Ultra-Strict Discipline for Jimmy

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Extreme regimentation and control for Jim.
4.8k words
4.09
23.4k
8

Part 1 of the 2 part series

Updated 06/10/2023
Created 07/18/2020
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Ultra-Strict Discipline for Jimmy

Part 1

She'd warned me repeatedly and I knew the rules by heart. While I lived in her house, a sprawling secluded mansion some ten miles from the nearest town, I was to remain chaste and be 100% obedient to her every command. That meant no playing with myself ever.

Ms. Valerie Severe, or Madame, is very strict with me and simply does not tolerate my masturbating. A magnificent statuesque auburn hair lady in her early fifties, she has piercing green eyes, a will of iron and stands an inch taller than me. She meets my sexual needs on her terms, if I am good, under her close supervision.

Unfortunately for me, she usually finds fault with my behavior which means that I often go denied for weeks at a time. But I still have to service her daily giving her lengthy massage sessions, tender caresses, and must lick her magnificent womanhood until she climaxes at least once.

She's auburn down there too. The only time that I am permitted to be erect in her presence is when I am servicing her, but god forbid that I should ever cum without her explicit instruction. On a very rare occasion, if I have been especially good, she allows me to make love to her.

Chastity devices are absent in Madame's household. She prefers that I suffer through the honor code and is happy to reinforce the rules with plenty of bare bottom spankings and other "maintenance" punishments.

She discovered early on in our relationship that I was a natural submissive who yearned to be under her command. Dominant that she is, she jumped at the opportunity to mold me into her perfect toy.

Dressed in a skin tight white t-shirt cut just above the navel and very short thin latex shorts that fit me like a glove and leave nothing to the imagination, I have become her thirty year old boy toy.

A thick seam up the back of these shorts digs deep into my bottom and always offers a tempting target. They come in two colors depending on Madame's mood: baby blue or bright pink. Any lewd thoughts that I might entertain are easily detectable in these shorts and invariably earns me a spanking.

I always blush crimson whenever any of the household staff see me dressed in this humiliating uniform. They are a married Indian couple who carry out all of Madame's wishes eagerly and without question. I am most definitely the low man on this totem pole, however, and must be obedient and follow their instructions to the letter.

Ms. Vandana, a petit buxom brunette only a few years older than me always dressed in a tight short maid´s outfit, who doubles as a maid and cook, is often seen exiting Madame's bedroom in the middle of the night with very little on. She loves her husband Raj very much, yet I have often heard her complain to Madame that he is far too big for her and that it is very hard for her to comply with all his sexual desires.

Mr. Raj is a giant of a man in his early forties. Strong and muscular, he is a good eight inches taller than me and at least eighty pounds heavier. He maintains the extensive grounds around the mansion and I assist him with the gardening and the mowing. From time to time he also acts as the household driver.

Mr. Raj is a very demanding task master and he is very strict with me. He never misses an opportunity to swat my bottom to improve my efforts or to give me a sound bare bottom spanking for any serious failings on my part, whether real or imagined. This is very much encouraged by Madame.

Recently, whenever we are alone, he has also begun to greet me in a powerful embrace pinning my arms at my sides while he squeezes my ass and kisses me deeply. He knows I am not allowed to get an erection without Madame's permission, but Mr. Raj has no such restrictions and embracing me I can feel his monstrous cock rise through his light cotton dhoti pants.

Ms. Vandana and Mr. Raj supervise me whenever Madame has to go on a business trip. As soon as Madame leaves, the mood in the house turns festive for them, but not for me as I am usually sent to bed early for some trumped up charge which I am never allowed to contest and which earns me another bare bottom spanking. Woe betide me if I complain or make any noises in my room as Mr. Raj will come right back in and give me another dose, as many as needed to quiet me down.

During the day when Madame is away, I get to do all of Ms. Vandana's chores as well as Mr. Raj's under their watchful eyes with plenty of swats to encourage my efforts. For them it is a day off and for me it is a heavy day of work.

