Doing Business, Part 41 [Season Finale] (Patreon)

Can you believe we've reached the end of the second season? Me neither. Need a recap of how we got to this point? Here's all the prior chapters in one handy place: https://www.patreon.com/posts/78092358

Forty-One

Nothing lasts forever. Not a fresh diaper. Not a full baby bottle. Not the humiliation of having loudly climaxed in my pants at a restaurant because of a remote-controlled vibrating plug inserted in my bottom by Mommy.

This little ‘business trip’ with Mommy, too, was sunsetting. We had one last night together in the suite. Tomorrow, at this time, I’d be back home again. Back in the world of Evan and Lyndie. Ava. Ms. Beaufort. It had only been a few short days, but it felt like weeks, somehow.

Nothing lasts forever. I had that stuck in my head. I tried writing it off as just being a little moody because my trip with Mommy was ending, but the feeling persisted no matter how much logic I applied to it. Maybe because I couldn’t stop myself from looking further ahead than just this weekend.

One day, this thing that I had with Mommy would be over.

I supposed that I could be wrong about that. Maybe there was, somehow, a scenario where Ms. Heller and I lived together in a retirement community and she was still wiping my dirty bottom. But I doubted it. At some point, something had to change. Maybe she’d leave the company. Or I would. Maybe one of us would realize that this arrangement wasn’t working anymore. Maybe the joy would have worn off.

“I don’t really care for that look,” Mommy said.

“Wh-what look?”

She laughed, shaking her head. “Really? You’re going to pretend that I can’t read you like a book? What’s wrong?”

My cheeks glowed a little, as I was feeling foolish for getting so upset about possibilities that were–hopefully–quite a ways off in the future. “I’m good.”

“I didn’t ask whether you were good or not. I asked for you to tell me what’s on your mind that’s giving you that sour look on your face. I’d have guessed that you pooped your pants, but…” She took an exaggerated sniff of the air. “...I don’t detect anything especially stinky.”

“I don’t want to trouble you with it, Mommy. I already know that I’m being silly, and–”

“I’ll be the judge of how silly you’re being. Come on now–out with it.”

“I was just thinking about…” The words suddenly seemed even more ridiculous than I thought they did in my head. “The end?”

“Of what? The weekend?”

“Sure. But, also…us? The inevitability of this little thing we’re doing ending one day?”

I expected her to laugh, or to just shrug and confirm that I was overthinking things. Instead, she sat down next to me on the couch and wrapped an arm around my shoulders, pulling me closer to her. She kissed the top of my head softly.

“Change is a scary thing,” she said. “Diaper changes? Absolutely frightful, depending on how badly it smells.”

I laughed. There were so many amazing things about Mommy that I rarely considered how funny she could be when she wanted to be.

She continued: “I don’t suspect I have much to say that you haven’t thought of yourself. The future is as unknowable as it is inevitable. We’ll see what it is when we get there.”

I nodded.

“I have now doubt this is already in the back of your mind. But take it from me–someone who’s a little more grown up than you: Just live in the moment.”

I took a deep breath before nodding. She was right–I already knew that to be the right answer, though it felt good to hear her say it too.

“But that advice can be deceptive,” she added. “‘Living in the moment’ doesn’t just mean that you take life as it comes at you. I mean, yes, you’re enjoying the moment that you’re in–but you’re also taking the steps that put you in the direction you want to go next. Nothing is certain, but you can at least try.”

It felt odd to laugh at that moment, but I couldn’t help myself.

“Is that funny?”

“No…not at all. But this is such a deep conversation and meanwhile, I’m over here…wetting my diaper again.”

She laughed herself, putting her hand between my legs to feel the diaper as it grew warm and swelled. “See? Living in the moment.”

“Thank you, Mommy. Not just for this conversation. But…for everything.”

“Of course. And thank you.”

I was finally smiling, though my cheeks still felt plenty warm.

“Now then,” she said. “I did have one little thing left to show you. One little gift in my suitcase that I haven’t shown you yet. I was saving it for the last night and, well, here we are.”

“Wh-what is it?”

“Words would do it no justice, my dear. I think you need to see it for yourself.”

I nodded, skeptical but nonetheless excited.

“No time like the present, right?” she asked. “Why don’t I go to the bedroom and get it ready for you. I’ll call you in when I’m ready for you.”

“Of course,” I said. “Thank you, Mommy.”

She kissed me on the head one more time before standing up and walking to the bedroom, closing the door behind her.

