Jennifer's Road to Submission

Warning: This story is a 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.

This is a prequel to the Mistress Elaine series. It chronicles how Jennifer met and became submissive to Mistress Elaine.

Mistress Elaine - late 40'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 - late 30's, married and has latent desires for women that she has suppressed. Short dark hair, glasses, full figured, but not heavy, with a short temper.

Laney - All-American girl, blond, attractive, tall and lean whose innocent appearance conceals a very dark side that Mistress Elaine has learned to exploit.

Chapter One

Mike DiPietro was driving his wife to the mall in their sensible sedan on a nondescript expanse of New Jersey freeway, and with the drone of the Mets game on the radio and the blandness of the passing landscape Jennifer DiPietro's mind was encouraged to wander elsewhere. She enjoyed the monthly visits to the upscale Mall at Short Hills but instead of focusing on what she was interested in buying she started thinking about her body, other women's bodies, changing clothes, the feel of clothing and the secret stories she had read about women in dressing room adventures with one another. She enjoyed the guilty pleasure of these salacious thoughts, but with a pang of her Catholic ingrained morality, pushed those thoughts away as not being at all appropriate for a married suburban woman in her late 30's.

Mike predictably played the role of the unhappy spouse. He was making his usual noises about how shopping was mind numbing and Jennifer made her usual suggestion that Mike visit the Godiva store and pick up chocolates and then park at Starbucks until she was done. The suggestion was gladly accepted. Jennifer knew that Mike was good for at least an hour, with the chocolates, the coffee, and the Mets game that he could stream on his phone.

Jennifer was still working part-time at an insurance agency and wanted more clothes that were business appropriate but could be used for nicer personal events. She knifed into Nordstrom's, weaving her way through the cosmetic aisles to the women's specialty clothing departments in the back. She made sure she wore her best set of heels, a pair of DKNY black platform pumps, to try on with her new outfits. Jennifer loved these pumps because their ultra-high heels best flattered her calves and the lines of her legs and also enhanced her relatively short 5'3" stature.

Jennifer took a left through the lingerie department, glancing as usual at the elegant pieces which would never fit her. Even the bland mannequins looked sexy in their cream colored embroidered delicate and lacey bras and sheer lace teddies, tiny bits of fabric skimming over slender bodies. She had always been the much curvier type, needing supportive constructed bras and well cut panties, not lacy thongs. She loved sexy details and colorful matched sets, but Mike managed to ignore whatever she wore so the lingerie was for her pleasure alone.

As she wandered around the racks of dresses she found a number of dresses in her size 12 that were of interest. She flipped through the dresses and selected three that she took a liking to and laid them flat on a nearby counter. She continued to shop, looking at silk blouses that might go with her skirts.

While she was looking at silk blouses a well-dressed, well-coiffed woman in her late 40's fingered the blouses as well and said "I think the Dolce & Gabbana pencil skirt would flatter your figure the best."

Jennifer was somewhat startled by the unsolicited opinion. "Excuse me?"

The woman repeated her recommendation.

Jennifer stepped over to the skirts and the woman followed. "Why the Dolce & Gabbana?" she asked.

"You're a beautiful full figured woman and the shape of the skirt will flatter your curves. That's what you were looking for, wasn't it?"

Jennifer, always quick on the draw, was not in this instance as she was taken aback by the woman's bluntness, her flattery and her Grace Kelly good looks. "Uh . . . yes. Of course."

"You should try it on with a cream colored silk blouse. It will look great with your pumps."

"Yes . . . Yes . . . I think I'll do that."

Jennifer perused through the rack with the silk blouses, picking one, and with the skirt in hand went to the changing rooms. She put on the outfit in the changing room and looked at herself in the three panel full length mirror and then turned around and looked over her shoulder at the back. The woman was absolutely right. The outfit looked fabulous on her. Jennifer sat on the dressing room bench in her new outfit and reflected on her unexpected encounter. The woman was exactly the kind of woman she envisioned in her fantasy of an illicit dressing room rendezvous - - well-dressed, assertive and insanely attractive. Her mind again wandered off to the possibilities her tryst with the woman would present, only to be snapped to reality by the realization that Mike's one hour timer was halfway done.

