Headmistress Roberts

This story is set in Ed Miller's "Miss Sheila DeVille's School for Wayward Boys" universe, which was further expanded upon by Lurker B. in his own "Miss Deville's Academy: Lucas's Story." I thoroughly enjoyed both stories and decided to offer my own interpretation. As always, here is Ed Miller's original disclaimer.

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This is a story involving explicitly described sex. If you think you might be offended by it, or you aren't allowed by the laws of the place in which you live to read such a story, don't. If you read past this warning, any offense you take or laws you break are your problem. I've warned you.

Permission is hereby given to archive this story anywhere on the Internet, so long as the author is credited, it is reproduced in its entirety (including this disclaimer!) and no fee is charged to access it.

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Miss Deville's School - Headmistress Roberts

Chapter 1

Of course, by the time the final bell rang she was as relieved as herstudents to start the weekend.

As the bell's remnants echoed through the halls, Headmistress Roberts gave a long final yawn at her desk and checked her watch. 3:00 p.m. on the dot. She smiled to herself. She loves when her school is run efficiently.

Standing up and buttoning her jacket, she looked around her office and took inventory of what final work there was to be done before she could return home after her long day. The meeting with the Pep squad? Finished. The budget proposal meeting with all the department heads? Pushed until Monday. Interview for the school paper? Finished (luckily for Miss Roberts, who otherwise might have had to come in to do the interview Sunday morning.)

Perfect, she assured herself, that will give me more time with Scott.

The reminder brought a smirk to her face. Scott had been showing much promise as of late. Their one-on-one 'mentoring' sessions had been getting progressively more... successful, and the Headmistress had been very pleased with his recent performance. While momentarily lost in her thoughts, Miss Roberts' hand slowly began to creep off of her desk, eventually finding it's way into her lap hidden below the mighty, finished oak and slowly began caressing that which it had found.

The sound of doors swinging open and her students filing into the hallways to begin their weekends jogged Mistress Roberts out of her daze, returning her thoughts to the task at hand. She plopped her briefcase on her desk and opened it while continuing her mental checklist. Mail? Already retrieved, read and properly dealt with. Staff checks? Issued presumably, although to be sure, best confirm with Hilda. Perfect.

"Then that leaves only..."

Her eyes hone onto the one last item of business for the week, a sealed white envelope sitting atop her desk papers bearing nothing more than the name of it's intended recipient, "Coach Camella." Putting the letter aside Headmistress Roberts proceeded to quickly file all other loose documents away into her briefcase, taking care not to misfile a single paper. The bun on the back of her head bobbed and swung as she finished clearing her desk. Grabbing her briefcase and smoothing her skirt, she stood up and walked around her desk, dragging her finger along the edge of the paddle proudly displayed on her desk's edge, smooth and thick in all it's glory. Pocketing the letter, she opened the door and looked back upon her office for a final survey, and with a sigh of satisfaction flipped the light off and shut the door.

Pulling the key from her locked door and turning around, she discovered a student, waiting in her leather waiting chair, head down in shame. Her secretary began to explain.

"It's Timmy again," began Hilda. "He began acting up during last period and just arrived here moments ago."

Timmy briefly looked up and caught The Headmistress' eye, which at the time was looking down at him with a combination of disappointment and authority. His gaze quickly returned to the floor. Miss Roberts checked her watch impatiently and sternly replied.

"I haven't the time for this. Tell Timothy here that it is his lucky day, that he is free to go enjoy his weekend."

Sporting an immediate smile Timmy jumped up, pleasantly surprised by his good fortune. He turned to leave but was grabbed by the arm and spun back around by his dominant Headmistress,

"HOWEVER, don't think for a second that you are off the hook. I expect to see you first thing Monday morning in my office for a meeting. Is that clear?"

"Ye...yes Ma'am." A frightened Timmy stuttered. After a few seconds frozen terror, Miss Roberts excused him and he scuttled off in a hurry, already dreading his upcoming "meeting."

After the door closed behind him, the two women looked at each other and after a pregnant silence burst into laughter. Their monstrous melons shook mightily as they laughed up a storm, prompting a few passing students to stop and ogle them through the office door's window, amazed at the voluptuousness that can be possessed by only two women. Sending a glance their way, the boys scattered, trying casually not to meet the eye of their Headmistress.

