Doing Business, Part 36 (Patreon)

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Thirty-Six

“What’s in this, anyway?” Kylie asked, pulling her mouth from the nipple for just a moment–strings of saliva stretched between the bottle and her lips.

“Is it good?” asked Mommy.

“Is it just milk? I can’t remember the last time I drank a glass of milk.”

Mommy laughed a little to herself–a knowing chuckle that Kylie might look back on in hindsight and consider an omen. I was grateful Mommy didn’t look in my direction–I was barely holding back some laughs myself, and I definitely would have lost it if Mommy and I made eye contact.

Instead, I focused on the fresh diaper that Mommy had put me in not that long ago. I emptied my bladder into it–just a little seconds-long stream–with barely any thought or pause. This seemed to be happening more and more as of late. At times it seemed a little concerning, though never to the degree that I thought I needed to make a change in my lifestyle. It didn’t feel like my potty-training had just…expired. I still felt like, if I really wanted to, I could make it to the toilet before it was too late. The new routine was not having a routine at all–if I had to go, there was little point in holding it, and so I’d just let it go.

Actually, maybe that’s exactly what losing one’s potty-training is…

Kylie continued to slurp away at her bottle. I was actually kind of surprised that Kylie, herself, didn’t question the contents of the bottle more than she had. Mommy had explicitly told her, earlier today, what was in the bottle in the fridge and what it was for. Had Kylie just not been paying attention? Or did she have all the sense paddled out of her?

The room was completely silent as Mommy and I watched Kylie down the milk.

“All done,” Kylie said, thrusting her hand out towards Mommy with an empty bottle in hand.

“You drank that quicker than I thought you would,” Mommy said. “Was it good?”

Kylie blushed a little, wiping away a small dribble of milk from the corner of her mouth. “Yes…”

“You’ve taken to infancy rather well.”

“This isn’t going to leave this room, right?” Kylie asked. “You’re not going to tell anyone? You’re not going to parade me around town in a diaper?”

Mommy laughed. “You’ve earned my silence. And as much as I’d love to take my babies around town, I think you’ve been cooperative enough that I’ll spare you that experience.”

Kylie nodded, the answers to her questions seeming sufficient enough for her to share more. “I…like this.”

“Yes, we know,” Mommy said.

“Thank you,” Kylie says. “I needed this.”

“We knew that as well. Didn’t we, Baby?” she asks me.

“Y-yes, Mommy.”

“Now, babies, I had to rush back to the hotel room to take care of this little situation–I should’ve never left a baby in charge of a baby. Thankfully, I had finished the conference panels I was on at that point, though I suspect there’s a few people who wanted to talk to me there who are wondering where I ran off to. I’ll need to make a few calls in the other room. Is it at all possible that I can leave the two of you alone for a little bit without worrying about you getting into trouble?”

“We’ll do our best,” I said.

Kylie just shrugged.

“I’ve got plenty of energy left in my spanking hand, just keep that in mind.”

We said nothing, as we both believed that to be the truth. Mommy left the room, returning to the bedroom, closing the door behind her. In less than a minute, I could hear the muffled tone of her voice talking on her phone.

“Well,” I said, turning to Kylie, “welcome to…babyhood, I guess.”

Kylie sighed, looking a little flustered. “I…I’m sorry.”

“For what?” I did think that she had a lot to be sorry for, I just wasn’t sure what this particular apology was for.

“Oh…a lot of things. I was mean to you, for one.”

I felt my cheeks warm a little. There seemed to be little point in withholding the truth from her at this point: “I liked it.”

“You probably did,” she said. “But I didn’t want you to like it.”

“It’s fine,” I said. “Believe it or not, I’ve experienced much worse.”

Her ears perked up a little. “Like what?”

A rush of memories played in my head like a highlight reel. Getting passed around the laps of the executives in the boardroom. Messing myself in front of Lyndie. Being marched through the office in disgusting diapers. Pizza Girl standing in my doorway, looking down at my diaper and smirking.

I finally just laughed, shaking my head. “Probably anything you can imagine. And if I haven’t done it yet, I assume that it’s only a matter of time before it happens.”

