Doing Business, Part 18 [Season Finale!] (Patreon)

[Author's note: Per usual, there's a naughty word or two that is censored, as to not upset the Patreon overlords.]

Eighteen

To the side of the large conference table, a row of chairs had been pulled back against the wall. The executives–the adults–were positioned at each chair.

Nobody needed to tell me how this was going to work, I could already see it for myself. This was a gauntlet.

I’d be passed down the line of execs, each having their moment with me, before I was finally passed back to Ms. Heller. And at the end of this process, I’d officially be indoctrinated into this weird kinky world of theirs.

I eyed up the order. Mr. Morris. Mr. Yang. Ms. Tamberlin. Ms. Beaufort. And finally, Ms. Heller.

Mommy.

On the other side of the room, I watched Ava and Lyndie join the other assistants. Megan was running her fingers through hair, seeming a little distracted. Bradley looked on nervously–either remembering his own initiation or maybe this was just the way he always looked.

“Come on now,” said Mr. Morris. “Get over here.”

I shuffled over to where he sat. I expected us to have a conversation, or that there’d at least be some sort of preparation for what was to come. Instead, he seemed to leap right into it. He reached forward to begin unfastening my pants. Instinctively, I brought my hands up to block him, but he just effortlessly batted them away, reminding me that he was now in charge.

“You shouldn’t have come back with pants on,” he said. “We were just going to take them back anyways.”

“Well you can’t have him walking around the building in just a diaper,” Ms. Beaufort said from further down the line.

“See, this is why I think we need to consider having a dedicated floor of the building that we use as a playspace,” Mr. Yang said, throwing his hands into the air.

“The board doesn’t love that idea,” Ms. Heller said. “But I still believe they can be convinced.”

The board? There was a board too? Did they know about the weird kinky lives the execs lead at work? Were they in on this game too?

“Now then,” Mr. Morris said as he tugged on my pants. “Let’s see that clean new diaper of yours.”

A ripple of giggles spread over the conference room from both sides as my girlish diaper was exposed.

I tried to explain: “It…it was all that was in Ms. Beaufort’s office and…”

“Baby, is your pacifier in your pocket?” Mommy asked from further down the line.

“Yes…”

“Be a doll and pop that into your mouth, please.”

I fished the plastic dummy from my pocket and did as she asked. As was likely her intent, I had felt especially chastised and childish by her command.

“Yes,” Mr. Morris said, running his hands over my pretty diaper, “this is a rather sissy look for you. Is your Mommy about to start putting ribbons in your hair?”

“I think I’d like to keep him as a baby boy,” Ms. Heller said. “Sissies are more Mr. Yang’s department.

“Sissies?” Mr. Yang rolled his eyes and shook his head. “Megan isn’t a sissy.”

“Over my lap,” Mr. Morris says to me, ignoring the other banter. “I assume you know where a little toddler belongs for a spanking.”

Not exactly, but I could figure it out. It had been a very long time since I was last pulled over someone’s knees for a sp*nking, but those memories never really fade.

Just like climbing into Daddy’s lap.

I threw myself over his legs, hearing a few more muffled chuckles scattered about the room as I did. He did the rest of the work himself, grabbing the waistband of my diaper with a single strong hand and pulling me into place.

There was no warning–he just immediately went into it.

SMACK!

I didn’t feel much of it. I felt the thick padding get shoved against my skin, but most of his blow was dispersed throughout the diaper. I assumed he knew this, of course. The sp*nking wasn’t intended to hurt–it was intended to humiliate. My pants were off, I was in a girly diaper, and I was over a man’s lap getting sp*nked–all while at work.

The mission is a success.

He throws a barrage of loud and firm slaps my way, each rebounding off the bottom of the diaper–the sounds echoing through the conference room.

“I’m hoping to spend more time with you,” he said to me finally.

“Yes sir,” I said. Adding, only because it seemed like the polite thing to say: “Likewise.”

“Alright, I think you’ve had enough fun,” Mr. Yang said from the next chair over. “Pass him along, will ya?”

Mr. Morris gently nudged me off his lap, and my feet slid back to the ground again. A short waddle later, and I was at the lap of Mr. Yang. I didn’t bother waiting for the cue to throw myself over his knees–I knew the request would be coming soon enough–and I planted myself atop his lap.

“Oh wow,” he said. “A real go-getter, this one. I can see why you’d want him to be your assistant.”