So while I am most definitely sexually denied, exploited and even treated with a degree of cruelty, I am nearly always on a sexual high in Madame's household which only gets magnified with my chastity and sexual denial. Servicing Madame intimately, the constant fondling and deep French kisses from Mr. Raj, even the spankings, ensure that I remain in a very agitated and sexually charged state of mind.

For better or worse, I am the center of attention in this household and I never feel that the severity of my station isn't worth it. Besides, Ms. Valerie Severe is a very wealthy lady, and in addition to the free room and board, she has promised me a sizeable bonus when I leave her household. Ms. Vandana and Mr. Raj have similar financial inducements, as well as the sexual bonuses that come from sharing her bedroom every so often.

Madame enforces an open door bathroom policy for me because she believes that I might be tempted to relieve my sexual control and frustration with a quick hand job in a locked room. She often walks straight into the john when I am doing my business. This practice led to a significant turning point in our relationship.

It had been three weeks since I had been allowed to cum and in my very randy and blue balled frame of mind the simple act of showering on one late Friday morning, lathering and rinsing off the soap, had me rock hard and erect. I wasn't playing with myself, but since I had not released in weeks, any stimulus, no matter how small or innocent, got me going.

Unfortunately for me, that's when Madame decided to enter the bathroom unannounced and stared in shock at my erection through the glass encased shower. She was furious and began shouting at me before she yanked me out of the shower, threw me on the ground and began to thrash my wet bottom silly.

She was still livid when she finally stopped spanking me and told me to get dressed in my t-shirt and pink shorts and report back to her in the library in twenty minutes. I dried off as quickly as I could, donned my "uniform" and stood at attention outside the library door within 5 minutes, waiting for her to let me in as I had done so many times in the past for a maintenance punishment session.

I could hear that she was on the phone, but couldn't understand anything that she was saying. The minutes dragged on and the butterflies running through my stomach were turning me into a nervous wreck anticipating yet another painful spanking or worse. But the moment she opened the door I saw that she was calm with an amused twinkle in her eye that I had come to dread.

My life would change in the next few hours, taking a turn to a much higher standard of discipline and regimentation than I had ever known before.

"Jim, I am so disappointed in you! How many times have I told you not to play with yourself?"

"B-but, Madame, I was only..."

"Silence! Do you think you can talk your way out of what I saw you doing in the shower? You were up to your filthy habits again and I simply won't stand for it in my house!"

I knew that tone, and when Madame gets so riled up it's better to just listen and respond when asked a direct question.

"Young man, you have a choice. You can end our relationship right now, collect what's due you, leave and never come back again. Or you can agree to submit to a much higher level of supervision, control and discipline.

"Since I can't run the family business and provide the kind of extreme regimentation and close supervision which you obviously need, I have asked my dear friend, Ms. Dominique Pegsworth, if she would be willing to be your new supervisor and disciplinarian. Dominique is a registered nurse and had been the head disciplinarian at the Adult Behavior Correctional Facility until she took early retirement in December.

"We have known each other since we first met in France during our college days when we were polishing our French. She admitted to me just weeks after leaving the Correctional Facility that she missed the daily routine of controlling and disciplining young men and women.

"So when I spoke to her about you, well, she took an immediate interest and wanted to meet you. We were planning to have her come over for a social visit to get to know you, but after your disgusting little display in the shower, I called her and she was as angry as I was! She would like nothing better than to discipline you and correct your disgusting behavior!"

I was blushing with embarrassment at having my predicament so openly discussed with a lady that I had never met, nor heard about until today. But I was also acutely aware that Madame was forcing me to make a choice and that if I did not submit to her terms, I would have to vacate her premises immediately.

"Make no mistake, Jim," Madame hissed as she cupped my balls and began squeezing until I was forced to stand on my tip toes.

"Ms. Dominique Pegsworth is an ultra-strict disciplinarian, and if you agree to these new terms you will have to obey her completely. She would be given full authority over you. There would be no more carefree jerk-off sessions in the shower for you young man! No more disgusting masturbation skulking in the john! She would bathe you herself and she would also see to all your needs.

