Doing Business, Part 29 (Patreon)

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.”