Doing Business: Memorandums, Part 4 (Patreon)

Note from QH: This marks the last chapter for Memorandums...for now. But seeing as how this little series has been well received, it's definitely something I'd like to come back to later. 

Just a reminder, there won't be a Doing Business chapter posted next week. But the week after will kick off Season 3!

Need to catch up? Check out this list of chapters of the Doing Business saga thus far.

Four: Crybaby

“He’s a nice boy,” Nancy Tamberlin says. “As sweet as can be. Still, he can be a bit much at times.”

Lyndie sits back in her chair a little, almost excited for Ms. Tamberlin to spill a little tea. “How so?”

“He’s clingy, for one. Honestly, I’m not sure if he’s just that infatuated with me or if I’m just the only person he knows all that well, so he hovers around me at all times so that he’s not alone. It can be endearing. But…he can also feel like a barnacle.”

“Is it just that he needs attention?”

“No, I don’t think so. Like, we can go for hours without talking to each other. He just needs to be around me. Honestly, there are worse problems I could have with him. But, you know, he’s just such a…”

“Baby?”

Ms. Tamberlin laughs, nodding. “Yes, exactly. It’s a miracle that he’s gone this long without wearing diapers at the office. Can you believe the boy actually survived high school and college? The other kids must’ve eaten the poor thing alive.”

“He’s a bit…soft.”

“Honestly, Lyndie, he’s a sweetheart. I just wanted to give you a heads up–he’s probably the babiest baby in this entire office.”

- - -

She knocks on his cubicle wall with just enough firmness to stir him from his deep stare into his computer monitor. He slides his headphones from his head and sets them aside.

“Oh, h-hi, Lyndie. How are you?”

“Doing well, thank you, Bradley. And you?”

“G-good, thanks.”

“What are you listening to? Anything good?”

He nervously glances towards the headphones and then the computer, as if to double check that there’s no way for her to see what he was actually listening to. “Oh, uh, just some playlists.”

“Well, I thought I’d stop by and check in on you. Y’know, see if you need to be changed or anything.”

“Oh, I’m, uh, good. Thanks.”

“I really wish I could take your word for it, Bradley. But I kind of need to check for myself.”

“N-not here, I hope…”

“Why don’t we take a little walk over to my office and we can check there, hmm?”

“Sure. Y-yeah, that sounds good.”

He rises from his chair, his pants making an unmistakable crinkling sound as he does. It’s unlikely anyone else has heard it–he’s in a remote enough area of the office. But both he and Lyndie hear the noise, and that’s enough for his face to turn a little pink. He quickly fumbles with his keyboard, trying to lock the screen–but in doing so, he pulls up his music program long enough for Lyndie to see the name of the playlist: 20 Hours of Children’s Sing Alongs.

By the time he successfully locks his computer and looks back to Lyndie, his face is even more red.

“Ready?” she asks, a little knowing smirk on her face.

“Yes…”

Lyndie never has much trouble talking to Ava and Clark. Maybe it's because, at this point, she considers both to be her friends outside of work. Whether they’re having a conversation or there’s just silence, it never feels awkward. But it's different with Bradley. There’s just so much nervous energy to him that she worries a simple question about the weather would cause him to burst into a fit of tears.

Still, as they walk to the nursery, she makes an attempt at small talk: “Have any plans for the weekend, Bradley?”

“N-not really,” he says. She waits a moment or two, wondering if he’ll have anything to add to that, but no.

“What do you usually like to do on the weekend?”

“Not much.”

She takes in a long breath through her nose, doing her best not to get frustrated. Not everyone is a talker, and it’s probably hard enough for the guy to contend with having to wear diapers in the office and having to get them checked, let alone carrying on conversations.

At the nursery, she closes the door behind him.

“Alright, mister. Let’s get your pants pulled down so I can take a look at your bottom.”

“B-but…I’m dry, I promise. Really, you don’t have to check.”

Her eyes narrow and she shakes her head. “I don’t know what it is with you babies and your insistence on lying about the state of your diapers. You’re already wearing a diaper–you’re not saving any of your dignity by trying to convince me that it’s still dry.”