"Your privacy, what little of it you still have left, would be a thing of the past; for example, all your bathroom privileges would be suspended the moment she walks into this house. You will have to ask her to go every time you need to be relieved and believe me there are a lot more severe forms of denial than moaning about emptying your pitiful little blue balls. She will also be present every time you use the potty as you most definitely cannot be trusted by yourself!"

"Your new disciplinarian is also a stickler for regularity which means that you will be getting lots of castor oil treatments and at least one big enema session per week. In fact, all your daily routines will be closely supervised by Ms. Dominique including what you eat and drink, your bedtime and how much time you spend in bed, what you wear, and how much hair you are allowed to keep.

"She will also oversee your exercise routines to keep you fit and monitor your study hours. Oh yes, young man! Ms. Dominique will also become your teacher and will make you learn lots of useful subjects. I know her to be a strict grader and a very demanding teacher. French will definitely be one of the subjects which you will be made to learn."

I shuddered knowing that French had always been my weakest subject at school. I simply don't have a knack for languages and when I had a choice at college, I gave up after one semester. I believe I had mentioned this to Madame several months ago when we initially met. She laughed at the time and I was baffled, telling me that she would see to that omission in time. I guess she was about to make good on her word.

"When Dominque spares you from your daily regimen, that is, during your "free time", you will be expected to help Raj with his chores. Of course, you will still have to follow Raj's as well as Vandana's instructions to the letter. Indeed, Raj tells me that you have been shirking some of your tasks recently and that he has had to discipline you often. He also mentioned that sometimes he's caught you looking at him in a queer way and that you seem to be fixated on his crotch!"

I blushed crimson at that remark squirming since it was not true, nor was it true that I was avoiding my work. But I also knew that in this household my opinion never carried much weight and so I remained silent.

"Your new disciplinarian will look into Raj's concerns. He really is an enormous bull, and I am sure that Dominique will make all the necessary preparations so that you can better cope with his demands. It would also be a blessing to take some of the pressure off poor little Vandana, who is so sore from Raj's demands!"

Relaxing her grip on my balls, she looked deep into my eyes and said, "So Jim, what's your decision?"

Stooping a bit to ease the pain in my balls, and though disconcerted by the plans that Madame had apparently concocted with Mr. Raj and Ms. Vandana, I swallowed all my misgivings and said, "Madame, I am so sorry for having disappointed you! I agree that I need a higher level of regimentation, control and discipline and I am truly grateful for your having taken the time and to contact Ms. Dominique Pegsworth and that she has agreed to be my supervisor and disciplinarian. I would like the opportunity to let Ms. Pegsworth know just how grateful I am to her if that might be arranged."

"Excellent! You won't have long to wait!" Madame continued, "Did you hear that Dominique? Jimmy has agreed. Can you come over now?"

I realized then that the speaker phone had been left on and that my new supervisor and disciplinarian had heard the entire conversation.

"I'll be there within the hour Val, and I can't wait to begin training Jimmy. By the way young man, you won't be touching yourself again under my watch! I can assure you of that!"

After she hung up the phone with my new supervisor and disciplinarian, Madame smiled at me with that ominous twinkle in her eye.

"You know Jimmy, I have a little confession to make. Dominique and I have been planning this day for months! You would have heard the construction going on in the south wing of the house. Well, it was finished earlier this week and that's where you will be spending most of your time with Ms. Pegsworth from now on. I want to show it to you before she arrives."

I followed Madame out of the library and towards the south wing trying to imagine what surprises might be in store for me.

Madame has a fertile imagination which I have come to respect and dread. Warned to stay clear of the south wing, I had never set foot in it. I only had access to the center part of the mansion, the northern wing and the extensive grounds around the building.

The mansion was really three houses rolled into one with Madame residing in the largest central unit and Ms. Vandana and Mr. Raj living in the second floor of the north wing. Their apartment had an ample living and dining room area, a large bedroom, a spacious bathroom and a walk-in closet. The first floor of the north wing had a large six car garage, parked nose to tail, as well as a storage room and a workbench area filled with tools and lawn equipment. I imagined that the south wing would be similar in design, but it was in fact very different.

As we entered the south wing Madame said, "Jimmy this first room is where you will be kept in shape."

