Rolewell Place Chapter One: Mommys Boudoir

 

Jamie Morgan dashed through the busy city streets, struggling to hold on to the half a dozen cups of coffee in his hands. Why had he agreed to get the coffee order for the office, again? It was the third day in the row that the young admin assistant had been picked to take the coffee run, even though it wasn’t his turn. It should have been Sheila or Derrick out here, vainly attempting to keep the hot liquid from spilling out of the plastic lid. Next time he will definitely tell the boss that someone else should get coffee. Definitely… maybe… The poor lad let out a sigh as he knew that deep down, he wouldn’t speak out. As his father had always told him, he didn’t have the balls to stand up for himself.

Jamie was so engrossed in his self-pity that he didn’t look where he was going, leading him to collide into a tall figure in shiny black.

“What is the meaning of this.” Jamie heard after falling to the ground. The voice was harsh and hinted immediately threat to his personal safety, but there was a husky charm. Somewhat dazed, he looked up to a figure that was at once but beautiful and terrifying. A tall stunning woman, with shining blonde hair, was staring down at him. Her gorgeous face, with ice cold blue eyes, looked upon with contempt and anger.

“I’m so sorry, I was rushing and I did not see where I was going.” He peeped out.

“Is that all you have to say? That’s your pitiful answer for ruining my dress?” Jamie looked away from the woman’s piercing eyes and was horrified to find that the coffee cups he was carrying had spilled onto the woman’s outfit.

“Do you have any idea how much a dress like this is worth? No of course you don’t, as if someone as uncouth as you would ever care about one’s appearance.”

The woman continued to berate Jamie, who meekly picked up the remains of his office’s coffee order. Getting back up, he got a better look at the woman and found himself drawn to his clothes. She was wearing a stylish jacket of shiny black material and a pair of expensive looking leather pants that clung to her supple well-toned body. She also had a pair of leather gloves and a pair of knee-high leather boots, with a very sharp high heel.

Jamie's cheeks reddened slightly as the woman tapped her steel stilettos impatiently.

“Are you going to gawk all day?”

“No ma’am, sorry ma’am.” Jamie looked back down, and clutching the remains of the coffee, started to walk away from the woman. If he had kept looking, he might have noticed a hint of a smile on the woman’s stern cold face. She felt pity for the poor boy, but seeing him cower so submissively made her feel other, more deviant thoughts.

“Hold it. We have something more to discuss.” She called. Jamie immediately stopped and turned around.

“These pants are very expensive, but I can tell that you will be unable to pay for the cleaning. I have an idea. What is your name?”

“Jamie, ma’am. Jamie Morgan.”

“Nice to meet you, Jamie. My name is Ms. Kensington. Now can you tell me why you blundered into me like a panicking rhino?”

“I was carrying the coffee order for my office. They don’t like it to be cold and they always want it for this coffee shop that’s five blocks away ma’am.”

“I see. Brunei’s is the store I assume?”

“Yes, that one. It’s my boss’s favourite.”

“Hmm, I know it all. As a matter of fact, I know the owner. Come along with me Jamie.”

“Excuse me, ma’am?”

“I said come along now. We need to get your coffee refilled for your office.” The strange woman then had Jamie follow her to her sports car, drove him to Brunei’s, and after quickly talking to the owner, got Jamie his entire order again free of charge. She then promptly drove him all the way back to his office.

Jamie was stunned in silence the whole time, amazed that the woman was not only doing all this

“Give me your phone, Mr. Morgan.”

He knew he shouldn’t give his phone to a complete stranger, especially one who just half an hour ago looked like they were about to rip his head off, but her authoritative manner made Jamie dutifully hand over his phone. He even made sure to unlock it first.

The woman quickly used the phone to make a call to her own phone, which she picked out of her Gucci purse.

“There now I can contact you when I have need of you.” She said, handing his phone back. “Run along Jamie, I’ll see you again soon.”

She then moved past him and continued her way, walking over to her sports car and drove off, leaving a mystified Jamie standing dumbstruck, until he remembered he had to go back to the coffee place to get another massive order.