“But…”

“No ‘buts.’ Just show me your diapered butt.”

He does as she asks, carefully and methodically unfastening his belt and opening his pants before shimmying them down his legs until the waistband is just above his knees. She doesn’t have to look too hard to see the telltale sag of the diaper. He’s most certainly wet.

“See?” she says. “Soaked, by the looks of it. Why couldn’t you just say that?”

Tears well in his eyes, with a single droplet managing to escape and slide down his face. “I…I’m sorry.”

“Are you…crying? Bradley, you’re not in trouble. You’re supposed to be using your diapers. I’m just here to help you take care of them.”

“I’m sorry, I’m sorry… I just…”

“I know,” she says, sighing a little as she tries to compose herself before she bursts out in laughter at the pathetic creature standing before her. “It’s really not that big of a deal.”

“Is it bad?” he asks, sheepishly looking down at his diaper.

“Well, it probably can’t hold much more. You don’t want to leak, do you?”

“N-no, I guess not.”

“Alright then. Up onto the changing table, let’s go.”

It’s not the first time she’s changed his diaper since taking on her new position as ‘corporate-babysitter,’ though his squeamish nature sometimes makes every new diaper feel like the first time all over again. She wants to laugh as much as she wants to grab him by the shoulders and give him a good firm shake.

No, no, you’re not supposed to shake babies.

She wonders how long it will take for him to act more like Ava or Clark, accepting diaper changes as just a normal part of their jobs. It’s a little ironic, she thinks, as Bradley seems so much more like a baby in almost every other way. She’s surprised that he wasn’t already wearing diapers when he started this job.

“So,” she says, pulling his pants down his legs, “is this really your first time wearing diapers? Here at this company?”

“Since I was a baby, I guess,” he says. “Why?”

“Oh, they just, uh, suit you.”

“Are you calling me a baby?” Again, his pouting tone almost brings her to a giggle, though she holds on tight.

“I mean…not exactly…”

“People have always called me a baby,” he says. “Or a crybaby. Or a little boy. Well, people call me a lot of things, I guess.”

His pants are off and she begins to pull back the tapes of his saturated diaper as she attempts to prod a little further. “Do you like it when people call you those things?”

“I don’t think I’m supposed to. Sometimes people are trying to be mean.”

“That’s not what I asked. Regardless of whether or not you think you’re supposed to like it, I’m asking if you do like it.”

“Sometimes,” he says, though the answer comes so quickly that he might as well have just said ‘yes.’

She separates his legs and pulls open the diaper, noticing how heavy the front of the diaper feels as she unfurls it. He must’ve wet himself at least twice in this thing.

“Did you get bullied a lot growing up?”

“I get bullied a lot now.”

She laughs. “Do you think that I’m bullying you?”

“N-no,” he says. “I just mean, like, not many people really respect me.”

She’s close to teasing that he would be a hard person to respect while his moist and flaccid penis hangs between his legs atop an opened pissy diaper, but it doesn’t seem like the time. Instead: “Do you want people to respect you?”

“Uh…”

She laughs as she draws a moist wipe from its package and begins to clean the skin in his diaper area. Smooth and hairless–she wonders if this was his own decision or if Ms. Tamberlin had insisted on it.

“Some people are just good at being doormats,” she says. “People try to say things about how everyone should stand up for themselves or whatever, but I don’t think that’s true.”

“No?”

“Gabrielle has a saying, you know? Actually, she never said it to me directly, but she’s said it to Clark a few times and then he said it to me. It’s something like: ‘There are leaders and followers. And each needs the other to exist.’ So, yeah, you’re a follower. But that’s not a bad thing.”

“Are you defending people who bully me?” he asks.

She laughs. “Oh, no, I don’t think so. Who bullies you?”

“Do you know Megan?”

She nods, though the truth is that she actually doesn’t know her all that well. The only executive assistant in this little cult who doesn’t wear diapers, though she seems to have an interesting enough story of her own.

“Really? What does she do?”

“She teases me a lot. Pokes at the bulge in my pants. Calls me a ‘crybaby.’ Or a ‘pissy-pants.’ Or a ‘thumbsucker.’ Well…she calls me a lot of things.”

