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Mistress Elaine Ch. 08-10

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Warning: This story contains graphic scenes depicting pain and humiliation and has one watersports scene.

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.


Chapter Eight

He had his instructions now. The day after his video with Jennifer, Mistress Elaine had an Uber driver pick him up at noon. The wipers swished in a steady rain as he rethought the experiences he’d had. A smile crossed his face when he recalled the heartfelt thank you from Jennifer. That simple acknowledgment of his worth made all the humiliation he was subjected to miniscule in comparison to the satisfaction he felt. Whereas yesterday he was dressed like and sissy in pink panties and a cock cage, today he was wearing gray flannel dress slacks with a navy blazer and crisp blue shirt under his raincoat, like someone headed to the country club for Saturday lunch (though he was wearing the blue frilly panties and the lacy halter bra that were in the bag marked “Friday”).

The car brought him north on a winding road running alongside a rushing river to a brick house set back in the dense stand of tall trees. The car pulled up next to the house. The driver ignored him as he disembarked the vehicle. The tall trees were dripping large drops of rain on him as he sought the cover of the house. He could smell the damp air, and it reminded him of the happier days of his youth and his visits to summer camp. As instructed, he found his way around to the side door. It was located on a small porch with a modest V-shaped overhang that provided a partial cover from the large drops. He rang the bell, hoping this was the right place. There was no answer for several minutes. The temporary glow of his memory was replaced by anxiety as the rain drops cascaded off the porch roof and onto the shoulders of his raincoat. He was relieved when Jennifer opened the door; she was casually dressed but angrier than the day before. He was crestfallen to see that he had clearly not won her over.

She did not invite him in, but let him stand on the porch with the rain continuing to splash on his raincoat and now his head.

“You again. Don’t get your hopes up. I did make Mistress Elaine cum when she watched the video. So you did not win Mistress’s little bet. I ended up getting punished severely anyway, thanks to your stupid fantasy. Here, everything off and in the basket – – and put on what’s in this bag.” She leaned against the door frame and watched as he stripped and put his carefully folded clothes, undergarments and then his socks and shoes in the basket, as if he was expecting to be graded on his work. The small bag (labeled “Saturday”) she handed him had bright red thong panties and a matching red halter bra. She watched as he pulled on the panties. He struggled with the hooks on the bra behind him. She didn’t move a muscle to assist him. It took several minutes of gyrations to finally get the two hooks into the corresponding eyes. He was now shivering as the rain was now pelting his almost naked body and his bare feet were standing in a thin layer water on a cold concrete surface. Satisfied with his appearance, she handed him the collar, leash and leather cuffs he wore the previous day. He again struggled with the collar. She was amused by his struggles and his discomfort, which were small recompense for the punishment Mistress Elaine had meted out that morning on her defenseless bottom. Once finished, she clipped the cuffs so his hands were behind his back.

Wordlessly, Jennifer pivoted and walked into a small foyer. He entered the foyer and backed into the door to shut it. He had to walk quickly to keep up as Jennifer led him down the hall of Mistress Elaine’s house on the leash, awkward with his hands cuffed behind him. They turned into a breakfast room, with comfortable furnishings and a large multi-paned bay window looking out onto the rainy back garden. There was a modern kitchen beyond, and open French doors to a dining room. It was a warm country house, and the only thing out of place was him in his exposed costume.

“Here, slip these on to finish your ridiculous outfit.” She pointed to a pair of shiny black high-heeled pumps on the floor, obviously in a large men’s size, that showed slight wear from their previous occupants. With hands still cuffed behind him he had to work his bare damp feet into them, and once they were on he felt the odd sensation of standing on a slope with his hips and chest thrust forward. The pumps were at least a size too large, which made the effort of standing in them and walking that much harder for a novice.

Jennifer guided him to stand in the doorway, facing the garden, as she clipped the rings of the wrist and ankle Tipobet cuffs to loops of cord she had wrapped around the hinges of the open French doors. In only a moment he was secured in an X position, standing in his heels, facing away from the door. He was surprised to see that his cock was erect given the position he now found himself in.

“You see, no need for a dungeon or special gear, but with the same effect. Now, pay attention!” She slapped his flank hard with her open hand, leaving his skin stinging. Jennifer knelt at the floor by his side and they waited in silence.