---

A week passed and the visage of the woman in shiny black haunted Jamie. Everywhere he looked he thought he caught a glimpse of her. Walking through the street, driving past in her luxury car, even in the supermarket he found himself thinking he saw her walking past the aisles. Obviously, he knew that was impossible. A woman like her would never deign to set foot in a Woolworths or Coles. Something so mundane, so unkempt, it was beneath her. ‘beneath her like me.’ Jamie thought. He didn’t know why she wanted his phone number. What could someone like her want with a boy like him?

He got the call from Ms. Kensington as he was about to leave the office for another coffee run. He looked down at his phone and felt his heart pounding. What did she want from him? People like him were meant to be forgotten.

“Answer the bloody phone, Jamie.” His boss yelled, “and get out of here already. Don’t be late again.”

Jamie picked up the phone and answered.

“Hello, Jamie.” Came the sweet dulcet tones of Ms. Kensington. “How is my clumsy errand boy.”

“I’m… I’m good ma’am.” He stuttered. He got up to move outside while talking. “I’m actually on my way to do another coffee run.”

“Are you? You are a conscientious worker, Jamie. That coffee run should have to be put on hold for the moment. I have need of you. I am sending the address of my offices. I request that you visit me as soon as possible. I have a proposition for you.”

“Ma’am? I have work, I can’t just leave it in the middle of the day?”

“Oh, but I assure you that you can. Your bosses have no real need of you for quite some time. They have just handed busy work. I have something far more important for you. Now get yourself here, Jamie. You do not want to disobey me.”

Ms. Kensington then promptly disconnected, and Jamie received a text detailing the location of her offices in the financial district of the city.

At that moment, Jamie realised that this would be a defining choice for him. If he did indeed go to see Ms. Kensington, then he would never be allowed to come back to work. Rick, his petty tyrant of a boss, deprived of his daily cup of expensive coffee, would fire him immediately. Jamie could imagine the fat bastard giving him a cruel mocking grin as he packed up his desk.

Yet, if he did not go to Ms. Kensington, if he did not follow the white rabbit in black leather, he was certain that he would be filled with regret for the rest of his dull simple life. The tantalising, terrifying possibilities that Ms. Kensington presented were so strange and full of danger. What could someone like her have need of someone like him? All his life, people like her took no notice of him. What was different? He had to know.

As Jamie wrestled with this decision, he received another text from his boss Rick, telling him to stop being a pansy and get his fucking coffee. Half an hour later, Jamie was standing outside Ms. Kensington’s building.

It really was her building. Even without the directions, Jamie could tell that it was her building. A towering skyscraper of shiny black marble, it emanated her menacing and beguiling aura, reminding Jamie of Sauron’s tower.

He entered the building and after introducing himself to the front desk, he was promptly directed to a special elevator that would take him to Ms. Kensington’s office. Apparently, they were told to be expecting him. The elevator took him to the top floor very quickly, shooting up like a rocket.

The doors opened, revealing to Jamie a modern looking office, not that dissimilar to his own, if with better furnishing, and less fluorescent lights. He immediately noticed one key difference, it was exclusive staffed by women. Beautiful women. Exquisitely beautiful women, and each and every one of them was dressed in tight shiny clothing. Jamie resisted the urge to gawp like a fish seeking food and walked into the office. The office women paid him no mind, except for one, a cute redhead in an emerald green rubber skirt suit, who motioned him to come towards her desk. It was situated next to a pair of ornate Maplewood doors that had the gold lettering of Ms. Penelope Kensington, C.E.O.

In a chipper voice, the woman spoke “Hi there, welcome to Baroness Incorporated. You must be Jamie. Ms. Kensington will be with you shortly. Please take a seat.”

Jamie sat down on an office couch and continued to gawk at the office. All of these beautiful women, wearing these extremely sexy clothes, and they were just going about their day as if they worked in a normal office.

