Mistress Elaine Ch. 01-07


Warning: This story is published in the BDSM category. It contains graphic scenes depicting pain and humiliation and 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.

Boxwood. This is your fantasy. Hope you meet your Mistress Elaine.



Was this sub space? He’d heard the term, and now his mind was overloaded with sensations, so maybe this was it. Not just with pain, also longing for his release. He was watching Mistress Elaine and his prone body, not from his eyes, but from afar as if he had no control over his movements. He channeled his thoughts to her in hopes that she would receive his mental SOS. She held the key to his release.

Chapter One

They had started talking back in the dawn of the Web, when a bad snapshot in an Instant Message was a big deal. The one photo he had of hers showed her in a charcoal grey wool gabardine suit with black leather boots with pointed toes and 4 inch heels, shot looking up on a vast green expanse of lawn. They had chatted over coffee for hours at Starbucks and one too-elaborate dinner, but nothing more. It was a Thursday night, and he was at home in the Englewood apartment when the bell rang. He was surprised to look out and see her, wearing a long navy blue cashmere coat and pulling a small roller bag.

“Hello, wow, Elaine, I had no idea, a surprise, come in…” He was stupidly fumbling for words.

“Mistress Elaine, you mean.” She was not smiling.

“Yes, of course, Mistress Elaine, please come in.” She had never offered the title before, and he stepped back as she brought her bag into the entrance hall. She slipped off the navy overcoat and he saw she was wearing boots similar to the ones in the picture. He also saw dark stockings with an elegant fitted evening dress with a plunging neckline that glimmered with burgundy beading.

He was trying to think quickly but failing; should he offer a drink or a joke? He felt he was losing the moment. During his moment of hesitation she reached into the side pocket of the bag and took out a riding crop. He knew what it was, in an abstract way, but the words died on his lips.

“You make me curious, Boxwood. I was wondering if you have real feelings beyond your theoretical discussions of erotic novels. Let’s see what you can feel without a lot of negotiation and role play games. Will you cross the line?”

She laid the crop across the floor in front of her and walked back a few steps to sit in the tall leather side chair. Here in his own familiar room his heart was pounding and he had to think back on everything he had read. He was wearing jeans and a shirt, and he carefully removed and folded them and then after a pause the boxers too. She was fully dressed, observing him naked in his room now, still not smiling. He knelt on the oriental rug and slowly bent forward. On hands and knees, he put his mouth to the crop to pick it up. He tasted the braided covering on the hard shaft and lifted his head to look at her.

Her lips moved towards a smile as she studied him and he ached with want as he looked at her long shapely supple legs, her dress, the swell of her breasts, her elegant neck, her heart shaped face, her jade green eyes and her long strawberry blond hair. She crossed her legs and briefly reached inside her beaded dress and under her bra to cup her own breast. He felt his cock hanging below him harden as he tightened his teeth on the crop and slowly crawled to her. As he got to her he lifted his head to offer the crop.

“Good start Boxwood. You have been studying.”

She reached into the bag beside her and brought out a collar, a well-used dark leather collar several fingers wide, not a toy or a costume item. As she buckled it on him he remembered their chats and thought about the other men and women who had worn it before. The wide stiff band lifted his chin awkwardly as she clipped a chain leash to it. It had the smell of its many prior owners.

She glibly said, “Calls for a drink, wouldn’t you say?”

Mistress Elaine went into the kitchen and brought out a chilled bottle of the Beringer Private Reserve Chardonnay they both liked with a corkscrew and one stemmed wine glass. He watched, naked and leashed, as she opened it and poured a full glass for herself.

“Oh, would you like some too?”

She zipped open her travel bag and pulled out a scratched steel dog bowl and put it on the rug and splashed the wine into it. She them dipped the toe of her boot in the bowl and swished it in the wine. He put the crop at her feet and crawled closer to kiss the wine soaked toe of her boot, then turned to the dish. With the collar he had to bend his arms and lean on them to lower his face into the dish. He lapped Tipobet chilled wine and felt it dribbling into his chin. He was very hard now with wanting her, and as he drank he realized he had said nothing, just accepted the role she knew he wanted.

