Mistress Elaine and Jackie

This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters in sexual situations are 18 years or older.

This story is dedicated to Boxwood.

Jennifer DiPietro ran her hand across the supple leather of her driver's seat, a light brown calfskin, in the sports car her husband Mike bought for her 40th birthday. As she gazed out the windshield onto the slow moving traffic on the Garden State Highway, her mind wandered to the feel and scent of Mistress Elaine's leather flogger -- the flogger that was most recently used on her bottom as punishment for her continuing insolence.

A small smile curled up on her lips as she recalled her last weekend at Mistress Elaine's Connecticut weekend house, a weekend spent performing the most mundane of chores until her smart mouth, complaining again about the drudgery of her assigned tasks, brought yet another session in her Mistress's "playroom," a room created expressly for the discipline of her stable of subs. Jennifer was one of a half dozen subs who routinely spent time in the service of Mistress Elaine. Jennifer's smile came about because her insolence became a trigger point for her punishments -- punishments that she hungered for.

Jennifer was spending a lot of time driving now, since meeting Elaine as an insurance client, and then as Mistress Elaine. It had started with invitations to her country house, but now it was a routine that Elaine had made for her. It had been two years since the two of them met at a department store where Jennifer was clothes shopping, and since then Jennifer escaped spiritually (but not physically) from her loveless, and almost sexless, marriage. Jennifer hadn't known about her submissive tendencies until Elaine identified, and then exploited them, for their mutual pleasure. Jennifer knew she would never turn back to her vanilla existence. Acting as Mistress Elaine's sub was the only time she felt truly alive.

Every other Friday she made excuses to leave work early, and made the drive 55 miles to Elaine's Connecticut house, prepared to stay for the weekend ... or not. The house was modern stone and glass, not really a mansion but still a massive structure with a large adjoining pool and pool house on a heavily wooded lot. As instructed, she parked in the gravel lot around back, a lot reserved for service people, then used her key for the mud room entrance that adjoined the spacious country kitchen.

As she stepped into the kitchen she saw her reflection in the floor to ceiling glass panels framing the breakfast nook and felt ridiculous -- a professional woman, in her mid-40s, here to do the bathroom cleaning she hated most, but nevertheless feeling giddy, with her heart thumping at the prospect of serving her Mistress. At least today it was rainy, and there were no other cars, but her instructions were the same whether the house was occupied or not.

She paused as she gazed at her reflection, a short buxom blonde whose curvy body and tight abs belied her middle age. She corrected her posture, thrusting her hips and chest out, admiring her best physical attribute, her large rounded breasts topped by long, always hard nipples that poked out from her scanty lace bra and gossamer thin silk blouse. The beeping of the alarm pad broke her admiring glance. She kicked off her heels and padded silently on her bare feet, feeling the cold tile floor as she entered the code to turn off the alarm.

As usual, there was a line of blue tape on the slate floor. She glanced up at the camera blinking red in the corner, then quickly undressed and folded her clothing on a wooden stool. Naked and barefoot, she stepped across the line and reached for the shopping bag on the row of coat hooks.

It amused Mistress Elaine to choose her clothing for her day as a house servant, and it might be anything. Sometimes it might be a worn maid's work dress, shortened and with most buttons removed, or an old faded bikini, or a complex corset with stockings. The short blonde shivered and opened the crumpled bag to find a scuffed pair of high heeled pumps and denim shorts. She tugged on the slightly too-small jeans shorts, with the button removed, and stepped into the pumps. Her phone went into the pocket, in case Mistress might choose to text her.

There was nothing else, except a pair of wrap-around sunglasses that obscured her eyes. Elaine had left her a small mirror on a hook, below the camera, so she could see herself and further her humiliation. Now she felt even more ridiculous, an older woman dressed like a cartoon girl in a teen movie, with her C cup breasts swaying and exposed and the jeans half open to show the womanly pubic hair that Elaine made her leave untrimmed. At every step, her breasts moved to remind her how she was displayed. There was a deep red lipstick taped to the mirror, which Jennifer applied to her lips and to her nipples, now rock hard in the cool air.