Mistress Elaine came in wearing a tweed skirt cut six inches above her knees, a tight thin cream colored cashmere sweater, and beige cut away pumps with three inch heels. “Ahhh . . . my two video stars, together again. I thought of you, Boxwood, as Jennifer licked me to an a quick orgasm last night. I could see that maybe there’s more to your relationship with each other given Jennifer’s real orgasm as you fucked her ass. So no, you did not win her services. And she ended up getting punished anyway for not treating you with respect while she was there. She was not authorized to pee in your lunch. Her bottom felt the sting of my cat for that infraction.”

Jennifer glared at Boxwood when Mistress Elaine was lecturing him. He resigned himself to the fact that the goodwill earned yesterday was but a distant memory.

Mistress Elaine continued, “What you need to focus on for the next two days is learning to give, to offer your body rather than taking. I asked you to dress up today, just to heighten the contrast for you and where you are now. We’ll work on those small tits of yours first.”

She stepped closer to where he was spread out, cupping and massaging his breasts in the soft lace bra, then sliding her hand in to pinch and roll his nipples. As the nipples tightened, she pushed aside the bra to lick and suck them, raking her teeth and tugging on them. He shuddered and arched his back to push them toward her. Jennifer watched with annoyance.

“Lovely, you seem like an easy slut already. But I think you need to be bigger and more sensitive to really understand how to offer these. And we are ignoring your clit for now? ” Mistress Elaine slapped the front of his panties and his hardening cock.

She reached into her pocket and held a small device for him to see – – a short wide clear plastic tube with a squeeze bulb. “With training we can make your nipples larger and more sensitive. Perhaps later I might decide to have them pierced and fitted with rings or bars to remind you of what you are. For now, we will just make a start in the right direction.”

Fitting the tube over his right nipple, she held it in place as she pumped the bulb. He looked down as he felt the suction and saw the nub of his nipple pulled into the tube and extended. Tugging it toward her, she slipped an elastic band off the tube to hold the swollen nipple, then repeated the process on the left. She stepped back and smiled at the effect, with his two extended nipples, and flicked her finger at the right one, causing him significant pain.

“We’ll just leave these on for 5 minutes now, but with repeated training you’ll be able to take more and they will stay permanently larger.”

She pulled his bra back up where the lace rubbed against his sensitive flesh. She ducked under his extended arm to walk behind him and as he tried to focus for a few minutes on the rain and the garden outside the windows. His attention snapped back as he felt his panties pulled down and her fingers with cold lube probe him from behind and a narrow plug pushed in. He felt the waistband pulled back up, then she stepped in front of him again holding out her phone.

“See, that feeling brushing the back of your thighs is the plug with a tail you’re wearing now as a reminder. Tits and ass, as they say, that’s what you have to offer now.” She snapped a couple pictures for posterity.

Mistress Elaine pulled the bra aside for a moment and he felt the swelling pain as she removed the bands and blood flowed back into his sore nipples. His penis hardened again as she pinched and rolled the tender nubs and he arched his back to offer them to her. She stepped away with a laugh.

“You are beginning to get the idea – – all you are now is a slut wanting to be used, not a real man who would be thrusting that cock at anyone now. “

Mistress Elaine started to go back to her bedroom. She paused momentarily and turned to talk over her shoulder with a last word. “I’m going to leave you now with Jennifer. She knows what she needs to do. I think I’ll draw a bath and listen carefully from my bathroom to make sure she does a good job.”

Jennifer couldn’t conceal her smirk. She carefully freed him of his bonds and led him with the leash to the coffee table in the living room. He was directed to kneel in front of the coffee table and then lay forward so his chest was pressed against the cold glass of the table. She then attached the cuff Tipobet Giriş on his left wrist to a chain and fed the chain under the coffee table and attached the other end of the chain to the cuff on his right wrist. He was pinned to the coffee table on his knees with his ass fully exposed. He heard Jennifer leave the room. He also heard water running in the master suite. He strained to hear more. The water ran for a few minutes more. Then he heard faintly,

“Yes, Jennifer . . . just a bit lower . . . yes . . . . right spot . . . . slut . . . . ahhhhhhhh.”