The red-headed secretary put a finger to her earpiece and turned to Jamie. “She’s ready for you. Please go in.”

After taking a breath, Jamie got and went to open the heavy oak doors. Inside, Ms. Kensington sat behind her desk, looking radiant in a white leather jumpsuit, awaiting him like a queen awaits her royal subjects.

“Come in Jamie. Do not be shy. You and I have much to talk about.” She spoke.

“We do? I’m sorry Ms. Kensington, but I am having trouble understanding why someone like you would require someone like me.”

“Are you so surprised, I can find need of anyone. I have a talent for seeing the potential of people. And I definitely see the potential in you. I see someone of budding greatness.”

Jamie blushed, and bashfully denied the idea that he could amount to what she was referring to.

“Are you implying that I am incorrect?” Ms. Kensington said, a slight irritation showing in her voice.

“No, no of course not,” Jamie replied. “It’s just… look at me.”

“I am looking, and I see a young boy who is being wasted getting coffee for a third-rate businessman. I can offer you a far grander purpose. You saw my secretary outside? Esme, she was once like you. A shy little boy struggling to survive in the city. Drowning in despair and self-hatred, now she shines like an emerald.”

“She does look very… wait…”

Ms. Kensington grinned, “you noticed I said, boy. Yet looking at Esme you would see nothing but female perfection. You would say the same thing about the rest of the lovely ladies of my company. And each and every one of them began their lives with boring male bodies. Some of them still keep their male forms, gross as they are, but they hide it extremely well. As for the majority of my staff, they have bloomed into beautiful women both physically and mentally.”

Jamie could not believe it. All those women out there, those visages of feminine beauty, were once men? It seemed impossible, yet looking in Ms. Kensington’s eyes, he knew that she was telling the complete truth.

“I’m sure you have many questions, and one day I might even answer them, but right now I want you to focus on one thing. I have a proposition for you Jamie, one that I suggest you consider very carefully. I want you to join my staff. I believe you can do great things here. I can offer you an excellent contract here at Baroness Incorporated, far better than your current position. Alongside a very substantive salary package, working for me includes full healthcare, room and board at our very luxurious apartment complex, and a very generous stipend for office attire.”

Jamie realised that today was going to be one shock after another as he considered Ms. Kensington’s offer. It seemed so ludicrous that it took him a while to realise the full reality of what she was offering.

“If I were to work for you, would that mean that…”

“Yes, as I wish to mean maintain a certain image with my workforce, you would have to give up your current male appearance. You have an option of temporarily hiding your male body, but I think we both know what you truly want.”

“To become a woman…” Jamie almost whispered.

“In body and soul.” Ms. Kensington stood up from her desk and walked to her bookcase. With a leather-gloved hand, she reached out for a book whose spine said “Ovid’s metamorphosis” She pulled it down, causing the bookcase to shudder, and like in a spy film, opened up to reveal a hidden room. It looked like an old-fashioned dentist office, with a big dentist chair right in the middle.

“Now Jamie, I am a very busy woman, so if you are to take my offer I suggest you take it quickly. You are not the only one in the city pointlessly holding onto a masculine façade. I can give you a new better life as your true self, I just need you to agree.”

Jamie stood still, staring at the examination chair that he knew was no normal examination chair. He knew that if he sat in that chair when he got back up, he would no longer be Jamie. At least he would no longer be the Jamie that he had presented himself as being to the entire world. The false Jamie. The male Jamie. He would be Lisa.

“How did you know?” He said softly.

“You aren’t my first darling, I tend to recognise the signs.” Ms. Kensington chuckled. “Do you have an answer for me?”

“I want this.”

“Can you say that again for me please?”

“I want this.”

“A bit louder darling.”

“I want this!”

“Once more with feeling.”

“I! Want! This!”

As if a dam had broken, Jamie strode into the foreboding room with a sense of purpose he did not have before. He sat down in the chair and eagerly awaited whatever would come.

Ms. Kensington went up beside him and said. “Now I know you are eager, but we got to keep you nice and tight so you don’t hurt yourself.”

