Mistress Elaine and Jackie

Jennifer and Boxwood were still in the kitchen, now sitting in the breakfast nook. Jennifer's ears perked up when she heard the front door open, and her body became rigid and her posture upright when her name rang out. Boxwood's semi-erect cock became flaccid. He looked around for the direction of Elaine's voice. Both of them knew the reckoning for their screw-up would come sooner than they expected. Jennifer got up and walked briskly to the front entrance.

"Jennifer," Mistress Elaine spat out on seeing her sub appear, "What were you up to before I got here?"

Jennifer's eyes shifted to the floor. "Nothing, Mistress. I was just finishing my chores."

Elaine's eyes sparkled when her blonde slut uttered the words they both knew to be untrue. Jennifer was intentionally making it worse. Already horny and craving submission, giving Boxwood an impromptu blowjob made Jennifer's want palpable to the experienced Domme. Elaine used a finger on her right hand to tip up Jennifer's chin so they were making eye contact. She used the forefinger of her left hand to wipe off a glob of cum still clinging to Jennifer's chin.

"What's this, my dear?" asked Elaine, brandishing her cum splattered finger under Jennifer's nose.

"I ... I ... I don't know," sputtered the buxom blonde, reflexively dropping to her knees.

Elaine looked down at her wayward sub, trying to suppress her smile. Jennifer looked so vulnerable, so sexy, kneeling with her luscious tits on display. Jennifer didn't know that she was one of Elaine's favorites, and that the Domme had scheduled Boxwood and Jennifer to be in the house at the same time, hoping for exactly what had happened. Elaine enjoyed meting out punishment as much as Jennifer enjoyed receiving it. Boxwood's coming humiliation would just be a bonus.

"Playroom ... now."

Elaine stood there, arms folded, as Jennifer scrambled to her feet and made her way to the playroom. The tall Domme glanced in the entranceway's mirror and then made her way to the master suite in the back of the house.

* * *

Elaine put her purse down on her canopied bed and then went into the walk-in closet to pick out the clothes she wanted to wear. She sat on a black leather padded bench and called out to Boxwood. She waited there patiently for the older man to arrive. He arrived moments later, slightly winded.

"Mistress Elaine ... it's so good to see you." He dropped to his knees in front of his Mistress, his eyes looking at the floor.

Elaine scooted her high heel forward, pressing the pointed tip against Boxwood's scrotum. She pushed until she could see a visible grimace on his face.

"You've been a naughty boy."

She pressed harder, Boxwood's eyes now wide open. She waited for his reply as a bead of sweat popped out on his forehead.

"I ... I have ... Mistress."

"Well?"

"It was Jennifer," the sub blurted out. Mistress Elaine's accusation confirmed Boxwood's suspicion that Elaine had watched them via the camera in the kitchen.

"You could have walked away."

Boxwood had no cogent response. He dipped his head lower, knowing his punishment was coming.

Then, in an unexpected turn of events for the sub, Elaine made an unusual request. "It was a long trip from the city. Rub my feet and be quick about it."

Boxwood relaxed at the temporary reprieve. He rarely got to touch Mistress Elaine, so her request for a foot rub was surprising and pleasing. He carefully removed each of her designer heels and placed them on the floor. He started kneading one of her feet, trying to imprint the sensation of her soft skin in his mind. Elaine uncrossed her legs, allowing him a glimpse of her black lace panties. A smile curled up on the corners of the strawberry blonde's face as she saw Boxwood's cock stir. Boxwood's emotions were so easily manipulated, she thought, as she unbuttoned her blouse, allowing it to fall open.

Boxwood's mouth was slightly agape, seeing Mistress Elaine's matching bra and panties. In any other circumstance, he would have thought she was trying to seduce him. For Elaine, it was simply a tease. She wanted his expectations to rise, which made the fall that much sweeter. There was a curious sympatico between the elegant and coldly distant Domme and the overweight and balding sub. Boxwood desire for humiliation seemed to have no bounds, as was Elaine's penchant for meting it out.

Elaine rose up from the bench and Boxwood sat back on his haunches. She casually unclasped the hooks of her bra in the back and let it slide down her arms. It was the first time Boxwood had seen his Mistress's breasts, the evenly shaped B cup breasts looking as perfect as the rest of her. His cock was unabashedly erect.

