A Maid’s Tail Ch. 02: Training

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Monday – Day 1: Training

There was a lot to be said about the countryside and it’s natural beauty. Most of it involved descriptors like ‘boring’, ‘flat’, ‘bland’ and Kim’s personal favorite: ‘quiet’. Having grown up on a quiet stretch of country road, the stillness was familiar in the way an old friend was. Unfortunately life had taken her away from wide open fields, miles of wood fencing and calm of rustling grass. It was only on the lonely stretch of road did she really miss it.

It had been so long…

Kim leaned back, taking in the warm sun glinting from the rows of junk cars and farm equipment that dotted the sides of the road in front of homes older than she was. Idly, her thoughts turned to her new employers.

There was something to Sylvia and Elliot, a strange kind of dichotomy that made them appear as if they were two sides of the same coin; both were firm and demanding in their own way. Sylvia was kind of a bitch, but maybe there was a story behind that.

She’d soon find out, one way or the other. Kim followed the directions she’d been given through the old roads until she rounded a bend near a copse of pines. The road dipped into an unassuming property with cobblestone walls running along the street at waist level, interspersed with stone pillars every few dozen feet. Back from the road was a large house that looked as though it had been uprooted from the plantation era and dropped in a sea of golden grass. Off-white and sprawling for dozens of feet in every direction, the home had a wide walk around porch ringing a stately two story southern design with wood pillars supporting an awning over a brick patio. Though the property was clean and well maintained, the gravel path leading from the street to the patio made for an eye sore.

The hunter green BMW parked neatly beside the patio, however, gave Kim the impression that the road was a work in progress. As her Pontiac trundled up the drive, she became acutely aware of this strange new turn her life was taking; for the first time in a long time she actually had a sense of looming dread. Working for someone else was always a toss up with none of the freedoms or securities (and insecurities) of being self employed. The fact of the matter was that she hadn’t sold a story in months, though. This wasn’t about pride any more, this was about basic survival.

“You can do this… Just put on a smile and pretend you give a shit.”

Following the time honored tradition of broke people and the mechanically inept, Kim climbed out of her driver’s side window, straightened out her blouse and bounded up the porch. She reached up to give a knock on the wide double doors, but Sylvia beat her to the punch by opening it. When Kim found herself looking at those mismatched eyes, she faltered. “Uh, hi.”

“You’re early,” she said flatly.

“I thought it’d be a good idea in case I got lost.”

Sylvia looked at her thoughtfully for a moment, Kim wondered what she’d be like if she smiled more; she would’ve been pretty beautiful. It also meant something had happened at some point to make her the miserable tart she was now. At least that was Kim’s uneducated opinion. “Yes,” Sylvia muttered as she turned away, leaving the door open for the new housekeeper to follow. “I think it’ll fit you. Maybe a little tight around the midsection, but you can loose some weight.”

Tch. Kim licked her lips, smoothly changing the subject. “You have a lovely place…” At least that much was true, the place was wide open and spacious, packed with furniture suiting the era in which it was built with quasi-Victorian couches, chairs, a wide bar separating the kitchen from the dining room. The plush carpeting that tracked the floor was a deep ruby color that stood out like blood against the soft ash wood flooring underneath.

Walking behind Sylvia, Kim couldn’t help but notice she had lithe curves; a dancer’s body wrapped in Bitch of the Month Club t-shirt and jeans. It was a shame, really, Kim thought idly, watching her little body stroll gracefully through the hall. She had a firm ass in skin tight jeans, unlike Kim who was thicker in almost every way. Not quite fat, but definitely… soft compared to Sylvia. “Stop it.”

“My husband’s design. He… liked Georgia.” She cast a glance back, perhaps sensing Kim’s gaze on her ass. She didn’t seem to mind.

Maybe she could salvage this. “You don’t sound too thrilled. Did something happen?”

“Not really.” They rounded the hallway into a massive observatory with bay windows overlooking a well tended garden and plenty of hanging ferns that dangled from hooks around the room. In the center of the semi-circular room was an easel with a little stool and a smattering of paints across a tired drop cloth under it all.

Then she saw it. Hanging from a metal coat hanger in the back of the room was a simple black dress with white trim. It was short sleeved with a pleated skirt and deep cut V in the chest area that was İstanbul Escort Bayan filled in with a flowing weave of white fabric. A frilly white half-apron was tied around the waist, hanging loose from the outfit and holding on to a pair of black cuffs that matched the dress perfectly.

