby. I’d never see any of them again.

That was…pretty exciting.

Diaper was fastened. Pants were pulled back up. The offensively dirty diaper was triple bagged before being thrust back into my hands. I might have been spared having to wear a soiled diaper on the tram, but was it any different if I had to carry said diaper in my hands?

Thankfully, I spotted a trash can at the tram platform. I gleefully tossed my naughty garbage into it, briefly pondering how long it’d sit there until someone disposed of the entire trash bag. Long enough to stink up that area too? I was already worried that we’d return from Seattle to find that Ms. Heller’s car still smelled like my dreadful diaper–the poisoned air trapped in place for days with no opportunity to escape.

A future-me problem.

There were just a few other people on the tram as we were taken into the airport, all of them looking like they were already over the airport experience. It was an interesting test run for the very baby-ish scent I was carrying around with me now.

It was hard to say how noticeable it was. I was getting a few glances, though it was hard to say if they were any different than the glances they’d give any other random person. The two middle-aged women who passed by Ms. Heller’s SUV were there too, though. Their eyes seemed to linger a little longer than everyone else’s. It’d be impossible to know for sure, but it was easy to imagine them connecting a few dots if they had overheard Ms. Heller’s earlier comment about a diaper change, and now catching the scent of baby powder.

Never one to miss an opportunity for creating chaos, Ms. Heller flashed me a sly grin. “So, what do you think? Will that diaper last you the whole trip?”

I imagined myself melting into the floor and disappearing completely. I was extremely disappointed that I didn’t. Now people were looking at us.

As much I wanted to stay silent, I knew better than to leave one of Mommy’s questions unanswered. “Y-yes…it’ll hold.”

“Once we land in Seattle, I’ll check for myself. I wouldn’t want you to get a diaper rash so early in our trip.”

That got some reactions. The two middle-aged women were whispering things to each other. One of them was staring directly at my mid-section.

What else could I do but grin and bear it?

But perhaps this was also the perfect introduction to our trip. Without having any clue what was coming, this was the kind of low-ish stakes humiliation that could help prepare me for whatever was next. I’d need only remember that I didn’t know them, and they didn’t know me. After this moment, I’d just be a fuzzy memory for them. A story they told later, maybe.

Maybe I could at least try to embrace that.

“Y-yes, Mommy,” I said, loud enough that anyone paying attention could hear.

That look on her face? That look of pride? That was all I ever wanted.

As exhilarating as the tram ride had been, I was praying for the action to slow down a little. If every moment between now and Seattle were filled with this sort of humiliation, I was likely going to explode–if not my body, at least my cock.

“We have a little time before the flight,” she said as we walked together through the terminal. “Are you hungry? Thirsty?”

“Well…I guess it’s been a while since breakfast. And we’re not going to be in Seattle for a while, right? So maybe I could go for…”

“Wait just a second,” she said, rifling through her shoulder bag.

The fool that I am, I thought she was looking for her wallet, like she was going to buy us lunch. Instead, she pulled out a baby bottle.

“Wh-what…”

“Here,” she said, handing it to me. “You may drink this.”

“But…I… M-mommy…”

“Look around,” she said. “Do you recognize anyone here?”

I didn’t have to look. “No.”

“So what do you care if they see a young man enjoying his ba-ba?”

“Well…what’s in it?”

“Baby formula.”

I could only imagine that I looked as disgusted as I felt. She took one look at me and laughed while shaking her head.

“I’m kidding, silly. It’s a protein shake. Vanilla-flavored, or so the canister claims. It travels better than milk does. Plus, it has all the nutrients a growing baby like yourself could ever need.”

As unpleasant as that sounded, it still didn’t sound as bad as it could’ve been.

“Do I have to drink this?”

“What a funny question. Every drop,” she said. “And you’ll have to do it soon. I don’t think they’ll let us take that past security.”

I carefully lifted the bottle’s nipple to my lips, cautiously scanning the crowd around me as we walked forward. As best as I could tell, nobody was looking at me. I took a small sip, suckling at the latex tip. I was immediately greeted with a surprisingly thick spurt of vanilla liquid. I could’ve done without the aftertaste, but the flavor wasn’t the worst.

“Good baby,” she cooed to me. “Go on now. Drink it all up.”

The more I sipped from the bottle, the easier it became. We were walking by all sorts of people, and nobody seemed to pay any mind to the young man walking around drinking from a baby bottle. Maybe, to everyone else, it just looked like I was drinking from a water bottle.

“Mommy,” a toddler yelled to my left. “That man has the same bottle I do!”

I felt my face ignite, and I turned and buried my face in Ms. Heller’s side. She laughed, putting a comforting hand around me, patting my shoulder. As embarrassing as having been called out by a child was, my reaction was almost more embarrassing. Had I really just clung to Mommy like that, desperate for her comfort?

“Poor baby. It makes sense, of course. Babies can just recognize other babies, you know?”

I wasn’t done with my bottle, and I intended to finish it. Embarrassment or not. Ms. Heller, too, seemed quite pleased that I was going back to the nipple after my little scare, giving me a supportive pat on my crinkly bottom.

Shortly after her checked luggage was carted away, we’d enter the line for our security scans. It hadn’t occurred to me until this moment that I was at risk of being frisked in my diaper.

“D-do you think they’ll know?” I asked Ms. Heller. “About my, uhm, diaper?”

“If they’re doing their job, they will,” she said with a confident nod. “But it’s not illegal to wear a diaper, little boy. It’s nothing you should worry about.”

This did little to calm my nerves.

“Besides, if either of us should be nervous, it’s me. The things in my checked baggage? Hell, the things in my carry-on? I’ll probably get a few raised eyebrows.”

I desperately wanted to ask about what was in her bags, but I kept my mouth shut. It was probably better that I didn’t know.

At the security line, Ms. Heller was in front of me, and I watched the faces of the TSA agents as her carry-on bag went through the conveyor belt. It was surprisingly hard to read the agents–either they had already seen everything there was to have seen, or they were trained to just not give away all that much information.

“Step into the body scanner, sir.”

Deep breath. Well, they’re going to see what they see.

“Alright,” the woman at the machine said after I had stepped inside. A whirl of air and electronic noises surrounded me, dissipating as quickly as they had arrived. “Step over here, sir.”

I stepped out of the machine and to the left where an agent quickly felt around my body. Areas of interest, I suspected.

“What is this?” the agent asked, lightly tapping the front of my pants with the back of their hand.

“Uhm…a diaper.” My face blushed furiously at having needed to say that aloud.

“Alright, head on through.”

Was that it? It seemed to be.

I found Ms. Heller soon after, not even realizing that we had been separated in the process of being escorted through the checkpoint.

“As painless as you hoped it would be?” she asked.

“Relatively.”

“Barring any diaper-blowouts while we’re thousands of feet above the ground,” she said, “I’d say the hard part is behind us.”

I looked out the window, to where a large plane had just left the runway and was ascending up and into the clouds. My heart beat rapidly as I tried to, once more, imagine the worst case scenarios.

“We’ll be boarding soon,” Ms. Heller was saying. I spun around to see that she was talking on the phone. “He was a good boy and filled his diaper on the car ride here, so I think he should be good for the flight.”

I wondered who she was talking to. Ms. Beaufort? Lyndie? Someone else entirely?

There was something very familiar about Ms. Heller’s oversharing on the phone.

It must’ve been a mom thing.

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  • quietlyhumiliated changed the title to Doing Business [Season Two: Business Trip] [Part 26 posted on 1/3/2023]

Twenty-Seven

From: Nancy Tamberlin <ntamberlin@xxxxxxxxx>

Date: Friday, April 1 at 3:14 PM

To: Gabrielle Heller <gheller@xxxxxxxxx>

Subject: FWD: Workplace Concerns

Gabby,

Earlier this week, HR received an email from an employee named Thomas Pritchard. Thomas seemed pretty upset about the recent promotions of Clark and Lyndie, feeling that he had been unfairly passed over for advancement. I met with him this week for a one-on-one chat in an effort to quell his anger.

At the time, I thought the conversation had gone well. I thanked him for his service, explained that the recent promotions were based on a litany of factors and were approved by the Board, and I even offered him a one-time bonus as a way to say ‘thank you’ for his hard work.

However, since our meeting, he has gone on to tell any employee who will listen to him that he plans on attending the next meeting of the Board of Directors to ask them, directly, about the recent promotions.

I’m sure there’s a number of ways that we could handle this situation, but I thought I’d present this to you first to see if you had any suggestions.

I don’t want to interrupt your trip for this matter, so we can discuss it further upon your return. Please do enjoy your time in Seattle :)

***

In a relatively short amount of time, Ms. Heller–Mommy–had gotten to know me quite well. She didn’t know my favorite band or my favorite place in town for pizza. She didn’t know about that time I barfed on Susie Chepske’s shoes in the second grade–though I’m sure she’d have loved to hear about it.

But she knew me, as a human. I had my tells, and she was getting better at reading them. She knew when I needed to go potty–often before I did. She could recognize when I was getting hungry. Or bored. Or tired.

Par for the course of a Mommy, really. That was the sort of skill you had to have.

But that street went both ways, and I was slowly learning about her as well. The way her eyes gleamed when she had a particularly devilish thought. The little breath she took to compose herself when she was overstimulated–usually by me.

And there was that miniscule–almost undetectable–grunt when something came up that frustrated her.

I caught that grunt as our plane arrived in Seattle and we sat on the tarmac for a few minutes. She was checking her phone, and whatever it was she read–she didn’t care for it.

“Is everything okay?” I asked. It could’ve been argued that I was being nosy. Mommy was an important woman, and she probably dealt with far more complicated situations than I could even fathom. But, I knew her well enough to believe that I could get away with offering her an ear to complain to.

“Do you know who Thomas Pritchard is?” she asked.

“No. Should I?” My imagination got away from me for a moment, and I wondered if this was yet another executive in the company–some other important fellow with a hard-on for punishing people dressed like infants.

“Some insignificant whelp in our employ,” she said, rolling her eyes as she lowered her phone. “Apparently he’s trying to make a big scene out of your promotion.”

“M-my…promotion?” I felt a heavy weight on my chest, as if this–whatever this was–was my fault.

“This happens from time to time,” she said with a shrug. “Some worker-ant gets it in their head that they’re the only person keeping the lights on in the building, and take offense when the company doesn’t bow down to kiss their ass.”