Jennifer went out of the changing area to find the woman to confirm her recommendation and to gaze upon her one more time. She wasn't in plain view among the sea of clothes. Disappointed, Jennifer then sought a salesperson to let her back into the locked changing room. As she was walking to the checkout desk she saw the woman, now flipping through leather jackets. The woman turned her head and her eyes lit up when she saw Jennifer in her new outfit.

"My, my, the outfit looks even better than I expected."

Jennifer nodded in agreement. "You were right. This outfit is a winner."

The woman approached Jennifer with her right hand extended. Jennifer noted that the woman clearly had money, as she was wearing a designer outfit and a very expensive set of heels. She was an attractive woman sporting a beautiful diamond and sapphire necklace and diamond stud earrings that looked to be at least 2 carats each. However she was not wearing a wedding ring. She had long strawberry blond hair and was a bit taller than Jennifer.

Jennifer shook her hand. "Jennifer DiPietro."

"Elaine Harris."

As they shook hands, Jennifer flushed as Elaine held the contact a bit longer than appropriate and raked her over with her piercing blue eyes, like the men she usually tried to avoid. Elaine's eyes lingered on her mouth and breasts and then slowly appraised her hips and legs, making Jennifer feel transparent. She felt herself beginning to respond to her feelings about other women but pushed it away.

After the awkward handshake they exchanged pleasantries and then business cards. Elaine's card said "Engineering Consultant" with a New York City address. Jennifer's card had her insurance agency on it with her Parsippany address.

"Maybe sometime we'll get together for coffee," said Elaine as she pivoted to continue her shopping. Jennifer tucked Elaine's card in her purse, soon to be forgotten.

Jennifer retrieved Mike from Starbucks. She attempted to show Mike her new purchases but his astounding level of indifference made Jennifer think better of it so she left her shopping bags unopened and carried them to the car.

About three weeks later, on a Monday, Jennifer was at her desk in the insurance agency office when Elaine walked in. It took Jennifer a moment to make the connection, but a stunning strawberry blond with impeccable fashion sense was not easily forgotten.

"Elaine, is it?" she cried from her desk. Jennifer felt the same feelings of want as a high school crush.

"Oh, Jennifer, good to see you."

Elaine approached her desk, and Jennifer felt her prolonged gaze again - - standing and looking down into her blouse, seeing that hint of her lace bra, assessing the shape and fullness of her breasts before sitting down. She wished she had worn something not so tight, or more flattering, but at the same time she felt her body respond to a woman's interest.

"Jennifer, I just bought a summer house and I need to insure it before I close escrow. I happened to run across your card and thought maybe your agency could help me." All of what she said was true, although what wasn't said was that Elaine was very attracted to Jennifer's curvy body and wanted to see her again. Elaine saw Jennifer's wedding band and viewed it not as a deterrent but simply another obstacle to overcome. Jennifer suspected Elaine was pursuing her and had already decided to assign the interior inspection to herself to satisfy her curiosity.

They made an appointment for the following Friday for the exterior to be photographed and measured and for Saturday for the interior of Elaine's house to be inspected and measured. Then Jennifer could supply a competitive quote. Elaine did not have to be home for the exterior inspection but did for the interior inspection.

The week flew by. Elaine always looked forward to Fridays. She was able to escape the constant drone of noise and the crowds in New York City for the peaceful Connecticut countryside. Driving out to the country house, Elaine luxuriated in the feeling of the powerful burgundy Range Rover and the excitement of another new conquest. She enjoyed playtime with her stable of subs and the thrill of controlling them, but what was most exciting for her was the first seduction, seeing the woman or man lose control and go outside the narrowly painted lines of their vanilla lives. She thought again about Deb and the college experience that showed her the way to this role.

