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.
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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 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 then clean her too."