In an instant, all my worries about ‘the end’ were washed away, and I was suddenly fully committed to trying to imagine what this last surprise was going to be. Given what amazing toys I had already seen, I tried to imagine what was left. An even bigger diaper? An even smaller cage for my cock? A literal cage–like a dog’s crate–that she was somehow able to assemble from parts she kept in her suitcase?

With one hand still on my warm diaper, gently squeezing the squishy padding, I decided to distract myself with my phone. I had a missed text message.

Lyndie: Well, this is the last night, isn’t it? How has the time with Mommy been?

Me: It is. And, as amazing as you could imagine it being.

Lyndie: And how are you spending your final night with her?

Me: I don’t know yet, actually. She has something planned, but it’s a surprise.

Lyndie: Oh. I think I might know what it is…

Me: Seriously? How do you know?

Lyndie: She might have sent me some pics of her arsenal the other day. And it’s one of two things, I think.

Me: Well, she used the remote control plug on me earlier today…

Lyndie: I wish I was a fly on the wall for that.

Me: Don’t worry, the rest of Seattle got to see it.

Lyndie: Damnit. I need a camera crew to start following you and Gabrielle around.

Me: Don’t tell her that. She’d probably think it’s a good idea.

Lyndie: Tempting…

Lyndie: But that means that I know what this final little treat of hers is.

Me: I don’t suppose you’re going to tell me?

Lyndie: [gif of an older Steve Rogers, with text reading: ‘No, I don’t think I will.’]

Texting Lyndie had only made me more curious and excited about what was happening on the other side of the door that seperated me from Mommy. I was tempted to crawl towards it and put my ear on the door.

Patience.

And, really, patience was the answer to all of my woes. Worried about the future? Worried about possible endings? Patience. Savor the now.

I was certainly enjoying this wet diaper. It was amusing to think that there was once a time when I didn’t wear, or even think about, diapers. Now? Even if Mommy was to actually dissipate into thin air tomorrow, I couldn’t imagine myself going on without diapers.

The door finally opened, just a sliver.

“Baby? Come here. But make sure you’re crawling. And make sure that you’re wearing only a diaper.”

That was an easy enough request to honor. I was only wearing a diaper and the undershirt I had been wearing since brunch this morning. I pulled it off and tossed it on the arm of a chair before flopping down on the ground on my hands and knees.

Was there a time when crawling had ever felt strange to me? I couldn’t remember. I’m not sure that I’d say it felt ‘natural’ now, but it at least felt ‘right.’ Expected.

I crawled forward into the great beyond.

She was standing near the bed in just a robe. Or, I assumed it was just a robe. Her slender bare legs stuck out from the bottom of the robe, and the gap between the two halves in front revealed enough cleavage to suggest there was nothing else holding them in place. The key to my cage still hung from her neck, gleaming in the room’s light.

She had a simple question for me: “How does sex sound?”

“W-wait…are you serious?”

“I think it’s finally time, don’t you?”

“Y-yes,” I said, nodding so hard I wondered if my head would roll off my shoulders.

“I thought you’d be excited about that.”

“A-are you going to…unlock my cage?”

She laughed. I knew that laugh all too well: the ‘oh, you’re such a silly little baby’ laugh.

“I don’t think we need to do that,” she said.

“But…then, how do we…”

She pulled open the robe, revealing her final surprise. Her final gift. Attached to her body by a harness and a series of straps was a bright pink nylon cock.

I was speechless. I looked up at her and her impressive new shaft with my mouth hung open and my eyes wide.

“Well? What do you think, Baby? Think this’ll do?”

I slowly nodded.

“It came with a number of dongs in different shapes and sizes,” she said. “This particular one is recommended for newbies to backdoor adventures. I suspect that you, the little butt-slut you are, could handle a bigger one, but this seemed like a good starting place.”

“Y-yes, Mommy.”

“I’ve put a number of things in your bottom this weekend, and I think we’ve both had a good time with it. But this is what I’ve been working towards–the moment where I get to fuck you. I’ve been looking forward to this for a good long time.”

My nose whistled a little as my breathing came in short bursts, fueled by sheer want.

“P-please,” I said. “Please…fuck me?”

She stepped forward and ran her fingers through my hair. “I think you’ve done enough begging, Baby. You’ve been a good boy this weekend, and you’ve earned this. Up on the bed, now. Let’s get you good and fucked.”

In a matter of moments, I was face down on the mattress with my ass and legs hanging over the edge of the bed. She carefully pulled down the back of my diaper, just enough to expose my backdoor, while leaving my caged cock immersed in the moist padding.