“You pooped your pants at the mall,” she said, grinning a little. “That has to rank pretty high on the list of the worst things you’ve ever done.”

“Probably. I’m, uh, sorry I ruined things with that guy.” I wasn’t actually sorry, but it felt like the right thing to say.

She shrugged. “That probably wasn’t going to happen anyway. Or, at least not like I thought it would.”

“Is that something you do often? Go to new cities, meet strangers, and try to charm your way into their pants?”

She laughed and shook her head. “I sometimes think I want to be that kind of girl. But Ms. Heller kind of put things into perspective for me.”

“She has a knack for that. But…how so?”

“I’m just reminded that I really miss being a, uh, little girl. I guess. My mom stopped holding my hand at a pretty young age, you know? Figuratively and literally. And in my social scene back at home, you kind of have to grow up fast. It’s all about pretending to be mature and sexy and powerful and… I just miss drinking a bottle of milk and coloring with some crayons.”

“You’re in good company, then.”

“Fuck,” she said, rubbing her belly.

“What’s wrong?”

“My stomach doesn’t feel…good.”

“Oh. Something you ate? Or…” I glanced over to the countertop where Mommy had placed Kylie’s empty bottle.

“I dunno. I haven’t drank milk in a long time, so maybe it was just drinking so much of it at once.”

“Yeah,” I said. “That’s probably it.”

I was feeling guilty. It was one thing to push Kylie into diapers, but it was another to give her laxatives without her knowing. It seemed especially cruel to me. And while I wanted to tell Kylie the truth, it also felt like it’d be a betrayal of Mommy.

But what if, just this one time, Mommy was wrong?

It seemed a little too late for this epiphany, given that Kylie had already downed the entire bottle. But, I figured, I could probably do the next best thing.

“So…actually, I have something I should tell you.”

“Hmm?” She shrugged a little, as if there was little left in this world that would surprise her. “Did you poop your pants again?”

“N-no,” I said, my cheeks automatically warming at her guess. “But…you might.”

She squinted and tilted her head quizzically. “I don’t really see how that’s possible.”

“The, uh, bottle of milk,” I said, pointing to the empty bottle on the counter. “It’s the one Mommy…er…Ms. Heller left for me this morning, remember? The one she told you to give to me in case I needed it?”

I had quickly tried to image all the ways in which Kylie might have reacted–the possibilities ran the gamut from her punching me in the face to her getting up and running out of the suite and never being seen again.

Instead, she laughed. She just laughed.

“Are you okay?” I asked. “Like, you understand what I’m telling you, right? The bottle probably had some sort of laxative in it.”

“Ah, fuck,” she said, laughing again as she shook her head. “You people are something else.”

“I’m sorry,” I said. “I actually feel kind of shitty about it.”

“But not as shitty as I’d feel, right? If I pooped in a diaper like you do?”

I sighed. “You have every right to be mad. It was kind of irresponsible to…”

“I’m not mad,” she said. “It’s just kind of silly. Did you think that I’d really squat down and mess myself in a diaper?”

“I guess I didn’t really think about it all that much…”

“Is Ms. Heller really expecting me to poop my pants? Like is this yet another hurdle I’m expected to jump through so that she doesn’t talk to my mother?”

“I have no idea.”

“At some point, I can’t keep playing this game anymore. What’s next? She’s going to make me suck on her tit before she puts me to bed in a giant crib?”

“Look, Kylie, I don’t really know what to tell you.”

“It’s fine,” she said. “Like I said, I’m not mad. Just a little amused. But, like, laxatives don’t make you uncontrollably shit yourself, right? Or else nobody would take them.”

I shrugged, having no idea what Mommy put in the bottle. “I suppose you’re right.” If the bottle had been intended for me, she was probably counting on the fact that I’d just mess my diaper whenever the urges came over me.

“I’ll just go to the bathroom when I have to go,” she said with a shrug. “Easy peasy.’

“Or…”

She laughed. “Or?”

“What if you just…did it.”

“Did it? You mean, what if I just…filled my diaper up like a baby? Like you did?”

I nodded, bracing myself in case it wasn’t too late to experience that punch to the face. “Yeah…”

“What in the world makes you think I’d want to do that?”

