Mistress Elaine Ch. 11-15

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Warning: This story contains graphic scenes depicting pain and humiliation.

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 are 18 years or older when in sexual situations.

This is Boxwood’s and Mistress SWP’s shared fantasy.


Recap of Characters and Chapters One through Ten

Boxwood – gentleman living in Englewood, near New York, divorced, professional worker, late-50’s, slightly overweight, interested in submission and humiliation. Polite, respectful, Met Mistress Elaine originally just for conversation, now a probationary sub of Mistress Elaine. Grand Life Master at duplicate bridge.

Mistress Elaine – early 50’s, independently wealthy from sale of patents developed while working as an engineer. Attractive strawberry blonde, interested in fashion, not leather costumes. Somewhat cold and distant, controlling personality, a slightly sadistic edge. Interested in mind play and lesbian seduction.

Jennifer – early 40’s and married but prefers women. Short dark hair, glasses, full figured, but not heavy, has been a sub of Mistress Elaine for a number of years.

Galina – early 30’s, Russian, slender blonde, former ballerina, master chef, cold and calculating, recent sub of Mistress Elaine

Valentin – early 30’s, Russian, slim, muscular, shirt sandy hair, said to be married to Galina, new sub to Mistress Elaine.

In Part I, “Mistress Elaine Chapters 1-7,” Mistress Elaine unexpectedly visits prospective new male sub Boxwood at his home where she tests him and begins to take over his life. The following day she sends over her female sub Jennifer to take charge of him. Mistress Elaine finds it amusing to direct and humiliate them both during a video call session, to the great annoyance of lesbian sub Jennifer.

In Part II, “Mistress Elaine, Chapters 8-10,” the story and the training continue with Boxwood sent to Mistress Elaine’s country cottage where Jennifer supervises his continuing humiliation and submissive training including pegging. Later that day he serves at a party of Mistress Elaine’s friends and competes for their amusement, hoping to win favor with Mistress Elaine. Boxwood cheats at the competition and both Jennifer and Boxwood are punished.

Chapter Eleven

It was a warm spring day in rural Connecticut, with a hazy sky and no wind, and he was already dusty and sweaty and tired. Raking and bagging the dried leaves, he was doing spring cleanup in the large yard behind Mistress Elaine’s country cottage after cleaning out her gutters. He hadn’t known what to expect from his training weekend but it wasn’t this. He still wore the collar, along with a worn, oversize t-shirt, plastic clogs, and lime green panties labelled “Sunday.” After feeding and watering him, Jennifer had added the ankle cuffs and linking chain, so as he worked he was constantly reminded of his submission and that he was now a willing applicant to Mistress Elaine’s stable.

Mistress Elaine was ignoring him now, sitting in a lounge chair on the terrace in the distance, with her coffee and the Sunday Times. She was casually dressed now, in a short yellow sundress with her hair pulled back in a ponytail. She shifted her legs to admire the nail polish Boxwood had expertly applied that morning to her toenails. She then focused on her thighs and thought about his reward last night, kneeling between those thighs to service her as Jennifer gave a running commentary on Boxwood’s expert oral skills and her rousing orgasm. She was pleased with Boxwood’s progress and with Jennifer’s burgeoning jealousy as the interplay between the two of them was an endless source of amusement. As she was musing about Jennifer’s jealousy as if on cue she came out of the house in short shorts, a tight t- shirt and heels with a silver coffee urn on a tray, and turned to glare at Boxwood as she refilled her Mistress’s coffee mug. Boxwood took note of Jennifer’s sex kitten good looks and the icy glare she gave him and went back to his yard work.

The sound of a car on the gravel drive got his attention and he looked down the hill. A slim blonde woman got out of a red late model convertible, 30-something and wearing a scarf on her head, oversized sunglasses and a fitted sleeveless blue dress. Next to her he saw a man, about the same age, wearing a brown leather bomber jacket, aviator sunglasses, slim jeans and loafers. The man seemed to be slender yet muscular, with very short sandy hair. As the man unloaded the luggage Mistress Elaine waved to them to come down to the terrace. He knew it was Galina and Valentin. He dropped his rake and walked slowly in his chains to the terrace, with dirt and bits of leaves clinging to his sweaty face and body.

When Boxwood arrived at the terrace he expected to see what he was seeing but it was startling nevertheless. Mistress Tipobet Elaine was standing and Galina and Valentin were kneeling in front of her, each kissing a foot. Mistress Elaine paid heed to Boxwood’s arrival. “On Boxwood, so good of you to join us. As you can see Galina and Valentin have returned from their trip to Russia. Galina and Valentin, please get up so I can make the introductions.”