It probably wasn’t the reaction she was supposed to have, but Lyndie couldn’t help but think that she now wanted to get to know Megan. She sounded fun.

“Maybe she actually likes you,” she suggests.

“Huh?”

Lyndie tucks the used wipes into the old diaper and balls it up before discarding it. She walks to the well-stocked diaper shelf, showcasing a wide assortment of large diapers in many colors and designs.

“Do you have any preferences for the next diaper?”

“No…you can choose.”

“Careful with that,” she says. “I’m always going to choose the most embarrassing option.”

He offers a slight shrug, and she responds with a shrug of her own.

“Okay, fine,” she says. “But I don’t want to hear any complaints about what I pick out for you.”

Her fingers slide across the selection of plump folded diapers on the shelf until one catches her eyes. She believes these are called ‘Princesses’–shades of light pink and darker pink with little feminine faces, tiaras, and unicorns printed across them.

“Wait, no…I’m not a girl!”

She swears that there are tears in his eyes again. “Look, buster, you didn’t want to choose, and so I chose one for you. This is the diaper you’re getting.”

“B-but, Megan…”

“Does Megan actually see your diapers?”

“Not always. But sometimes she tries to pull down my pants. And if she does it again, she…well, she’d never let me hear the end of it for wearing a girly diaper like this.”

“You think?” Lyndie asks. “I mean, maybe she’d find it a little relatable, y’know? Given that she’s also into, uh, girly things.”

“Maybe…”

Lyndie is a little curious about how Megan and Bradley interact with each other. In the scheme of things, she knows the least about the two of them–though she’s quickly getting caught up on him. It’s Megan that still remains a mystery. No diapers, but still considered to be one of the ‘sex toy’ assistants. She makes a mental note to schedule some time with Megan later.

“Oh, for goodness sake,” she says, looking at his face again as she unfolds the diapers. Sure enough, some fresh tears are rolling down the sides of his face while his lip quivers. “What are you crying about now?”

“I’m not c-crying.”

She rolls her eyes. “Are you sure about that, bud?”

“These are, uhm, tears of…happiness.”

She’s not entirely convinced of that, but chooses to roll with it anyway. “And what would be making you happy right now?”

“You,” he says. “This? Just talking and stuff.”

“Ms. Tamberlin doesn’t talk to you?”

“She does… But I don’t think she wants to, like, be my friend or anything. We only talk about business. Or how I can please her sexually. And, uh, I do like doing that for her. But…I guess, I just wish we had something deeper. Like what Ava has with Ms. Beaufort. Or what Ms. Heller seems to have with Clark.”

Lyndie is simultaneously flattered and confused by his explanation of ‘happiness.’ Is he so starved for companionship that some small talk while she changes his diaper is all that’s needed to bring him a little joy? She ponders it further as she slides the fresh pink diaper under his bottom. Maybe there is something to that–Ms. Tamberlin has often said that she had no interest in changing his diapers, and there was something admittedly intimate about this whole process. Maybe she was missing an opportunity to be bonding with Bradley.

She notices the way that he stares up at her as she shakes baby powder into his diaper. The way his cock–completely average sized, if she was to rate it–suddenly grows a little firmer under the white cloud of powder. Goddammit. This boy is probably crushing pretty hard right now. She pretends that she doesn’t notice.

“Th-thank you for doing this for me, Lyndie,” he says.

“Of course,” she responds, overly critical of her own tone and how it might be perceived. Is he going to think that I like him in the same way? She adds: “It’s what I’d do for anyone who needed their diaper changed.”

Still, there’s something about that pathetic puppy-dog look on his face that breaks through the wall of cynicism she usually prefers to stand behind. Though, if she was being honest with herself, that cynicism had started to fade a little since being invited into Ms. Heller’s surreal little world.

“What are you doing for lunch?” she asks, pulling the tapes of his diaper into place so she can seal it shut.

“I brought a sandwich from home,” he says.

She grimaces a little. She finds homemade sandwiches to be the most boring thing one could subject themselves to for lunch at the office. “What if, after you get your pants on, we go and grab some lunch together at the cafeteria? My treat?”

