Ashley's New Boss - Chapter 1 (Patreon)

A new short story, commissioned by an anonymous Patron, and kicking off with a supersized first chapter.

"Just take a seat over there and Anna will be right with you," the secretary smiled, gesturing over to the waiting area.

Ashley froze for half a second, fear coursing through her veins before she calmed herself with an internal chuckle. Anna was such a common name... There was no way she could be unlucky enough that it would be the Anna she was thinking of. "Thank you," she said politely, stepping over to sit on one of the couches.

Despite what she'd told herself, she couldn't help thinking of 'her' Anna as she waited, fidgeting. She knew for a fact that she hadn't worked here then, had intentionally avoided trying to get a job where Anna did work, although it had been long enough now that Anna could easily have switched companies, in which case, it would hardly have shocked Ashley that she'd wound up in a position already where she had the power to hire people. 

She fit right into this sort of corporate environment, was practically made for it, as much as she loved to control everything, to manipulate it... That had served her well in her career; in their relationship, it had been the death knell, the thing that had prompted Ashley to ghost her. She'd been too scared to even tell her that she was breaking up with her, had waited until she was going to move to a new apartment building, not told Anna about it, then blocked her phone number and all of her social media accounts.

It had felt cowardly then, and it still did, if she was being honest. Anna wasn't unreasonable... She'd probably deserved better than that. Ashley had just been scared that, if she talked to the other woman about it, she'd wind up letting herself be convinced to stay, and she'd known that would be a bad idea.

It would be an even worse idea to work for her, no matter how appealing the job listing she was applying for was, so her heart sank when she saw the office door open, the occupant stepping out, as tall and beautiful and intimidating as ever. Ashley gulped, head spinning, unable to believe her bad luck. She squirmed on the couch, eyeing the elevator she'd ridden up on, wondering if she could sneak out before Anna spotted her, before the secretary pointed her out. 

If it was possible, Ashley was too slow for it, Anna turning, locking eyes with her with a familiar grin. Ashley felt her body lock up as her ex-girlfriend approached. "Well, hello, there," she purred. "How nice to see you. Why don't you come into my office?"

"I-I don't..." Ashley shook her head.

Anna paused, her voice softening. "Come on, Ashley," she urged. "Please? We can handle this like adults."

Ashley had never really felt like an adult next to Anna; she was so much taller than her, so much prettier... And that was definitely the case now, too, as she could feel a small dampness growing in her panties, one she prayed Anna wouldn't notice. Her bladder had always been tiny, like her, and weak, and Anna had gotten so annoyed with her whenever they went out to bars, and it would take barely a full drink before Ashley had to worry about having an accident. 

That had been the source of one of their biggest fights, Ashley going over to Anna's place so they could go out together and discovering that she had bought her diapers, of all things. "Come on," she'd told Ashley when she, naturally, protested. "They're purple! That's your favorite color!"

"I don't care if they're my favorite color!" Ashley had rolled her eyes. "They're diapers! I'm not wearing diapers!"

"Well," Anna had countered, "I'm not going out with someone who I know is going to humiliate me by pissing her pants twenty minutes after we get there!"

"I-I'm not going to!" Ashley had whined. "I-It doesn't happen that often!"

Things had devolved from there, with Anna listing every time it had, Ashley trying to dispute them, to say some of them had been spilled drinks, that some of them hadn't been that bad... In the end, they hadn't wound up going out that evening at all, with Ashley going back home in a huff.

And now, here she was, in Anna's office, underwear wet, proving Anna's point. "I-I..." Ashley stammered, overwhelmed.

"Please?" Anna repeated. "It would mean a lot to me."

Reluctantly, Ashley followed her into her office, taking a seat in front of Anna's desk. "I-I changed my mind," Ashley finally spoke up. "I-I don't want to work here. Y-You can delete my application, I-I..."

"Ashley," Anna interrupted gently, "I want you to know how sorry I am about what happened between us."

Ashley nibbled her bottom lip, staring up at Anna. "R-Really?" It did look like she was being sincere, though when it came to Anna, it was difficult to tell sometimes when that was the case, or when she was being manipulative. "Y-You're not mad about...?"