Galina and Valentin rose up and were facing Boxwood. The couple looked like they had jumped off the cover of a European style magazine. Boxwood was painfully aware of his appearance, an overweight man in an ill-fitting t-shirt, women’s panties, and dirt and bits of leaves clinging to him. Both Galina and Valentin were unable to suppress the smirk that arose when they saw Boxwood’s appearance.

“Boxwood,” said Galina in lightly accented English.

“Good to meet you sir,” said Valentin in a similar accent.

“I look forward to serving you,” replied Boxwood.

Mistress Elaine turned to Jennifer, who was standing to the side. “Jennifer, don’t you want to welcome Galina and Valentin back?”

In a forced voice Jennifer said, “Welcome back.” A laser beam was shot from Jennifer’s eyes to Galina. All could see that there was no love lost between the two of them.

“Well,” declared Mistress Elaine, “Now that we have said all our pleasantries, Boxwood, go finish the yard and then report back to me. Galina and Valentin, you sluts get ready to meet me in my bedroom. Jennifer, go help Boxwood bag the remaining leaves.”

Boxwood was already crossing the lawn when he turned to see Jennifer following at Mistress Elaine’s orders. Her face was dark with anger at her sudden public demotion from personal servant to yard worker.

As a woman in her 40’s, older than the new arrivals, she was a bit too old and too curvy for the sexy outfit she wore as part of her humiliation for misbehaving yet again. The tight stretchy gray short shorts molded to her lower body, accentuating her slender bare legs. Her strappy high heels were already dusty and certainly awkward for yard work. He could not help staring at her large, swaying breasts, obviously braless under the tight silvery t-shirt. Her hair and makeup, so flawless when she was serving on the terrace, were already in disarray as she sweated while working her way up the slope of the yard, and her glasses were slipping down her sweat slicked nose. Even with her disheveled appearance Jennifer still looked like a Goddess to him. He fondly remembered being allowed to use her body once, and her gratitude for the pleasure he gave her, and his cock went rock hard in his panties.

“That bitch, Galina! The two of them, trying to look cool, not like the lower slaves they really are. Now both of them are sucking up to Mistress, fighting for my place. I knew her first! And you, what are you looking at you pathetic loser?!” He lowered his eyes and turned back to his raking, but he couldn’t stop thinking about Jennifer’s sensuous body and was unable to suppress the bulge in his thin green lace panties.

Boxwood’s obvious erection was not lost on Jennifer. “All you can ever do is think with your penis, like most men! So annoying and disgusting! Stand still, and hold that rake over your head!” He spread his hands on the thin wooden handle and held it over his head, feeling his shirt ride up to expose the panties more.

Jennifer grabbed handfuls of dried leaves out of the tall paper bag he had been filling and stuffed them roughly up his shirt. The scratchy leaves were pressed against his skin as she packed more in. As he kept his arms up, she stuffed more leaves and debris into his panties until his legs were dusted with a shower of dirt and broken leaves.

“Now, just keep your mind on the work. Rake!” She held the bag open, and he went back to raking and lifting bundles of leaves to fill the bag. As he moved, the dry leaves stuffed into his clothes crackled and chafed; her sharp look told him to keep his eyes down.

“Yes, Miss Jennifer.” They had worked their way along the tree line, filling a dozen bags, and the noon sun was beating down on them when they heard a bell. Mistress Elaine was back on the terrace, in a long bathrobe now with a towel on her hair, ringing it and calling them back to the cottage. Both of them were sweating and covered in dust, and the shredded leaves inside his clothing were itchy and painful.

Mistress Elaine waved them off. “No, no, both of you are a mess now, clean up before you come back to the terrace.” She pointed them to the hose at the corner of the house, then crossed her arms to watch.

Jennifer picked up the hose. “Boxwood, everything off now.” He was too tired to resist as he pulled the shirt off over his head, then tugged the panties down. Mistress Elaine laughed as leaves fell out of his clothing. Jennifer gave Boxwood a bracing shower, spraying him with cold water while paying extra attention to his cock and balls. Before she could finish Mistress Elaine spoke up.

“Boxwood, undress Jennifer Tipobet Giriş then clean her too.”