“Oh, I…uh, well, I don’t want to impose.”

“You’re not imposing if I ask you to go with me,” she says, rolling her eyes again.

“That sounds very nice. Thank you.”

- - -

Lyndie doesn’t think about it too much in the day or two that follows. Sure, she thinks about it a little–she thinks about how it was nice to have extended a hand to Bradley. Maybe it makes him feel a little better about his place in the office, if he was having doubts about it before. Truthfully, she feels a little better about herself. Maybe this isn’t the position she ever imagined herself being in, but it feels more right to her than most anything else ever has.

And then, early in the afternoon, there’s a timid knock on the door to the nursery. She can guess who it is before she even opens it. It’s a surprise for many reasons, namely that he’s never come to her before–she’s always had to go and fetch him.

“H-hello, Lyndie,” Bradley says, hands folded in front of him as his cheeks glow a slight pink.

“Bradley, hi. In need of a change already? I thought I just took care of your soggy bottom an hour or two ago.”

He quickly leaps into the nursery, closing the door behind him so as to not let this conversation reach any ears it shouldn’t be.

“Well, no, I don’t need a change. Just yet.”

There’s something about the ‘just yet,’ that gives her pause. “So, then, what brings you by, babypants?”

His cheeks blush a little brighter at her playful jab. “I was just, uhm, hoping we could talk for a minute?”

“Sure. What’s up?”

“So, like, I don’t normally do this sort of thing,” he says, running a hand through his short hair. “But I was wondering if, maybe, you’d…uhm…help me do something I’ve never done before?”

She grimaces again, imagining him pulling down his pants and holding his dick in his hand. But she decides to give him the benefit of the doubt and at least hear him out before she sends him on his way. “What, exactly, did you have in mind?”

“Well…so, I was thinking about it, right? And…I’m sure you change all kinds of diapers…”

She’s not entirely sure where he’s going with this yet, but she can’t help but crack a tiny smile. There’s something really adorable about watching this boy trying to stammer his way through whatever absurd request he has. “Uh huh.”

“And, like, I know I’ve wet my diapers an awful lot since I started having to wear them again. But one thing I’ve never done before…because, you know, Ms. Tamberlin really doesn’t like the idea of it…”

“Bradley,” she says, holding a hand out for him to stop talking for a moment. “Do you want to poop your pants? Is that what this is all about?”

“I just never have before,” he says with a sheepish shrug. “But I’d never, uhm, want to just barge in here and force you to have to deal with that.”

She laughed, shaking her head. “Believe me, you wouldn’t be the first to do that.”

“So…with your permission…maybe I could…?”

Her smile grows a little as she stares down the fragile little boy in front of her. He’s refreshingly transparent–what you see is what you get.

“If you want to poop your pants,” she says, “then you should go ahead and do it.”

“A-are you sure? Because…”

“Bradley, yours wouldn’t even be the first dirty diaper I’ve seen today. Why don’t you take off your pants, relax a little. And when you’re ready, just…let ‘er rip.”

His face turns a deeper red, maybe because of her phrasing, or maybe at the fact that she’s actually allowing for this to happen. He fumbles with his belt for what seems like ten minutes before finally shoving his pants down his leg, revealing the same light green diaper she had put him in an hour or two before–he had been sure to pick his own diaper this time.

No, Lyndie isn’t normally thrilled about having to change another messy diaper. She likes the concept of a messy diaper more than she likes the actual experience of having to clean up after one. She can watch big babies filling their pants all day long, though–she’d never get sick of watching their faces scrunch as they pushed something unbelievably naughty into their diapers like they were 20-something years younger than they actually were. But changing dirty diapers is starting to feel like work. At least she gets paid for it.

But this scene that is starting to play out in front of her now, is very exciting. She’s proud of herself. She’s proud of Bradley. This, to her, feels like validation of her abilities as the ‘babysitter.’

“Go on,” she coos. “You can do it whenever you’re ready.”

“I…I don’t know if I can–”

“You do have to go, yes?” She doubts he would’ve come to her if he didn’t have to.

“Y-yes. Very much so.”

“Well?