“Oh.”

“But, and you would know this better than most, the company doesn’t reward people who need their asses kissed. The company rewards people who kiss the company’s ass.”

My cock ached as I thought of Mommy–an avatar for the company as a whole, if there ever was one–sitting on my face.

“So what are you going to do about it?” I asked.

“My gut reaction is to fire the clod and move on. But…maybe I can do better than that.”

“How so?”

“I haven’t decided yet. But that’s a problem for later.” She slipped her phone into her purse. Short breath. She had composed herself.

“So, Seattle, huh?” I looked out the window, though there wasn’t much to see yet beyond large expanses of blacktop and buildings.

“We made it,” she said, putting her hand on my thigh. “The flight wasn’t so bad, was it?”

“No, Mommy.”

“Just that one little accident?”

I nodded. Somewhere above Wyoming, I had wet my diaper.

“You’ll be okay to sit in that a little longer, yes? You won’t leak?”

“No, Mommy. I think it’ll hold.”

“Good boy.”

I’d be tempted to say the flight was uneventful, aside from pissing myself again. But believing that was only proof of how commonplace humiliation was in my everyday life now. At one point, early on in the flight, the flight attendant in first class asked Mommy and I if there was anything she could get for us. Without missing a beat, Mommy had handed over my empty baby bottle, asking if there was any milk that could be used to fill it.

The flight attendant looked baffled for a moment, scanning the other seats around to see if there was a baby or toddler she wasn’t aware of. But to her credit, she maintained a professional demeanor and gladly took the bottle to fill it.

The bottle then sat in the tray in front of my seat for the remainder of the flight. I sipped at it here and there, when I didn’t think anyone would see me. But I was wrong far more often than I was right about who could see me. The flight attendant alone must’ve seen me drinking from the baby bottle half a dozen times.

“And you two have a wonderful day,” she said to us as we walked past her on our way off the plane.

“Oh, we most certainly will,” Mommy said, giving my bottom a playful smack. The loud hollow rumple of my diaper seemed obvious to me, but I’d never know what the attendant thought.

After we picked up her checked luggage, we made our way towards the exit. I assumed that we’d have to hail a cab or that she’d arrange for an Uber to pick us up. But, no. Standing in front of a sleek black Town Car was a man holding a sign that read ‘HELLER.’

I thought that sort of thing only happened in movies.

“H-he’s for you? Us?”

She laughed, patting me on the head condescendingly. “Baby, don’t forget. I’m very important.”

“Ms. Gabrielle Heller?”

“The one and only.”

“My name is Joel, and I’ll be your chauffeur this evening. And you are joined by…”

“This is my assistant,” she said. “But you are only to refer to him as ‘Baby.’”

“Y-yes, of course.” His face had glowed as pink as mine.

I could already tell that this was the way this trip was going to go. Humiliating moment after humiliating moment. In a place where absolutely nobody knew me or would remember me? She was going to absolutely destroy me. And I was going to let her.

As we sat in the back of the car, en route to wherever was next, I decided to text Lyndie.

“I’m in Seattle now.”

I started typing out a message to Ava too:

“Hey Ava. I just made it to Seattle and was thinking about you.”

But I deleted it before sending it. This probably wasn’t the time to open that can of worms.

“Let’s see,” Ms. Heller said, reaching between my legs to squeeze the plump padding under my pants. “Are you any wetter than you were before? Need a diaper change yet?”

I glanced up to the windshield where I caught Joel’s eyes looking back at us in the rearview. The latest in a series of strangers who probably had an interesting story to tell later. The women from the tram. Maybe the TSA agents. The flight attendant. Joel.

“I…I should be good.”

I hadn’t invested a lot of thought into it, but it was an idea that kept springing up in my mind since we left the office: Not just embracing my humiliation, but leaning into it. Could I even pull such a thing off?

“You sure, Baby?”

Her gentle squeeze of my diaper, feeling the soggy padding press against my cage, had me feeling a little inspired. This seemed as good a place as any to test my ability to become the biggest baby possible.

“M-mommy…”

Her eyes lit up, already impressed that I had taken on the infantile affectation I had only ever used in the privacy of her office.

“Yes, dear?”

“I…uhm…might have to…make poopies in my diaper. Uhm…later.”

This wasn’t true. My earlier eruption in the passenger seat of her SUV had cleaned me out. But I needed to say something, and I needed it to sound as pathetic as possible. Judging by the look on her face, and Joel’s wide eyes in the rearview, I was successful.

“Of course you do, Baby. But we don’t have to worry about that now, do we? You just let Mommy worry about when your stinky bottom needs to be changed.”

“Y-yes, Mommy.”

“Besides,” she continued, “you wouldn’t want to stink up Mr. Joel’s car now, would you?”

There were his eyes in the mirror again.

“Uhm…no…”

Joel said nothing, a testament to his professionalism.

“Trust me,” Ms. Heller said to Joel. “He makes the smelliest diapers of any baby I’ve ever met.”

“Well, uh… I guess I’m grateful that I don’t have to deal with that,” he finally said.

There was only so far I could take my diaper talk, unless I wanted to just start babbling like a baby. I didn’t think I was ready for that just yet.

She moaned to herself a little as she squeezed my wet diaper again. “I’ll never get sick of feeling your soggy diaper, Baby.”

“I…like it too.”

“But you wish you could like it more, yes?”

“Uhm, well, yes.”

“But that pesky little cage around your little cock stops you from getting hard, doesn’t it?” Her voice had become cloying, possibly even sarcastic.

“Mmmhmm.”

“Do you wish you were free from it? So that you could get hard and squirt to your little heart’s content in your diaper?”

“Y-yes, Mommy.”

Fuck. I wanted that so bad. Obviously, it didn’t make much to push my buttons while in this state. But she wasn’t pressing the buttons–she was mashing them with an open palm.

“You’d do just about anything for release, yes?”

“Yes, Mommy. Anything.”

“I’m going to hold you to that,” she said.”

“Please.” I was nearing a point of no return–the point at which I was so desperate and needy that I lost control of myself. I had been pushed close to the point before, but I had never actually been pushed past that point.

“You want to jizz in your dirty diaper for Mommy?”

“Yes…”

“You want to suck on Mommy’s titty while she rubs your diaper?”

“Uhm, yes…”

“Do you want Mommy to stick big thick things up into your bottom?”

“F-fuck… Yes, Mommy.”

“Hmm,” she hummed to herself, nonchalantly. “Good to know.”

Her hand slid off of my crotch and her attention was back on her phone again. I felt as if I had just been pushed into a deep pit with no way out. I was practically trembling in the backseat of the Town Car, desperate for her to even touch me–let alone unlocking me. But she was ignoring me. And Joel, consummate professional, kept his eyes on the road and didn’t get involved.

Lyndie, with the perfect timing, returned my text.

Lyndie: “Having fun so far? I doubt she’ll waste any time before embarrassing the hell out of you.”

I gave her the truth:

Me: “It’s been non-stop. Even as we speak.”
Lyndie: “Sounds about right. I don’t want to interrupt anything.”
Me: “Actually, could you do me a favor?”
Lyndie: “Perhaps”
Me: “Do you have any idea who Thomas Pritchard is?”
Lyndie: “Should I?”
Me: “All I know is that he’s an employee. I guess he’s causing some trouble because of our promotions. I was thinking that maybe if we found out who he was, we could just talk to him before things get out of hand.”
Lyndie: “I’ll ask around and see what I can find out. But don’t worry about things like that right now. Worry about keeping your diaper full for Mommy.”
Me: “I’m already pretty wet…”
Lyndie: “Of course you are.”

I looked out my window as the city whizzed past us. I’d never been in Seattle before, and this part of it didn’t look all that different from any other city I had ever been in. Big buildings. People. Cars. I had no idea where we were going–now and for the rest of the trip. Everytime the car stopped at a light, I wondered if I’d see one of these buildings again. Would we go into that bar later, where she’d loudly ask if I had pooped my pants? Would we take a walk through that park later while my diaper sagged between my legs to the point where I had to hold it up with my hands?

“What are you thinking about, Baby?” she asked, putting her hand back in my lap again.

“Just…trying to guess what’s next, I guess.”

“I could tell you,” she said. “If you wanted.”

I saw a cluster of young women out the window, about the age of Lyndie and I, standing on a street corner. They were talking and laughing, having what looked to be a really good day together. I bet they’d get a kick out of seeing me in a dirty diaper and a caged cock. Maybe Mommy would humiliate me in front of them. Or anyone else.

Mommy and I, we didn’t know everything about each other yet. But we knew a lot. We knew the tells. And she already knew that I didn’t want to know what lied ahead. Nothing kept me under her control better than the fear of the unknown.

“That’s okay.” And, without even thinking about it, I added: “I’m, uhm, wetting myself again, Mommy. J-just a little.”

Joel was looking back at us via the mirror, curious as ever.

“Of course you are, Baby. We’ll get you changed soon enough.”

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  • quietlyhumiliated changed the title to Doing Business [Season Two: Business Trip] [Part 27 posted on 1/9/2023]

Hello! Just one of those periodic reminders to say: A) Thank you for continuing to read this story. I do appreciate you sticking around! B)If you are dying for more of this story, Tier 1 subs to my Patreon get access to new chapters before anyone else. Right now, there are 5 more chapters of this story to read there. Also, if you decide to sub to a higher tier, there are many (many) short stories and series available to read that are exclusive to the Patreon. Drop by and help support the cause, if you can! (The cause = making people read naughty stories, I guess.)

 

Twenty-Eight

I could’ve been more observant. I could’ve taken notes of the streets we had turned on to get to the hotel. Hell, I could’ve noticed what the hotel itself was actually called. But details like that only seemed important to adults.

In the last few minutes of the drive, I was thinking about the number of details that I didn’t care about when I was a kid. When my family took vacations, I was just there, enjoying whatever was put before me. I didn’t think about the hotel reservations. The plan for our meals. Getting tickets for an amusement park. Travel accommodations.

I had been tempted to ask about things like our accommodations, or what her schedule would be like, but I bit my tongue every time. Those were adult concerns that only Mommy would care about. It felt good to just…not care. I couldn’t remember the last time I was able to just sit back and let life happen around me without being an active participant. Bills, work, meal planning, grocery shopping. All of those things still existed–and eventually I’d be back in that world. But not right now.