He was naked and shivering, still dripping cold water off his hair and body, but his penis hardened as he stepped closer to Jennifer. She handed him her glasses which he set down on the window ledge behind him. She lifted her arms and he carefully peeled off her tight sweat soaked t-shirt, now stuck to her curvy body like a second skin. As he pulled it over her head her breasts bounced free in front of his face. He knelt to pull down her shorts and slip off her heels as Mistress Elaine smiled with approval.

“Here Boxwood, all of my ladies have to be washed properly.” Mistress Elaine tossed Boxwood a new bar of soap.

Much to his surprise Boxwood caught the flying bar of soap with his right hand. He picked up the nozzle of the running hose with his other hand and starting wetting Jennifer’s naked body, starting with her hair. He rinsed her hair, running his fingers through Jennifer’s short dark hair. He was mindful of his painful erection, trying not to hit her with his erect penis as he rinsed her hair in close quarters. He soaped his hands and washed her face and neck, then kinked the hose to allow only a gentle spray to rinse it. Jennifer wondered if she was being too harsh with him as he was treating her with the utmost of respect after her continuing efforts to degrade him. If anything she needed an ally if she was going to deal with Galina and Valentin. She chided herself for her quick temper, taking her frustrations with Galina and Valentin out against Boxwood. Why should she feel threatened by an old overweight man who worshiped her?

Lost in his own thoughts Boxwood washed her arms and hands and then was confronted with her breasts, now with nipples hardened by the cold spray of the water.

Mistress Elaine could see Boxwood’s dilemma. “Make sure her tits are squeaky clean Boxwood.”

Boxwood lathered his hands and lifted up Jennifer’s right breast to wash underneath it. The softness of her breasts was accentuated by the soapy film. He had never felt anything as luxurious in his life. He then focused on Jennifer’s left breast and starting washing it as well. He was caught up in the eroticism of the moment and got too close, inadvertently brushing his erect penis against Jennifer’s now soap slick stomach. The contact was too much for Boxwood. Before he could back away his penis had ejaculated on Jennifer’s stomach. Boxwood had his back to Mistress Elaine so she could not see his faux pas. Jennifer was startled by the sensation of Boxwood’s warm cum against her cold skin but said nothing. Instead, she rubbed his cum against the skin of her tummy as if it were soap and gave Boxwood a knowing smile. Boxwood was puzzled by Jennifer’s silence, but gratified that she had somehow had a change in heart.

Boxwood continued to wash Jennifer as if nothing had happened, and was happy that his penis had now softened, taking away at least that point of embarrassment. He took joy in washing Jennifer’s pussy and anus and took note of the fact that Jennifer widened her stance without being asked to allow easier access to her nether regions.

Mistress Elaine was amused by Boxwood’s infatuation with Jennifer. “Dry her off, let her dry you, then go around to the kitchen door.”

Chapter Twelve

The smells of a country farm style lunch wafted out of the kitchen door. Boxwood and Jennifer entered the kitchen door, noting that there were two neatly piled sets of clothes on the floor. Jennifer was rewarded with a new set of matching panties and bra, a red jersey dress with fine white polka dots and sandals. Jennifer went back to the servant’s quarters to reapply her make-up. Boxwood retrieved a new halter bra and matching panties, short shorts, an “I Love New York” t-shirt with a large red heart on it, his collar and his ill-fitting high heels. He dressed slowly and waited for Jennifer to return.

A few minutes later Jennifer returned, looking no worse for wear, refreshed in her pretty red dress. Boxwood took another loving look at her ample cleavage.

“Come in, come in, it’s time to eat,” said Mistress Elaine with surprising warmth. “Galina and Valentin have whipped up something special for our two hard workers.”

Boxwood noted there were only place settings for four people. He then spotted a worn and scratched dog dish in the corner. He went over and stood next to it. He could smell fried chicken on the stove and could see Galina busily making waffles in a waffle iron. There was already hot coffee on the table.

Jennifer awaited her Mistress’s instructions before sitting. Mistress Elaine, now sitting at the table, motioned to Jennifer to sit next to her. Jennifer beamed.

Valentin put a heaping platter of fried chicken on the table. Galina followed with a stack of waffles and a small carafe of maple syrup.

“Excellent,” declared Mistress Elaine. Turning to Boxwood she added, “You know that Galina and Valentin are professional chefs.” Jennifer scowled Tipobet Güncel Giriş at the accolade but was so hungry she couldn’t keep her eyes off the golden brown fried chicken.

