Doing Business, Part 50 (Patreon)

Holy cow. Can you believe it's been FIFTY chapters? And that's not even counting the Memorandum chapters, or all the chapters that are written that you haven't even read yet. Wowzers. I just want to thank everyone who is still reading along with this story. I hope you're still enjoying reading it as much as I'm enjoying writing it.

And, as always, if you missed a chapter, or just need a refresher, don't forget that there's a list of Doing Business chapters so far, right here.

Fifty

My entire romantic history was embarrassingly brief and forgettable.

My first kiss was with Becky Sewart during a game of 7 Minutes in Heaven when I was in 8th Grade. Our names had been drawn at random from a hat–one from the ‘boy hat’ and one from the ‘girl hat.’ We were ushered into Nicole Greenwood’s bedroom and the door was shut behind us.

Becky and I had never talked before that. I wasn’t entirely sure we went to the same school. Honestly, I wasn’t entirely sure what I was doing at this party. ‘Boy/girl’ parties weren’t really my scene, and I was only there at my friend Daniel’s request. While I had no doubt that there were girls at this party who would’ve scoffed at the prospect of making out with the shy kid in the Beatles tee, Becky was not one of those girls.

Becky was very upfront with me. She had never kissed anyone either, and she wanted to. She was ravenous. And so we clumsily grasped at each other, mashing our mouths together in an effort to unlock the mysteries of kissing. It was fine. We never saw each other again after that.

It would be another three years before I kissed someone else again. This time, it was my partner in Chemistry Lab, Michelle Slater. We had been making eyes at each other for most of the semester, though neither of us seemed especially adept at flirting. We would eventually start ‘dating,’ which wasn’t all that different from being friends. We ate lunch together, talked on the phone on occasion, and shared small kisses when we were absolutely sure that nobody else was looking.

We finally managed to get some solid canoodling in when her parents went out of town for a weekend. All I had to do was avoid being spotted by her older brother–easy enough considering he had never left his bedroom–and we had most of the house to ourselves.

That was when I had lost my virginity–somewhere amidst the kissing and experimental touching, we stumbled into sex. Admittedly, it didn’t last all that long–I didn’t last all that long–and I’m still not entirely sure either of us actually enjoyed it.

We broke up two weeks later. Eventually, she’d come out as a lesbian–leading to the few who knew our history together to tease that being with me had been so bad that she swore off men altogether.

They might not have been wrong.

All this to say that it was a surprise to me when Ava pulled her lips from mine again so that she could say: “You’re a really good kisser.”

We had meandered into a small park by this time, a quiet place that was free of onlookers and bright lights. We had started by sitting on a bench as we made out with each other, but somewhere along the way, we ended up on the grass.

My cock throbbed in my cage as her lips connected with mine. As her diaper rubbed against my diaper. As my fingers snuck under her shirt to touch her skin. As she moaned into my ears.

As frustrating as it was to be denied the ability to let my cock grow, it didn’t feel like the worst thing to have the cage in place. If I had access to my manhood, I’d probably use it. And considering that I hadn’t gotten the pre-approval from Mommy that I once said I’d get before a situation like this, maybe it was good that something was stopping me from getting into any more trouble.

But, fuck, I wanted trouble. I wanted it so bad.

“Your diaper must be pretty wet by now,” I said, my hand slipping between her legs to feel the bloated padding through her pants. “With all this excitement?”

“Everytime I think my bladder is empty, I feel another little stream trickle out of me,” she said.

Her hand stroked the front of my pants again. I knew what she was looking for–the firm lump of a stiff cock buried in my diaper. But everytime, I could almost feel the confusion in her fingers when she only found the stiff cage in its place.

“I wish I had a key,” I said.

“Me too,” Ava said. “Do you think Ms. Heller would give it to me if I asked nicely?”

“There’d probably be some stipulations,” I laughed. “Like, we could have sex–but only if she watched.”

She shrugged. “Fine by me.”

“R-really?”

“I mean, that sounds really fun while I’m all horny like this,” she said, laughing. “If I actually had to do that? I dunno. Maybe I’d poop my pants and cry.”

I felt another pang of discomfort in my crotch. “Is it bad that I, uh, think that sounds kind of hot?”

“You’re such a dirty little baby, Clarky.”

“Takes one to know one.”

We didn’t actually know each other all that well. We knew about each other’s diapers. We had the shared experience of our surreal work environment. But I didn’t know her favorite color. I didn’t know what sorts of hobbies she had. We could be incompatible in almost every other way.

“What’s your favorite color?” I asked, figuring I had to start somewhere.

“Purple, I think. But also blues and pinks. Cooler colors. You?”

“Green,” I said. “Favorite TV show?”

“Uhm, don’t judge me,” she said. “Downton Abbey?”

“Why would I judge that?”

“It’s so…basic.”

I laughed, realizing that I didn’t know all that much about Downton Abbey or the social ramifications of being a fan of it. “Well, as long as we’re not judging, I’ll admit that my favorite show is, uhm, Mythical Knights of Far Earth.”