"They never learn do they?" Hilda choked out, as their laughter finally succeeded.

Miss Roberts shook her head in amusement. "Of course if they could learn on their own, we would all be out of jobs, wouldn't we?"

Hilda giggled as Miss Roberts placed the letter on Hilda's desk. "Did the employee checks go out on time?"

"Of course Ma'am."

"Just what I like to hear. Now please make sure this letter gets to The Coach will you Hilda? Before she leaves for the day to be safe."

Hilda picked up the letter and looked it over.

"Of course. I will deliver it to her immediately."

Miss Roberts flashed Hilda a goodbye smile and began to walk towards the door, waving over her shoulder without turning her head.

"Have a splendid weekend Hilda."

"I know you will Ma'am."

Miss Roberts stopped with her hand on the door and turned. The light shone off her midnight black, pulled back hair, highlighting her aura of dominance. Her plump deep red lips parted into a smile.

"So you've heard, have you?"

Hilda smirked slyly back.

"The professors have been talking, things get around. All I have to say is congratulations. He seems like a good fit."

Miss Roberts returned her friend's smirk.

"Let's hope so."

Chapter 2

Miss Roberts enjoyed taking the scenic route back to her mansion on the edge of campus. It took her through the center green, where students studied under the sun and basked next to the fountain. It took her past the fields, where the football and baseball players began to warm up for practice, stretching their muscles and doing exercises in the heat, MDA displayed across their uniforms. Her ample breasts pressed against her business jacket and her glamorous features distracted most of the boys she passed, and she was content knowing that as she passed the boys their stares moved south onto her toned, muscular ass. The trees, the fresh air, the sun. The smell of fresh cut grass. They gave her a moment to observe and reflect.

Miss Roberts was pleased that she could provide such excellence to boys who otherwise would have ended up in jail...or worse. Seeing the bustling campus life brought joy to her eyes and reminded her how far these boys had come and why she loved her high-demand, difficult job. It also reminded her of how she has been able to accomplish so much and build such a supportive community of young men. It reminded her that everything she has (and has built) is a direct result of her fierce attitude.

She had always been a woman of accomplishment. Straight A's throughout elementary, middle, and high school, not to mention her swimming championships. After finally graduating from an Ivy League college Suma Cum laude, (and subsequently being inundated with lucrative job offers) she received a letter, telling how her accomplishments had caught the attention of the soon to retire Headmistress of a school called 'Miss DeVille's Academy for Wayward Boys' who wanted to meet with her. Needless to say, Andrea Roberts was thrilled. Finally, a job that gave back to the community. A job where she could do some real good, and would be given the tools to be a great leader.

While her maternal side relished the opportunity to give troubled boys a new chance at life, her dominant side also relished the respect. And the power. She had always felt that due to her ultra-feminine looks, her assertive attitude came across as 'bitchy' in many circles, while her intelligence came across as being a 'know-it-all.' She never saw men face such troubles. But finally she found a job where those qualities aren't only useful, but necessary to be successful.

Her biggest moment of pride came on the retirement day of the previous Headmistress, when she was ceremoniously handed down the paddle that now sits displayed on the front of her desk. This was accompanied by a banquet in her honor and a one-on-one meeting in the office of the (exiting) Headmistress, who gave a final rundown of the job. It was a very distinct memory.

Chapter 3

"The job is hard, the job can be downright frustrating at times," the Headmistress Sonja Dawson began, her silver hair and dignified wrinkles demonstrating she has the wisdom and experience to back up her words. "But you will have the tools you need to be great."

Mistress Dawson reached in the lower drawer of her desk and began fishing around. A young Andrea Roberts waited patiently in the chair across the desk, with a burning wondering of what she is in for.

"As has already been demonstrated for you, the paddle is for disciplinary action." With eyes that never faltered from Miss Roberts' own, Miss Dawson put an unseen object in her lap. "And as you know, it is the major factor for MDA's unrivaled success."

The woman paused, gauging Miss Roberts' reaction. She continued.

"However, there are special cases that require special attention. Which is why you will need this." With that, Miss Dawson dropped a foot-long strap-on dildo loudly onto the oak desk. Miss Roberts looked puzzled.