“He’s certainly a catch,” she responds from further down the line of chairs.

“I don’t have much more to add than what Mr. Morris has already demonstrated,” Mr. Yang says to me. “Though it looked like he was having fun slapping around this big poofy bottom of yours.”

WHAP! SMACK!

A short flurry of slaps rebounded off my diaper, again filling the room with the humiliating noise. Something was happening back there. Maybe the repeated slaps were breaking down the diaper’s thick qualities, or maybe it just took so many blows in the same spot before I began to feel it.

But I was starting to feel it now.

“Give him here,” Ms. Tamberlin said.

“Hold on,” Mr. Yang said. “I’m not done yet.”

SLAP! WHACK!

Another batch of smacks landed on my diaper. If asked, I wouldn’t have admitted that it was painful yet. But some of that sting was starting to make its way through.

As I was only halfway across the gauntlet, this didn’t bode well for me.

“Don’t be greedy,” Ms. Tamberlin said, expressing a little more frustration in her tone. “I want to play with the baby.”

“You don’t even like babies,” retorted Mr. Yang.

“I like them when they’re not mine.”

“Fine, fine.”

I was handed off again. I hopped off one lap and into Ms. Tamberlin’s. I glanced across the room as I did so, taking in the faces of the peanut gallery–the other assistants and Lyndie. None of the assistants seemed to look much different from the last time I saw them. I wondered if they’d seen this all before–aside from the time they had experienced it for themselves.

It was Lyndie’s reaction I was most interested in getting a glimpse of. Her smile had grown wider, and her hands seemed tightly clasped in front of her, like she could barely contain her glee.

SMACK!

Ms. Tamberlin wasted no time in walloping my diaper. I felt that one, and it smarted. The diaper’s protection seemed to have been worn down by the last two laps. Not only that, but it seemed like Ms. Tamberlin was striking harder than her peers.

CRACK! WHAP!

Her hand seemed to move faster, and the impact sounded louder when she made contact. Had the men just been showing restraint?

“I probably should’ve warned you, Baby,” Ms. Heller said. “Nancy is also the Director of Corporal Punishment.”

“God, I wish,” Ms. Tamberlin said. “Could you imagine how cool those business cards would look?”

SMACK! SLAP!

Another sharp delivery of swats arrives. My ass feels hot, and I bet it’s warm to the touch.

I’m now in pain.

I feel my eyes watering. My bottom lip is trembling. I didn’t see this coming minutes ago. Moments ago, even. And looking ahead–I know it’s only going to get worse.

“About done with him?” asked Ms. Beaufort in her delicious French-tinged accent.

“Just about,” she said. I couldn’t see her face, but I was pretty sure I could hear her smiling.

SLAP! WHACK!

A pathetic “Guh!” was forced from my mouth as her final smacks were felt through the worn padding of my diaper. This seemed to elicit a favorable reaction on both sides of the room.

I feel a heavy teardrop rolling down my cheek.

“There,” said Ms. Tamberlin, sounding content with what she had accomplished. “Now you can have him.”

I’m ready to flop myself over Ms. Beaufort’s lap next, but she stops me.

“Perhaps your bottom could use a break, yes?” she asked.

I nodded, sniffling a little.

“You’re looking a little beaten down, Clark,” she continued. “Does your little tushy hurt?”

I fought the urge to turn around and see how the other assistants were reacting. I simply stared forward at Ms. Beaufort, offering a little nod.

“I may have a little something that could help.”

“Oh?”

“You’re going to love this,” Ms. Heller remarked.

To my astonishment, Ms. Beaufort was unbuttoning her blouse. There was no shame or hesitation on her part, she went about it like she was at home, alone, with nobody watching her. She just made her way down her blouse, unfastening each button along the way, until she got to the last third when she stopped.

She reached into her open blouse to expose her lacy white bra. I may or may not have previously appreciated the size of large breasts in passing, but the more I saw of them now, the larger they appeared to be. And once her bra was exposed, she carefully hoisted her left bosom from it.

There it was, completely exposed to everyone in the conference room–her plump breast and its generously-sized nipple. And there appeared to be a little drop of moisture at the tip of it? A rogue droplet on the underside of her breast?

I wished I had a little more decorum, but out of surprise, I blurted: “Are you…lactating?”

There were some more scattered giggles throughout the room. I suspected everyone else–save for Lyndie–was already well aware of this.

