Keeping a Watchful Eye on Jimmy

Keeping a watchful eye on Jimmy

By

Maamsboytoy

Part 1

My wife and mistress, Ms. Sandra, dominates and strictly controls me. She is a beautiful petite brunette with an iron will and a playful sadistic streak which comes alive every time she embarrasses or humiliates me at home and in public.

I am by nature submissive and obedient. Ms. Sandra's discipline and micro management style thrill's me to the core and I am truly grateful for all the attention she gives me. Our relationship of more than ten years, however, sometimes has me wonder what I have gotten myself into.

Although my wife is independently wealthy, she insists that I be a provider in our family of two. After we got married, she made me leave the firm where I had achieved noticeable success and a high salary.

"James, you married me, not your work. You spend far too much time there instead of with me and you come home exhausted. That´s not what either of us want. Besides we don´t need you making that much money anyway since I have more than enough. And I have found a perfect job for you, dear boy, that will be much better for us," she said with her arms crossed and a determined look on her face.

I made the mistake of challenging her decision.

"But, Ms. Sandra, I have an excellent job at a top accounting firm in the country and I am being promoted on a fast track," I pleaded referring to her formally as she always demanded from me. "Mistress, can´t you please reconsider?"

"You don't listen, James," she said with a steely look in her eye. "The decision has been made and you will be starting on your new job next Monday.

"Instead of thanking me as you should be, you are questioning my judgement and that is completely unacceptable. Strip, boy, and get over my knee for a well-deserved spanking," as she picked up a heavy hairbrush.

Saucer eyed, realizing that I had better resign myself to a new career, I laid over her lap buck naked, and said, "I am sorry, Mistress, for having questioned your authority."

"Not as sorry as you are going to be," as she brought down the hairbrush with a painful whack followed by forty-nine more. At the end, I was crying like a baby over her knee.

Ms. Sandra arranged that I be admitted into a female run accounting firm where the pay is much less and the work load a lot more tedious than my previous job. My mistress gets my entire pay check sent directly to her account. I get pocket money, if I am good.

The new job has non-financial attractions from Ms. Sandra's point of view which sealed my fate. The head of the firm, Ms. Joyce, is the best friend of my wife. They agreed that I would work from 9 am to 3 pm, Monday through Friday, with the provision that if there were any work assignments that had not been completed during the work week, I would have to complete them over the weekend at home.

I am also watched very closely at the firm which is the real reason why Ms. Sandra had me join Ms. Joyce´s firm. My contract stipulated a lot of conditions, which are highly unusual, but Ms. Sandra thought they were perfect for me.

Suffice to say that I consented to be courteous, respectful, cheerful and obedient towards all the female employees of the firm. I am obliged to complete their business requests no matter how trivial, tedious or time consuming.

Any mistakes or slip ups on my part or indeed anything short of presenting a cheerful and submissive demeanor as well as a prompt execution of tasks that must be flawless, get reported to Ms. Joyce, who in turn calls and explains my deficient behavior to Ms. Sandra.

"James, I had another call from Joyce today about your behavior," said my angry Mistress as soon as I got home. "Something about your putting up a fuss about doing a chore. We can´t have that, boy. Strip and get over my knee, right now."

"Yes, Mistress," I said resignedly, having learned that I am never to question the veracity of any complaint lodged against my behavior at the firm.

My loving wife set up a special purpose office at home to make sure that I had the right environment to carry out my "homework" in the basement of her estate. My home office also doubles as my punishment room. It resembles a school classroom with a small desk and chair for me to work in and the ever-present stiff wooden back chair for Ms. Sandra to put me over her knee for a sound bare bottom spanking.

There is also a sturdy vaulting horse with straps to hold my wrists and ankles when a more severe punishment is in order with several spanking instruments hung on the wall behind the horse including paddles, straps, a tawse, a heavy hairbrush, and a vicious cane. My little school desk faces the horse and the spanking instruments to incentivize me to focus on my homework.

Mistress Sandra carefully reviews my weekend assignments. Any errors or messiness are dealt with harshly.

So, the arrangement works fine as far as Ms. Joyce is concerned, especially since my Mistress also happens to be one of the most important clients of the firm.

About one year into our marriage and nearly as long at Ms. Joyce´s firm, Mistress explained that I would be called "Jimmy" from that day on and not James.