There were splashing noises, then noises as if someone were rummaging in a closet, then footfalls.

It was Jennifer. “I’m back Boxwood with a friend.” He heard the sound of Jennifer squeezing a tube as the air swished out and then into the tube.

“Here, meet my good friend Boxwood.” He felt a cold, hard, wet presence at his anus. He tried to clench his cheeks as a gesture of futile resistance.

“Uh, uh Boxwood. Unclench those cheeks or its going to be worse.” Boxwood then heard Jennifer slip off her shoe. Moments later he felt the impact of the heel of her shoe as she spanked him with multiple hits.

“Owwwwww,” he cried as the heel connected for what felt like the hundredth time.

He then felt the cold wet presence again. He tried to relax his anal ring and wasn’t sure he was successful. He felt a great deal of pressure, then suddenly a feeling of fullness as Jennifer’s fake cock slid deep into his ass.


Jennifer was delighted she went balls deep on the first thrust. “You’re a natural Boxwood. You were made to take a cock all the way up your ass. Let’s see how you do with a hard fucking.” Jennifer demonstrated her acuity with a strap-on and executed rapid strokes in Boxwood’s distended ass.

“Shitshitshitshitshit” reverberated off the walls of the living room. His screams were easily heard by Mistress Elaine in her bathtub. Boxwood was experiencing a searing pain from his anal initiation at the hands of a very unsympathetic handler.

Jennifer reached down to stroke Boxwood’s embarrassingly erect cock. His cum dribbled onto the hardwood below.

Jennifer pulled back out of his ass and then unhooked him. She pulled him to his feet. Her fake lubed cock was lewdly protruding from her harness. Boxwood couldn’t believe the full length of that massive fake cock was moments ago buried in his ass. Jennifer turned around so Boxwood could see her bare ass and the back of her legs. All of it was crisscrossed with red stripes from Mistress Elaine’s cat-o-nine tails.

“Looks like we’re even now Boxwood. Now get on your knees and lick up your cum before Mistress Elaine gets back.”

Chapter Nine

Things had changed so much his mind was spinning. It was less than 2 hours ago that he was getting into the Uber car, dressed like a senior professional, and now he was standing for the first time in Mistress Elaine’s home, half naked in panties, bra and heels. His ass was sore where he had been spanked and used and his lips were sticky with his cum which he’d licked off the oak floor. Standing next to him was the naked 40- something woman who had just taken him. With her glasses and short brown hair, Jennifer looked like someone he might see in an upscale book store but with her full breasts exposed and the strap on and harness at her waist. Both of them waited silently for Mistress Elaine to return.

When Mistress Elaine came in she was dressed for a casual rainy day at home in a soft cashmere sweater and slacks with low heeled shoes. Her normal dress made their nakedness and lingerie even more humiliating.

“Well, enough fun for now, both of you have work to do today. The guests will be here at 6:00, and the party is not going to prepare itself. Jennifer, put your toy away properly. We need six dozen of those little cocktail snacks you so so well, with the melted cheese and the olives. You also need to set up the bar, and of course supervise Boxwood here.”

“Yes, Mistress, thank you.”

“And you, Boxwood, you can learn to put others first by doing the cleaning, and then by helping Jennifer. You’re already dressed for it and the things you need are in the kitchen. Jennifer will tell you the rules so do as she says.”

“Yes, Mistress Elaine.”

” You forgot to say ‘thank you.’ Jennifer, give him 10 strokes of the crop for that later. Now go, both of you. I’ll be in the library.”

She left, and he turned to see Jennifer smirking again, as she removed the strap-on and picked up the crop. “Why wait? Grab your ankles, Boxwoooooood.” She purposely drew out his name to mock him in his sissy outfit.

He was bent over, head down, legs apart, as she stung his ass and thighs with sharp smacks, and he counted them off. He stood and waited while she went out of the room until she returned dressed in a short gray skirt and a cotton shirt with plastic clogs. She handed him a cleaning bucket with tools. He couldn’t help letting his Tipobet Güncel Giriş eyes go to her bare legs and her breasts swaying under the shirt and he felt his cock harden.