The four at the table engaged in idle chit chat, mostly revolving around Galina and Valentin’s trip to Moscow to visit relatives and their “secret” recipe for fried chicken that included the use of a buttermilk brine. Boxwood watched as the stack of waffles and the pile of fried chicken dwindled on the platters.

As the meal concluded Valentin took the leavings on the platters and scraped them into the dog dish. The chicken bones were piled high in the dish and then topped with soggy half eaten waffles. He then took the remainder of the cold coffee and the carafe of maple syrup and poured them over the pile of food.

He went over to the counter and retrieved a pair of handcuffs. Without being asked Boxwood put his arms behind his back. Valentin handcuffed Boxwood’s arms together.

“Enjoy Boxwood.”

The conversation continued as Valentin was attending to Boxwood’s “meal.” As Boxwood stood in the corner while Valentin was serving him he studied Mistress Elaine and her three subs. Mistress Elaine was elegantly but casually dressed as always, and clearly very wealthy in some way he did not understand. She was her usual cool and collected self, but now glowing from her recent session with the Russians, yet she still held herself at arm’s length from everyone. Jennifer was fuller figured and very sexy in her new red dress, and he hardened as he thought about his intimate knowledge of her body and his innate ability, despite her resistance, to please her. The two Russians seemed unconcerned about his presence. He knew he should not underestimate them, as the Russians were the grandmasters of chess, and were likely already thinking three moves ahead of Jennifer and Boxwood. Galina was slender, in a blue dress that molded to her high, small breasts and showed her dancer’s legs. When Galina did pay notice she glared at him in his ridiculous outfit. Valentin glanced at him often, in the superior way of a more handsome and fit man, dressed in European sportswear and fine Italian shoes. Boxwood shuddered to think of how they would treat him.

Now he was on his knees in handcuffs, gnawing at the leftover chicken bones in the dish and slurping cold coffee and soggy waffles. After a morning of hard work he was hungry and ready to accept his new role. The women soon left the kitchen, still carrying on their conversation without a glance backward at Boxwood. Valentin stayed behind, apparently waiting for a private moment to gauge his new rival.

“So Boxwood, is it? What kind of name is that?”

Boxwood lifted his head from his dog dish, with syrup coated pieces of chicken and waffles sticking to his face. “I’m English.”

“So you are. It looks like you, like the British Empire, are relegated to the leftovers of the world.”

Boxwood was not about to get into a political discussion while he was kneeling with his hands cuffed behind his back. “I imagine you’re right.” He thought it best to give ground so as not to give cause for further abuse.

Valentin was pleased with the reply. Boxwood would not put up any resistance.

“So Boxweed, I think when I was at the airport I had a piece of gum stick to my shoe when I was in the restroom. Can you please remove it?” Valentin could see that Boxwood’s hands were cuffed so there was only one way to do it. He lifted up his expensive Italian loafer and sure enough there was a wad of gum, now encrusted with bits of dirt and rock.

Boxwood shimmied forward on his knees and used his teeth to scrape the gum off Valentin’s shoes. He spit the gum out on the floor.

“No no Boxweed. That’s part of your lunch.” He bent over and put it back in Boxwood’s mouth. “Now chew carefully like your Momma taught you.” Boxwood swallowed the wad whole, while the entire time trying not to retch up his entire lunch. Valentin looked at the bottom of his shoe and nodded his approval. Then before he left the room he veered over to Boxwood’s dog dish and casually used the toe of his now clean shoe to tip the contents of the dish across the floor.

“Ta Ta Boxweed.”

Now the gauntlet had been thrown down. Boxwood knew that the Russians had something more insidious in store for Jennifer, as she was already a trusted member of Mistress Elaine’s stable. It looked like he was going to have to join forces with her if either of them were going to survive.

Chapter Thirteen

Boxwood was just finishing gnawing on the chicken bones in his dish when Galina came into the kitchen to fetch him. She stepped up right next to him so his back was close to the wall. “Boxwood, Boxwood – – you seem to do nothing but get dirty like a small boy. Mistress wants you upstairs; she says you have more tasks to do. “

She watched as he struggled to stand up with his hands still behind him. She was still dressed casually (but fashionably), now wearing an untucked white cotton top (with no bra), an unbuttoned navy blue cardigan sweater and skinny pink jeans with white canvas tennis shoes. He was very conscious of her body and her high breasts so close to him. She used a kitchen towel to roughly wipe the food and grease from his face, then gripped his chin.

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