She touched some buttons on the back of the chair and it began to vibrate. Metal clamps appeared and slammed tight over Jamie’s wrists, ankles, and neck. Breathing heavily in anxious anticipation, he watched Ms. Kensington grab a gasmask whose hose was attached to a purple tank.

“Take deep breaths darling. You are going to want to get as much of this inside you as possible.”

She latched the gasmask onto his face and Jamie, following her instructions, breathed in deep the purple gas flowing into him. The gas tickled his throat and made him cough. The coughing got harder and harder to control and his body began to spasm. Locked in the chair, his body lurched around violently. The gas was changing him, altering his body on a molecular level. His body hair fell out, leaving him with smooth slinky skin. His legs and arms thinned out, becoming sleek and toned. The fat in his gut went in, moving into his hips and butt, straining against his pants. Two fleshy mounds rapidly grew on his chest, pushing up against his shirt, causing buttons to fly off as he gained a pair of nice firm breasts. His hair grew past to his neck and gained a red tinge, as his face reformed into a sweet feminine visage.

Jamie eventually stopped spasming and Ms. Kensington removed the gas mask. She tapped the chair’s buttons again, releasing him.

“That was… exhilarating.” He spoke his voice a slightly higher-pitched version of his original voice.

“Yes, I’m sure it was. But we are not done yet. Remove the remnants of your boy clothes and get changed. Stage two requires a special suit.”

She directed Jamie to a dressing section in the room behind a privacy wall. There he found a black latex suit that was to cover his entire body up to his neck, including attached socks and gloves. Jamie removed the tarred remains of his male clothes and once he was naked, saw himself in the mirror. He was amazed at how much he had transformed.

From a distance, one would immediately think he was a woman, although up close things would get more confusing. He had a general build of a woman, though very slight. One could mistake him for either a boyish girl or a girlish boy. The bulge down between his crotch continued to confuse things. Looking at his reflection, he could no longer think of himself as a ‘he’. ‘They’ felt much more accurate.

Jamie picked up the latex bodysuit and slipped their body into the rubber. The inside was well covered in lube, meaning they were able to slide in with not too much trouble. Once it was fully on, Jamie reached behind their back and pulled the zip all the way to the top of their neck, sealing them in.

Jamie took another good look at themselves in the mirror, the rubber helped hide their bulge and emphases their curves and budding breasts. Still, they felt only halfway done. They definitely weren’t Jamie another, but they weren’t Lisa either. Who was Lisa really? Who was she going to be? More importantly, what did Ms. Kensington want Lisa to be?

Jamie walked out from the divider to Ms. Kensington, who gave an appreciative chef’s kiss. “You are on your way to becoming a fine mademoiselle, my dear.”

“Yes, but why? Why are you doing this to me? It can’t just be out of the goodwill of your heart.”

“Now you are asking questions? That’s good I suppose. Your eagerness for femininity has stopped blinding you.  You are correct, it is not out of the goodwill of my heart. I’m not even sure such a thing is possible. What I do is I find exquisite creatures like yourself, beauties trapped in dull male forms, and bring about their true feminine essence.”

“Yes, I got that from the tits on my chest. But why?”

“Because, once someone is gifted their deepest desire, they tend to become very loyal to those who did the gifting. I have an extremely dutiful workforce, supplied through this process of feminization. By granting you the opportunity to rebirth as Lisa, I will have a new member of staff who will most likely serve me well.”

“So that’s what I am? Another addition to your staff?”

“That is what you are to me. What you are to yourself is another question that I am sure you will discover once you finish your transformation. Now chop chop. Stage 2 awaits.”

Ms. Kensington led Jamie to a high-tech chamber, a four glass-walled rectangle similar to a shower, with the top and bottom outfitted with diodes and wires. Ms. Kensington handed Jamie a rubber hood and gas mask. “Put these on as well, you will need them for the procedure.”