"James, you keep acting like a badly behaved boy, so from now on you are going to be treated like the naughty boy that you really are. A boy badly in need of strict discipline and control. And we are going to start by calling you Jimmy."

Although I did not like the idea, I was secretly grateful that it wasn´t anything more belittling or humbling. I simply said, "Thank you, Mistress, and I hope to improve my behavior to your satisfaction."

"You better, Jimmy-boy, you better," she said threateningly.

She went as far as informing Ms. Joyce about my new name. Soon everyone at the firm started calling me Jimmy. The ladies quickly warmed to the idea and the two other men that work at the firm, Bob and Tim, the former as I learned, the husband of Ms. Joyce, snickered a bit at first, but soon began calling me Jimmy too.

The three of us "boys", as Ms. Joyce was fond of calling us, are very hard workers. We arrive promptly at 9 am and leave at 3 pm on the dot. We are all handed a large satchel of "homework" every Friday afternoon to be completed over the weekend.

My male colleagues are very respectful towards the ladies of the firm. They stand up when any of the ladies enter our small fishbowl glass encased work area in the center of the office. The door to this work area locks from the outside and there is no handle on our side.

So, if we need to exit the work space, we must remain seated at the circular table which the three of us share and raise our hand. We need to wait patiently until one of the ladies lets us out.

The table that we share is also a bit cramped for three grown men. It is less than a meter in diameter and our arms and legs wind up rubbing against each other unless we keep our forearms on the table and our feet neatly tucked below our chairs.

I fell into the work routine quickly enough standing at attention as soon as any of the ladies entered the boys' work station and raising my hand to be let out when I needed to use the bathroom. But I was taken aback when Bobby asked me, "Does your wife demand that you be respectful around ladies?"

"Yes, Bob, she does," I responded without giving the matter much thought. Ms. Sandra has drilled into me that I must always answer any question that I am asked truthfully and completely, no matter who asks.

"And does she spank you if you don't?" he asked as he stared into my eyes.

I gulped. Bob's question made me blush from head to toe and he and Tim, who perked up hearing the question, were the last people on earth that I wanted to know about the way my Mistress treats me at home.

But given Ms. Sandra´s instruction to answer every question fully, I felt trapped. After a pause I confessed in a low voice turning beet red with embarrassment, "Yes, Bob, she does spank me."

Reaching over he gave my bottom a playful pat and said, "That's all-right, Jimmy-boy. Tim and I are also in a female led relationship and our loving wives sometimes spank us too."

In retrospect the revelation made perfect sense. The men employed at Ms. Joyce's female led firm were those married in a female led relationship. Comradery sprang since we instinctively knew how we were treated at home. Yet, I was soon to learn that not all of us boys were treated equally.

The eventful day that Ms. Sandra started calling me Jimmy was also memorable for the rapid changes that would take place at home. From that day on, I was made to wear baby blue tight short spandex shorts, with a nasty seam up the back that digs into my crack.

The shorts fit me like a glove which means that she can readily spot if I am getting a bulge or if I become erect. I am not allowed to get aroused unless she authorizes it. I get spanked if I have the temerity of getting hard without her permission.

Indeed, I have been regressed to naughty boy status, badly in need of discipline and control, precisely because I do not have self-mastery over my sexual impulses.

"Jimmy, if I catch you getting hard again tonight, you are going to spend the rest of the night over the horse with twenty from the tawse. Got it, boy?" she said sternly.

"Sorry, Mistress. I don't know what I was thinking, Maam!" I said as politely as I could.

Anyone invited to our home will see me in this ridiculous "uniform" usually only complemented with a very short and tight white T-shirt that barely covers my navel.

At Ms. Joyce's firm, however, I am always dressed in one size too small thin beige chino slacks which are very tight in the butt, a rather short white button-down short-sleeve shirt which often pops out the back of the trouser when I sit at my chair, and a blue bow tie.

The one article of clothing that I wear to "keep me out of trouble" is a pair of bright pink satin panties. I take pains to ensure that while seated at the boys' table, I don´t show my panties, which is difficult since the chinos are low rise and the shirt too short. On one occasion Bob noticed as I leaned over the table top concentrating on resolving a work issue.

"Are you wearing panties, Jimmy?" I blushed hearing the question and sat bolt upright in my chair. But I was trapped and somehow Bob had figured that he could needle me by asking me questions and that I would always answer him fully.

"Yes, Bob, my wife makes me wear panties to keep me out of trouble."