This mentality, combined with the distance we were from everyone else I knew or cared about, was making it incredibly easy to fall into the babyish state that Mommy wanted me in for the next few days.

Who was I kidding? I wanted to be in the state too.

“Well?” Mommy asked as we took a few steps into her room. No, not a room–an entire suite. “What do you think?”

I had wide-eyes and an open mouth. My head was shaking. “Th-this is nicer than my apartment.”

“No offense,” she said. “But it better be. Go ahead, take a look around.”

The living room we were in seemed to act as a central hub to the suite, with doorways branching off a kitchen, a bedroom, a bathroom, and…another room? The thought of there being another bedroom–and the possibility of being sent there to sleep with Mommy, was a little distressing.

I jumped from room to room, quickly scanning everything. Everything was immaculate. Everything felt designed. Curated. Just by walking on the carpet with my cheap sneakers, I felt like I was corrupting this space.

King bed. One of the biggest TVs I had ever seen. A fridge already stocked with assorted beverages and snacks. I felt like every time I turned a corner, I was in awe of something else.

I was admiring the jetted tub in the bathroom when I heard Mommy walk up behind me.

“That should make bathtime fun, yes?”

“Y-yes, Mommy.”

“There’s a toilet and a bidet too,” she said, pointing to the units on the opposite side of the room. “Not that you should get too excited about that. You certainly won’t be needing them.”

It was a very obvious point, but one that still made my cheeks glow.

“You have one room left to investigate,” she said with a smirk.

The other bedroom–which I had started to write off as just excess space that we wouldn’t need. But now that she was trying to shepherd me to it, I was curious.

It was, in fact, another bedroom. Except the bed had been pushed all the way against the wall, leaving a large space in the middle of the room, which was now occupied with a playpen. Among other things.

“What…is all this?”

“Surprise,” she said, wrapping her arms around me and hugging me. “It’s not the full-on nursery I wanted–but there’s not much you can do when we only have the place for a few days.”

Next to the playpen was a large flat pad on the ground, next to some neatly stacked piles of diapers. The more I looked around the room, the more I noticed. The pacifiers and baby toys. Clothing laid out on the bed. Baby food jars and baby bottles.

“H-how did you do all this?” I asked.

“I made some calls,” she said. “I’m an executive, that’s what I do–execute. I ordered some things and had them sent here. Hired someone to set it all up. It was a piece of cake, really.”

“All this for…me?”

“Let’s not pretend that I don’t get anything out of this,” she said.

I wanted to cry. I might’ve been, a little bit. I couldn’t think of the last time that someone had gone this far out of their way to create such an experience for me. She was right–this was likely just as much for her. But it made me feel like the most important baby in the world at that moment.

How do I thank her for this?

There was only one real answer. I’d just give her what she wanted.

I immediately dropped to my knees, my thumb in my mouth. I looked up at her face, hoping my face would express how spoiled this pathetically dumb baby was feeling.

“Look how precious you are,” she said, running a hand through my hair. “Are you ready? To just be my baby and nothing else?”

My head was automatically nodding. My entire body felt consumed by the lust I felt for her.

“Let’s get you out of these clothes,” she said. “I think I’d like to see you crawling around in just your diapers for a bit.”

Such a simple desire, but it was something we never really had the space to do. Aside from the confines of her office, there wasn’t anywhere that I could just be a free-range baby.

“It’s not a changing table,” she said, pointing to the long pad, “but I thought this would do nicely for the next few days. A changing pad. Why don’t you lie down on it so that Mommy can undress you.”

I quickly crawled over to it, flopping myself down on my back. My feet were already up in the air without her asking–eagerly anticipating her hands to free me of the useless adult clothing I wore.

She plucked my shoes and socks off first, followed by my pants. Then, she helped me out of my shirt and tee–leaving me entirely nude except for my diaper.

“Quite wet,” she said, grasping the bottom of the diaper and squeezing. “But I knew this. You made a pee-pee in the ride over, didn’t you?”

I nodded, my thumb back in my mouth again.

“Poor Mr. Joel, he probably had no idea what to make of that little scene, huh?”

I shook my head. I thought back to the things I had said while in the backseat of the car. I could barely believe that was me. Had I actually said the word ‘poopies’ out loud?

“It’s wet enough for a change,” she said. “But…I don’t see a point in changing you if you’re going to need a diaper again soon. Do you need to go, Baby?”

I could feel some pressure in my bowels. There wasn’t a dramatic urgency yet, but it was enough that I could probably coax something into my diaper if I wanted.

“Yeth, Mommy,” I said, the thumb giving my words a perfectly infantile lisp.

“Why don’t I leave you in this diaper for now,” she said. “Go on and crawl around. Explore. I’m going to be unpacking a few things.”

“Uhm…Mommy?”

“Yes, darling?”

“Wh-what if I…go.”

“Say the word, Baby. I know that you can.”

“P-poop. What if I…poop?”

“What do you mean, ‘what if?’ I’m expecting you to. Don’t think about it. Just do it.”

“But…thould I find you? Or…”

“I’ll find you,” she said. “Trust me, I’ll know if it happens. When it happens.”

I was on my own in the makeshift nursery. I started to climb up to my feet, but I thought better of it and got back down on my hands and knees again. Even when Mommy wasn’t here watching me, I wanted to be a baby. And, strangely, when left to my own devices, I found it even easier to let that headspace take over.

I crawled. And it was so fun to have room to crawl around that I did a few laps around the room. Such a stupid thing. Only a baby would enjoy this.

I grabbed one of the new pacifiers and slid it into my mouth, letting my slobbery thumb land back on the soft carpet again without any regard for things like germs or dirt. Next, I clumsily pawed at the new toys she had bought for me. Oversized plastic keys. A rattle. A plush dinosaur. Giant chunky blocks.

Do babies actually like these sorts of things? What are you even supposed to do with…

But then a few minutes quickly passed as I sat in my soaked diaper, idly shaking stupid baby toys around in my hands.

I’m such a baby. I felt my cock straining in my cage. Such a baby.

Fuck. I couldn’t get enough of those words. I’m a baby. A baby. That’s me. I’m a big baby now. A big stupid toddler. A diaper-filling little…

I got back on my hands and knees again and began crawling around the room again, the plush dinosaur–a stegosaurus that felt like a ‘Spike’ to me–still clutched in one of my hands. I didn’t even realize what I was looking for when I started my latest loop around the room, but then it dawned on me: I was looking for a place to poop.

A summer or two ago, I was at a summer barbecue hosted by my cousin. They had a little girl, maybe no older than 2. At one point she waddled out of view of everyone, prompting my mother to ask where little Jessie had gone.

“She only really does that when she has to make a dirty diaper,” my cousin had said. “She’s at that age where she knows she’s supposed to start learning how to use a toilet, but chooses to use her diaper anyway. So she’ll sneak off and poop her pants while nobody’s watching.”

I could relate to that. I found a nice little place alcove between the playpen–which I only then realized was quite large–and the bed where I felt like I could do my business.

I’m not sure if it felt right, but it certainly felt safe.

I grunted and pushed, expecting my body to offer more resistance. It didn’t, perhaps having already given in to the same primal and babyish urges my brain was being overwritten by. Most of it was pushed into the diaper all at once, a firm mess that expanded the back of the diaper considerably. I reached behind myself and felt the bottom of the diaper as I pushed again, getting the last of it out–each push expanding the diaper’s size a little more.

I had messed my diaper plenty of times in the last few weeks. In front of people. With the help of suppositories. In places that I probably shouldn’t have messed myself. But even when it felt good–and, honestly, it always felt good–it didn’t feel like it did now. There was something about being in this room, surrounded by these things, and being left by myself, that made this feel better than it had ever felt before.

My hand glided back and forth over the back of the diaper, feeling the shape and size of my mess. I squeezed at it a little. “Unh.” My cock strained again.

Fuck. This was a mistake. My hormones were all over the place and the pleasure-center of my mind was combusting. What was I supposed to do? All this sexual energy. All this desire. And absolutely nothing to do with it.

I let myself fall back on my ass, squishing the sizable mess between my ass cheeks and the diaper. I slid back and forth in my diaper a few times, just little movements, feeling the mess spread even further.

I needed Mommy so badly. I needed her to tell me how much of a naughty little baby I was being. I needed her to tell me how badly I smelled–because I was already quite stinky. I needed her to…literally do anything. If she wanted to throw carrot sticks at me, I’d have gladly accepted that.

I needed Mommy to fuck me.

No plan. No thought. No conscious decisions being made. I let my head fill itself with fantasies and wishes while hips continued to gyrate back and forth in the diaper, smushing the contents into a disaster that I couldn’t begin to grasp.

Just a big stupid baby. Look at me. So stupid. So fucking horny. Stinky. Making poopy diapers and helplessly squirming around. So pathetic. So, so, fucking pathetic. Such a hopeless little…

“What’s going on in here?”

My body froze in place and my neck craned to the door where I found Mommy in the doorway.

I had no idea what to say. I wasn’t even sure if I could form words if I wanted to.

“Believe it or not, it wasn’t the stench of your dirty diaper that got me back in here,” she said. “It was the sound of a diaper crinkling so much I thought you were wrestling with it. And…maybe you were?”

I clutched Spike tightly looking down at the loaded diaper between my legs. I had completely forgotten about shame–it’s an emotion seemingly reserved for people who know better–but it was finally washing over me. What was I doing? What had I let myself become?

“Just look at you,” she said, shaking her head. “This is…apocalyptic.”

Was it that bad? I had no idea. No clue how to even gauge how bad things might be.

“I’m not sure how you did it,” she continued, “but this is a certified blowout. Look at you. It’s coming out the waistband. And the leg bands. And you even got it on the carpet!”

I looked down at my diaper again, lacking the entire picture she was seeing, but seeing enough.

“Come here,” she said. “Crawl over here, to the changing pad.”

I did so, finally showing a little caution as I slowly lifted my dirty bottom from the carpet so I could crawl back to her and the changing pad. It was a short distance, but it might as well have been an entire pad. Her eyes were fixated on me as I lurched forward, one knee or forearm at a time, with my absolutely filthy diaper swaying in the air behind me.

“I’m not upset,” she said, her lips forming back into a small smile again as I laid back down on my back on the padding. “But I am a little curious as to what was going on in here.”

I pulled the pacifier from my mouth, taking my time with the words as I re-learned how to speak: “I got…carried away.”

