Ashley's New Boss - Chapter 2 (Patreon)

Ashley had been so prepared for Anna to suggest diapers, the way she had when they were together, had been ready to tell her no, but, to her surprise, she had, instead, recommended a doctor. "They accept our insurance there," she'd said. "And they're pretty close. You can go wherever you want, obviously... I just think trying for that doctor's exemption will be your best option. I bet I can get them to squeeze you in today, too."

Anna was right; Ashley didn't really like that, either. She doubted anyone enjoyed going to the doctor, didn't think she was special in that dislike, though that didn't change the fact that she'd rather have been almost anywhere else after work that day, other than sitting in the exam room, squirming on the table, feeling cold and vulnerable, having just gotten extensively poked and prodded and probed, now waiting for the results to see if all of this had been worth it.

She flinched at the sound of the door opening, turning to see the doctor return, clipboard in hand. Ashley wriggled on the table, hearing the paper cover crackling beneath her, grateful to see the other woman sit down, as opposed to going for the latex gloves again. "S-So," Ashley spoke up anxiously, "what's the verdict?"

"Hmm?" the doctor glanced up at her, over her glasses. "Ah, yes. The 'verdict.'" She let out a dry chuckle at the choice of words. "Well, dear, I'm afraid I can't help you."

"Wh-What?!" Ashley squeaked, brain filling with anger at having gone through the whole appointment for nothing, and despair, not knowing what she was going to do at work now. "Why not?!"

The doctor blinked, surprised at the harsh tone coming out of the otherwise meek girl. "Because I can't diagnose something that doesn't exist."

There had always been some part of Ashley that had feared this would be the case; it was why she hadn't gone to a doctor before now. That, and, as inconvenient as it could be, it hadn't been as big of an issue until now, until it was affecting her life at work. "S-So, there's nothing wrong with me?"

"Not medically, no," the doctor shrugged. "There is a medication you could try, but there's no guarantee it would make any difference, and if it did, it would take a few weeks, at least, to kick in. It could help expand your bladder capacity, though. It's still in testing, so how much is hard to say, and..."

"A few weeks?" Ashley's stomach twisted, her mind having wandered from what the woman was saying after that. "B-But... What am I going to do until then?"

"I could prescribe you some protective garments," the doctor offered.

And there it was, the thing Ashley had been terrified, coming in, would be the only solution, the thing she'd avoided the last time Anna had wanted her to do it, the thing that she'd assumed Anna was going to go straight back to. "D-Diapers?" she whined. 

"Yes," the doctor replied. "I know it's embarrassing, but I think you'd be surprised how many young people your age have to wear them. And if the drug works, it would only be temporary."

That was true... This wasn't the whole thing, just a part of it. If nothing else, it might help her get by with those three bathroom breaks she was allowed, as gross as the idea of peeing herself and sitting in it was. "O-Okay," she agreed reluctantly. 

"Very good," the doctor nodded, jotting something down on her clipboard. "I'll have the nurse bring a package in for you to get you started."

Ashley didn't love having to wait even longer here, or having somebody else know about her new secret, but she could at least get up off the table now, pace around the room nervously until the nurse came in. "Hello," she smiled. "I believe these are for you."

The package was big, especially considering how few diapers it said it contained. Ashley's nose crinkled as she took it, wondering how bulky and thick they were, how difficult it was going to be for her to keep them hidden under her clothes.

"Do you need any help putting them on?" the nurse asked. "I can give you a tutorial while you're here!"

"N-No!" Ashley shook her head, cheeks glowing. "I-I'll be fine!"

She was less certain of that - as humiliating as it would have been - the next morning, when she was getting ready for work. It didn't help that when she ripped open the package, she saw that they were purple, just like the ones Anna had bought for her, but it was too late for her to go buy herself some that didn't remind her of that, or that were thinner, or for her to take back what she'd said and have the nurse show her how it was done, because it seemed much less obvious now that she had to do it.

She fumbled with it, taping it on as best she could, then found an outfit that she thought mostly hid it, though, looking at herself in the mirror, turning this way and that, frowning, she was pretty sure someone who knew what they were looking for would definitely be able to tell what she had on. 

The diapers were so large, she couldn't fit as many into her purse as she'd hoped, either. She groaned, trying in vain to stuff just one more inside, wishing she hadn't been so much of a chicken the day before that she hadn't bothered to try any of this. If she'd known what to expect, it might not have been so bad, but having it all at once now, first thing in the morning, was overwhelming.

There wasn't even time for her to stop by Anna's office to see if she'd managed to find a way to get her ID working at the bathroom again for the day. She didn't particularly want to face her, but, if Anna hadn't done it, Ashley would have to do it anyway. As big as the diapers were, she didn't trust them to last her the whole day, so she'd have to change somewhere...

The first test came sooner than she'd anticipated, when she'd barely had time to boot up her computer. She locked it, scurrying to the bathroom, holding her breath as she scanned her ID, waiting...

Red light. She groaned, trying to squeeze her legs together as she stared at it, blushing as she heard the diaper crinkling, felt the padding bunching up, refusing to let her thighs get too close together, which only made it harder for her to hold it. She could go back to her seat, pee her pants...

No. It wasn't fair! She had made it on time! She didn't have to use her diaper! She marched herself to Anna's office after all, determined... And then froze when she peered inside, saw Anna talking to her bosses in there. She definitely didn't want them to see her in a diaper, or marching in and borrowing Anna's bathroom, for fear that they would forbid her from using it in the future, closing that loophole for her altogether.

She trudged back to her chair, the realization of what she was going to have to do slowly setting in as she went. She did make it all the way, but almost as soon as she sat, as her body was in the position it had longed to be in - though preferably on a toilet - she felt her bladder let go. She wrinkled her nose, squirming, the stream of warm pee pouring out of her, soaking into the diaper beneath her, making it so much squishier, even more humiliating to be wearing.

She waited as long as she could possibly bear it before scrambling back to Anna's office, ready to go get changed. After what had happened, she'd decided she wasn't going to tell Anna about the diapers until the next day, if she didn't spot them, but that wound up not being an option.

"I told you, Ashley, you can't come in here every time you need to use the bathroom," Anna sighed. "Did you see the doctor?"

"N-Not yet," Ashley lied, not wanting to admit that she wasn't able to get an exemption from her. "Pl-Please? Just this once?"

Anna rolled her eyes. "Fine." As Ashley toddled towards the bathroom door, however, she snapped. "Ashley! Did you already go?!"

"H-Huh?" Ashley frowned, fidgeting, reaching behind herself, heart pounding as she felt a dampness there. "Oh, no..."

"Honestly! You are soaked, Ashley! I bet you ruined your chair, too! I'll have maintenance bring you a new one, but I expect you to apologize to them for the trouble, young lady! Now, come here." Ashley couldn't bring herself to resist as Anna grabbed her by the hand, pulled her closer, sliding her skirt down, revealing her diaper. "Just as I thought. I'm glad you're finally taking my advice, Ashley... This tape job is horrendous, though. I guess people are going to have to talk, because you clearly need somebody to help you diaper yourself properly."

"I-I'll do better," Ashley squeaked.

"I don't think the office furniture can survive long enough for you to figure it out," Anna scoffed, before softening, seeing the mortified tears beginning to well within Ashley's eyes. "Sorry," she apologized. "Hey, it's only until you get that doctor's exemption."

That only made Ashley, feeling so pitiful and pathetic, standing there in front of her ex-girlfriend in a drenched diaper, about to have it changed by her, cry harder... And pray that the medication she'd been given instead was actually going to work.