She had to move now, she knew the timer was ticking since she first opened the door. In the kitchen, she took out the bucket and the bathroom cleaning supplies as the next camera blinked on. She never knew whether Mistress Elaine got messages to watch her in real time, or whether the video was saved for later viewing -- or even if there really was any video at all. Was she featured now in some "Topless Maid" camera site, or was all this just a reminder of the degradation she secretly craved?

Jennifer trooped up to the third floor, breasts bouncing and swaying, to start work in one of the guest bathrooms, reaching high to scrub the tile in the shower then on all fours, breasts hanging low, as she scrubbed the toilet and the floor.

Mistress Elaine knew she hated domestic chores, so this was her task every time, to clean every fixture in every bathroom, whether it was already clean or grossly used, to finish her chores dirty and sweaty, but to never be allowed to shower later or clean herself up. Putting on her own clothes later, driving home sweaty and used, would remind her of her place. Crawling and scrubbing, Jennifer's mind was full of her desire for Elaine, who would mercilessly tease her, but seldom touch her. On a good day, she might be allowed to play with another female sub as their Mistresses laughed.

As she cleaned, Jennifer also flashed back to the humiliation of her first visit there, when Elaine made her help male slave Boxwood with the lawn care, then had him scrub her clean outside with the hose, using his hand and roughly soaping her shivering body. She was only bisexual in a technical sense now, since Elaine sometimes instructed her to please her mostly disinterested husband, but from time to time Elaine used it against her and made her supervise or work with Boxwood as punishment. He was older, balding, a bit chubby and not attractive, but her skin went flush now as she thought of his thick cock in her mouth as he manhandled her tits, all for Mistress Elaine's amusement.

Jennifer lugged the bucket of soapy water to the next bathroom, dreaming of submission while her work kept her grounded in reality.

* * *

Boxwood entered the familiar Connecticut address into the mapping app and settled into his car. He knew the way, of course, but he was an organized guy who always checked for the best route and any traffic problems. Since Mistress Elaine had found him, among all the on-line chat subs, he had found the intensity of service he was looking for, so he was excited to have this routine. On random Fridays, she would text him to go to the house, and be prepared to stay over. He knew now to park at a nearby gas station and walk a half mile over the hill to her back yard, where he had a key to the pool house.

It was mid-morning by the time he made the 60 mile drive, walked over, and let himself in. He was soaking wet from the rain as he unlocked the pool house door. The pool house had a bench and shelves, and a closet full of pool and yard tools. His assignment was maintaining her home, mostly outdoors, but with some inside cleaning. He knew that Elaine had other subs coming and going, with specific tasks, like the slut Jennifer, who was forced to clean the bathrooms. He seldom saw the other subs, but was always hopeful someone would be in the house working. He always checked the gravel parking lot before he came in, hoping to see Jennifer's sports car. Of course his most fervent hope would be that Mistress Elaine would be there, but his true reward was just being part of her stable of subs. On this day his heart raced as he saw Jennifer's cute little red sports car parked in its usual spot.

As expected, the service entrance was unlocked and the alarm disarmed. He entered the mud room and stopped before crossing the line of blue tape and stripped quickly, since the camera high on the wall had started blinking red when he opened the door. His cock hardened in the chilled air as he fumbled with the bag of clothing Elaine had left for him. As with all her subs, it could have been anything, her point was always to remind him of his submissive status. There was an old and worn bra today, probably from a thrift store, and a torn grey housekeeper's dress, with the buttons removed and cut off just below hip length. He recognized it as Jennifer's uniform from months ago, and a shiver went through him as he recalled her straddling him while he laid naked on the cold slate tiles of the kitchen, licking the big-titted blonde to a slow and excruciatingly long orgasm while Mistress and others watched during one of Mistress's cocktail parties.

He tugged on the pink bra, and saw that this one had small pebbles taped into the cups, to make him look as if his nipples were comically hard all the time. Elaine liked him in a bra, to emphasize that he was not fully feminine, like the real women she loved, and at the same time not some masculine stud either. His body itched where he had used the electric trimmer; Elaine found it amusing to keep some subs roughly trimmed, and others wild and hairy.