Admittedly, I felt a slight pang of disappointment as I felt the well-lubed member sneaking past my tight muscles and into my hole. Make no mistake, I loved the feeling immensely, and the feeling of the artificial cock being pushed into me still forced a guttural groan from my mouth. But it was a feeling I had experienced a few times this weekend already.

And then, with just the slightest movement of her hips, she made me realize that I hadn’t experienced anything like this before.

The feeling of the prosthetic shaft inside of me was incredible, as it always was. But it was so much more than that. The feeling of the front of her thighs pressing against the back of mine. Her hands positioned on my hips. Even just the way that the cock moved inside of me–she didn’t have the same range of control over it with her hips as she did when she was fucking me with it while holding it in her hands. It just felt…real.

I had no idea if she had ever done a thing like this before, and this certainly wasn’t the time to ask. It seemed like she knew what she was doing, though–and she was doing it very well.

“Fu-uuu-ck…”

“Do you like that?” she asked. “Does that feel good?”

“Yessss,” I hissed, feeling my brain slowly liquify as she continued.

I’m getting fucked senseless.

“Tell me you’re a little baby,” she commanded.

I could barely think, but I opened my mouth and began to vomit words, hoping that they made some semblance of sense: “I’m a baby… I’m a baby. Just a little…unh…tiny…unnh…pathetic baby. Just a fucking disgusting little diaper-filling…oh…baby who needs his Mommy to…fuck…fuck him. Just… Fuck. Just a baby. A big… No, a little… No, I mean, uh, a big…little…? Little…big? Stupid little…unh…baby.”

“As always, you go above and beyond what I ask to make me happy,” she said. “But do you like it? Do you like being a ‘stupid little baby?’”

“Y-yeah…” I muttered, in between desperate breaths and primal grunts.

“Do you like being my stupid little baby?”

“Yes, Mommy,” I practically shouted. “I’m yours!”

“Mmm,” she moaned, deep satisfaction in her tone as she continued to fuck me with her cock. “Yes, you are. You’ll do anything I tell you, won’t you?”

It was getting harder to fit in words between my short breaths and increasingly louder moans. I threw my head up and down, hoping that it came off as a nod.

“When we return to the office, should we just do away with our attempts at illusion? Do we really need people to believe that you are just some college-age adult, taking his first, heh, baby steps into the corporate world? Or should we let everyone see who you really are?”

“Mmmm…”

“Maybe there’s no reason to keep you in adult clothes while you’re at the office. You could be the office baby. I mean…you are, though perhaps not everyone knows that yet. But they should, yes? They should see the baby in his big plump diaper and onesie, crawling around on the floor of the office with a pacifier sticking out of his mouth.”

“Mm. Mm…mmuhhh…”

“It’d probably be good for morale, right? It’d be like having a puppy. An office baby–everyone would love that. Everyone could take turns coddling you. Until you pooped your pants, I suppose. Then, I imagine you’d be sent to Lyndie or I to be changed.”

My body rocked forward and back in rhythm with hers as she fucked me. The longer we went, the better it seemed to get. She probably had a better handle on pleasing someone with a cock than most men–not that I was thinking about that in the moment. My mind was long gone, and all I could do was let her have her way with me. Of course, even if I had my wits about me, that’s all I would’ve wanted anyway.

At one point, I realized my thumb was in my mouth. I was completely sure when that happened, but it felt like it belonged there.

Stupid brainless baby, getting fucked by Mommy while he sucked his thumb in a wet diaper. It seemed so perfect. That dangerous sort of perfection that I’d probably be chasing again for the rest of my life.

But, too, if this wasn’t the end…maybe there were other levels of perfection that I hadn’t even witnessed yet.

“Ah, maybe someday,” she mused aloud, continuing to pound me from behind. “The world just isn’t ready for a completely exposed office-baby.”

And then she laughed, very hard.

“Of course, I could just have my own office building, right? One that encourages babies to crawl around without clothes to conceal their diapers.” Then, as if mostly talking to herself, she muttered: “Of all the fucking times to have an epiphany…”

I’m sure I’d have loved to process that idea a little more, if only she wasn’t bringing me closer and closer to another climax while my cock remained in its cage. Which was fine. Maybe I never needed to be unlocked again if she was going to keep fucking me like this.

Everything ends, I managed to think. Even this.

“Say it again,” she said. “Tell me again how you’re Mommy’s little baby.”