“Don’t be shy,” Ms. Beaufort said. “Don’t you want a taste?”

Of course I did. I was practically salivating. But did I want a taste of her breastmilk here? With an audience?

“Really, it’s okay,” Ms. Beaufort said.

“Everyone’s had a taste,” Ms. Heller said, motioning towards the other assistants.

“I haven’t,” said Mr. Morris from the other end of the executives.

“If you’d like to serve as my assistant too,” Ms. Beaufort rebutted, “I’m all for it. But diapers are a mandatory part of my assistants’ dress code.”

Mr. Morris didn’t seem to have anything else to interject.

“Just a taste,” Ms. Beaufort said to me again.

I had never known how badly I wanted this before. And with another pathetic sniffle, and just after wiping the last of the tears from my eyes, I leaned forward and gently placed my lips on her breast. I had no remembered life-experience with actually suckling from a nipple, though the motions did remind me of sucking on a pacifier.

When the first drop hit my tongue, I immediately regretted having tasted it at all. It wasn’t enough that it made me feel so completely small–it also tasted magical. Like sweetened milk, or milk mixed with honey. I needed more, and I already knew that I’d later be craving more.

“Oh goodness,” Ms. Beaufort exclaimed to the delight of the others in the room. “He’s a thirsty one, hmm. Gabby, maybe you ought to consider lactation training yourself?”

I pulled myself away from her breast, suddenly remembering where I was and who I was still amongst. I had only been suckling for a second or three–but that was all it took to instantly brainwash me into thinking I was an actual baby again. My cheeks turned bright red as I tried to compose myself.

“Some babies can’t get enough,” Ms. Heller said with a shrug. “I’ll consider the suggestion, but if you have enough to share…”

“I do,” Ms. Beaufort says with a smile. “Anytime baby gets hungry and wants a little snack, you just let me know.”

And that just left one chair left: Mommy’s.

Having been sufficiently sp*nked, poked, prodded, and even breastfed, I wasn’t sure what else there was to endure now that I’ve made it to the end. Instead of throwing myself over Ms. Heller’s lap–as much as I would’ve liked to–I stood still and waited for her direction.

“I wanted to give this to you sooner,” she said. “But this seemed like a more fitting time for it.”

I tried to imagine what it might be. A key to her office? Her home phone number? A new pacifier?

She handed me a box, wrapped in red wrapping paper. “Go ahead. Open it.”

My eyes scanned across the conference room again, hoping to read the reactions of everyone else before taking any more guesses as to what it could be. But they seemed just uncertain, and curious, as I did.

Here goes nothing. I tore off the paper.

For a moment, I wasn’t entirely sure what I was looking at. I could see a picture of the contraption on the box–whatever it was, it looked sleek and made of stainless steel.

“Read it aloud,” Ms. Heller said. “What does the box say?”

“It says, uh…this is the ‘LilNub.’”

There were some giggles and chuckles coming from behind me. I still felt like I was missing something and I stared at the box harder. Then, suddenly, it clicked.

“That’s right! It’s your little chastity cage. What do you think? Ready to slip it on? Ready to be fully under Mommy’s control?”

It was something that had been in the back of my mind since she first mentioned it to me. I had always known what the cage entailed, and symbolized. Hell, I had even fantasized about such control being imposed on me by her. But holding it in my hands felt more real than it ever did before. This was real. This was really happening. And once it was on me, I was hers.

“Well?” she asked, still waiting for a response from me.

What else was there for me to say?

“Thank you so much, Mommy. I love it.”

Her face glowed as she smiled widely. “You’re such a good boy.”

“Well?” asked Ms. Tamberlin. “What are we waiting for? Lock that baby up.”

“Is that what everyone wants?” Ms. Heller asked the rest of the room. “Should I lock him up? Right here, right now?”

Lyndie started it: “Lock him up!”

Mr. Morris and Mr. Yang joined in: “Lock him up!”

The rest of the assistants, even timid little Bradley, had joined in: “Lock him up!”

Ms. Tamberlin and Ms. Beaufort joined in: “Lock him up!”

And the entire room became a unified chorus: “Lock him up! Lock him up! Lock him up!”

“And you,” Ms. Heller said to me. “What do you want?”

I was sure that she knew the answer. Everyone in the room probably did. But I said it anyway.

“Lock me up. I’m yours.” 

[Thank you for reading this story, and I hope you've enjoyed it so far. Season 2 starts the week after next.]