"Do be a dear and unlock the door to the playroom. Jennifer should be waiting there," the Domme said dismissively. Boxwood left the closet, but not before looking back and taking one more glance at Elaine, now bent over smoothing a thigh high stocking that she had drawn up on one leg.

Elaine slipped on her highest pair of heels. They were uncomfortable, but she loved the height it gave her, and in dispensing punishment, the visual was just as important as the punishment itself. Elaine always wanted to project the image of control, and was well aware that the way she dressed sent a message that she was both desirable and unattainable. She checked herself again in the full length mirror, adjusting the back seam of her thigh high stockings and smoothing the top of her tight, short black skirt. She was pleased at seeing the outline of her black lace bra under a cream colored silk blouse. She unbuttoned one more top button, now satisfied at the cleavage she was showing.

* * *

Boxwood and Jennifer were in the inspection position when Elaine walked into the playroom. Even though their eyes were trained on the floor, they could see in their peripheral vision that Elaine was dressed differently than usual. Gone was the elegant attire and in its place was a much sexier, severe look, as she towered over the two of them. She pushed the play button on her phone and held it so the two of them could see it. It was a snippet from the kitchen camera, showing Jennifer on her knees, Boxwood's cock making her cheeks obscenely bulge outwards.

"What do you sluts have to say for yourselves?"

Boxwood and Jennifer remained silent, their backs now slightly rounded and their heads bowed even lower.

"I thought so."

Elaine stood by the door, tapping a wicked looking riding crop on her hand as Jennifer and Boxwood stewed in the play room. One of the main features of the play room was the bench, really a wide padded low platform. They took the positions she had taught them, side by side on hands and knees, eyes ahead. They were naked, except for the dark glasses which prevented any eye contact.

"I'm disappointed in both of you, and you need to be punished. Stay as you are, and think about that."

Boxwood shifted his knees to get comfortable and resisted the urge to glance over at Jennifer. His mind got ahead of him, though, and as he pictured her on all fours, with legs apart framing her wet cunt and her big meaty tits hanging, his cock stirred and hardened.

Jennifer held her position, with flecks of his cum drying on her face, and thought about being displayed with her legs apart. The thought pleased her. Here, she could be the slut she wanted to be without judgment from others. Elaine made adjustments to their positioning, and once satisfied with the position of her subs, left the playroom to retrieve Jackie.

* * *

Jackie was a wild thing that Elaine rescued off the streets of New York City to be her driver. She caught Elaine's eye because of her cool, hard edged look, and her overt sexuality. She had long, chestnut brown hair, tied back in a French braid that went down to the middle of her back, her arms were tatted with colorful floral designs from her wrists to her biceps, and her firm C cup breasts boasted nipples pierced with gold rings. She was buffed, and thought of herself as a butch lesbian, but her two years of being with Elaine as her driver showed her a glimpse of a world where men and women in her stable lived out their submissive fantasies.

When she took Elaine to the country house, she would often see her subs toiling around the estate in the skimpiest of clothes and had once walked past the playroom when the door had been inadvertently left open. From early on in her job as Elaine's driver, she had found herself aware of the tall strawberry blonde's aura of power and easy control, and as she experienced Elaine's interactions with what she realized must be her collection of submissives, her mind raced with new thoughts. She began to explore the ideas of this new world, and eventually worked up the courage to ask if she could serve Elaine. Today was the first time Elaine had ever responded and recognized her desire.

After Elaine left her in the driveway, she walked into the service entrance, for the first time as a guest and not as Elaine's employee. She looked around the mudroom, noting the camera high in the corner, and took a deep breath. Her uniform as a driver was simple and conservative -- low heeled shoes, dark wool slacks, and a fitted dark grey wool jacket. She removed her clothes first, folding them and placing them on the shelf, then shed the simple lace bra, panties, and low stockings she wore. She kept her glasses on, and then stepped over the blue tape line, naked and shivering.

The contents of the shopping bag surprised her. She had expected something racy from her imagination, but this was elegant, expensive clothing, and included a small cloth bag with make-up inside. The lacy Japanese bra held her large breasts gently and the panties were snug, and the dark thigh high stockings were sheer and smooth. The very high heels with the red soles were the most expensive shoes she had ever worn. She buttoned the low cut, thick creamy silk blouse and slid on the dark tweed pencil skirt. There was even a necklace of grey pearls. She felt a bit out of balance, so dressed up, as her normal daily attire, when she wasn't in uniform, consisted of a pair of ripped jeans and black t-shirt.