“Baby!” I shouted, barely able to think of many words beyond that. “Me baby!” I wasn’t especially aware of what I was blurting out.

“Yes,” she giggled. “Go on. Tell me more.”

“B-baby… Mommy’s, unh, baby…”

“You’re trying so hard to use your big boy words, aren’t you? I don’t see the point. Go on. Talk to me like the little baby you are.”

“Uhhhhh…” I paused for just a moment before spitting out a series of babbling noises: “Muh…mmghhhh…buh-buh…”

“Good enough,” she said.

I hoped, and believed, that she’d fuck me forever. But I could feel something brewing in me–that unmistakable tension of sexual energy that had just about boiled over. I sucked on my thumb even harder, bracing myself for the end.

I ended. I thoroughly ended, all over the inside of my diaper as I moaned and brayed like a mule, my body convulsing from what was likely the best end I’ve ever had in my entire life.

I think I might have blacked out. Maybe not literally, but I had become so lost in that moment that I had become disconnected from reality. I might have even had an out-of-body experience, watching from elsewhere in the room as Mommy gave me the last few thrusts that caused me to dump my load in my diaper.

“Are you okay?” she asked. The cock was still in my bottom, so it couldn’t have been that long after my climax–though it felt like years had passed and I was just waking up from a coma.

“Mmhmm.”

“I’m pulling myself out now. Are you ready?”

“Mm.”

There were, no doubt, thousands of articles and internet comments written about this very sensation, but it was one that was entirely new to me–her cock had stirred up my bowels something good, and the stimulation had left me badly needing to evacuate.

“D-diaper,” I muttered.

“Oh dear,” she said, likely sensing what was coming. She wasted no time in pulling my soggy diaper back into place.

Flump.

In a single, uncontrollable, moment, I filled the back of my diaper effortlessly. The best sex of my life, followed by, probably, the single best mess of my life. My poor hole–worn out from intense use–barely even registered the forceful exit. But the feeling of the mushy mass against the skin of my bottom was so good that it made up for the inability to feel myself pooping.

“I’m surprised this hasn’t happened sooner while we played with your backdoor.”

My face had turned a deep red as I slid my thumb in my mouth again. “Thowwy…”

“Oh, there’s nothing to be sorry for,” she said. “It’s what babies do, right? I choose to take it as a compliment–your complete and total transformation into Mommy’s little baby boy.”

That sounded good to me. I nodded slightly, though I was unsure if she saw that or not.

“What do you think?” she asked. “Should I get you cleaned up? Fresh diaper? Maybe a bath?”

I shook my head.

“No?” she asked, laughing. “Then what would you like to do?”

“M-maybe…I could just stay like this for a while?”

“I see nothing wrong with that. Why don’t we do this: I’ll sit on this big chair over here. And you’ll come over and sit on my lap in your stinky and sticky diaper. And we’ll just cuddle for a while. Does that sound good?”

“Yes,” I said. “Yes, Mommy. Please.”

I crawled up into her lap, balling myself up as best as I could in my mushy diaper.

“Tell me another story,” I said.

“I think I know one you might like,” she replied with a wry grin.

“Oh?”

“It’s not quite like my last story. That one had already happened, you know? But this one has yet to occur. But it might.”

“What’s it about?”

“It's about a woman who, at the strangest moment, realizes she’s done everything she’s ever wanted to. She’s achieved everything. She’s at the top of the world. And she wonders if it might be time to set some new goals for herself. Try new things. She wonders what it might be like to stop doing things for other people and to start doing things for herself.”

“Like…she doesn’t want to be a mommy anymore?”

“That might be the one thing she wants to do,” she said. “It’s the rest of it she could do without. The corporate life.”

“I’d like to hear more of that story,” I said.

“Me too,” she said, gently kissing me on the forehead.

She may or may not have had more of that story to tell me, though I’d never know. Exhausted from sex–exhausted from the weekend as a whole–I quickly passed out in her arms.

Everything ends eventually. I had made my peace with that. If I couldn’t stay like this–cuddled into a ball in Mommy’s lap while my bloated diaper’s scent permeated the entire suite–forever, I’d at least stay there for as long as she’d allow.

Epilogue

Somewhere in the midst of being railed from behind my Mommy, I had missed a text message from Lyndie:

Lyndie: Hey do you remember that guy you told me about? Thomas Pritchard? You said he was trying to cause some trouble because of your promotion. Well I did some snooping around and I figured out who it was. We know him. But we called him a different name because we didn’t know his real one. Anderson.