Kimberly blinked. “Uh…”

Sylvia crossed her arms looking at her. A wolfish smirk crossed her lips. “What’s the matter?”

“W- Well, I… Really?” She eyed the uniform. “I mean, really?”

“If you’re not interested in the job-”

“I didn’t say that!” It came out faster than she intended and Kim blushed, looking away. “I just didn’t expect you and your husband meant a real maid’s uniform.”

Sylvia’s dual-tone gaze turned to the uniform briefly. “There’s more to it,” she looked to Kim. “We have very specific expectations.”

Kim was almost afraid to ask. “Like…?”

“The house must be clean top to bottom daily. You’ll be expected to cook dinner, get groceries, do the dusting and the laundry, clean the floors and turn down the bed twice weekly. Right now, we’d like you here Tuesday through Saturday but that might change as… We decide.” After a moment she sauntered over to the uniform, smug in her apparent control over Kim’s reaction to the turn of events. She knew Kim couldn’t turn this job down, that she’d agree to pretty much anything to keep it.

Strangely, some deeper part of her didn’t want to resist. Kim licked her lips, eying the uniform.

“Now, when you’re here, I expect you to be in uniform. Complete uniform.” Then she turned the hanger around. Kim’s breath caught in her throat. Attached to a piece of cardboard was a hay colored head band with black cat ears on it in the middle of the card was a frilly white choker with a little bell on it and a black bowtie at the back. If Kim had thought the uniform was strange, miles out of her comfort zone, then the tail was a trip to the moon by comparison. The thick, bushy black tail was probably as long as her arm, but the method by which it was meant to stay ‘on’- more accurately ‘in’ made Kim blush a furious crimson. It was a small butt plug not much bigger at its widest part than her two fingers put together.


Kim’s breath came in quicker sips as she stared at the little plug. Could she really do this? Her heart punched into her throat as she thought about the bills waiting for her at home. When Kim didn’t immediately respond, Sylvia closed the distance with a casual strut, holding the uniform between them so she looked up at Kim over the smooth fabric. Her mismatched eyes flickered with amusement and mischief. “Well?”

“Uh-” Kim swallowed. “Cat got my tongue?” That earned her a smile. She relaxed a little. “W- Can I ask something? What happened to your last maid?”

Sylvia looked at her oddly, shook her head and cracked another faint smile. “You’d be the first… We just moved here a few months ago.”

“Ah-… s- so.”

“So.” She said with finality.

Kim sucked in a long breath as she considered the uniform and the woman holding it. This was strange territory, nothing like she had imagined in fact. Her entire body bristled with goosebumps and the heat of uncertainty. Absently she became aware she was sinking her teeth into her lower lip, wondering just where this strange, exotic chapter of her life might take her. “The bills, too. Can’t forget about the bills.”

Of course, it wasn’t entirely the bills that made her say, “Uh do you have a bathroom? S- So I can change?”

Sylvia grinned slyly. “Right this way.”


A little while later, Kimberly was standing in front of the full length mirror beside the bathtub, blushing deeply while her reflection stared right back at her in disbelief. Her lightly tanned flesh was coated in goose bumps and her own awareness of every brush of air over her bare legs made her all the more conscious of her being exposed.

Sylvia had been right, the maid’s outfit was a little tight in the stomach area, but the cut of the fabric around her chest only accented her generous bust, making her look fuller and proudly displaying her cleavage behind the thin white veil between either side of the low cut top section. All this, of course, made the satin choker more pronounced. Even the bell attached to it seemed to jingle a little louder than it had when she was putting it on.

The tawny color of the headband blended in with her natural hair color pretty smoothly leaving only the cat ears poking up through her blonde mane- she put her hands on her hips and turned her body slightly this way and that, checking that the length of the skirt was right. Her long legs had always made it hard to find appropriate skirts; they were inevitably too long or way too short. This particular dress seemed to lean towards the ‘too short’ side, stopping just a hair above mid-thigh.

Then there was the tail…

Kim licked her lips, glancing at it uneasily. She hadn’t İstanbul Escort mustered the courage to try it on, though she had held it under her skirt to see how it would look- but with no belts or sashes to hold it in place, there would be no way to fake it.