I saw a padded mat on one side of the large gym with plenty of equipment. There was a tread mill, a bicycle, an ellipse, a rowing machine, pull-up bars, leather padded benches, and a wide assortment of weights. The other side of the room had a large wet area with a glass encased steam bath, an open shower and sink, a free standing toilet with an adjacent bidet and a wide massage table. Certainly no privacy here I thought to myself.

The wall separating the gym from the next room was lined with mirrors and when we passed through Madame said, "And this is the school room where you will learn your lessons."

The room had an intimidatingly large teacher's desk and chair on a high dais, several black and white boards, a high punishment stool at the back of the room, and two small pupil desks and chairs. Two student desks I thought to myself and wondered who the other might be.

Madame pointed out the tawses, martinets and canes lining the walls and said, "You better study your French with the utmost diligence Jimmy, or else!"

Seeing me wince Madame gloated and said, "Come upstairs boy, there are more surprises in store for you on the second floor."

I imagined that it would be similar to the north wing and, roughly speaking, it was. The living and dining room area, however, was smaller with one unique piece of furniture: a large adult baby high chair with straps for legs and arms as well as a locking tray.

Noting my wide eyed reaction, Madame said, "I don't understand why you are surprised about the chair, Jimmy. I told you that Ms. Pegsworth would supervise and control you're eating and drinking from now on and there is no better way to modify your habits than to have you nicely strapped into that adult baby chair and feed you herself.

"I can picture you at breakfast with a big bowl of hot porridge, liberally laced with that foul tasting castor oil, knowing that she will probably make you eat at least two full servings and wash it down with plenty of prune juice and milk. We've talked about your meals and all the energy you will need for a hard day of exercise, school lessons and garden work with Raj. So we will want you really stuffed at breakfast, right after your first morning workout in the gym.

"Of course your new supervisor Ms. Dominique might not let you use the bathroom for a while after breakfast to instill discipline and character. But you can count on her keeping you hydrated with a lot of juices, milk and water. You will be learning to beg her to be allowed to pee soon enough young man."

Amazed and beginning to realize just what I had agreed to, we exited the living-dining room, and entered the bedroom which was significantly larger than the north wing's. Madame noted that the king size bed was Ms. Pegsworth's and I saw that the bathroom was much bigger in this wing. It was also completely open to the bedroom, no door or wall separating the two rooms. Anyone in the bedroom would be able to observe everything going on in the bathroom. No privacy at all.

The bathroom area had white tiling on the floor and on the three surrounding walls creating a cold clinical atmosphere. I spotted a toilet, a bidet and a sink. No showers in this bathroom, but there was an oversized stand-alone bathtub in the middle of the room. I cringed as I saw an assortment of water bottles and thick nozzles hanging on stands and hooks from the walls.

"That's right young man, that's your enema kit and I am sure that your new supervisor and disciplinarian will put it to very good use to keep you nice and clean. But let me show you one last feature of your new quarters."

She then pointed out the dark walk-in closet which on this southern wing of the mansion had a large floor to ceiling window separating it from Ms. Pegsworth's bedroom. I thought, that's odd; why would anyone bother to put a window looking into a closet? Madame soon clarified the matter by switching on the overhead light of the "closet".

"Jimmy, this is your bedroom." I was saucer eyed and taken aback by what I saw. The room was sparsely furnished with a narrow elevated cot with plenty of restraining straps and a high back wooden chair which I assumed would serve to give me bedtime spankings before putting me to bed. The light switch for this tiny room was also on Ms. Pegsworth's side of the wall.

Slipping open the two sturdy door bolts that kept my little bedroom locked, we walked in and I immediately realized that there weren't any locks on my side of the door, not even a doorknob. Once I was locked in this room, someone would have to let me out. But what really rattled me was looking back on to Ms. Dominique's bedroom since I could only see our reflections in the high sheen floor to ceiling wall mirror.

Trembling at what awaited me, Madame laughed and said, "That's right Jimmy, it is a one way mirror and you will never quite know who it is that will be looking in on you in your tiny little bedroom cell. You better get used to it young man."

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