Jamie pulled on the mask, stretching it over their head. They then strapped on the gasmask, leaving fully enclosed in rubber. Looking in the reflection of the chamber’s glass walls, all they could see was a strange rubber creature. A shiny beast showing only the idea of a human form.

“Step in the chamber darling, Lisa awaits.”

Once Jamie was inside the chamber, Ms. Kensington closed the glass door, and locked them in.

“What you are about to experience to something akin to what Mary Shelley once wrote in Frankenstein over a hundred years ago. With enough electricity, the scientist brought his creation to life. I will do the same. All you have to do is think of Lisa.”

Ms. Kensington then let out a big cackle and pulled down a giant lever attached to the chamber. The top and bottom of the chamber began to spark. The sparks became bigger and more violent, they started to zap at Jamie, whose rubber skin deflected the damage. The sparks continued, increasing in frequency. Zap, zap, zap. The rubber could only do so much, dulling the pain but not negating the impact. Each spark pushed Jamie’s body further into their transformation, slowly ridding any sign of maleness. Their hips widened, and their breasts increased in size and girth, stretching against the rubber. The zaps hit against their groin, causing them to writhe and shake in pain. The genitalia, still crudely male, recoiled from the shocks, receding deeper into the body.

The pain was excruciating, but Jamie persevered. They had to, there was no other option for them. The tantalising joy of becoming the girl they wanted to be was worth all the pain. So, they endured. They thought of Lisa, who she could be. Back in Jamie's quieter moments, the shy boy thought of a beautiful ingenue. A nice pretty girl with a smile for everyone. She would wear her cute rubber outfits for Ms. Kensington and serve her well as a sexy secretary. She would walk behind her boss with a wiggle and a charming jaunt, ready at a moment's notice to provide support, professional or otherwise. That is what she wanted, right?

Amidst the pain, Jamie contemplated, really contemplated on who Lisa was. Not on what Ms. Kensington wanted Lisa to be, not on who Jamie used to be, but on what Lisa could be. Lisa did not have to be defined as being another version of Jamie. So, who could Lisa be then? Through the foggy lens of the gasmask, Jamie looked at Ms. Kensington, who had a vicious smile on her face. The transformation process was as rapturous for her as it was painful for them. Jamie understood that life for Ms. Kensington was about taking what she desired, taking men like Jamie and remoulding them into pretty little girls. If only life was like that for Jamie. Why shouldn’t it be like that? Why shouldn’t Lisa have a life like Ms. Kensington? If anything, she deserved a life like that. She demanded a life like that.

The shocks continued, but they weren’t painful anymore. A determination had set into Jamie’s mind. They would be in command of their transformation. They would be the commander of their fate.

The changes in Jamie’s body were reaching fruition. The rubber creature in the glass chamber was ready to be born and set free. Ms. Kensington watched from outside and her gleeful smile faltered as she noticed that the transformation was going a little differently. For one thing, the yelps of pain had become yelps of joy. Another thing was that usually at this point the subject would shrink in size, but Jamie appeared to be gaining height, matching Ms. Kensington’s own. Ms. Kensington had never seen a transformation like this before, except that one time many years ago. A silent “oh my” escaped her lips.

The zaps, guided by Jamie’s now indomitable will, focused intently on their crotch. What was left of their pathetic maleness was being pushed deeper and deeper, causing Jamie to moan. The penis and testicles receded into the body, reforming into a feminine slit, finalising the transformation.

The chamber ceased its actions and the glass door opened. The black rubber figure, now 100% female, stumbled out of the chamber, heavy breathing coming through the gas mask. Ms. Kensington went to help her, but the new woman pushed her back, quickly straightening herself out. Reaching back behind her neck, she removed her gas mask and unzipped her rubber hood.

Ms. Kensington let out a gasp as she saw the new woman’s face. Long bright red hair, slightly matted and damp from the rubber hood, fell down to her back. Her face was beautiful, regal, and sultry at the same time. This wasn’t the cute girl Ms. Kensington had expected. This was a woman.

“Lisa.” Ms. Kensington spoke, the name left her lips like a soft invocation to a goddess. “How do you feel?”