“You seem excited already for your day as a sissy maid. The one rule you need to know is no touching that clit yourself – – if you need to use the bathroom you come and see me.” Jennifer stepped closer to loop a long scarf around his neck and used it to tie his right hand behind him. “Slower, one- handed cleaning will make you think more about what you are becoming now.”

Then he was alone in a little- used upstairs bath, awkwardly spraying and scrubbing with his left hand, his feet and ankles aching from the ill-fitting high heels and feeling the uncomfortable binding of the bra and panties. Part of his mind was on the dirty and sweaty work, but part was on how ridiculous he looked like this, almost naked in a stranger’s home, and on his memories of tasting Mistress Elaine and Jennifer’s bodies. Hours later, he was back in the kitchen with his bucket, on aching feet. Jennifer was at the stove, surrounded by trays of food.

“Miss Jennifer, may I use the bathroom now please? I finished upstairs.”

“You’re a slow worker, Boxwood, we have had other maids here who were better at this. So, I guess you must really seriously need to go since you’re asking for this?”

Jennifer was smirking again as she led him to the small bathroom in the back hall. She didn’t move to untie his hand, and she was standing very close to him as she pulled his panties to his knees. He waited for her to direct his penis, but instead she opened her shirt to expose her full breasts and laughed as he began to harden. Now she held his cock and started stroking it, and the effect was to make him harder and to make it almost impossible to pee.

“Go ahead Boxwood . . . pee now. I don’t have all day.” His erection made hitting the bowl accurately impossible. Jennifer kept stroking his cock as he concentrated on urinating. Even though he used his free hand to guide his cock the stream out of his penis was misdirected and most of the pee went on the rim and the floor below.

“Boxwood, you’ve really done it now. The guests will be arriving soon and the guest bathroom is dirty again. We don’t have the time to fetch a clean towel so what shall we do? I think you should use your bra and panties to soak up what you can and you’ll need to lick up the rest.”

Jennifer glared at Boxwood and started tapping her foot. Boxwood took off his bra and panties and used them to swab the toilet rim and then the floor. The bra and panties were so saturated there was still some residual moisture on the floor. Boxwood leaned down and licked the floor clean. He thought that his humiliation was complete. He was wrong.

Jennifer leaned down to inspect the floor. “I guess that will have to do. Boxwood, did I give you permission not to wear your bra and panties? Put them back on, now.”

Boxwood put the urine soaked bra and panties back on.

Jennifer looked annoyed. “Now we really do need to get you cleaned up so that you can serve the guests.”

He was back now in the living room, watching the darkening sky, with Jennifer holding his leash. After taunting him before, she was smiling now. Mistress Elaine had inspected them after the cleaning and the cooking, and laughed to hear about how Jennifer had further humiliated him in the bathroom. She approached Boxwood and sniffed the air. “Boxwood, you stink. I’m amazed that you can’t handle the simplest of bodily functions and had to pee all over my clean floor.” She had sent them off to get ready, but with strict instructions he was not allowed to cum.

Jennifer took him to the first bathroom he had cleaned, then stripped him and showered him in cold water with rough scrubbing. As he dried off with paper towels she showed him the clothes Mistress Elaine had chosen for them.

“This is a basque, Boxwood, sort of a short satin corset but it offers your tits and leaves the nipples exposed. You have dark stockings and higher heels to go with it, and a matching thong. I have this new cocktail dress, and a present from Mistress – this lovely Wacoal matched bra and panty set. Now watch and learn.”

He had to stand silent and naked as he watched her shower and dress, hardening as he saw her body and ached to touch her, then feeling her hands all over him as she fitted the stockings and zipped him into the basque. Now he saw in the dark glass of the shower door his new costume, like an aging Rocky Horror character, with his nipples rouged, on her leash. Behind them, he heard a new buzz of conversation.

“…so glad you could make it here in the rain, I was hoping we could use the patio. Jennifer is here, and a new project I’m working on, still a bit rough but with potential…”

He was nervous now, trying to hear who Mistress Elaine might be bringing to join them, when Jennifer slipped the blindfold over his eyes. At the same time she gave the leash a sharp tug and pulled him forward. He stumbled, to find his hands pulled forward to rest on the back of a low chair. He felt her reach down to slip cuffs around his ankles, then heard the rattle of the chain as she spread his ankles around the coffee table where he had been bound before.

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