God, how badly did she want this job that she had even considered it? She blushed deeper still, the fine hairs on her forearms bristling to full attention as she eyed her reflection, then the tail. Herself, then the tail. She wasn’t even sure it was an issue of self respect any longer. It wasn’t like she had anything to be ashamed of…

No, nothing at all…

It was part of the job. Yes, that made perfect sense when taken into context- Kim’s heart fluttered as she looked at her reflection once more. Her breathing came sharp and short. Tiny sips of air. She could do this, she could be the best damn maid these people had ever seen, just like she had done when she pretended to be a snake wrangler when she had been doing research for one of her books.

Then again, two people almost died, maybe that was a bad example.

“Oh, shut up,” she whispered to the empty room. In her sudden rush of irritation she plucked the bottle of KY jelly from the sink and the plug end of the tail. She was going to be the best damn cat… maid… thing she could be.

At least that was the intention; turning the little glass plug over between her fingers gave her a whole new shock. She was actually going to do this, she was going to submit her anus to strangers for a paycheck… Her shoulders felt heavy with this thought, the shame of being brought to this. Yet, there was something else to it; she wasn’t being forced into anything… Sylvia might have been a bitch, but she wasn’t in the room trying to force the plug up Kim’s ass. She had an expectation. A demand.

Kim bit her lower lip, eying the mirror. She couldn’t let her employer down, now could she? Kim swallowed down her misguided pride and carefully slathered the little plug with the silicone based lube, then eased her panties down enough to coat her rosebud. At the touch, her skin rippled with a wash of naughtiness. The chilly lubricant only made her quiver more.

She was really going to do this… Holy shit, this was not what she had expected. Nibbling on her lower lip hard enough to turn it white, she massaged her fingers around her most forbidden entry, circling her rosebud with new curiosity she’d not felt before. Curiosity lead to a creeping sense of wrongness and shame- yet she persisted, working little circles around her sphincter muscles… Gingerly, she pressed her lubed up finger against her asshole. Her gaze turned to the mirror reflection. Cheeks flushed, nipples hard as glass even through her bra and the uniform.

Oh, this was something she shouldn’t have done. “No,” she told herself. “No, stop before you-” but it was too late, her finger’s pressure eventually won over the resistance of her body and slid. Kim sucked in a breath, arching her back slightly, tilting her head so she faced the ceiling while the new sensation rippled through her. It wasn’t unpleasant, at all. Still she struggled with her breathing as she circled her inner muscles for the first time, reveling in the private naughtiness of the experience.

In a stranger’s bathroom, dressed like a maid, Kim was fingering herself in the ass… Oh, if she had known sooner… She stole a glance to the door, then pushed another finger against her butt. This time the pinch and pressure were much easier to overcome and before she knew it she had both fingers in her ass and no breath in her lungs. She planted a hand on the mirror for balance, clutching the tail. She experimented a tiny bit, spreading her fingers, sliding them in and out, testing the limits of her new found pleasure before she drew out. The real show, she quietly promised herself, would have to take place at home…

After a few short breaths, Kim brought the tail plug to her ass, symbolically and literally ‘sealing the deal’ on her employment. The little bell at her throat jingled cheerfully as she pushed the plug in. She exhaled a low sight when the base of the plug mated firmly with the space between her cheeks. She stood half bent over for several seconds, getting accustomed to the feeling of the fuzzy tail tickling her. She was panting softly when she looked to her mirror reflection, she mouthed the words “Bad kitty.”


Walking with the plug was a new and interesting experience- having that feeling of fullness was only the beginning though. Sylvia took her on a tour of the entire property, up stairs, downstairs, over every square foot of hardwood floor in the house- and there was plenty of it- and then out around the perimeter of the building. By the time they got back to the doorstep, Sylvia’s attitude had relaxed a bit and Kim had become accustomed to the sensation of the plug, and the fine hairs brushing her inner thigh and ass cheeks.

Even accustomed Escort İstanbul to it, Kim was never able to get entirely comfortable. Sylvia noticed, too. As they walked into the house, she stopped outside of the kitchen, “Make us some iced tea, would you?”

“Uh- Yeah, sure.”