“I feel…” Lisa replied, her voice a pleasant mezzo-contralto, “I feel alive, for the very first time.”

Lisa reached behind her back and unzipped herself out of the catsuit. Her smooth alabaster skin was dripping with sweat as she eased herself out. She handed it to Ms. Kensington. “I think this needs a wash, Penelope.” She said, using Ms. Kensington’s first name as if they were equals. “I think I need one as well.”

“Oh but of course. Follow me. I have my boudoir.” Penelope took Lisa to a room next to her office that functioned as a mini apartment, complete with a full bathroom and fully stocked wardrobe. Lisa gladly took the shower first, eagerly exploring her naked body under the warm water. Once clean, she dried herself off and helped herself to Penelope’s wardrobe.

“You do have a marvellous selection of clothes, Penelope.” Lisa searched through Penelope’s collection of latex and leather, silk, and satin. “Perhaps one day I might have a selection of my own.”

“Yes, perhaps you will darling,” Penelope replied, somewhat melancholic.

Lisa strode out of the wardrobe in her new outfit. A catsuit the same bright red as her hair, with buckles across the front zip, one which was now stretched up against her large breasts. On her collar, there was an added cowl that made her look like a villainess from some 50s sci-fi show.

“MMM, this feels amazing Penelope. How can I ever repay for all of this?”

“There is actually something we need to discuss Lisa,” Penelope said gravely, taking Lisa by the hand and leading her to her bed.

“I take it you understand that your transformation is not usual.”

“I suppose I do,” Lisa answered. “I was under the assumption that once transformed I would start calling you Mistress.”

“Yes well, that is usually the case. Though I prefer my girls to only do so in my boudoir. You may want something different. Allow me to explain. Most subjects are simply submissives who desire a kind of femininity that allows them to live their dream of servitude. They are transformed and become loyal slaves, partly enslaved by the intoxication of their own new femininity. You though are different. You were never truly submissive. As Jamie, you were simply being held back by wretched masculinity. Now as Lisa, you have gained a femineity that is far from submissive. Tell me, if I ordered you to get down on your hands and knees like a dog, and then lick my boots till they are clean, would you do it.”

“Of course not, I would slap you for such an insulting idea.”

“Exactly. As a woman you know your worth, and that is not as a slave, but as a Mistress.”

“A Mistress… Mistress Lisa… I like the sound of that.”

“Of course you do. I was once the same. Back when I was Gary”

Lisa’s green eyes widened.

“Oh don’t look so shocked. You are going to find that a lot of people are not who they used to be in your new life. This brings me to my next point. There are only a few people like you and I, those who were shackled by your original selves and need transformation to let their true dominant nature out. We have a calling, to lead others like my girls out there and help them blossom.”

Lisa thought about the cute Esme at the reception desk, that she was once a man until Penelope led to a new life. Lisa imagined herself doing that, shepherding weak men into feminine servitude. It created a warm suggestion in her crotch as she envisioned taking men and turning them into such devilishly adorable girls, dressed in rubber of course. They would look at her with clear devotion, and bend to her indomitable will. Oh what power she would wield, what immense power!

“Would be nice.” She spoke.

“I’m sure it would indeed. Unfortunately, a city can only handle one woman like us. Too much dominant power would wreck the ecosystem here. We would take too much, and create an empire, one that would invite challengers. Far better to rule our fiefdoms in secret.”

“Does that mean I must leave? Carve out my own fiefdom?”

“I am afraid so. You must find your own city. Find individuals like sweet Esme, and break them down into submission. Alas, I will be unable to see it. You are a beautiful creature, Lisa.”

“As are you, Penelope. I don’t have to leave right now, do I? Maybe we can simply enjoy the moment, and I can reward you.” Lisa reached out for the zip on Penelope’s white leather catsuit, gently pulling it down.

“I guess one night is alright.” Penelope agreed, glad that at least for one night, she had found an equal.

(A very late gift for https://jamies-latex-lust.tumblr.com/)