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Made Maidenly by the Boss

For blazingpelt

By Draconicon

William, or Billy, as his boss tended to call him, was having a bit of a bad day. He kept looking down at the drawer at the bottom of his desk, knowing that the cat had left him something to wear down there, and he knew that it was going to be as humiliating as all the other times that he had been kept after work for one of Mr. Jake's 'private sessions.'

His cheeks burned as he remembered last week's session. He'd been given a pair of latex gloves and boots, as well as a tight pair of latex pants, and he had been made to strut up and down the cat's office, showing off...everything. Not even a hint of his body had been spared the glare of the camera lens, and he knew that the boss had been 'enjoying' it over the course of the day. Mr. Jake hadn't been shy about showing that off, either.

And now it was Friday again, which meant that there was another package for him in the drawer, just waiting for the hours of the work day to be done before he was called back to the boss's office to show off, again. The raccoon gritted his teeth, his ears sliding down to lay flat against his head, his tail twitching like made.

This is wrong, this is wrong, this is wrong, he thought. I should just...I should just quit.

That might have been what he told himself, but doing it? That was probably not going to happen anytime soon. Not with the way that he had a criminal record hanging over his head and the boss was the only one willing to employ him across the city. He knew that for a fact; he'd been applying for other jobs for nearly three weeks and hadn't heard back from anyone in that time.

Just...why? Why can't I...

It was the burglary conviction, he was sure of it. Anyone that had even a small mark against their record was hard to employ, and anyone that had something bigger, like he did, was darn near unemployable. He grimaced as he thought about being stuck here with the boss for another month, even, and -

"Billy? Billy, are you there?"

The speakerphone. He groaned, biting his lip. If he could just get up the nerve to tell the boss to shut up and shove it...but no. He needed this job. The raccoon reached out, tapping the button.

"Here, boss."

"Excellent. The floor should be emptying out in about five minutes. You have permission to open the drawer and see what I have for you."

"Do I have to?"

"Yes, Billy, you do. Now, open the drawer for me, that's a good boy."

He hated hearing that, but it was better than the implied 'good girl' that he sometimes heard in the office. Shaking his head, he pulled on the drawer grip -

And then immediately slammed it shut again. He blushed hard, hoping that he had been seeing things. He opened the drawer again, and found that he hadn't.

"Slamming drawers? Tsk tsk. Naughty. That could be damage to company property if you keep that up, and that's far more expensive to work off."

"Sir, please, you can't...you can't be serious."

"Oh, but I am. Now, wait until everyone is gone, and put it on. I don't want to see any of your work clothes when you come back here. See you soon."

Click. The short call cut off, and he groaned. Leaning back, he looked down at the drawer. The black and white of a French maid's dress was impossible to miss, as were the gloves, the panties, the stockings...everything. He groaned under his breath, rubbing his face as he shut the drawer more gently, looking around and hoping that nobody had seen anything. This was going to be hard enough to explain as it was.

Damn it...damn it, damn it, damn it...

Ten minutes later, he was standing in his cubicle in nothing but the dress and its accessories. He blushed worse as he felt the way that the silk panties were pushing his cock up, making him have a cute little bulge in the red silk undergarments. He groaned, shifting from foot to foot, the sheer stockings clutching tight to his legs.

"This...is...humiliating."

"Office, my good little maid. Now."

"Coming."

At least he didn't have to walk in high heels. There had been no footwear in the drawer, so he hoped that this was just going to be a posing session like last week. He wanted to just get this done and go home, and walking in high heels would make that all but impossible.

The raccoon rounded the corner of his cubicle, walking down the long aisle that split the cubicle sets in half. The boss's office had all the windows blanked out, the screens pulled down on the other side, and he imagined that Mr. Jake was probably already getting off to the idea of him being there, dressed like this. He swore if he had any chance of getting another job, he would have taken it by now.

Just a bit longer. Just a bit longer.

The skimpily-dressed raccoon knocked on the door, and the boss answered with a chuckle on the other side.

"Come in."

He did as he was told, as he had been doing for far too long, and stepped through.

Mr. Jake was dressed in a white suit today, and the cat looked over his desk with his hands folded together, his pointer fingers tapping against each other as he looked the raccoon up and down. William - Billy, rather - did his best to hold still, to not look as furious and humiliated as he felt.

"That dress suits you," the cat said eventually, smiling. "Now, turn for me."

Groaning, the raccoon spun in place, feeling the stockings squeezing his legs more, feeling his toes sliding against the tips of the socks. They were so...so sheer, and he could feel the other man's eyes on him the whole -

"And stop."

His back was to his boss, and he blushed as he swore he could feel eyes on his ass. It got worse when the cat cleared his throat, and he knew what he was supposed to do. Slowly, his ringed tail began to rise, lifting the skirt with it, and he felt his panties and ass cheeks come into view.

"My, my. Barely enough for that bubbly butt of yours, isn't it?"

"Mmmph..."

"Turn around, Billy."

He knew what was coming, yet he still blushed as he turned around and found himself face to lens with the boss's camera. The cat tapped the button on his phone a few times, snapping shot after shot of the crossdressing raccoon. He bit his lips, trying not to get turned on, but there was something about this humiliation that was sending a few twitches and tweaks of pleasure all the way down to his dick.

He shifted from foot to foot as the pictures continued, gripping his arm in embarrassment until -

"And now, lift the skirt."

"Nnngh. Why do you make me do this?"

"Because you've got nice girly curves, and I can. Now, up."

Mr. Jake was not a kindly cat, and he knew better than to make the other man wait. He grabbed the base of his skirt and pulled it up slowly, dragging it up to his waist, and then a bit higher as the cat gestured for him to show off more. His cock was starting to stiffen in his panties, and he could feel them gripping his shaft that much more.

Click click click went the camera, and he groaned as he felt his cock rising in response to the sound.

"Oh god...oh god..."

"Mmm, you look quite good like this, Billy. You're such a good girl."

"I'm...I'm a guy."

"Of course. But for now, you're a good little girl. My good little girl."

His cheeks could not have been redder if he had painted them with tomato juice at that point. He groaned as he felt his cock keep rising even when it shouldn't, and he tried not to look at his boss. It was very difficult, particularly as he could see Mr. Jake's other hand moving very busily beneath the desk.

"Now, turn around again, and lean against the chair. I want you to push your ass out good and far."

"Mmph. I swear..."

"Do it, and you'll see a bonus on your next check. Fight me on it, and you'll see just how long you last out there."

He knew that there was no point to trying to sound more manly, to fighting this, and yet he kept trying. Why? Why did he think that this had any chance of actually succeeding? He was just fooling himself.

As the raccoon leaned over one of the chairs, he felt the boss's eyes staring right up the skirt, looking at his panties, looking at his ass. As the clicking continued, the pictures getting snapped, Billy thought of something else, and promptly wished he hadn't.

How long until he goes from photographing me to fucking me?

Billy pushed the idea back down, but it was too late. He had already thought of it, and now it was in his head. But surely, his boss had some levels of propriety. Surely, he wasn't going to push it quite that -

"And now, lean forward...and pull those panties down."

"..."

"Now."

Oh god, oh fuck, oh god...

The End

Summary: William, known to his boss as Billy, is a raccoon with a record, and who has a boss that is ever so happy to take advantage of how much Billy needs his job. So far, it's been merely some humiliation here and there, some bits of titillation, but what happens when the boss decides to take it further?

Tags: M/M, cat, raccoon, office, crossdressing, panties, humiliation, exhibitionism, bulge, camera, posing, feminization, blackmail, sissification, abuse of power,