Sylvia stopped her. “When you’re on duty, you’ll refer to me as mistress; as in ‘As you wish, mistress’, or ‘I’d love to, mistress.'”

Kim blinked, heat flushing her face. “A- All right… Mistress.”

“Good,” Sylvia touched her lower back, ushering her into the kitchen. “Something else you’re going to find.” She leaned over the bar between the dining room and the kitchen. “You’re going to have to get used to… our expectations.” She smiled when Kim glanced back at her. She had a nice smile.

Kim filled the glasses and slid one over, vaguely aware of how hungry she still was; skipping that jar of pickle juice was a bad idea apparently. With a smile she didn’t believe in, Kim leaned against the bar. “Ah… speaking of those-” Kim’s voice fell when Sylvia put her finger to the maid’s lips.

“You’ll learn,” she said firmly. “In the meantime, I want the house cleaned up, start with dusting and then you can make dinner.” She leaned forward a little, glancing down at Kim’s cleavage. She met the cat-maid’s gaze and smirked wryly, causing her to blush again.

“O- Okay… Anything else?”

“Not for now, no. There should be plenty of food to cook with- we had fish last night, so find something else for us.” The younger woman glanced at Kim’s cleavage again before she got up and turned away. “I’m going to paint. If you need anything, I’ll be in the observatory.”

“Ah… All right, uh, mistress.” Kim fidgeted a little. “When did you want to eat?”

“Mmm, good. Maybe you are a quick learner. Elliot will be home at six thirty, have dinner ready by quarter after six.”

Kim looked after her. Absently, she heard herself say “Y- Yes, mistress.”

The rest of the day proceeded as one might expect; cleaning was straightforward once she found the duster and cabinet with cleaning supplies. Every inch of the ten room house was as immaculate as she could make it without spending hours on her hands and knees. It was cathartic in a way. Kim let her imagination roam over some new story ideas while she cleaned, stopped only when she had to ask permission to enter the bedrooms or go to the bathroom- which with the plug always seemed as though it was a constant need.

That part of the job was going to take some real getting used to.

Around five she was finishing up with the dusting when she approached one of the smaller side rooms, a kind of guest bedroom that overlooked the ten acre property from the front of the building. She came across a small dress form with a half made dress clinging to it, but what struck her most was the large sapphire necklace hanging from the neck stump. The gem had to have been the size of a bottle top, ringed with what she presumed were diamonds and set in silver or white gold- maybe even platinum. Good grief, these people were loaded. She dusted it off carefully, afraid to touch it for fear it might slap her with a law suit or something for smudging it and then headed downstairs.

Kim plodded down the steps in her sneakers to find Sylvia standing at the edge of the hall with her canvas smock on, she looked at Kim with a mix of amusement and thoughtful concern. “Finding everything all right?”

“Yeah- uh. Yes, Mistress. No problems. If…” she grit her teeth. She knew better than this, but somehow Kim got the impression it needed to be said anyway. “If you’d like to check over my work-”

“I don’t think that’s necessary, do you?”

“Not really, but I thought I’d mention it.”

“Tell me something…” Sylvia prowled closer, “How do you like this arrangement?”

“It’s only been a day. I mean… You know, it’s fun and all? I can’t say I’ve ever done anything like this.”

The younger woman smiled a private little grin. “Good. I think I was right about you, but I guess we’ll see.”

Kim’s brow knitted beneath her cat ears. “Right about what?”

The younger woman stepped up beside Kim and ran her hand down her back in one slow stroke that intentionally traced the lines of her back, her delicate fingertips running along her spine. In a low, throaty voice, she said “we’re going to train you how to be a proper maid and a proper… well…” her hand slid lower, over Kim’s butt. The older woman straightened- Sylvia took it one step further; she gave a gentle tug on Kim’s tail.

“Ah-” Kim hissed air through her teeth. Her choker bell jingled playfully at her sudden shift in weight.

“Good kitten.” Sylvia patted her lower back and strode past. “Don’t disappoint us…”

Kim clenched inwardly, letting out a soft sigh and wondering- not for the first time- what the hell she had gotten herself mixed up in.


After the incident in the hall, Kim kept an eye- and ear- out for the tell tale creaking of the flooring and stairs while she made dinner. It had been years since she had cooked anything more than hamburgers or scrambled eggs, so maybe ‘made dinner’ was a bit of an overstatement.

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