“I’ve never even heard of that,” she said.

“It’s…anime.”

She tried her hardest to keep her laughter contained, but it still managed to explode out from her lips: “Ha!”

“I know, I know…”

“I never really thought of you as the anime type.”

“I’m not. Or, well, I guess I’m not into it as much these days. But I was when I was in high school.”

“Educate me,” she said. “What is Mythical Knights of Far Earth about?”

I sighed, unprepared to have to summarize the epicness of a series I doubted she’d have much interest in. “Well, it’s, like, a fantasy story. With knights and dragons? But there’s also spaceships and lasers and…”

“I’m kind of loving this already,” she said. “Is it streaming?”

“No…it came out, like, 15 years ago, I think. It was never super-popular but it has a pretty big cult following. I, uhm, have the DVDs, so if you want to see them…”

She nodded. “I’d like that very much. And, if you liked anime, there’s another show I really like that you might know.”

“Which one?”

“Stargirl Regine in Love?”

I could imagine the DVD case–it was something I must’ve seen countless times in my teenaged, more anime-obsessed, years: A young woman with a flowing cloak, surrounded by countless smiling, boyish, faces.

“I know of it,” I said. “But I don’t think I know anything about it.”

“You’re in for a treat, then. It’s about Regine, obviously, a sorceress who always has to save the world with her magic, right? But she can only activate her powers when she kisses someone–and it has to be someone she’s never kissed before.”

“That actually sounds pretty fun.”

“It’s mostly dating antics with the occasional battle against a monster,” Ava said. “And I have those DVDs.”

It felt really assuring to have more in common with Ava than diapers. It wasn’t just that we both had our favorite anime–it was the excitement in our voices as we talked about them. The way our hands continued to touch each other as we talked.

“Looks like we’ll need to have some sort of viewing party,” she said.

“The only bummer is that we’d have to wait.”

“Wait?” she asked. “Wait for what?”

“For Ms. Heller to, y’know, unlock me from chastity.”

She laughed, playfully shoving my shoulder. “Dirty little baby.”

“What? You weren’t thinking the same thing?”

She shrugged playfully. “Wouldn’t you like to know?”

“Anime and chill?” I teased. “Marinating in our diapers?”

My smile faded a little as I said the words aloud. Soon, if she went through with her plan, Ava wouldn’t be in the office. She might not even be in diapers.

“I didn’t leave yet,” she said, reading my face.

“But you are leaving?”

She nodded. “But that doesn’t mean that we can’t ever talk to each other again. In fact, I hope that we talk to each other more than we’ve ever talked to each other before once I leave.”

“I hope so too.”

Her hand stroked the front of my pants again. “Can I see your diaper?”

I cautiously looked around us. The park was deserted–I didn’t even see people walking on the sidewalks around the perimeter. The windows in the closest houses were either dark or the blinds were pulled closed.

“Only if I can see yours.”

“Deal,” she said.

I quickly unfastened my pants, opening them up enough to show her the front of my diaper. She wasted no time in reaching forward to grasp it, gently squeezing the saturated padding.

“Pretty wet,” she said.

“That’s what they’re there for,” I said, shrugging.

She quickly repositioned herself a little, giving herself enough room to open her own pants, shimmying them down her thighs far enough that her diaper was almost completely exposed. Even in the dim light of the park, it was clear that it was very wet. Wetter than mine, were I to guess.

I watched as she took a look around the park herself. Deeming the coast to be sufficiently clear, her grin turned a little more playful as I watched her push her pants further down her legs. All the way down. When they reached her ankles, she pulled her sneakers off and set them aside, allowing her to completely remove her pants.

“Ava, wh-what are you doing?”

“Living my best baby life while I still can,” she said. “Lie back.”

She pushed against my chest with her palm, lowering my back to the grass. She took another cautious look around the park before throwing one of her legs over my horizontal body so that she could straddle me. Her wet diaper was now atop mine. I felt her slowly shift her hips, seeming to find just the right position. In a moment, it became clear what she had been looking for–the bottom of her diaper settled atop my caged cock.

Her body swayed back and forth ever-so-slightly, grinding her diaper against my cage. I wouldn’t have guessed she could feel the rigidness of my chastity through two wet diapers, but there she was–moaning softly into the night air.

“I…I wish you could feel this,” she said.

“I do too,” I replied.

Though it wasn’t like I didn’t feel anything. My cock was, of course, straining against the confines of its enclosure, while the rest of my body felt electrified with pleasure–likely compensating for the inability to grow hard.

“Y-you don’t mind if I, uff, use you a little bit, do you?” she asked.

It was certainly nice of her to ask. “Not at all.”

“I think about you a lot,” she said. “Like…when I’m touching myself.”

“If I could touch myself, I’d be thinking about you too.”

“W-wouldn’t it be fun if, uhhm, you could fuck me? And we were both, like, in our diapers?”

“Mmhmm,” I moaned. I had definitely thought about that before.

“Is it bad that I want you to fuck me while I’m in a messy diaper, Clark? B-because I think about that a lot.”