She eyed the bag of make-up. She rarely wore make-up, and the assortment of expensive cosmetics proved a challenge to her. She tried to remember how the saleswoman at the department store demonstrated the use of eye shadow and eye liner on her, and tried to replicate it with the help of the small mirror mounted high on the wall. She traced the outline of her lips with dark red gloss and looked at herself once again. Satisfied with her efforts, she walked into the kitchen, noticing that another camera blinked on, and looked at her reflection in the floor to ceiling window. She didn't recognize herself, a high school dropout who lived her first twenty-one years within the underbelly of New York City, and now a glamorous woman in a large country estate. She practiced walking on the heels, surprised that she didn't fall over. She was looking at herself in profile in the window when Elaine breezed into the kitchen.

"Why Jackie, you clean up nicely." Elaine's eyes swept over her young charge, surprised at Jackie's transformation from her rough and tumble roots to an elegant woman. Jackie's pride swelled at her new appearance and Elaine's compliment.

"I ... um ... kind of like this new look."

"It becomes you." Elaine walked around her driver, adjusting the fit of her clothes. She picked up the make-up bag. "Look at me."

Elaine used her hand to tilt up Jackie's face so she could fix her make-up. She took the mirror off the wall and held it in front of the dark haired beauty. "See?"

Jackie glowed with her refreshed appearance. "Let's go to the playroom, shall we?" Elaine led and Jackie, still a bit unsteady on her heels, followed.

The door to the play room was closed. Jackie's heart started pounding in her chest as she approached the room that was the centerpiece of Elaine's world of domination and submission. This would be her first good look at this new world, where women and men voluntarily subjugated themselves to this outwardly cold and distant Domme. Elaine carried herself with quiet confidence, but how did that translate in this lifestyle? Elaine always kept everything so neat and orderly. What kind of chaos lay behind that door, she wondered?

With even Jackie's heightened expectations, she wasn't prepared to see a balding overweight man and a voluptuous blonde, naked and on their knees, each wearing nothing but a ridiculous pair of wraparound sunglasses that were omnipresent in retirement communities. Her jaw dropped when she saw the wide assortment of implements neatly arranged on the far wall -- floggers, whips, ropes and other devices she couldn't identify. Her eyes focused again on the two wayward subs.

Boxwood and Jennifer had been waiting on their hands and knees for what seemed like an eternity when they both felt a cool breeze as the door to the play room opened. Neither of them dared turn their heads to see who entered, but they did hear two distinct set of footsteps. Elaine was talking as they entered.

"...had this room done so I would have a place for special training. So, anyhow, these two are Jennifer and Boxwood, who both need some correction."

Elaine and Jackie walked in front of the subs so that they could see them. Jennifer and Boxwood were surprised to see a young woman in elegant attire, dressed as if she was attending one of Elaine's fancy cocktail parties. Jennifer squinted, and even through the sunglasses, recognized the younger woman as Elaine's driver. She wondered why Elaine's driver would be dressed so differently, and in the play room, to observe their punishment. Her mind wasn't allowed to wander long.

There was a loud snapping sound. Then Jennifer realized an instant later that Elaine had hit her bottom with the riding crop she had been carrying. She bit her lip instead of crying out. The flash of fire burned brightly, and just as the pain was dissipating she felt another, then another, until her thighs were trembling and tears were flowing freely down her cheeks.

Over the roar in her ears, she could hear snippets of Elaine talking, but not to her.

" ... little slut ... punished ... loves it. You'll see."

Elaine leaned over and cradled Jennifer's weeping face in her hand. "Do you like this Jennifer? Do you want this?"

"Y ... Yes ... Mistress," she stuttered, between sobs.

Elaine went around behind Jennifer and dragged her fingers between the dripping folds of the blonde's sex. Jennifer shuddered at the unexpected touch, the incendiary glow in her bottom lighting a raging fire of lust. Elaine ordered Boxwood to remove his sunglasses and lay underneath Jennifer in a 69 position.

"Lick her Boxwood. I know you want to."