“I just…I dunno. I mean, you seem to like diapers a little bit, right? And the way that, uh, Mommy treated you earlier? You just know she’d love to clean you up if you did. So, like, if you think you’d ever be curious about seeing what it feels like…maybe this is the time to do it?”

The room fell silent for a moment, and I watched the gears slowly turn in her head as she processed my words. From behind the bedroom door, I could hear Mommy talking on the phone. I couldn’t make out the words, but I could hear Mommy’s professional tone. She’d probably be tied up a while longer.

“Are you actually suggesting that I just…mess my diaper?”

I shrugged. “You don’t have to do anything you don’t want to do.”

“I know that.”

“Forget I said anything,” I said, suddenly realizing how insane it sounded to ask someone else to use their diaper like I did.

“Now hold on,” she said, stroking her chin. “I didn’t say that I wouldn’t.”

“R-really?”

“Maybe we could barter?”

“Barter? Like…how?”

“I can think of something–no, two things–I’d want in exchange for me making a mess in my diaper.”

My heart began beating faster. I wasn’t sure that I liked giving her any sort of leverage over me, especially when it came to her pooping her own diaper. But…I was at least curious to see what she had in mind.

“Like what?”

“I want to see your dick in its little chastity cage. That is what she has you locked up in, right?”

“Y-yeah.” That didn’t seem like that bad of a request. If she had asked, I might have even shown it to her without expecting her to have used her diaper in exchange. “And what was the other thing you wanted?”

“Since you’re the one who gave me the tainted bottle, I think you should have a front-seat view for the action.”

“How so?”

“I want your face pressed against the back of my diaper while I mess it.”

I immediately felt my cock strain within my cage as my face turned an entirely new shade of pink. I…wanted that. I wanted that very badly.

“Oh…” was all that I could muster.

“So? Do we have a deal?”

“Y-yeah. I think that’d work for me.”

“Okay, good. I guess we have a little time, right? I should probably wait for the laxatives to really kick in. I could make it all dramatic, right? Holding on for as long as I can before finally giving up the battle and just letting it all go?”

I’ve definitely been there before. “Well…whatever you want to do, I guess. Do you think you could…go? Now? If you had to?”

She shrugged. “Maybe? I’m feeling kinda…full. I don’t think I’ve gone in a bit, and I wonder if a bottle of milk, by itself, wouldn’t have been enough to get my insides going. But I could probably hold out a little longer.”

I nodded, feeling a little too overstimulated to know how to respond.

“But that means we have plenty of time,” she said. “If you, like, want to show me what’s in your diaper.”

I sighed. What would Mommy say? If she were here? She’d probably reach over and pull down the front of my diaper herself.

“Yeah,” I said. “I guess. But, like, you have to promise me that you’re not going to just run off and use a toilet later, then. We have a deal.”

“Yeah, yeah,” she said, sarcastically rolling her eyes. “But don’t forget that you need to jam your sniffer into my diaper while I’m taking a dump in it.”

My caged cock continued to throb. “I assure you, I didn’t forget.”

“Well then? C’mon. Show me what she’s got you locked up in.”

“Okay, fine. But…”

“I’m not going to promise that I won’t laugh at you,” she said, very likely reading my mind.

“Fair enough.”

I reached between my legs and unsnapped the bottom of the onesie, letting my mildly-moist diaper sag a little. Kylie made no effort to stifle her giggles at this sight–not that I could blame her.

“You must really want to see me use my diaper, huh?”

I laughed as I began to tug at the front of my diaper. Not only did I want to see her use her diaper, but I found myself very excited about the prospect of having such an up close and personal view of the action. Yet I was actually laughing about how easy it would’ve been to have gotten me to show my cage earlier. All she really had to do was ask.

And that, I think, went for everyone in the entire world. I’d probably do anything if I was asked to. Looking cute and wanting to humiliate me only made it easier.

I pulled down the front of the diaper just enough to allow my locked up manhood to flop out from it. There it was. Forever stuck in a state of softness, thanks to the LilNub.

“Holy shit,” she said. “That’s so…pathetic.”