Goddamn, I wanted to be free of that cage so badly. “That would be so…naughty.”

“You think?”

“Only, like, the naughtiest thing ever.”

“Mmmmm.”

Her body continued to rock atop me steadily. I could feel her shifting more of her weight from her knees to her bottom. It was as fantastic as it was torturous. So close to being inside her, yet so far away. She was using me, and I kind of loved it. I almost wanted to run and tell Mommy about it after. I suspected she’d love to know all about how Ava got off at my expense.

I could feel some fresh dampness on my skin, and realized that one of us–maybe of us–had a leak. It shouldn’t have been a surprise, as both of our diapers were quite saturated, and with the way she was grinding on me it seemed inevitable. I didn’t mind it. I liked feeling the wetness seep into the fabric of my pants.

“Maybe you’d, ooh, mess yourself too,” she said. “A-and our dirty diapers would just, like, mush against each other as you fucked me.”

“You are an absolutely filthy little baby, Ava.”

“Fuck,” she hissed as her back arched. “I…I can’t believe I said that out loud.”

“I’m glad you did,” I said.

“I think, uhm, I’m…uff…going to…”

She didn’t have to say the word for me to know what was happening. Her legs tensed while I watched her shoulders buck and twist. She sputtered a series of sounds from her mouth, half-words like “Guh-” and “Ba-.” And when she was done, she slid off my body and collapsed beside me.

“I…I’m sorry,” she said. Not too sorry, I suspected–given her grin. “I’m not sure what came over me.”

“You have quite the imagination,” I said.

“It wasn’t too much, was it?” she asked, her voice faint with exhaustion.

“Not at all. I’ve never seen that side of you before.”

“Nobody has.”

“And you want to leave the company? You want to leave this? Are you sure about that?”

“No, I don’t want any of that,” she said. “But I need a place of my own. And I need a job that doesn’t make me lust after the naughtiest things on earth. And I need a good relationship with my mother. After I have those things? Then I’ll put a diaper on again.”

“And poop in it?” I asked, smiling.

She laughed. “A big one. The stinkiest one I can manage. And I’ll invite you over to be the first one to sniff it.”

“Don’t tell me things like that,” I said. “I’ll end up staring at my phone 24/7 until I get the call.”

“You let me know when you’re out of your cage first,” she said.

“Fair enough.”

For a while, we just laid in the grass, looking up at the night sky and taking in the ambient sounds of the park. At some point–and I wasn’t exactly sure when, as I had begun to doze off a little–she had slid herself back into her pants again.

“What do you think?” she asked. “Should we call it a night?”

“Do we have to?”

She shrugged. “I’m sure my mother already has a few questions about what I was doing tonight. The sooner I can answer them, the sooner I can go to bed.”

“Tonight was nice,” I said.

“Even the part where I rubbed my diaper on you?”

“Especially that part,” I said, my hand stroking my pants–still feeling the dampness from whatever pee Ava had managed to squeeze out of our diapers.

“D-did I get your pants wet?” she asked. “I didn’t mean to do that.”

“Laundry day is tomorrow,” I said. “Or, at least, it is now.”

We helped each other up and we took a minute or two to straighten and recollect ourselves. She put her shoes on and fixed her hair, while I zipped my moist pants up and brushed some grass and dirt from my clothes.

“I think I’m just going to call an Uber to drive me home,” she said. “Are you okay to get home?”

I nodded. “I’ll be good.

We had a few more minutes together as we waited for her car to arrive. We somehow managed to avoid talking about work or diapers for a whole ten minutes–instead revisiting our earlier conversation about obscure anime that we thought the other would like.

And then she was gone.

I was tempted to just walk home. It wouldn’t have been a short walk, but the weather seemed perfect for it. Not to mention that I’d have loved the time to just think and process the evening. Though–it wasn’t a trek I wanted to make with a sopping wet diaper like the one I was wearing. That was just asking for a painful rash. But I looked around the park again, finding that it was still completely silent and deserted. I lowered my pants one more time, removed the diaper, and heaved the heavy blob into a nearby trash can.

Walking home in damp pants, sans diaper or underpants, probably wasn’t much better of an idea–though I did it anyway. I took my time, rotating through the thoughts that weighed most heavily on my mind.

Ava.

Mommy.

My mother.

Lyndie.

Lyndie… I really didn’t want to be mad at Lyndie. I didn’t want to have a reason to be mad at Lyndie. The answer was quite simple, I realized: I’d have to talk to her. Tell her what I knew, and then see how she responded. It was all I could do.

I’d have to put on my big-boy pants tomorrow and do that. Figuratively speaking, of course–I was sure that my diaper wouldn’t be clean when it came time for that conversation.

I also briefly humored the idea of talking to Mommy about what had happened with Ava tonight. Somewhere in that conversation, I could even pepper in the fact that I’d like to be freed from my cage–even if it was just for a single evening.

But, no. Not yet. For now, I wanted tonight to be just mine and Ava’s.

Besides, before I did anything else, I’d need to deal with Lyndie.