Mistress Elaine stood up to walk around him and observe him as he knelt with his face in the dish and his ass up. He felt the pointed toe of her boot nudge his legs wider apart, then lightly tap his exposed balls. The crop was in her hand now; he felt the sharp sting of the leather tab on his rear at the same time he heard it whip through the air.

“Count them Boxwood.”

“One.” His face was already flush and he was already wondering how many strokes he would have to endure.

He was shaking and sore after ten strokes. He wanted to show his Mistress that he was brave and suppressed the tears that wanted to flow freely.

“Thank you Mistress.”

The leash slacked off as she returned to the chair.

“No more chatter, just show me without words how much you want this.”

She shifted in the chair, with her legs slightly apart now, and studied him as she sipped her wine. He looked at the smooth polished black of her boots, her knees in the gray stockings, and the shadowed space under her skirt and tried with his eyes and his face to show what he felt. He had never wanted any woman so intensely. She slid her hand seductively under her dress and bra and cupped her own breast again, lazily stroking her thumb and index finger against her nipple, and watching his reactions. He was shaking now with his desire to see her body and taste her breasts.

“I want your full attention for a long time Boxwood, not just that erection that’s driving you now.”

She shifted to extend one leg under him, tightening the leash, so that he felt his hard cock on the leather of her boot. He sensed his role, and began to hump himself against her boot as she pressed her leg against him, and soon the novelty of the act and the friction and the shame of needing this had him cumming and spurting. She pulled back her leg to hold the boot to his lips. He eyed the creamy white discharge splattered on her boot and without hesitation licked it clean. His tongue tasted his own salty cum along with hints of boot wax and wet leather. It occurred to him that this was not the ideal pairing with the chardonnay he had been saving for a special occasion.

She pushed him back so that she could lift the hem of her dress and sit back with her legs splayed wide. His cock was maddeningly soft now as he saw the lacy gray stocking tops on her pale bare thighs and the exciting shadows beyond. The leash pulled him closer and suddenly his face was resting on her stocking tops and he could see that she had carefully planned everything, including this intimate detail of arriving at his apartment pantyless. He was staring at her neatly trimmed strawberry blond pubic hair. Her pussy lips were swollen and bore the moist evidence of her desire. He felt her hands push the back of his head firmly against her sex. He eagerly plunged his tongue deep into her sopping wet cunt. Everything else had left his mind.

Chapter Two

His tongue began to ache as he felt Mistress Elaine pull gently on the leash. The skirt of her dress was pulled up over her hips, but with his face buried between her thighs and all he could see now was the skin of her belly. The stiff leather collar kept his head up and he varied the way his tongue penetrated, licked, and sucked her. His nose was in her musky, damp hair and he felt her thighs against her head. His mouth was full of the taste of her as he traced her hard clit and he thought of a Billy Joel song, about worshipping at the delta, as he felt her shudder under him.

Then it was over, as the leash went slack and she pushed him away with her booted foot. He was kneeling naked and deflated on the oriental rug in front of her as she tugged her skirt down. She was breathing harder, but still not smiling. He kept his hands at his sides and felt her juices coating his face.

“That was a good beginning Boxwood and with more practice you might be useful. You just need to keep your focus and not get distracted by your own needs. Lie down now, right here.”

He slid from his knees to lie back on the rug, seeing mostly the ceiling. He heard the zip of her bag, then she was standing over him with the crop and a small box. She reached with the riding crop to nudge his legs wider apart and tapped his cock lightly with it.

“Hold still and pay attention.”

He was silent as she knelt next to him and laid the crop across his chest. Then he felt her hands on his soft cock, lifting and tugging, the cool feel of plastic pieces around it. With the wide collar he could not look down at her so he saw only the ceiling. Her hands worked on him then he heard and felt a sharp click. She stood up and the pressure continued. He realized now that his cock was curved into the shell of a chastity device.

“Stand up now and come over Tipobet Giriş here.”