She chuckled softly as she began to untape the diaper. “What were you thinking about?”

“You. The diaper. Everything…”

“Everything,” she repeated. “That’s a lot.”

I nodded. “It felt like a lot.”

The diaper was pulled open, completely exposing the messy contents within. I didn’t dare look down at myself to see what I had done. Instead, I looked up at her face. She looked as composed and confident as she always did, even if I could tell that she was unsure of where to start in the cleanup effort.

“I thought this thing would make things a little easier for us,” she said, gently jostling my caged manhood. “A ‘set it and forget it’ sort of thing, you know? But it seems to have turned you into the horniest little babe who’s ever lived.”

“I…I’m sorry,” I said. It felt worth repeating: “I got carried away.”

“It’s nothing to be sorry for,” she said, stroking my cheek with the back of her hand. “I like you like this.”

“R-really?”

“Don’t pretend you didn’t already know that.”

There was more I wanted to tell her, but I wasn’t sure if I should or not. As it turned out, I wasn’t so far out of my baby-space that I could stop myself if I wanted to. “I just want to c*m so badly.”

Her smile got bigger as she pulled the first damp wipe from the package.

“Of course you do. Do your diapers make you horny?”

“Unnnh,” I groaned–a guttural reaction I hadn’t seen coming.

“Probably not just diapers,” she said. “But specifically dirty diapers, huh? I bet you just love the feeling of them.”

She was right, though it was far more than that. It was, literally, everything. Everything made me horny.

“I promise you, I’ll give you your c*mmies,” she cooed to me as she began to carefully clean away the mess from my skin.

“N-now?”

“No,” she said, giggling. “Not now.”

“Then…when?”

“You’ll know when it’s time. I promise you that.”

I could’ve whined some more, but I didn’t want to sound any more pathetic than I already did. Besides, the more I whined, the more at risk I was of convincing Mommy that she should postpone my cock’s relief.

“Yes, Mommy.”

“Good boy. Now, I’m afraid I have some news that you might not be entirely happy with.”

My heart sank in my chest. “Yes?”

“An old colleague of mine is in town for the same conference. It was a last minute decision on her part, apparently.”

“Oh,” I said, expecting this to be the part where she told me that she’d be spending some time with her friend instead of with me.

“She’s asked me to get drinks with her this evening. Maybe go to some clubs. But, I have other plans.” She smiled at me.

“So…”

“I won’t be going out to the club with her tonight. Still, social obligations being what they are, I can’t not see her while we’re both in town, so I agreed that we’d meet her for dinner.”

“We?”

“Afraid so. So, assuming we’re ever able to fully clean this stinky catastrophe you’ve created, we’ll need to get downtown to meet Gretchen.”

“D-does she know about my…diapers?”

“She doesn’t, actually,” she said, laughing. “Let’s see how long we can keep this a secret from her.”

“So do I…have to wear a new one?”

“Oh yes,” she said, playfully booping me on the nose. “You’re still a baby. You’ll always be a baby.”

I accepted this change of plans very quickly. As always, I trusted her. The details of what we did, who we met, and when we did any of it, were far above me now.

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  • quietlyhumiliated changed the title to Doing Business [Season Two: Business Trip] [Part 28 posted on 1/14/2023]

Twenty-Nine

Text message from Lyndy (1 of 3):

“I found Thomas Pritchard in the office directory, but that doesn’t exactly help me know who he is. At least I know where he sits now. I’ll take a look on Monday.

Text message from Lyndy (2 of 3):

“Bradley was sent to the nursery today for the first time with a wet diaper. Poor little boy didn’t know what to do with himself, having his diaper changed by someone he didn’t know that well. I’m sure he’ll get used to it.”

Text message from Lyndy (3 of 3):

“I don’t know what’s up with you and Ava, but she seems pretty bummed about it. I told her we’d get drinks together tonight. I hope you’re having fun with Mommy. Thinking of you.”

***

I don’t ask any questions about Gretchen. I don’t ask about her last name or where Mommy knows her from. I don’t ask where she lives now, or where it is that she works. Adult details that are unimportant to me.

When we arrive at the trendy downtown eatery, Gretchen and Mommy embrace, exchanging pleasantries.

My first observation: Ms. Heller doesn’t seem to like Gretchen as much as she likes her other friends, like Neve Beaufort. I wouldn’t say she’s unfriendly, but there’s caution in how she talks to her. She doesn’t feel like she can be her true self around Gretchen. If I was to guess, the two seem more like rivals than best friends.

My second observation: Gretchen did not come alone.

“I’m so sorry to do this,” Gretchen said to us. “But I had to bring Kylie with me today. She wanted to come to Seattle with me so that she could spend some time with a friend of hers who lives in town. But, wouldn’t you know, she’s sick in bed this weekend. Stomach flu, apparently.”

“Oh,” Ms. Heller says with a curious smile. “So Kylie is…”

“My daughter, yes. Say hello, Kylie.”

“Uhm, hi,” the young woman says from behind her mother. She’s tall and skinny with sun-bleached hair pulled behind her in a ponytail. It’s immediately crystal clear that Kylie has no desire to be here either.

Bonus observation: When in her element, Kylie is the queen of her social circle. I see it on her face and in the way she dresses. An alpha female, probably like her mother. Like Ms. Heller. Even if I wasn’t wearing a diaper and still recovering from my messy bout of lust, she was far out of my league.

“And this,” Ms. Heller said with pride, “is my superstar assistant Clark, who’s joining me in town for the conference.”

It hadn’t been long–just a few hours–since I was in the office. Subtly creeping around in my diapers, hoping not to be noticed. I should be a pro at it by now, but my brief foray into complete babydom back at the suite seemed to have set me back a little, and I found myself overly cautious about every movement I made.

I was sat next to Ms. Heller, but across from Kylie. While the women quickly fell into a conversation about the latest gossip in their lives, Kylie and I were left awkwardly staring at each other.

“So, you graduated high school this year?” I asked.

“Yes.”

“Uhm, well, congratulations.”

“Thanks.”

I sighed a little, feeling like it was trying to squeeze water out of a stone. Clearly, she had even less interest in talking to me than she did being dragged to dinner in the first place. Still, I felt like I should at least try to keep a conversation going. I’m sure Ms. Heller would be proud of me if I could.

“So what’s next for you?” I asked. “Going to college?”

“I’m going to Cornell,” she said, in a tone that also seemed to say: “Which is probably better than whatever school you went to.”

I nixed my plans to follow that question up with a query about what she’d be studying. Maybe there was no shame in just letting there be silence.

“How old are you?” she asked.

The question threw me for a loop, not just because I wasn’t expecting her to continue talking to me, but because the concept of age felt a bit…fluid as of late.

“21,” I said. “Why do you ask?”

She laughed. “Oh, just wondering.”

How could I not overanalyze a response like that? Did I look too young? Too old? Did she…hear my diaper crinkling and wanted to know just hold this freak was who still needed diapers?

Calm down. She doesn’t know anything.

I wondered if there’d be more questions, but none came. Kylie had turned her attention to her cellphone. That’d probably be the last I heard from her. Which I was perfectly okay with–I didn’t need this queen bee judging me.

Gretchen and Ms. Heller both ordered cocktails. I had been tempted to order a beer for myself, but even if Mommy had let me get away with that, it still felt like a betrayal of who I was supposed to be while we were away. I was stuck with water.

Food came. None of it was especially my type. Tiny portions of things, stacked on top of each other in the centers of large plates. I ate it without complaining. It didn’t taste bad, but it definitely seemed like a flavor profile wasted on the tongue of someone who was just craving a giant pizza.

Remember Pizza Girl? I wish I hadn’t thought of that. I felt my cheeks warming, and I quickly lifted my glass of water to my face in an effort to hide it.

“I was going to hit the little girl’s room,” Gretchen said, placing down her fork.

As if in tune with this social cue, Ms. Heller quickly responded, “I’ll join you.”

They were both off to the restrooms, purses in tow, to do whatever it was ladies actually did in restrooms.

“So,” Kylie said. “Are you fucking your boss or something?”

I just about spit my mouthful of water across the table and all over Kylie’s face.

“Wh-what? Why would you ask me that?”

“Oh please,” she said with a shrug. “I don’t know why she’d drag her assistant with her to dinner with a personal friend. And I’ve watched the way you two interact. She totally has you wrapped around her finger.”

“I, uh… I’m not sleeping with my boss.”

“Well, you’re definitely doing something with her. Because she’s leading you around like you have a collar around your neck attached to a leash.”

I felt myself blushing furiously. “No… She’s just my boss, you know? And it’s important that I stay close by in case she needs me and…”

“Don’t bullshit a bullshitter,” Kylie spat, smiling smugly. “All I do is lie to my mother. I didn’t come to Seattle to see a friend. I came here because while my stupid mother is distracted by her conference for the next few days, I have access to her credit card and free reign to do whatever the hell I want to do.”

I had no idea how to respond to this. Clearly she wasn’t going to take ‘No, I’m not sleeping with my boss’ for an answer. But the truth was probably infinitely worse than anything she was expecting. ‘So, I’m not sleeping with my boss. But I am allowing her to lock my penis in a cage while I poop my pants.’

“It’s complicated,” I said, hoping that this might suffice as an answer.

She laughed, shaking her head. “Knew it. You’re fucking her. You naughty boy.”

“Maybe…don’t tell your mother about this,” I said, suddenly realizing the chaotic possibilities if Kylie started telling her mother about this little discussion.

“I won’t…” The way her voice trails off worries me a little. I can sense a ‘but’ coming.

“But?”

“But,” she continues, “If I’m going to do you a favor, maybe you need to do one for me.”

Fuck. I can only imagine what sort of bullshit I’m being dragged through now.

“I don’t really know what I can do for you. But…”

“I don’t need much, okay? But you’re 21, right?”

“Uh…yeah.”

“Well I’m not. And I’d love to get my hands on some alcohol this weekend. Maybe you can help me out with that?”

I sighed. “Honestly, I don’t know if I can. Me and Ms. Heller have a pretty tight schedule and…”

“You mean that she has a pretty tight pussy, right?” she asked, giggling into her hand.

“N-no, I don’t mean it like…”

“Come on,” she said. “It’s not like you’re going to be with her 24/7, right? I know it said that it looks like she has a leash on you…but she doesn’t actually keep you chained up in her hotel room, right?”