Elaine had always been described as a leader or as bossy, depending on whether someone liked her or not. In her relationships, first with men and later mostly with women, she had always taken the lead to get what she wanted. One summer semester, living in a small house off campus, her roommate was Deb, a brunette California girl. A hot night following an even hotter day and two bottles of cheap wine, and Deb was making a bet on a silly board game they were playing. "If you win, Elaine, I'll be your slave for a week. If you lose, you have to clean the apartment for a month." It was such a random offer that Elaine didn't think much about it until Deb lost the game on purpose and was smiling. "OK, you win the bet, I'm yours now; what do you want me to do?"

It seemed like a joke, so Elaine started small: kneel, kiss my feet, rub my back, make me tea. With each step though, she saw that Deb wanted more, and needed more to complete her submission. So Elaine upped the ante to see what would happen: take off your shirt and bra, dance to amuse me, strip to your panties, make yourself cum, eat my pussy. Deb's excitement made her excited, and by the end of the week she was amused to be totally controlling Deb, deciding her clothing, meals, and bathroom privileges, keeping her naked and chained inside the apartment, and finally inviting Deb's former boyfriend and his new girlfriend over to see her humiliation and for the three of them to use Deb and each other sexually. It was Elaine's first sexual experiences with women and she found it to be more gratifying than her experiences with men.

Then the week was over and they went back to normal life for a while then split up, but the sense of combined power and sexual thrill stayed in Elaine's mind, and she sought the look she had seen then in Deb's eyes - - the going over the edge and accepting the power of submission.

Elaine's pleasant thoughts of her college days was interrupted when she rolled up to the house. She was glad to see she was the first to arrive and was hopeful that Jennifer would handle the inspection herself.

Jennifer was listening to her phone, trying to find the country house in her practical and slightly beat up Mazda sedan. "In 500 feet, turn right on West Mill Road. Your destination is on the right."

She was nervous and excited, running a few minutes late and thinking about seeing Elaine again. She remembered the look, as Elaine told her what outfit to buy, and the way she felt in the blouse, skirt and high heels. That's what she was wearing now, though not very practical for a property survey meeting, but very practical for showing Elaine that she was interested in her.

When she thought about Elaine, Jennifer's mind jumped to the look of her body, and to those few fumbling moments between girls at boarding school, and then her fantasies about being seduced and dominated by a beautiful woman. She and Mike had been married a long time, and things had settled into a mind numbing dullness. A long time ago he had shrugged off her cautious suggestions to spice things up and now he was a pretty basic guy - some non-functional gift lingerie for her on Valentine's Day and the possibility of an infrequent blow job for him. He didn't know and didn't appear to be interested in where the darker part of her mind was, imagining herself whipped and then taken in the shower, or being tied to the bed and then forced to do unmentionable sex acts with her captors. She had read the erotic classics a long time ago and in her mind she was always that girl forced to kneel and submit or straining against her bonds as her punishment was administered.

She snapped back to reality and took a deep breath. The house was a nicely restored Victorian, painted creamy yellow with gray trim, and a large porch with white Adirondack chairs, one occupied now by Elaine. Jennifer organized her professional smile, grabbed her purse, clipboard and tape measure, and climbed out of the car.

"Elaine," she shouted as she waved from the gravel driveway.

Elaine was pleased to see that Jennifer had decided to handle the interior inspection herself. She knew that she should trust her instincts because her instincts told her that Jennifer had every intention of exploring where this relationship was going to take her. Elaine also smiled when she saw that Jennifer was wearing the same outfit she tried on at Nordstrom's, down to the impractical high heels. Where Elaine was taller and more angular, Jennifer was curvy in all the right places.

"Welcome to Connecticut, Jennifer. I'm so pleased that you elected to handle the inspection yourself."

"I wouldn't have dreamed of asking someone else."

"Shall we go inside?" said Elaine as she opened the screen door.

They walked into the spacious cottage. Jennifer started with the entryway and then living room, measuring each room and taking copious notes. Occasionally she would snap a picture on her phone, but the whole time sneaking furtive glances at Elaine and sensing her seductive demeanor.

They finally came to a room with a locked door.

"What's here?" Jennifer asked innocently.

"It's a small playroom."

"Oh. I didn't know you had children."

"I don't. It's not that kind of playroom."