Boxwood slipped on the short dress and the plastic gardening clogs that were also in the bag. His semi- hard cock was barely exposed at the bottom of the dress, and it gaped open with only one button to show his shabby bra and rotund belly. She had also left wrap-around sunglasses to cover his eyes. He glanced at the stained mirror, then up at the camera again. Here he was again, of his own choice -- a balding older man, overweight and out of shape, half-dressed and humiliated, with a pool to clean and a yard to mow as Mistress Elaine's timer ticked down his day of service.

He went about his chores with enthusiasm. He knew that Jennifer was toiling away inside the house and schemed for a way to see her. He was permitted to use the restrooms inside, and just needed to be on the same floor as her to catch a glimpse of the sexy blonde. He had intercourse with Jennifer on two occasions, both of which resulted in the most memorable orgasms of his life. Even though he wasn't allowed to masturbate, he would occasionally break discipline and think about Jennifer's tits while he stroked his big cock until his cum would splatter his face. He would of course tell Mistress Elaine of his transgression, gladly suffering the punishment in exchange for keeping Jennifer's nubile body fresh in his mind.

On this particular day the pool was relatively clean, and with the light rain he couldn't mow the lawn, so he was able to finish his assigned tasks around lunchtime. That gave him a little over two hours of free time before he had to change back into his street clothes and go home if Mistress Elaine had no further use for him. He went into the pool house refrigerator to grab the sack lunch he packed for himself and then went into the kitchen in the main house to eat it in the breakfast nook. He was careful to whisk all of the dirt and leaves off of him before he entered the house, knowing the cameras would show that he was the one to track the unwanted refuse into the house.

He sat on the wooden bench in the nook, leisurely eating his roast beef sandwich, when Jennifer came into the kitchen to refresh her cleaning supplies in the utility closet adjoining the mud room.

"Boxwood," she said, noticing the older man eating his sandwich quietly in the breakfast nook. She didn't realize that he had been sitting there for over a half hour, still on the first half of his sandwich, waiting patiently for a glimpse of her. He noticed her the second she entered the kitchen, but kept his head down as if he didn't. He couldn't believe his good fortune. Jennifer was not only there, but she was wearing one of the skimpiest and sexiest outfits he had seen on her -- topless, with denin shorts and fuck me pumps. There was no mistaking that Jennifer was a slut, and a hot one at that.

"Oh ... Jennifer ... it's good to see you," he replied, mustering as much indifference as he could in his voice, although inside his blood was already boiling. He had to make himself not stare at the boobs of the topless sub. He held up the uneaten half of his sandwich. "Care to join me?"

Jennifer could see through Boxwood's veneer of indifference. She knew when men were secretly lusting after her tits, and with her rounded breasts laid bare and their long past history together, it was easy to see the overwhelming sexual desire in his eyes. It just so happened that Jennifer had only one more bathroom to clean, and that her impure thoughts while she was cleaning the bathrooms left her in a highly agitated state.

Boxwood rose from the table to greet her as the blonde approached the breakfast nook with a sparkle in her eye. He made no effort to hide the erection that sprouted from his gaze at Jennifer's pendulous boobs, bouncing in time with her step.

"Jennifer ..." he started to say.

"Shut up," said Jennifer, cutting their repartee short. She got on her knees and grasped his thick cock in her hand, stroking its length as she milked the first drop of precum out of the tip. She looked into his soulful eyes. "This is what you want, isn't it?"

"Yes," he said sheepishly.

Jennifer knew exactly what to do to pleasure him, and made quick work of him, forming a perfect "O" with her lips and looking into his eyes with her best slutty expression as she pushed her mouth all the way to the base of his turgid cock.

"Fffffuck ..." the older submissive groaned as Jennifer tensed the muscles in her throat to strangle his cock. She rocked her head up and down his shaft, feeling the hot, pulsing cock in her mouth as the older man gyrated his hips. When she knew he was close, she wet the middle finger of her right hand with the spittle dripping from her chin and used it to rim his asshole, jamming it inside him as his legs tensed.

"Uh ... uh ... uh ..." Boxwood grunted, trying to forestall his orgasm. He knew they would both get in trouble for this unscheduled tryst, although neither of them seemed particularly concerned about the consequences. They both enjoyed humiliation and punishment, and this particular episode would just be the latest in a long line of transgressions.