He had to use both hands to awkwardly roll to his feet and a tug on the leash pulled him forward. Mistress Elaine was beautiful, still in her beaded dress and boots, and they were standing in front of the tall walnut-framed Victorian mirror next to his sofa. She was almost his height, holding the loop of his leash, and he was the heavy naked man in the tall collar, looking totally out of place. His cock looked very small now, encased in the tinted plastic shell that wrapped it into a curve. He saw the small chrome lock dangling from the shell of it.

“Now put these on to complete your new look.”

Elaine held out a pair of hot pink panties. He had to watch himself in the mirror as he stepped into them and pulled them up over the small rounded shell of his cock enclosure. She reached down to feel the smooth front of his panties, then cupped his breast. He felt a mixture of shame and excitement, but at the same moment he felt the sear of pain of his cock as it was unable to harden in its curved prison.

“Did I ever tell you, Boxwood, in all those chats, that I actually find women much more exciting?”

He was watching in the mirror as she began to unbutton her dress, exposing her lacy bra. She opened the front of the dress down to her waist and slipped her arms out and unfastened the front catch of her bra. He was excited by her shapely bare breasts and hardening nipples, but instantly felt the pain of his trapped cock.

Now she shook her hips a bit as she opened the rest of the dress and tossed it aside. She was stunning, in just the boots and stockings, and he was aching and frustrated. He watched in the mirror as she used the leash to pull his lips down to her breast. Then he was licking and sucking, trying to ignore the dull pain of his cock. In the tall mirror he could see her finally smiling now.

Chapter Three

He was breathless and aching with want as his tongue circled her breast and his lips found the extended nipple, and without thinking about it his hand was on her side, holding her to him. Mistress Elaine pulled away, and the sharp smack on his thigh came from the crop he had forgotten about.

“No hands, Boxwood, this is not some sort of movie date! Maybe you need to be cuffed, your mouth is all I want from you now. I’m trying to get you to set aside your old masculine mindset, to be more like the women I prefer.”

She slid his arms down into the sides of the panties he wore, then pushed his shoulders down so that he was kneeling again. Leaning over him, with her arms on his shoulders, her breasts were hanging down like ripe fruit to be picked and he was straining to lick and taste them again. His need to be touching her this way was so strong now that the discomfort of his trapped cock and the loss of his hands were pushed to the back of his mind, and he felt a surge of submission as he connected with her body. He was lost in the tasting of her, his lips and tongue working and feeling the weight of her breasts and the hard nubs of her nipples.

Mistress Elaine shuddered and backed off, pulling him up so that he was above her now, supporting herself with one hand on his shoulder and the other cupping his ass in the panties.

“I want those tits Boxwood, be my good girl now.”

He forgot about his caged cock and pinned arms behind his back and arched his back to leave his small breasts hanging down and wanting to give. He offered his hard nipples to her mouth and almost cried out when she took them, licking and sucking and nibbling lightly. He was suddenly happy to have something to offer to her to want to use him in this feminine way. His arousal was painful, with his cock in its plastic shell, as he focused on giving her what she wanted from him.

Chapter Four

He woke to the smells of cooking and his back was aching. Last night after using him Mistress Elaine had led him to the bedroom and tied his leash to the bedpost, giving him only a pillow and a thin blanket on the floor. He had to listen from below to the sounds of her vibrator and her pleasure and feel his cock throbbing helplessly in its cage. Now he was naked except for the panties, collared and leashed in his own home.

Mistress Elaine slid out of bed naked and gently kicked him in the rear. “Have a good night, Boxwood? I’m thinking I will need to get you one of those padded dog beds, instead of the hard floor. How about breakfast? I need to get going, but you’ll be working from home today.”

She went into his closet and was now wearing his robe. Mistress Elaine took the leash and led him crawling to the kitchen where he smelled fresh coffee, eggs and buttered English muffins. He suddenly became aware that he was hungry, not having eaten since an early dinner the previous night. She sat at the table and tugged his leash closer and as she opened her legs he saw she was naked under the robe. He kissed her inner thigh and then her mound. Her scent was much muskier Tipobet Güncel Giriş and earthier than the night before.

“Oh Boxwood, I forgot to mention to you. I don’t shower until after breakfast. All my girls like to have their taste of their Mistress before she washes. You will too.”