My cheeks flared further and felt a new wave of shame wash over me. Even in a pair of diapers herself, and possibly on the verge of using them, she still seems to have the upperhand when it comes to humiliating me.

“It’s for Mommy, so…”

“Do you like it?”

“I like…her having that sort of control over me, yes.”

“But do you like the feeling of being locked up?”

“Not especially…”

“When’s the last time she took that off of you? I bet it’s been so long since you got off.”

“It hasn’t come off since she first put it on,” I confessed. “But…I got off last night.”

I immediately regretted saying that. It felt like too much information to have divulged, and I was only opening myself to more questions.

“Is that so? Did she fuck you in your ass or something?”

“Uh…”

She giggled again.

“You know about that kinda stuff?”

“I have the internet,” she said, shrugging.

“Alright,” I said, starting to slide my cage back into my diaper.

“No, wait,” she said.

“Hm?”

“Can I…touch it?”

My heart beat a little faster, and I felt my palms getting a little clammy. I took a cautious glance towards the bedroom door. I wondered what Mommy would say if she was here now. Who was I kidding, she’d probably love watching Kylie manhandle my cage.

“Y-yeah,” I finally said.

She reached forward and grabbed it, feeling the weight and size of it in her hands. She brought her face closer, doing a more thorough inspection. It was torturous, having a cute woman so close to my cock–grabbing at it with her hands–with no chance of me being able to actually enjoy it.

“Cute,” she offered, shrugging. “They make these plastic ones that are bright pink. You should ask her for one of those.”

“I’m not a girl.”

“What, a boy can’t wear pink? It’s not like you’re winning any ‘man-points’ while wearing a rainbow onesie and a unicorn diaper that you…” She quickly reached beneath me to feel the bottom of my diaper. “...a unicorn diaper that you’ve wet a little.”

“Point taken. But this chastity cage seems more than sufficient.”

“Well, be careful. If you don’t need to take it off to climax, she might as well just chop it off.”

“She’s not going to cut my dick off.”

She laughed, seeming to find her own scenario pretty hilarious.

“Well, what do you think? Ready to shove your face in my diaper?”

“Do you have to…go?”

“Not yet. Do these sorts of things usually take a while?”

I shrugged.

“Well, just put your face into my diaper anyway. I want to see what it feels like.”

I pulled open the front of my diaper and slipped my cage away and obediently crawled over to where she was squatting–her ass jutting out in the air behind her, just waiting for a foolish face to press itself into it. While this may not have been the most humiliating thing I’ve ever had to do, it might have, at least, ranked amongst the strangest. I leaned forward, slowly pressing my face against the bulky plastic padding of her diaper. It was as soft and crinkly as I expected it to be. Not exactly comfortable, though there was a quality to it that at least felt…’nice’ on some level.

And then I felt the diaper growing warm. I thought, perhaps, it was just from the heat of my blushing face pushed against it, but then the texture of the diaper’s padding seemed to change too.

“Are you…”

“Oh wow,” she said, moaning a little. “I had no idea how amazing it felt to wet a diaper. Keep your face there. I want you to feel all of it.”

She didn’t have to tell me twice. I could feel the diaper continue to get warmer and soggier. My ears were filled with the sound of the diaper’s crinkling and the faint sound of her stream making contact with the padding within.

I certainly hadn’t made note of the bedroom door opening and closing behind me.

“And…what exactly is happening with my babies?” Mommy asked. Her tone was crisp, but humored, cutting through the noise to make itself known.

“Oh, uh…” I eased my face from Kylie’s backside. “We were just…”

“No, no,” Mommy said. “Put your face back where it was. It looked good there.”

I did as she asked, feeling my heart pulse rapidly as I did.

“Kylie? Why is my baby boy planting his face in your bottom?”

“He, uhm, told me about the bottle,” Kylie answered, some of the wind being taken from her sails. I could sense the respect she had for Mommy’s authority. A good spanking will do that to anyone.

“And you somehow convinced him to shove his face into your diaper?”

“Yes…”

“Don’t mind me, then,” Mommy said, taking a seat on the loveseat near where we were stationed. “I have all day, and I don’t mind watching how this plays out either.”

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