"Ma'am, I don't understand..." began Miss Roberts.

"Nothing to understand, my girl." Interrupted the Headmistress. "Simply put it on."

Hesitantly, Miss Roberts reached out and grasped the monster. It wobbled as she examined it's smooth perfection. It was the most life-like dildo she had ever seen, thick as a summer sausage with a mushroom tip head that demanded respect. It had no scrotum, but still managed to emit an aura of power and dominance. It seemingly glowed in her hand, though she felt sure that it was just the lighting of the office. Miss Roberts stood up and pushed her chair back, creating room for her to strip. She reached behind her back and unzipped her black formal dress, letting her pristine boobs push the dress off of her, and watching it fall to the floor. Her matching bra and panties were white lace, which showed off her soft, feminine curves and her powerful hips with stunning results. She hooked her thumbs inside her panties cautiously and gave a look at Mistress Dawson, asking for confirmation. The Mistress Dawson nodded and Miss Roberts continued, letting her panties fall to the floor.

Her pussy was completely hairless. It glistened under the lights of the office, with her cute clit just barely poking out from beneath it's hood and her lips at full display. Even the Headmistress, with all her years of experience, was stunned by the sight of the naked angel in her office. Very warily, Miss Roberts proceeded place the strap-on on the floor and step between the leg harnesses. Pulling it up to her groin, she bucked everything in place and waited. And nothing happened. At first.

Suddenly the leather buckles which previously dug uncomfortably into her legs and ass became completely painless, which was followed by an intense warm sensation coming from her pelvis. Miss Roberts watched in awe as the straps melted into her skin, melting and melding until all trace of them was gone. The dildo remained, now being held up with no device or harness. The base of the monster schlong slowly attached itself to her pelvis, morphing the surrounding skin into a bubbling, putty-like substance. The bubbling continued as Miss Roberts felt her internal reproductive organs being changed and rearranged. Her eyes widened in disbelief. She felt her two ovaries slide down the inside her of body, sliding until they pushed their way out the base of her pelvis, stretching the skin as they continued to fall, until they formed a perfect, juicy scrotum. As the bubbling subsided and the transformation came to completion, Miss Roberts continued to stare downwards, eyes locked onto her lower parts.

The cock was now part of her, and she was now hung like a horse. She turned and look at herself in the office mirror, marveling at how her new hairless meat pole hung down to her mid-thigh. She grabbed her cock by the base. Completely real; organic. Her balls were no joke either, each bigger than a golf ball, and swaying, hanging like a pair of juicy apples.

She turned to Miss Dawson, mouth still open in shock.

"This is your tool. This will make you the undisputed Alpha at this academy. Combined with your intellect and unending determination, a cock as dominant and potent as yours insures that you will be a great and powerful Headmistress."

Miss Roberts tried to speak, but couldn't. A mix of gratitude and astonishment bubbled up from her stomach left her speechless. The Headmistress recognized this and gave her a piece of advice she surely needed.

"Sit here, in the Headmistress' chair."

Miss Dawson gracefully got up, her flowing, silver dress creating waves as she moved. She floated around the desk and moved over to the door, retrieving her long raincoat off the coat rack and donning it. Miss Roberts meanwhile walked around the desk and eased into the large leather chair. Suddenly a wave of satisfaction came over her and it all felt right. She was now the Headmistress. She gazed down at her erect cock, standing at full mast with her testicles resting on the leather, and reveled in her newfound sense of authority. The ex-Headmistress smiled and began to silently exit, leaving the Mistress Roberts to her responsibilities. Just before she took her final step out of the office she paused and turned to her successor for a final thought.

"If you're lucky, during your time here you'll find an assistant in one of your students. Someone who will be loyal and willing, and will be a great servant and mentee. Under the school law, the Headmistress may find one student to become what is known here as her "Wife," but let it be known, most Headmistresses never find anyone worthy of the position. My final advice to you is this...if you ever have the opportunity to take on a wife during your time here, do it. The advantages of having one are many and the opportunity of finding a worthy wife is hard to come by."

Sonja Dawson stepped out and closed the door of her office for the last time, leaving Headmistress Roberts to ponder the advice she had just been given.