There was a long pause as Jennifer processed that last answer. She was unsure what Elaine was saying. "Well, if you want me to include it in the contents calculation I'll need to take a look."

"Very well," said Elaine as she went to the kitchen to retrieve the key. She unlocked the door, opened it and turned on the lights.

In front of Jennifer was a floor covered by industrial grade carpeting, a plain wooden bench, a wooden highback ladder chair, some rings attached to the walls and ceiling, and a large armoire.

"Oh, this is an unusual workout room," noted Jennifer.

Elaine walked to the armoire and swung open the doors. There were a number of whips, cuffs, and ropes suspended from hooks installed on the back wall of the armoire.

"Ohhhhh," mumbled Jennifer.

There was an awkward silence as Jennifer stared at the contents of the armoire and her mind registered what the "playroom" was all about. Her secret fantasies all bubbled up to the surface of her mind. She felt lightheaded, as if she was about to faint.

Elaine stood immediately behind Jennifer. She cupped her hand and lifted Jennifer's skirt, resting her hand on Jennifer's damp panties.

"You didn't need to come out yourself to measure my place, did you?"

Jennifer sucked in her breath but didn't move to stop Elaine. She felt as she was incapable of movement. "No," she whispered. Jennifer now knew that all pretenses had evaporated and that her outfit had clearly signaled her intention to Elaine that she was prepared to be seduced.

"You could have used an outside contractor to do it, couldn't you?"

"Yes."

"You wanted to see me again, didn't you?"

"Yes."

"And you wore the outfit I picked out for you so you would look sexy for me, didn't you?"

"Yes."

Elaine put her other arm around Jennifer's midsection so her breasts were resting on Elaine's arm. "Tell me why you wanted to see me again."

"Because . . . because I've never known anyone like you. I've never been attracted to women but I'm attracted to you." Jennifer paused before continuing. "You're glamorous, beautiful, cold, distant and controlling. I find that to be an irresistible combination."

Elaine smiled when hearing Jennifer's accurate assessment.

Elaine started rubbing Jennifer's pussy through her panties. A gasp escaped from Jennifer's lips.

Elaine whispered in Jennifer's ear so she could feel Elaine's hot breath on her neck. "And you find me sexy, don't you? As sexy as I find you."

"More so. You're the sexiest woman I've ever met."

"Take your panties off and give them to me."

Jennifer hesitated for just a moment. Elaine withdrew her hand and Jennifer used both of her hands to pull her panties down to her ankles. Then she bent over to slip her shoes though the panties. She stood up and handed the panties to Elaine. They were now facing each other.

Elaine took the panties and held them between the two of them.

Elaine stated the obvious. "Wet."

"Very."

"Do you like having me tell you what to do?"

"Yes."

"Why?"

"Because I want to please you."

"Why do you want to please me?"

"Because I want you to want me."

"That's very good. You're right. When you do what I want, it makes me want you more. Now take off your blouse and bra and drape them over the chair. Then stand in front of me with your hands behind your head."

Jennifer carefully unbuttoned her blouse, draped it over the chair, then leaned forward and unhooked her bra in the back and slid the straps off her shoulders. Her breasts bounced free. Elaine drank in her first look at Jennifer's full luscious breasts. Jennifer stood in front of Elaine and put her arms behind her head. The combination of her hands behind her head and her ultra-high heels made her large breasts jut out even further than usual. It was too much of an erotic vision for Elaine; a person who prided herself on her self-control. Elaine pushed her head forward between Jennifer's breasts, feeling her cheeks rubbing against the soft skin of Jennifer's breasts. She then slid her head to the left to take Jennifer's erect nipple into her mouth. She began sucking and nibbling on Jennifer's nipple in earnest.

"Oh God, Elaine. This is divine." Jennifer felt her knees weaken and had to struggle on her heels to stay standing.

Elaine straightened up, letting go of the nipple and watching Jennifer's breast bounce once released.

"I couldn't help myself my pet. I've been dreaming about your soft creamy white breasts from the moment I saw you."

"I've never been with a woman before."