"No, Ashley," Anna said. "I mean, I was at first, obviously. I had no idea if you were alive or dead, and..." She shook her head, calming her voice, as it had been slowly building in volume through the last sentence. "I understand why you did it now, and I would have done the same, in your shoes. I've been wanting to find a way to make it up to you, but I didn't think I'd ever get the chance."

"I-I'm not going out with you again," Ashley told her, proud of herself for how steady she managed to make the words sound. "I can't, Anna."

There was a flash of what might have been disappointment in Anna's eyes before she nodded. "I understand. You're right, that's probably for the best. I would like to give you this job, though."

"I-I don't think that's a good idea," Ashley replied.

"I can approve you for an immediate raise," Anna said. "The maximum allowed. I know it would be way more than you're making now. And I promise, you don't have to worry about me hitting on you, or trying to pursue our relationship... That part of our lives is over, and I accept that. Please... I want to do this for you."

Ashley knew she probably ought to turn it down, but the pay on the listing was already enough to make it tempting, and with a raise on top of it... "Y-You promise?"

Anna smiled, reaching into her desk and pulling out a contract. "I do, Ashley. Come on... Just sign here."

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

Ashley looked up from her desk, not surprised to find Anna there, although the two cups of coffee she was carrying were unusual. "Thirsty today?" she teased.

"I am," Anna smiled, "But this one is for you."

"Oh." Ashley blushed, taking the cup. "Thanks." It was nice of her, Ashley had to admit... Anna was the manager, after all, so, if anything, Ashley should be the one fetching her coffee!

"I made it just how you like it," Anna said. "If you need anything else, you can feel free to let me know, okay?"

"Okay," Ashley nodded. It really did seem like Anna had turned over a new leaf, like she was desperate to prove it. It was kind of nice, if Ashley was being honest, seeing Anna so eager to please her, the way Ashley had felt like she needed to do for her when they were together.

"And don't forget you need your ID card to unlock any doors if you need to go anywhere," Anna reminded her. Ashley nodded again, took a sip of her coffee, pleased to find that it had exactly the right amount of cream and sugar, setting it down and getting to work.

She didn't think anything of it when her bladder twinged - if anything, it was right on schedule for her - and she hopped out of her seat to head to the bathroom, getting a few steps away before remembering to grab her work ID card. It was nice of Anna to refresh her memory on that, or else she might have made it all the way there and not been able to get inside, and, as far as her desk was from the bathroom, that might have spelled disaster.

It had seemed odd to Ashley at first when the secretary who had given her the tour had mentioned the bathrooms were kept locked, but as long as she was able to get in, she supposed it wasn't a huge deal. It was probably a security thing, she assumed, and a way for the higher-ups to keep track of where everyone was at all times.

Indeed, the lock beeped when she scanned her card, and she was able to open it right up and go inside. She let out a sigh of relief, half expecting to be denied, for this all to be a trick. There was still a little of that the next time she went in, and the third, but by her fourth trip of the day, it was second nature. She'd gotten used to how long the walk took, too, could time it out better, wait longer.

Which made it all the more devastating when, on her fourth trip, the lock gave a different beep, a red light flashing beside it rather than the usual green. "W-Wait, what?" she frowned, trying to push it open, only to find it still locked. She scanned her card again, heart pounding, with the same result.

"Oh, no," she groaned, squeezing her thighs together. She didn't know what to do, who to turn to, so, as much as she didn't want to, she found herself hurrying to Anna's office, whining, "The bathroom won't let me in!" desperately as soon as the door was closed.

Given their history, particularly with that, she wasn't sure Anna would do anything about it, but, thankfully, she took mercy on her. "Hurry!" Anna exclaimed, hopping up from her desk. "You can use mine!"

Ashley barely made it, shoving her pants and underwear down and plopping down hard on the toilet just in time, letting out a sigh of relief as she heard the tinkling coming from beneath her. When she finished up, wiped herself, started to pull her pants back up, she saw that she actually hadn't, not entirely. There was a small wet spot in her panties after all.

She hoped Anna didn't notice how much she was blushing when she emerged from her private bathroom, having to face her with damp undies yet again. "Th-Thanks," she said, trying to hurry for the door.

"Don't you want me to see if I can fix your ID?" Anna smirked.