Chapter 4

Headmistress Roberts opened the door to her mansion (paid for by the academy of course) and entered. The entrance room was massive, with two extravagant staircases along each side of the circular walls which wound up to a loft leading to the rest of the second floor. The entire gound floor was white and black marble, sporting intricate designs that wove across the house. The high ceiling and chandelier gave the room the feel of an old ballroom from the 1940's. Golden railing adorned the steps all the way down, and vases with flowers freshly picked peppered the place and gave it a heavenly smell. The giant glass windows surrounding the huge wooden double-doors were amazing and intricate, creating colorful spirals of light on the wall when the sun shone through the glass.

Mistress Roberts had only just closed the front door, set down her briefcase and removed her business heels when she heard the distinct clack-clacking of high heels as they made their way from a satellite part of the house, down a corridor to the front room. She knew it was Scott.

From out of the hallway the 2nd floor loft came a girl of awe inspiring fertile and feminine proportions. She was short, about 5'2" and very curvy. Today (per Mistress Roberts' instructions) she was adorned in a French maid's outfit, complete with low cut dress and a skirt that could hardly be qualified as such. Her round, soft, feminine face was stunning, with a delicate nose, pouty red lips and light blue eyes that emanated innocence. Long blonde hair fell down in golden locks onto her shoulders, giving her a coy look. Her slender, porcelain neck gave way to her exquisitely huge chest which surpassed Mistress Roberts' own G- cup melons to fill even a J-cup bra to bursting. Her impeccable gazongas were practically popping out of the top of her outfit, yet her most revered blessing was her ass. She had a slim waist attached to hips that could stop traffic. Her round, firm buttocks look straight from of a music video and jiggled whenever she took a step. Her epic donk was currently hanging out from her skirt, only concealed by a pair of small, frilly white panties running up her crack, hardly containing her double- scoop ass. She clacked as fast as she could over to her husband, placing her feather duster on a table as she passed by.

"Good afternoon, Mistress Roberts." Cooed Scott as he gave a polite curtsy.

Mistress Roberts smirked. She had trained him well. When he was first sent to her office, she thought him for a troublemaker. He was stubborn, unwilling to listen, and very sharp-tongued. But he always aced his tests, whether he studied or not. He was clearly a very bright boy. But bright boys are a dime in a dozen, while wives are not. After spending some time with him talking in her office she realized his potential. Though there was one test he still had to pass. When their conversation concluded, Mistress Roberts commanded him to strip and bend over her desk. Grabbing her 'special paddle' from its display, she gave him a firm slap across his cute teenage buns.

He immediately transformed into the most beautiful girl Mistress Roberts had ever seen. Although he was a full 18 years old, he had the appearance of a wide-eyed innocent 16 year-old. Mistress Roberts was stunned. She had never seen such beauty and hopeful innocence before. She eventually sent him back to class without further punishment, sending a memo to all teachers that no boy was to touch Scott in any way. Word quickly got around school that he was now the Headmistress' property, and that no boy should as much as look down his dress.

Before long Scott was ordered to the Headmistress' office every morning for one-on-one tutoring. Every day he was bent over by Mistress and transformed into a fertile young thing. He was subsequently paddled so frequently that his body permanently adopted his new female form, as well as a naturally submissive mindset. The two quickly grew a bond and after a few weeks, Mistress used the School Constitution's 'Wife Clause' to choose Scott as her wife. He was moved out of the dorms and into the Headmistress' Mansion permanently, where he was to take classes separate from the rest of the student body. Classes on cooking, beauty and exercise (as any other subjects she wished him to learn) would keep him busy and sexy for his husband.

"Good afternoon baby," smiled Mistress Roberts, as she put an arm around Scott's delicate waist, dipped him back and kissed him. His lips tasted of the cherry lip gloss she instructed him to wear. Good boy.

She put him on his feet and he blushed and giggled. Without a word he helped Mistress remove her coat, and put all of his husband's things away (shoes, coat and briefcase.) Minutes later his husband was sitting in a comfortable recliner in front a large fireplace sipping a rum and Coke Scott prepared for her and giving Scott a rundown of her day while he gave her an expert foot massage.