“But…”

“But what? I’ve seen plenty of stinky diapers. And I’m asking you to do it. I’m not sure if there’s any reason to doubt yourself now.”

“Yeah. Okay…”

The boy still seems wracked with hesitation, however. She thinks she can guess why–he needs to be told to go. It doesn’t matter how long he’s been holding it or how badly he needs to go now, he needs to be told to release it all into his diapers.

She’s not immediately sure how she feels about this. Thus far, she feels like she’s been acting as the hand of the executive management team–dispensing humiliation and aftercare, but only at their request. This feels different. She doubts that Ms. Tamberlin even knows he’s here right now. And so it’s now her decision when, and even if, he uses his diaper.

If it wasn’t for the painful look of discomfort on his face, she’d be tempted to make him wait a little longer.

“I want you to poop your pants for me,” she says, hoping that the words ‘for me’ really resonate with him. “Fill your diaper.”

In the split second before his face scrunches up and he drops his load into the diaper, he looks happy. Gleeful, in fact. Maybe the happiest she’s ever seen him.

She smiles while watching him grunt, the bottom of his diaper sagging more as the sound of his mess being expelled fills the room.

I could get used to this sort of power.

“Come here,” she says. “Let’s see what you’ve done.”

He takes a deep breath, both to recover from all the energy spent in squeezing everything out of himself and into his diaper, and to brace himself for the inspection of his diaper. Once again, there’s tears streaming down his face. The pathetic little thing is literally crying like a baby because he pooped his pants. How fucking delightful.

She takes great pleasure in watching him trying to walk again–the first time he’s ever had to walk in a messy diaper. After a few awkward and uncertain steps, he settles on an exaggerated waddle in which he leaves his padded ass sticking out in the air behind him. She’s not entirely sure the analogy makes sense, but she thinks of a duckling waddling out of a pond.

Maybe not now, but eventually, she’s going to float the pet name Duckling past him and see how he reacts.

“Well it certainly smells like you filled it up plenty. But let’s take a little peak. Turn around for me?”

He does so, slowly shifting his body around so that the expanded rear of his diaper is right in front of Lyndie. She pulls open the back of his garment, seeing exactly what she expected to see–that’s quite a load.

“Turn around again,” she commands.

He does so, his cheeks more pink than she’s ever seen them before. This time she cups the front of his diaper in her hand. Once more, she finds exactly what she was expecting to find–a firm cock buried in the padding.

“What do we have here?”

“Uhm…well…”

“It feels like someone might like their stinky diaper. Is that right?”

“I…uh…”

“There’s no need to be bashful about it,” she coos. “You like what you like. What if I helped you make the inside of your diaper a little sticky?”

He moans as he begins thrusting his diaper into her hand. It doesn’t take long.

- - -

“Have you noticed anything different about Bradley lately?” Nancy Tamberlin asks, sipping from her steaming cup of morning tea.

“Different?” asks Lyndie. “How so?”

“I’d say he’s more…chipper? Exuberant? I suppose he’s never been an unhappy boy. But there's been a little extra pep in his step the last few days.”

“Interesting,” Lyndie says. She can’t help but grin a little, though she tries not to be so obvious about it.

“Maybe it’s you,” Ms. Tamberlin says, shrugging. “Maybe he just needed a little extra TLC.”

“Maybe,” Lyndie says. “But I don’t think I’ve done anything all that different.”

“Well, whatever you’re doing, keep it up.”

Lyndie wears a goofy grin on her face as she makes the walk back to the nursery. It’s been a while since she felt like this. It’s kind of like the feeling she used to have when she was falling in love–but not quite the same. She’s not falling in love. She doesn’t see herself marrying, or even dating, Bradley. But she has power over the boy, and she can’t even begin to imagine the things she can do with that yet.

She finds a small bundle of flowers waiting for her in the nursery. No name on them, but she can guess who they’re from.

Is this dangerous? she asks herself. Am I playing a dangerous game? Playing with this silly little boy like this, someone might get hurt. Worse, he’s someone else’s little boy.

It seems like a problem for another day. For now, she’s going to think about the next time she makes Bradley squat down and fill his diapers for her.