Does a chastity cage count as a type of leash?

She pulled a pen and a scrap of paper from her purse to start writing something down. “If you get, like, a spare hour or two, just text me, okay?”

“Look, I don’t want to cause any drama with your mother and my boss and…”

She laughed, shaking her head as she slid the piece of paper across the table to me. “I don’t want any drama either, okay? I just want to go shopping, get drunk, and watch an unhealthy amount of romantic comedies on my hotel room TV while I try on the shit I bought.”

“I’ll see what I can do,” I said, taking the piece of paper and sliding it into my pocket. Just the adding of my hand to my pocket caused my diaper to crinkle under the table, painting my cheeks a little redder. “No promises, though.”

“I can make it worth your while,” she said, shrugging.

I wanted to ask ‘How?’ but I didn’t get the chance. Looking over Kylie’s shoulder, I could see Gretchen and Ms. Heller returning from the bathroom. There wasn’t much left to do now but wait and hope that I could figure out a way out of this new little debacle later.

“I hope you didn’t miss us too much,”Ms. Heller said, taking her seat next to me.

“Welcome back,” I said. I wondered if she could pick up my telepathic message: Get me out of here, I got myself into another mess.

“This was a lovely evening,” Gretchen said. “It was nice to catch up with you again.”

“Likewise,” Ms. Heller responded, notes of fakeness in her tone. “It’s a shame we don’t live closer to each other.”

“Well,” Gretchen said, glancing at the time on her phone. “We don’t have to call it a night there. Send your assistant home. I’ll send Kylie back to my room. You and I can get a few drinks.”

“I wish that I could,” Ms. Heller said, quick to counter Gretchen’s offer. “It’s going to be a long day tomorrow, and I promised Clark here that we could go over some reporting before it gets too late.”

“Staying up late on a Friday night to…go over spreadsheets,” Gretchen said, frowning. “What happened to the fun and free Gabrielle I used to know?”

“She got promoted to CEO. I don’t have a life now. Just work.”

“Hardly seems worth it,” Gretchen said. I wasn’t sure if she sounded sarcastic, or just whiny. Likely the latter.

It wasn’t long after, and Mommy and I were in the back of a car again. I had no idea what sort of car service she had access to, but she seemed to be able to summon classy town cars from the aether with a few taps of her phone.

“I’m sorry to have subjected you to that,” she said to me. “I didn’t mean to drag you along at all, but I had tried to use you as an excuse for why I couldn’t go in the first place. Of course, Gretchen just told me to bring you too.”

“It’s fine,” I said.

“How are things…down there?” She put her hand in my lap, edging her fingers between my legs. I was surprised that she wasn’t just saying the word ‘diaper.’ Maybe she was sparing this driver a peek into our personal life. Maybe, Gretchen had just exhausted her to the point where she wasn’t feeling especially naughty.

“Fine,” I said. “Just, uh, a little wet.”

“Usually when you say it’s a ‘little’ wet…”

“I mean it this time,” I said.

“I’ll check for myself back at the suite.”

“Yes, Mommy.” I immediately blushed, seeing the eyes of our driver in the rearview mirror looking back at us. I was reminded of my near-slip in front of Kylie earlier at dinner.

This seemed to help correct Mommy’s humors. She was smiling again, and her hand gave my diapered crotch a healthy squeeze, summoning a tiny moan from my mouth.

“I don’t actually like Gretchen all that much,” she finally said after a few long moments of silence.

“I kind of figured.”

“Such is the corporate life. It’s all about networking, and keeping your enemies far closer than your friends.”

“I don’t think Kylie liked her much either.”

Ms Heller laughed, shaking her head. “Did she tell you that? I didn’t realize you two talked all that much.”

“Just a little.”

“What did you talk about?”

I was torn on how to answer that. On one hand, I didn’t want to lie to Mommy–it was actually the last thing I wanted to do. But I wasn’t sure that I wanted to give her all the details of our conversation either. Maybe I thought I was protecting Mommy if I could help Kylie with her request.

Or, maybe, there was a very small part of me who was curious about Kylie’s offer of making it ‘worth my while.’

Ultimately, I didn’t think that I was opposed to telling Mommy the truth. I just didn’t want to do it at this very second. That felt like a pretty selfish decision, but one that I’d stick with.

“She told me she’s going to Cornell,” I finally said.

“Of course she is,” Mommy replied, rolling her eyes. For the time being, that was the end of that conversation.

Arriving back at the hotel, I was surprised to have Mommy grasp my hand after we got out of the car.

“Come, Baby. There’s some things I want to show you.”

It didn’t take much to excite me these days. And being led through the hotel by the hand was absolutely doing it for me. We briskly trotted through the lobby and into an elevator, where another middle-aged couple were already on board. My hand was still locked in hers.

I studied their faces as they studied ours. I could see them trying to process this scene. Who were we? Mother and son? Lovers? Something else entirely?

I also caught a playful smirk on Mommy’s face. She just couldn’t help herself.

“Don’t forget,” she said. “When we’re back in the suite, I’ll need to check your diaper.”

I could’ve sworn that smoke was coming from the couple’s ears.

When in Seattle… I chose to play along. “I need a change, Mommy. I’m very wet.”

“Is that so?”

I nodded. “And…I think I might have to do a…poopy too.”

“Oh dear. Well I hope this elevator gets to our floor soon, then.”

I watched as the woman reached forward, pressing a new key on the keypad so that the elevator stopped at the next floor. It probably wasn’t their floor. They probably didn’t care–so long as they got out of the elevator with these weirdos.

She shook her head and chuckled in amusement when the elevator door closed. “Impressive.”

“That was fun.”

“Are you sure you’re not just sucking up so that I take your cage off tonight?”

I laughed, shaking my head. “No, Mommy.”

“I’ll choose to believe that.”

In the suite, within the same second she closed the door behind us, she began to take off my clothes again.

“I think you’ve spent far too much time in adult clothes today.”

“Agreed.”

“Let’s get you back to the ‘classic baby’ look, yes? Just a diaper.”

“Yes, Mommy.”

“You were kidding about making another stinky diaper, yes?”

“Y-yes. I think the last one cleaned me out.”

“I should hope so. Otherwise, I wouldn’t know where a boy of your stature stores it all.”

I felt buzzed. Despite not having had anything to drink tonight, I’m tipsy–or high, or something else entirely–on just this experience. I was feeling like something is coming tonight, but I just don’t know what it is. But I watch the way she moves, and I hear the way she talks, and I can sense an energy about her. She’s excited too.

“Come here, Baby,” she cooed to me from the bedroom a little bit later.

I was on the floor of the living room when she called to me. I was crawling around in just my diaper, which had grown a little wetter. A little heavier. I promptly corrected my course and crawled into the bedroom, my padded bottom jutting out behind me.

She was atop the bed on her knees, wearing only a sheer black camisole. The top barely concealed her breasts, while the lacy hem at the bottom barely concealed anything below her hips.

My cock, once more, strained in its cage.

“You asked for relief tonight,” she said. “You asked to c*m.”

“Y-yes, Mommy.”

“I promise you now, you’ll make your little c*mmies in your diaper. One way or another.”

I wanted that so badly. Needed that. But her cryptic comments kept me a little suspicious. I felt that there was a catch.

She lifted her left hand, revealing a key dangling from a chain. “This is it. The key to your little cocklette. I bet you want this.”

“Yes, Mommy. More than anything.”

“Ah, but be careful when you say that, Baby. Because you have a choice.”

“A choice?”

“Instead of taking the key, you could also take what’s in my other hand.”

“But…”

“I promised you I’d get you off, right? I meant that. No matter what you choose, you’ll be rewarded. Even if your cage isn’t unlocked.”

What did that even mean? I couldn’t even begin to imagine how she’d get me to climax if I didn’t get to have my cock unlocked.

But…I was curious.

“Wh-what is in your other hand?” I asked.

She lifted her right hand slowly, revealing two sizable objects in her hand. I wasn’t completely sure what I was looking at for a moment, and I couldn’t figure out how anything would be comparable to her just unlocking my age.

But my eyes focused and I began to make sense of what I was seeing. One object was a vibrator, I think. Not, like, the kind that went inside of someone. It had a large white cylinder mounted on the end of it. A ‘personal massager,’ I think I had seen it advertised as in the past. The legendary Hitachi Magic Wand. Years of smut had taught me that the only thing it ever massaged was a woman’s vagina.

The other object? Well, that looked to be a purple cock.

“So, like, you would, uh…”

“I’d take this,” she said, motioning to the toy. “And I’d fuck your little bottom with it. We’ll start small…I think this is a good starting point for what is probably a tight little hole.”

“And the other thing?” I asked, pointing to the massager.

“I’d put the Magic Wand up against your cage,” she said. “I’m quite confident that I could make you c*m into your diaper with just one of these toys. But with both? I guarantee it will happen.”

Goddamn, I wanted to be unlocked from this cage so badly. I wanted to feel myself grow erect again. I wanted to fuck her. But…now, I wanted those toys. And just the idea that she could bring me to climax without even having to unlock me? I was quite alright with giving her that sort of power.

“I, uhm…”

“Yes, Baby? Tell Mommy what you want.”

“Please…fuck me.”

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  • quietlyhumiliated changed the title to Doing Business [Season Two: Business Trip] [Part 29 posted on 1/20/2023]

The pace of this story has slowed dramatically (6 chapters to cover one day).  This is common in murder mysteries and suspense novels, but not in fiction at large.  As the pace slows, there is a risk of having the chapters break apart, to become isolated vignettes.  Mystery and suspense writers often use a particular gimmick to prevent the narrative from losing its cohesion in this way, and that is to avoid completing a thematic scene in one chapter.  This is the proverbial leave the reader dangling strategy.  Sophisticated writers may not even conclude a scene in successive chapters, instead choosing to go off in a seemingly unrelated direction, only to double back later.  Ring composition first frustrates and then rewards, and this rhetorical trick has been in play for more than 2500 years.  

I would strongly encourage you to start playing around with this sort of thing, because your writing is definitely up to the challenge.  When the story is spread across many chapters that appear at roughly the rate of one per week, thematically complete chapters tend to read as short stories in and of themselves, rather than as an intrinsic piece of an overarching narrative.  I'm guessing that you want to avoid this.