The balding man laid on his back, the hairs on his back being painfully pulled as he shimmied his body on the wooden floor to slide under the kneeling blonde slut. This was nirvana for Boxwood -- to be ordered about by Mistress Elaine, and to be in the humiliating position of laying on his back, his small pot belly extending upward, as three women witnessed his submission. Jennifer's hanging tits rubbed against his chest and her wet cunt was above his eyes as he assumed his position.

Impatient at Boxwood's slow movements, she used her riding crop to hit the tender arch of his foot.

"Owww," he cried out at the unexpected correction.

"Be quick about it Boxwood. Lick her."

Boxwood could hear Elaine say in a low voice to Jackie, "You can play with yourself when you watch this. You're going to see what these sluts really want."

Jackie's eyes were wide open. She was watching the man, obviously willing to do whatever Elaine ordered, feverishly licking the blonde's weeping cunt, as the woman remained still. What Jackie didn't realize was that Jennifer was exerting every ounce of self-control to stay perfectly still and silent, when the perfect mixture of pain and pleasure made her want to thrash her body about and scream out in ecstasy. Boxwood was so hard his erection was painful.

Elaine knew this was the time to finish Jennifer's punishment. She used the riding crop to create a perverse checkerboard of red and white on Jennifer's ass, each strike of the leather tab leaving almost a perfect red square. Jennifer's body was now taut, each muscle tensed, as the pain was even and intense. Every cell in her body was crying out for relief. Boxwood unrelenting licking created a powerful cocktail of pain and pleasure, and Jennifer reflexively let her knees relax so her pussy was pressing hard against his lips.

Elaine gave her one last lash with the crop. "Make her cum now Boxwood."

Boxwood sucked the slut blonde's clit into his mouth, swirling his tongue around the hardened nub. Jennifer's thighs squeezed his head and a gush of moisture saturated his face.

"Oh God!" Jennifer screamed as the orgasm she had been obsessing about the past week wrenched her body. She held her breath, willing her climax to continue and hoping it wouldn't end. Boxwood gasped for breath as he was covered by Jennifer's bountiful deluge, and he felt as if he was going to cum without being touched.

Elaine was watching Boxwood and Jennifer, enjoying watching her two subs pleasure each other in their own way, while she peeked over to see that Jackie had slipped her hand under her skirt and was fingering herself as she witnessed the art of dominance and submission for the first time.

"Like what you see, Jackie?"

Jackie was too busy looking at Jennifer, her body still quaking from her orgasm, and Boxwood, almost being crushed and suffocated by the curvy blonde, with his erection still lewdly pulsing.

"Jackie?"

Jackie finally heard Elaine's voice. "Uh ... yes ... El ... Mistress?"

"Did you want to participate?"

Jackie had entered the play room with great anticipation ... and fear. She wasn't sure what she was going to see, and was fearful that she would like it. Before, it all seemed a bit perverted and comical, Elaine's subs walking around the house in ridiculous clothing performing menial chores, but that was just the slow build-up to what she had just seen in the play room -- consenting adults letting their deep seated sexual fantasies be brought to fruition under the skillful hands of Mistress Elaine.

The question pending was a momentous one. Would Jackie step over that puritanical line separating the vanilla world from Elaine's? Jackie thought that she was experienced at sex, but this type of role play had excited her in ways she hadn't expected. Her fingers, soaked with her own desire, bore her answer.

"Yes, Mistress Elaine. I want this."

Elaine was pleased. She thought that Jackie harbored submissive tendencies even she didn't know she had. Having her see Boxwood and Jennifer was the perfect introduction. In a moment of inspiration, she knew what should happen next.

"Boxwood, get up and stand in front of Jackie."

Boxwood had to untangle from Jennifer, his back aching from laying on the hard wooden floor. His cock was still painfully erect as he stood in front of the elegantly dressed woman.

"Jackie, use your hand and make him cum."

Jackie's mind raced faster. She was relatively inexperienced with men, but knew how to give a handjob. She grasped the middle of his cock and then started pumping towards the tip, precum flowing out of the head and onto the floor. Boxwood's knees weakened as he watched the fully dressed woman in expensive attire stroking his cock. His eyes met hers, glowing with the same desire he saw in Jennifer's.

"Use your hand and catch his cum," Elaine ordered, seeing Boxwood's legs tense.

"Uh ... uh ... uh," the older man grunted as spurts of creamy white cum pooled in the palm of the brunette's hand. She continued to pump until there was nothing more, except Boxwood's groans.