"O-Oh," Ashley paused, turned. "Y-Yeah, I guess so..."

It was nice of Anna to do that; Ashley wouldn't have even thought of it again until she had to return to the bathroom next, and this whole thing might have repeated... Ashley really did seem to be turning over a new leaf. 

She waited anxiously while Anna typed away at her computer. "Don't be nervous," Ashley chuckled. "I'm your boss, and I know you're here, so I'm not going to be mad at you for not working right now. I'm sure this is just a little glitch, nothing to be concerned about... Ah, there we are."

"Is it fixed?" Ashley asked, ready to leave.

"No, not quite," Anna told her. "I just found what the issue was. Did you already take three bathroom breaks?"

Ashley blushed, squirming. "W-Well... Yeah..."

Anna looked up at her, shook her head. "Ashley," she said, Ashley not liking how much it sounded like she was scolding her, like she was talking to a child. 

"I had to go!" Ashley grumbled. "It's not my fault!"

"You're only allowed three bathroom breaks in a day," Anna sighed. 

"W-Wait, really?" Ashley squeaked.

"Yes, really," Anna replied. "Too many of our employees were abusing their bathroom breaks, so we had to crack down, and that turned out to be sufficient for all of them. You can go in and out as often as your like during your lunch break, though."

"B-But..." Ashley fidgeted, looking at the clock, thinking about how much longer she had to wait before her lunch break, and how long she had after that... "Wh-Why didn't you tell me that before?!"

"It was in your contract," Anna shrugged.

"Well, why didn't you warn me?!" Ashley fumed. "Y-You know my bladder...!"

"I assumed you read it like a responsible adult before you signed it," Anna said, crossing her arms. "Don't get mad at me because I trusted you."

Ashley nodded, trying to calm herself down. "Y-You're right..." She should have looked more closely, she knew, she'd just assumed it was all the usual legalese she couldn't make heads or tails of. And, since it had come straight from Anna's desk, before she'd had any time to doctor it, she'd also assumed that it was standard. "B-But what if somebody is sick, or...?"

"You can get a doctor's exemption to have more added," Anna informed her.

"Can't you just... say I have one of those?" Ashley sniffed, batting her eyes up at her pitifully.

Anna shook her head. "I don't have access to that on my end, I'm afraid... But I'll see what else I can do, okay?"

"O-Okay..." Ashley agreed, not knowing what else she could do. The next time she had to go, she got up sooner, certain she'd have to visit Anna's office again, not relishing that interaction, letting Anna have that much power over her. To her surprise, Anna had come through for her after all, and the door opened just fine, as it did for the rest of the day.

Anna brought her coffee the next morning, too, and Ashley felt obligated to tell her, "Thanks. And thanks for what you did yesterday, too."

"Of course," Anna smiled. "But you should probably see about getting a doctor's exemption anyway."

"Sure," Ashley said, with no intention of following through. 

She had hoped that her bladder's over-activity the day before was due to nerves over starting a new job, but it was just as bad that day, too... And, frustratingly, her card stopped working again partway through the day, leading to her rushing to Ashley's office, hand to her crotch, making a desperate race to her private bathroom...

And failing. To her horror, she could feel the warmth soaking through her pants, beginning to cascade down her thighs, right in the middle of her ex-girlfriend's office.

"I-It's not fair!" she sobbed through the bathroom door as she attempted to clean herself up. "I thought you fixed it!"

"I did what I could," Anna told her. "But all I could really do was let you borrow bathroom times from later on in the week... And apparently, you blew through all of those already."

"W-Well, what does that mean?!" Ashley whined. "N-Now I can't use the bathroom for the rest of the week?!" Anna didn't respond, which told her all she needed to know. "C-Can I use this one?" she asked quietly, not liking having to give that much control over to Anna, but not seeing any other option.

"I don't know," Anna replied hesitantly. "If you're in here that often, people might start to wonder why, and, as clear as you were about not wanting to have a relationship again, I doubt you want people to make assumptions..."

"W-Well, what am I supposed to do, then?!" Ashley demanded, pushing open the door to the bathroom, face red, to confront Anna.

Anna couldn't quite hide her grin as she looked down at the smaller woman in her soggy pants. "I do have an idea," she smirked. "But I don't think you're going to like it..."