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Thirty

She dangled the key to my chastity cage in her left hand a little longer–a final tease that I had been so close to release–before casually tossing it across the room. It was gone, for now.

“What do you think?” she asked. “Is this a good look for me?” She had taken the purple dong and held it between her thighs. The placement wasn’t quite right, but if I squinted a little, it did almost look like she had a cock of her own.

I nodded. “Yes, Mommy.”

“This is what all the hubbub is about, huh?” she asked, playfully slapping her toy with the back of her hand so that it bobbled up and down. “Men are so silly.”

I had no rebuttal for this. If anything, it was probably my inability to conform to the social standards of “men” that had resulted in where I was now–crawling around the ground with a wet diaper while my boss stroked her cock in anticipation of using it on me.

“Have you ever wanted to be a girl?” she asked.

“No,” I said, shaking my head. “Well…I never thought about it.”

“Nothing wrong with that. You’re happy with the skin you’re in?”

“I think.”

“How does the idea of this going into your bottom make you feel?”

“Honestly? A little nervous.”

She laughed, gripping the shaft tightly in her hand. “But you want it?”

“Yes…”

“If you end up liking this, you should see what else I brought,” she said, nodding towards her suitcase. My eyes followed to the sealed luggage. What else was there?

For the sake of my own curiosity, I also hoped that I liked tonight’s toys.

“Come up here, Baby,” she said. “Up on the bed with me.”

She didn’t have to tell me twice. I crawled across the bedroom and climbed onto the bed. Her soft hands were on me immediately, easing me down onto my back.

“Do you know that I appreciate you, Baby?”

“Y-yes, Mommy. Of course.”

“You’ve done a lot for me in our short time together.”

Had I done all that much?

“More so than doing the tasks of an assistant,” she continued. “Of which, you’ve done very few so far. And more so than just pleasuring me or entertaining me with your humiliating antics. I think you–just being around–has been good for me.”

“Well…you’ve done just as much for me,” I said.

She straddled my body, hovering above me like an angel as she looked down into my eyes.

“You’re an excellent baby.”

“You’re an even better Mommy.”

She moaned a little, massaging my chest with her hands. Slowly, her hands spread out across my body. She rubbed my shoulders. My neck. My arms. Even my face–softly stroking my cheeks and running her nimble fingers through my hair. It was a feeling of bliss unlike anything I could remember experiencing before.

If she had stopped now, got up from the bed, and put her clothes back so she could go get a sandwich, I think I would’ve felt satisfied. It wasn’t getting off–but this felt like love. I felt loved.

“If I could make you cum without unlocking your little cock,” she cooed to me, her lips pressed close to my ears, “I probably wouldn’t ever have to unlock you again, yes?”

An absolutely terrifying idea, but one that sent pulses of pleasure through my body. Yes, fine. Destroy the key. Flush it down the toilet. Throw it out a window. Wrap it up in a dirty diaper and throw it in the dumpster.

I bit my tongue–scared that I’d blurt out something I’d regret later.

Fuck.

At the worst possible moment to have a conflict of conscience, I was reminded of my conversation with Kylie and my withholding of that conversation from Mommy. And I was just going to idly lie back and let Mommy pleasure me while continuing to keep this from her?

“M-mommy?”

“Yes, darling?”

“I…I, uhm, have something I need to tell you.”

“Yes? What is it? Do you have to make a poo? Are you going to make another stinky diaper for Mommy while I’m on top of you?”

I really wished that was what was happening.

“N-no. There’s something I didn’t tell you before.”

The smile faded on her face, just a little. “Oh? Interesting timing on your part for a serious conversation.”

“I just don’t think I could fully enjoy anything that would happen tonight if I wasn’t completely open with you.”

She remained on top of me, but she sat up, her moist pussy resting on my cage. “Go on.”

“It’s about…Kylie.”

She laughed. “That’s the very last name I would’ve expected you to say. What about her?”

“She asked me to do a favor for her.”

“Hmm. What sort of favor?”

“She wants me to buy her alcohol.”

She laughed, shaking her head. “A ballsy girl, eh? Did you tell her about us? This isn’t, like, a blackmailing situation, is it?”

“N-no,” I said, shaking my head. “I don’t think so. I don’t think Kylie has any interest in talking to her mother about anything, let alone us. I didn’t tell her anything about us either…though she certainly assumes we’re having some sort of…relations.”

“Well sure,” Mommy said. “I’m sure many people assume. Baseless speculation doesn’t scare me too much. Though I’m curious why you didn’t tell me about this little conversation sooner.”

“I’m sorry, Mommy. I guess…” I remembered that I still hadn’t told her everything. There was still the promise of making things ‘worth my while.’ But did I dare reveal that too?

As if able to, at least partially, read my mind, Mommy asked: “What did she offer you in return for fetching alcohol for her?”

“She just said she’d, uh… Well, she didn’t exactly say how she’d repay me.”

“But the implication was that she would find some way to return the favor?”

I nodded again, my cheeks bright red.

“Even with your little cocklette all locked up, you still manage to do a good amount of thinking with it. Impressive.”

“I’m sorry, Mommy. I didn’t want to keep it from you and…”

She put a single finger over my lips. “I don’t know what you thought you were going to get from her with your cock locked up and in a diaper, besides more humiliation. And if that’s what you wanted, I’m happy to help you reach that goal.”

“N-no, I just…”

“Let’s not worry about it anymore,” she said. “I’ll take care of Kylie. And, right now, I’m going to take care of you, baby.”

I took her for her word, and I let go of that little knot of anxiety I had been holding so close to my chest. It was a great relief.

“Do you wish you were a big boy?” she asked, grinding herself on my diaper where my cage was.

“Y…yes. Mommy, I really do.”

“Alas, Mommy’s kitty isn’t for little baby-cocks, is it?”

“No, Mommy.”

“You didn’t choose the key, you chose the toys.”

“Yes, Mommy.”

“Allow me to introduce you to this fine fellow,” she said, grabbing the purple cock and holding it in front of her. “Not the biggest I’ve ever seen, for sure. In fact, if I took a fella home and this was what he was packing, I’d be a little let down. But, for a little butt-virgin like yourself, I imagine this will do just fine.”

She could try and downplay its size, but I still couldn’t imagine that thing fitting inside my ass.

“Y-you said that there’s another one in your suitcase?” I asked. “A…bigger one?”

She laughed, shaking her head. “One thing at a time, Baby. I can’t wait to show you what else I brought with me. But, as they say: ‘Baby steps.’”

I could accept that. To stick to the infantile metaphors, I’d have to crawl before I could walk. I’d have to…get fucked by a smaller plastic cock before I got to see whatever was to come after.

Her hands were on my diaper, teasing at the tapes like she was going to peel them away. But first, she’d squeeze and grasp the stiff lump caused by the metal cage contained within. Each would draw a moan from my lips–more out of desperation than actual pleasure.

“You want it so badly,” she said.

‘It’ wasn’t defined, but it didn’t have to be. ‘It’ was anything that could get me to climax.

“Yes, Mommy.” I felt my voice fraying as she somehow managed to make me even more pathetic and desperate than I already was. “Please. Please.

“Oh,” she said, smirking. “Begging. I quite like that. Give Mommy some more of that, won’t you?”

There was no hesitation on my part, I simply turned on the spigot and let it run: “Please, Mommy. Pllllleeeease. I need it so badly. I’ll take anything. Everything. Can I please have it?”

“But why do you want it so badly?”

“Because you keep me locked up, Mommy.”

“Surely it’s more than just that.”

I took a deep breath. Fine, if you really want me to beg. “Mommy, I can’t be around you without getting turned on. Every single thing you do–every single thing you do to me–it drives me crazy. You have me. You have me…” Kylie’s words from dinner came to mind. “...wrapped around your finger. You want me to be a baby? I’ll be the best baby you’ve ever had. You want me to wear diapers? Poop my pants? Crawl around like a baby? Absolutely humiliate myself in front of my roommate, co-worker, pizza delivery girl, and the entire executive team for our company? I’ll do it. Because, at the end of the day, I’ll do anything for you. Any insane disgusting thing you want, Mommy. I’ll do it. Because if it makes you happy, it makes me happy. So, please. Please, Mommy. Make me cum. Make me explode. Stick anything you want up my ass. Destroy me, Mommy.”

She didn’t respond immediately. Which made sense, given the amount of information I had just vomited at her.

“The pizza girl, hmm?” she finally said. “You’ll have to tell me more about that later.”

“Okay…”

She started peeling back the tapes on the diaper. One at a time, slowly, filling the room with the sound of the stubborn sticky tabs being pulled away from the diaper. When she was finished, she pulled down the front of the diaper, laying it flat on the bed beneath me.

“I have to admit, this isn’t what I’m used to. Usually, when I open your diaper up, there’s a disgusting mess waiting for me to clean.”

I didn’t say anything, letting my glowing cheeks do the talking for me.

“Here,” she said, reaching for something off the bed and bringing it to my face. It was one of the new pacifiers, which she plunged into my mouth.

“There’s really nothing you need to say,” she said. “And you’ll still be able to do all the moaning and groaning you need to.”

I nodded.

“Now hold this for me.”

Before I knew what was happening, she had grabbed both of my hands, clasping them together above me and she then thrust the purple plastic cock into them.

It felt surreal, holding this toy in my hands. Perhaps it was a bit prudish on my part to have felt so strange, but I’ve never held a dong in my own hands before. It didn’t feel that different from what I had expected: firm, with a little flex to it. Soft to the touch.

It was then clear to me why I was holding it–she had the lube.

“When playing with little bottoms, it is of the utmost importance that everything be good and slippery,” she said. “That means both our purple friend here, and your little backdoor.”

She squeezed a glob of clear gel into her hand before slowly applying it to the toy, thoroughly covering every square inch of it. Now, under the room’s lights, it seemed to glisten and shimmer–as if some sort of holy relic.

“I’ll be taking Mr. Purple back,” she said. “Now, there’s a few ways we could do this, but I think a better angle–for the both of us–would be if you rolled over.”

I watched her squirt another batch of lube into the palm of her hand. This time, she carefully dabbed the fingers from her other hand into it, spreading it to her fingertips like an artist putting paint on their brush from the palette. Then she slid off my body, giving me plenty of room on the bed to flip over. I did, finding this new position to feel even more vulnerable than the last. My ass was sticking up in the air–hers to do as she wanted with. My caged cock now rested on the wet diaper under me. Fitting, really, that I should never be too far away from my diapers.