She pulled on his leash until his head was pinned against her cunt. She wanted him closer for his tongue to be able to access both her pussy and her ass. His tongue took broad strokes, starting in her anus and lapping across her clit. His cock was desperately trying to harden again inside the plastic shell. He shed the pain, as the pleasure of licking his Mistress’s most private of places far surpassed any sensations of pain.

He licked steadily until she pushed him away and stood up, leaving the robe open to show her voluptuous body and make him ache with want again.

“I found some things and made this delicious breakfast, would you like some? Coffee, juice, a nice ham and Gruyere cheese omelet, muffins and marmalade, it was very nice.”

He watched as she scraped the remains of her meal into the scratched steel bowl and put it on the floor in front of him. He was hungry now, and with his face in the dish, trying to lick up the mixed food, she added cold coffee to it.

“I want you to think about your new role, Boxwood, after you watch me get dressed. There’s a task list for you on the fridge, and I will be calling you to check in on video. If you are very good maybe you can be released from that cage tonight. Now, what do you say?”

He looked up kneeling on his kitchen floor with food on his face.

“Thank you, Mistress Elaine.”

Chapter Five

He was kneeling on his kitchen floor, forced to think about his change in status. He had designed the kitchen renovation himself, all cherry wood cabinets, dark granite, stainless steel appliances and LED lighting, and managed the construction of every detail.

Now he was naked except for the pink panties he wore over his cock in its plastic shell, and the wide leather collar. The chain leash was looped over a coat hook on the wall. His face was coated with the breakfast he had slurped from the bowl. He could smell the last day’s festivities on his collar, still soaked with wine from the previous evening and this morning’s breakfast.

Before she left, Elaine (Mistress Elaine, she reminded him) had casually slipped off the robe to prance naked around the apartment, humming as she got ready for work. She took a shower and came into the bedroom with water dripping from her hair and rolling down over her breasts and pubic patch onto the carpeting below. He was made to lick the moisture off her body as she dried her hair. She brought her roller bag to the dining area and he had to watch as she got dressed, aching with his desire for her. She made a show of it, knowing his hardening cock was painfully restrained. Shimmying into panties and giving him a daylight look at her blond pubic patch, sliding on the stockings so he could trace the line of her supple legs, then a pair of 4″ black patent heels that complimented her “smutty business” look. She laughed at his look as she strutted topless a few steps, then leaned forward with the tantalizing globes of her breasts hanging free, pausing to let him absorb this erotic visual, and then fit them neatly into her lacy cream bra. A silk blouse where the outline of her bra and the swell of her nipples was clearly visible, then that kind of sexy executive skirt he liked with the flat front and pleats that was cut 4 inches above the knee. She slipped in her jacket and cashmere coat, then reached into the roller bag.

” Sorry Boxwood, no touching, you are a mess. I would tease you more, but I have an early partners’ conference today at the office. Hands, please.”

He knelt with hands out, as she buckled on leather cuffs then clipped his hands behind his back and attached the leash to the hook with a small lock. He was helpless now, and along with the pain of his swollen cock he really needed the bathroom.

Elaine opened his computer on the breakfast bar so that he could see himself in the video feed.

” I used your account to email your office. You are out sick today. I will have someone check on you, have a wonderful day! And may I say how pleased I am by your manly silence, this is certainly where you belong now. Bye!” She left in a rush, leaving classical music radio playing on the computer. His knees were sore now, on the hard tile floor, and he had to sit awkwardly with his hands behind his back and his head restrained by the leash.

Chapter Six

When the doorbell rang his heart was pounding. He heard the door, then the click of heels in the entrance hall reverberating off of the walls. He scrambled to kneel again but was shocked. Instead of Elaine it was another woman, an attractive 40 ish brunette carrying a Whole Foods shopping bag. She was not as tall as Elaine, with red glasses and short smooth hair, dressed for casual shopping in a coat and skirt with low heeled shoes.

“Look, I can explain, who are you, please wait…” He was red faced and fumbling for words, but she held up a hand to silence him, then put a paper on the floor in front of him as she picked up the riding crop Mistress Elaine had left there.

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