Even though Jennifer was a submissive, she enjoyed humiliating Boxwood because he secretly loved her wicked ideas. She knew they would be punished, which would undoubtedly result in some inventive form of humiliation for Boxwood. She inserted a second finger, and that was a feeling of fullness and pleasure that rocketed him to an orgasm he couldn't stop. He thrust his hips forward, gripping a handful of her hair as his prodigious wad shot into her mouth.

"Mmmmph," escaped Jennifer's lips, as Boxwood's hold on her hair prevented her from pulling off. A small rivulet of cum ran down her chin. As the older man's orgasm subsided, he loosened his grip on her hair. She spat his cum on the breakfast nook table, gasping for breath.

"You motherfucker!" she exclaimed after she caught her breath. "You pulled my hair."

Boxwood's eyes showed terror. The last thing in the world he wished for was to hurt her. "I'm so sorry. I got carried away. It was so good ...".

"Don't do that again," scolded the buxom blonde, her tits bouncing as she vented her anger.

"I'm sorry ... I'm sorry ..." the submissive man pleaded.

Jennifer looked at the pool of creamy white cum on the table. Then she looked at Boxwood. He already knew what she was going to say, his mind reeling with the sheer depravity of the act she was about to request. His flaccid cock stirred, awaiting her order.

"Lick it up. What are you waiting for?"

Boxwood leaned forward, his tongue already out, as he dragged it across the highly polished wood surface, scooping up his cum and swallowing it.

"That's a good boy," she said with satisfaction. She knew they both enjoyed what they had just done. She looked up at the blinking light above the kitchen camera. "I hope you enjoyed this as much as we did."

* * *

The cameras were indeed working and Mistress Elaine happened to be watching from her phone as her driver made the last turn before arriving at her country house. She chuckled as she watched Boxwood eat his own cum and Jennifer mugging for the camera with cum dripping off her chin. This was precisely the reason she had a stable of subs -- to amuse, and occasionally surprise her.

Breaks in discipline were never tolerated, especially one as flagrant as this one, Boxwood for cumming without permission and Jennifer for engaging in an unsanctioned sex act with him. Elaine sat back in her seat and drummed her fingers on her leg pondering her choices. She used the flogger last on Jennifer to good effect. Maybe this time the riding crop? And for Boxwood? He loved humiliation. Maybe he should be made to bring Jennifer to orgasm, and then be denied his own? That would give him something to think about for the next week. As Elaine was pondering her choices, the gleaming black car pulled in the horseshoe shaped driveway in the front of the residence.

Elaine checked her make-up in the mirror mounted in the back seat and then stepped out of the open back door. Elaine looked up at the driver, a young woman in her 20's, who had expressed interest in joining her stable of subs.

"Thank you Jackie. I've taken the liberty of putting your clothes in the mud room. Just go around back to the service entrance. The door should be unlocked. There'll be a brown paper bag with your name on it. Put your driver's uniform in it. Boxwood should be in the kitchen. Ask him to show you the room upstairs I've reserved for my subs. He'll assign you one of the beds up there. Freshen up and be back in the kitchen in fifteen minutes. Is that understood?"

"Yes, ma'am, I understand." Jackie tried to maintain her composure. She was never sure Elaine registered her interest in becoming a sub, and now without warning she was about to become one. While she was trying to remember Elaine's instructions, her thought process was interrupted.

"Another thing. While we're here, my subs call me Mistress or Mistress Elaine." The strawberry blonde walked off before waiting for Jackie's reply. Jackie stood there, mouth slightly agape at the sudden turn of events. She would soon learn that Elaine always played her cards close to her chest, and that she jealously protected the element of surprise.

Elaine smiled inwardly at Jackie's reaction, almost a deer in the headlights. It was quite a change from her earlier experiences with the tall brunette, a cocky butch lesbian brought up on the streets of New York and formerly a bouncer at a bar that Elaine frequented. She entered through the front entrance, her designer heels clicking on the wood floor.

"Jennifer ... come here," Elaine's voice echoing down the hallway.