She began to carefully paint my bottom with the lube. I felt myself instinctively tighten up at her touch.

“You have to let me in, Baby,” she cooed from behind me. “Take a deep breath. Relax.”

I did exactly that: I took a near-infinitely deep breath. I relaxed. Relaxing wasn’t easy. With my body in this position, and with the knowledge of what was coming, it was hard to convince my muscles to cooperate.

Relax. You want this.

I felt myself loosening. Unclenching. She could probably already tell, but I felt it was important to tell her through my pacifier: “Mommy, I’m yourth.”

She hummed in delight and began preparing my backdoor once again. This time, her finger tips entered me; slow and steady. I bit down on the pacifier, channeling all the energy I would’ve liked to have used for my sphincter muscles into my jaw. It seemed to work.

“That’s much better,” she said. “What a good boy. I think that should do it. What do you think? Are you ready for Mr. Purple?”

I couldn’t decide if I liked this toy having a name or not, or if I just disliked the name ‘Mr. Purple.’ What was the alternative, though? Hank? If there had to be a name, this was probably the best option.

I offered an affirmative moan in response to her question.

She was prepared–I could immediately feel the stiff tip of Mr. Purple pressed against my hole. How? How was this thing ever going to fit? But with just a little push from her, it slid into me.

“Ohhhhhhh…

“I’ll assume that’s a good sound.”

“Yeethhh, Mommy.”

“I’m going to take it nice and slow, okay? Little by little. You tell me if I need to stop or remove it.”

“Mmhmm.”

True to her word, I felt the toy slide deeper into me. Toy? It seemed like an extension of her now. Mommy wasn’t using a toy. She was fucking me. Fucking me with her cock.

“Is this too much?”

“No… No, Mommy.”

“I’m going to keep going.”

“Pleath.”

I was losing comprehension of how deep she was now, and how much more of her cock there was to fit inside me. It almost didn’t matter–it felt all consuming. It filled me. Completed me. It was simultaneously overwhelming yet not enough. I can take more. I can take everything. I was likely overestimating my abilities to take a cock at this point. Yet I knew, for sure, that I was in love with what I was feeling at this moment. It was hitting all the nerves–nerves I wasn’t sure that I had ever had stimulated before.

“Unnnnnh,” I moaned, teeth still clenching the pacifier for dear life. “More. Mommy, more!”

“That’s exactly what I hoped to hear,” she said. “Look at my little baby, begging for more cock. Are you Mommy’s little butt-slut?”

“Unnh. Ohhhhhh.”

“I’ll accept that as a yes.”

I felt the cock reverse course, slowly pulling from bottom. Just as it had taken eons for her to fill me with it, it seemed to take forever to draw it back again. Again, it was hitting all those poor neglected nerves.

“M-more,” I stammered the best I could with my mouth still locked around the pacifier. I doubted I needed to let her know what I wanted, but it couldn’t hurt.

“That’s the hard part,” she said. “Now that you know you can take the whole thing, I can do it again…”

“Mm.”

“...and again…” She pushed it as deep into me, again, before sliding it back out.

“Mmmph.”

“...and again…” Another thrust.

“Unnnhhhh.”

“...and again…”

“Unnnnnnnnnnghhh. M-mommy…”

“Now that you’ve been introduced to the concept of getting fucked, we can talk about what’s next.”

Did I want whatever was next? I wasn’t even sure of anything anymore. I just wanted more. I didn’t care what it was. My own manhood, shriveled and locked away, could barely stand it, and I felt myself dribbling into the diaper–a near constant leak of anticipatory precum.

“It’s possible to make a boy cum just by playing with his bottom. I don’t even have to touch his cock.”

“Mmm,” I moaned. “Pleath.”

“It doesn’t come easily,” she said, giggling. “Pardon the pun. But we’ll get you there in time. For tonight, that’s where this other toy comes into play.”

BRRRRRRRRRMMMMMM

I could hear the Magic Wand activate behind me with its electric hum. She hadn’t even touched me with it yet, and still felt like its energy was coursing through my body. She reached through my spread legs with the wand and held it against my cage.

Is this what it’s like to be electrocuted? I could barely even process the waves of pleasure that immediately began to ripple through my body. The cage only seemed to amplify its contact with me, spreading its pulses over a larger area.

“And while the wand works its magic on your cage,” she said, “I push Mr. Purple deep inside of you.”

“Unnh. Unnnnnh. Unnnnnnnnnnnhhhh… Fuuuuuck.”

It couldn’t have taken any longer than half a minute. Almost immediately, I felt my cock oozing into the diaper–an eruption fueled by two weeks of hopeless desperation. I lost all the strength in my entire body and I collapsed on the bed, shaking and whimpering like a pathetic baby as my cock continued to leak between my body and the diaper.

She slowly withdrew her cock from me for the last time. The human body, so I was told, was an incredibly versatile machine. I’m sure that my asshole would be fine in the long run. But at that moment, it felt like it was the size of a tunnel on the highway. She could park her car in my ass if she wanted to.

Her soft hands were on my back, cycling between massages and gentle strokes.

“Was that worth it?” she asked. “Did you get what you wanted?”

It took a few seconds to remember how to speak again, and the words that finally came out of my mouth were unfiltered and raw from the forefront of my brain: “Throw away the key."

 

As always, thank you very much for continuing to read the stories. Bonus Appreciation Points (redeemable in the lobby) for those cool babies who like and/or comment the story. All the feedback is very important to me. 

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  • quietlyhumiliated changed the title to Doing Business [Season Two: Business Trip] [Part 30 posted on 1/28/2023]

Baby Steps! Fantastic. Love the detail that he was still laying on his wet diaper and the possibility opportunity of further humiliation with Kylie and the pizza girl. 

I also assume Mommy knows he's got a big crush on the babysitter.

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The 14th Annual Seattle Leadership Conference is pleased to welcome Gabrielle Heller.

Gabrielle Heller, CEO of [Company Name Redacted], will be joining the SLC for two panels on Saturday, April 2nd. In the first, “Future Paths,” Ms. Heller will be joined by a panel of executives from a wide range of companies to discuss the new directions business is taking as technology continues to evolve at a breakneck pace.

Later in the day, be sure to catch Ms. Heller’s second panel: “Relationships Within Command,” a deep look at her strategies in building a team that works together as a family, instead of just co-workers.

***

I felt as if I had been reborn. Maybe I had been.

The night before had been transcendent–feeling like the culmination of every single moment that had passed since the first time I ran into Gabrielle Heller in a random hallway while I tried to hang an award on the wall.

I awoke from a perfect sleep, finding that Mommy’s arms and legs were still wrapped around me, keeping my body close to hers under the covers. She wore nothing, while I just wore a diaper.

My diaper was completely soaked, and I had no recollection of when that happened. But it didn’t bother me. I barely even considered it. Why should I? This was what I did now. I liked the feeling of the swampy diaper pressed between her body and mine.

“Ah, the little boy has awakened,” she cooed to me.

My eyes darted to hers, not realizing that she was also awake. It actually made the moment feel even more special, knowing that she had chosen to stay in bed, clutching me close to her, even though she had been awake for who-knows how long.

“H-hello,” I said, my voice cracking and straining at its first use of the day.

“Sleep well?”

I nodded. “Yes. Very.”

“I wish I could stay in bed with you all day…”

“You can,” I said. “You should.”

“I have to be at the conference today,” she said. “They’d be a little bitter if I didn’t show up.”

“Will you be there all day?”

“Most of it,” she said. “But the good news is that this is the only day I have to be there. Starting tonight, I’m all yours.”

“N-no,” I corrected. “Mommy, I’m all yours.”

“Of course,” she said, laughing. “Always.”

She kissed me on the forehead, setting off a chain reaction of warm and pleasurable feelings throughout my body.

“What about me?” I asked–a half-cooked question that probably didn’t have enough context to make sense.

“What about you, Baby?”

“What should I do today while you’re at the conference?”

“Be a baby,” she cooed, running her fingers through the hair on the back of my head. “What else is there to do?”

“But…”

“I know. The prospect of being a little baby, all alone in a strange city, is probably a little overwhelming, yes? Not to mention boring.”

I nodded. Honestly, it was the boredom I was concerned about more than anything else. I wasn’t about to go toddling through the streets of Seattle in my thick diaper, but I also wasn’t sure how I was going to keep myself amused–especially when my cock remained sealed up in its cage.

“I’m sure I could find a way to spice up your day for you.”

This made me a little nervous, yet–as always–excited. I bet she could. And, knowing her, she already had a few ideas.

“First things first,” she said, patting the bottom of my sodden diaper. “We need to get you changed into something a little fresher, yes?”

“Yes, Mommy. Please.”

She released me from her grip, and I begrudgingly released her from mine. She slipped out of the bed and wrapped herself up in a thick terry cloth bathrobe. I was disappointed to see her cover up, but it was probably a good thing for my ever-strained cock.

It was no new revelation that Mommy had gotten diaper changes down to a perfect and efficient science. Yet this never seemed to detract from how much I loved them. The way she manhandled my legs. The effortlessness of her almost every movement. The way the baby wipes would zip across my skin, or how she knew the exact amount of powder to shake onto my skin. She was a wizard.

“Now that we’re out of the office,” she said, opening up her suitcase as my hands pawed at the loudly crinkly fresh diaper, “I feel like we finally have the chance to dress you in something more age-appropriate.”

My heart began pounding, as I could only imagine what she was going to reveal to me.

It was a sailor outfit. A navy blue onesie, with white trim that circled the sleeves and leg bands, a white-trimmed collar, and–the start of the show–a bright red tie.

“Is this not the cutest thing?”

My burning cheeks should’ve been enough of an answer, though I added: “Y-yes, Mommy.”

Truthfully? I loved it. Adored it, even. The deeper I fell into the baby abyss, the deeper I hoped to fall. Yes. Dress me up like a little baby.

“Aww, look at you,” she cooed. “Practically wiggling around in excitement, aren’t you?”

“I, uhm, I really want to wear that for you, Mommy.”

“You’re such a good boy.”

Soon, I was being led to the mirror by the hand so that I could see myself. There I was, in just my sailor onesie and a thick diaper. I probably would’ve looked quite babyish in just the onesie, but the puffy bulk of the diaper seemed to turn that dial to 11. She popped my pacifier into my mouth, completing the look.

I was just a baby.

Then, a peculiar thing happened–the hotel room’s phone rang. In the age of cellphones and laptops, I found it hard to believe that any landlines were ever being used–let alone one in a hotel room.

Mommy flashed me a mischievous grin as she walked to the phone and selected the button to answer it on speakerphone.

“Good morning, this is Edward from the concierge desk. Mr. Ashburn has a guest. I wanted to check with you before allowing them up.”

I felt my face grow white as I glanced back into the mirror. Who? Who was this and why were they looking for me?

“Does he now?” Mommy replied with an air of mock-confusion. “And who is this visitor?”

“This is Kylie Feldman.”

If possible, I became even whiter. My pacifier dropped out of my mouth and into my hand.  “H-how did she…”

“Send her up,” Mommy confidently said into the phone before ending the call.

“Mommy… How did she know where we were staying? I…I thought that…”

“You were quite sleepy after your big night,” she said. “You passed right out. So, of course, I took it upon myself to pick up your pants and I found the piece of paper she wrote her phone number on. And, remembering what you told me last night, I thought maybe I should reach out to her.”

“I don’t know if she should see me like this,” I said, looking into the mirror again. Yup, still a big infant.

“I don’t think it’ll matter,” she said, shrugging. “But why don’t you stay in here for a few.”

She left the bedroom, closing the door part way behind her. It was open enough that I could hear her walking through the living room, though it seemed to conceal me from any curious eyes that would come through the main entrance to our suite. Mommy seemed not to care that she would be greeting Kylie in just her bathrobe.

If Kylie thought something was going on between us before, wait until she sees this.

I had nothing but questions. Why did Mommy reach out to Kylie? What did she say to her? Why had Mommy agreed to let Kylie come here, of all places, while I was dressed like this.

There was a knock at the door. Fuck.

All I could do was listen.

“Good morning, Kylie,” Mommy said moments after opening the door.

“Oh, er, hi Ms. Heller. I…didn’t realize you were…here.” Kylie’s voice still carried those notes of sweet and cattiness, but it also sounded deflated.

“Surprised? Likewise, imagine my surprise to see that you’re stopping by.”

“I…was supposed to meet your assistant Clark here. Are you two…sharing a room?”

“We’re sharing lots of things these days,” Mommy said. “Like phone numbers.”

“Oh.” There was a lot of uncertainty in Kylie’s voice.

“Why don’t you come inside, Kylie.”

For a moment, I wasn’t sure if Kylie had come in or not. For all I knew, she had sprinted off down the hallway, never to return. All I could hear was the sound of the door closing again. I caught another glimpse of myself in the mirror. Still a baby. I kind of hoped that she had run for the hills.

But then I heard Kylie’s voice again: “Look, I didn’t want to start any trouble. I just thought that he could…”

“I know what you wanted,” Mommy said. “You were texting with me late last night, not him.”

“Look, I said a lot of things that…” her voice trailed off before she started again: “I thought I was talking to Clark.”

“I know,” Mommy said.

“You can’t tell my Mom,” she said. “Please?” Kylie sounded desperate. I wondered what else she had said to Mommy last night, thinking it was me.

“You graduated high school, yes?” Mommy asked her. “You’re over 18?”

“Yes.”

“So, you’re an adult. You have the right to beg boys for alcohol, while promising sexual favors in return. You have the right to send photos of your ass and tits to anyone you’d like to.”

My eyes widened. I really missed quite the conversation.

“But…my mother…”

“Ah, yes,” Mommy said. “Your mother–Gretchen–she’d disapprove, wouldn’t she? Probably cut you off from her credit cards. Maybe reconsider whatever investment she was making with Cornell to get you in as a student.”

“Please, don’t…”

“I see no reason to drag your mother into this conversation,” Mommy said. “I think we can help each other out.”

My heart was pounding even harder. What the hell did she mean by that?

“How so?” Kylie asked, sounding equally uncertain.

“Well, after I freshen myself up a bit, I’m going to be at the convention all day. And while I could take my darling assistant Clark with me, I think he’d be better off staying here.”

I looked in the mirror again. Yes. I was thinking that myself.

“But,” Mommy continued, “in Clark’s current state…I’m not sure I’d like to leave him to his own devices. He needs supervision.”

My heart sank. I could imagine where this was going…but it seemed far too surreal to actually be happening. Right?

Kylie laughed. “Are you asking me to…babysit your assistant? An adult man? Who is older than I am?”

“I’m encouraging you to stay here today,” Mommy replied. “You can call it whatever you’d like. But staying would ensure that our text messages stay between us. And, as long as you’re here…well, there’s a well-stocked fridge in the kitchen. If anything was to go missing…I probably wouldn’t even notice.”

“Sounds kind of like blackmail,” Kylie said.

“Funny. I had the same thought when Clark told me that you were asking for him to get you alcohol after you speculated about his relationship with me. So I don’t consider this to be blackmail, no. We’re just two people, doing favors for each other.”

My entire body felt tense as I braced myself for how Kylie would respond to this. I couldn’t begin to fathom the idea of Kylie seeing me like… I looked in the mirror again, feeling a shudder creep through my body.

“Fine,” Kylie said. “I guess I could stick around for a little while.”

“I thought you would.”

“He’s not going to do anything weird, is he?” Kylie asked.

Mommy laughed–a hearty bellow that suggested Kylie had inadvertently struck her funny bone. “I’m not going to lie to you, Kylie. Everything you see today is going to be weird.”

“Great.”

“Take a seat. I’m going to get myself ready for my day. Clark and I will be out in a few minutes.”

Without even realizing I had been moving, I found myself pressed to the other side of the partially-closed door–the single sheet of wood that, for now, protected the giant toddler from being spotted by Kylie. And soon, I won’t even have that. I scrambled back towards the bed as I heard Mommy walking back towards the bedroom.

“I suppose you heard that conversation?” she said, walking into the bedroom and closing the door behind her.

I nodded. I opened my mouth to say something, but I couldn’t imagine myself saying anything that she couldn’t tell just by looking at me.

“I know, I know,” she said, kissing my cheek as she floated past me to start getting some of her belongings from her suitcase. “This isn’t how you imagined today going, is it?”

I shook my head. “No, Mommy. Does she have to be here?”

“Two birds, one stone,” she said. “I wanted to hire a babysitter for you anyway. I thought it would’ve been fun. But then, of course, I got pretty busy and never got around to it. And I’m sure you can imagine just how hard it is to find a good babysitter willing to deal with such large diapers on short notice. And now, Miss Kylie seems to have just fallen into our lap.”

“But…” There were so many points to protest, where would I even start? I thought I’d pick the one that would, potentially, affect Mommy the most. “...aren’t you worried about her saying something to her mother?”

“No,” Mommy said, quite confidently. I expected her to have more to say, but that seemed to be it. Somehow, that simple answer felt plenty convincing to me, and I left it at that.

Still, I wasn’t even remotely thrilled about the prospect of having to not only reveal myself to Kylie, but to then spend the day with her.

“I don’t think she’ll change my diapers,” I said, an ever-so-slightly passive aggressive way of saying ‘I don’t think this is a good idea.’

“No, she probably won’t,” Mommy said with a shrug. “But that doesn’t mean that you can change your own either. I’ll take care of whatever she doesn’t when I get back.”

“But, what if…”

“You make a big mess in your diaper? You’ll probably stink up the whole suite. Oh well.”

There were many questions left, but only one I was going to ask: “Does it have to be this way?”

“Baby, if I say it’s going to be this way, then it’s going to be this way.”

I nodded.

“I’m going to take a shower and wash up, then get dressed and ready to go to the conference. You’re welcome to go out and greet Kylie yourself, if you’d like. But if you haven’t by the time I’m ready to go, I’m just going to drag you out there myself. I might even throw in an extra paddle or two on your padded bum. I can’t imagine you’d want her to see that.”

“M-maybe just a few more minutes, Mommy,” I said, feeling as pathetic as I probably looked.

She smiled. “Of course. But don’t keep your babysitter waiting too long.”

I sighed as I watched Mommy gather her things and strut into the bathroom. The last thing I saw, before the bathroom door closed behind her, was her robe falling to the ground, exposing her perfect body to me for just a moment.

I sighed a second time, grasping my thick diaper to feel my still-caged manhood within.

Behind one door was Mommy, naked and stepping into the shower. Heaven.

Behind the other was Kylie, completely unaware of the weird world she was about to be exposed to. Hell.

I’d have to go talk to Kylie before Mommy returned to the bedroom. But, considering that the water in the shower had just turned on, I had a few minutes.

I laughed to myself. Lyndie was going to get a kick out of this later.

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  • quietlyhumiliated changed the title to Doing Business [Season Two: Business Trip] [Part 31 posted on 2/03/2023]

Cliffhanger! And Kylie seems a little pissed off. I wonder if she had anything on today, such as meeting friends lol.

And I guess the blackmail/bribery doesn't have to stop here - Kylie can get Clark in some very compromising shots, though Clark could dob her into his mommy. (An old saying in Oz is "Dobbers wear nappies"!).

I hope Kylie takes to the role and gets a real kick out of it. Or perhaps she fails Ms Heller utterly and needs to be punished. A nice wry way of getting back at her rival.

 

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A nice cliffhanger.  Keep doing this, and you will see the story becoming a seamless whole ... and with continuity comes momentum.

Another thing to consider is how setting can hint at a story line later in the text.  For example, back in chapters 1 and 2, your description of Heller's office is short, and totally impersonal.  Didn't Clark look around?  Were there no family photos or other personal memorabilia of the type that decorate every executive's office?  Their absence, once noted, would have suggested to Clark that the lady is both unmarried and childless.  Just a passing reference, and then move on, not to return to the subject until Kylie enters the scene-- angry, self-loathing, destructive Kylie, whose mother bought into the nonsense about having it all, only to discover that success comes at a high cost, known as prioritizing.  Talking about Kylie would have allowed Clark to probe where this relationship is actually headed.  Is he filling a void in Heller's life, which holds out the possibility of 8/5 becoming 24/7, or will he remain a plaything for a woman who seeks nothing more from him than submission to abject humiliation?  The story has to have a resolution, and periodically scattering hints like this increases tension, and keeps the reader coming back for more. 

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  • quietlyhumiliated changed the title to Doing Business [Season 4] [Part 79 posted on 4/26/2024]

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