Both Bob and Tim burst out in laughter and spent the next ten minutes ribbing me which embarrassed me greatly.

It was clear that my male colleagues might be in female led relationships, but mine appeared to be a whole lot stricter than theirs. Their teasing also made me think, as Mistress Sandra kept pointing out, that I have no one else to blame but myself. I just don´t have the will power to exert self-discipline and control over my sexual impulses.

As soon as I get back home from work, I must strip and present my panties for Ms. Sandra´s inspection. If there is so much as a trace of pre-cum on this terribly easy to stain article of clothing, or any other stains for that matter, I am in deep trouble.

My chastity is in Ms. Sandra's hands. I am allowed one release per week under her close supervision, if I am very good. Ms. Sandra collects my ejaculations in a cup and I must swallow every last drop.

On the rare occasion when she wants me to make love to her, which I enjoy immensely, I must eat her cream pie afterwards until she is satisfied and perfectly clean.

Regardless of my chastity, I am required to bring my loving wife to orgasm at least once a day. While I am licking and sucking Ms. Sandra´s gorgeous pussy and beautiful ass, I am allowed to get hard. But woe betide me if there are any precum stains on my home uniform.

A tiny pearl-drop of precum on my pee slit is ample justification for a visit to the vaulting horse in my punishment room.

We follow an honor code at home, so I do not wear a cock cage. Ms. Sandra loves this code. At times I truly wish I were caged because my sexual frustration and very swollen blue balls have often gotten me into trouble. At the three-week mark of abstinence, I get erect over just about anything, and to Ms. Sandra's delight, she is always ready to spank me back into submission and presentable form.

Part 2

In the second year of our marriage, after four long weeks of chastity, Ms. Sandra caught me playing with myself in the shower, just stroking, nowhere near cumming. I simply could not resist the temptation.

That little episode had monumental consequences for me. It led to the immediate introduction of an open-door bathroom policy and much greater deprivations of privacy then I had ever experienced. Ms. Sandra is now present in the bathroom whenever I need to use it and she bathes me herself.

"You are a wicked naughty little boy who can´t control himself. I can't trust you not to play with yourself, so you only have yourself to blame for this situation," she often scolds me as she humiliates and embarrasses me regularly in the bathroom.

Her delight in my predicament is all too obvious when at bath time she edges me and digs a soaped finger or two into my bottom to make sure that I am whistle clean at both ends. I am allowed to get hard during the bath, but warned not to cum.

Only five days after instituting the open-door bathroom policy, and nearly five weeks without having had any sexual release, she skillfully edged me during my bath and I simply could not control myself and I came. Ms. Sandra was furious.

"You disobedient, ungrateful boy!" She said as she slapped my face hard with her left hand and kept slapping me as I pumped all my pent-up cum into her soapy right hand.

After I finished this unauthorized emission, she said, "Lick it up boy, every last drop!"

I spent the next several minutes licking up the soap and cum from her soaked hand which tasted awful. She then dragged me wet and naked to my punishment school room office, secured me over the vaulting horse and gave me the hardest spanking I had ever had with a leather tawse.

After the spanking she administered a large enema which I had to hold for one hour doing corner time in the living room while she watched the news on TV.

As I fidgeted and squirmed holding the enema, with my hands on my head, my nose touching the wall, and my feet spread wide, the door-bell rang.

Ms. Sandra got up to answer the door and I could see from the corner of my eye that it was Mr. Roberts, her stern fiftyish driver who was always amenable and deferential around her, but curt and demanding toward me.

He lives on the second floor of a garage-cottage which is part of the estate grounds of my wife´s home where we live. Even though I have a driver´s license Ms. Sandra does not let me drive nor use public transport.

"If you can´t control that little willie of yours, boy, you certainly are too immature for public transport and way too undependable to drive any of my cars," she says sternly whenever I ask if I can get out on my own.

So, Mr. Roberts drives me to the firm, every day, and brings me straight back after I have completed my work day.

As he spoke with Ms. Sandra, he kept his eyes rivetted on me and would have seen my face blushing as vividly red as my freshly spanked bottom. Embarrassed to the core, I knew better than to move an inch from where Mistress Sandra had left me.

They spoke out of my ear range for what seemed like an hour, but it must have been only ten minutes or so. He finally left and Mistress resumed watching the news.

"You still have another half an hour to go before I let you anywhere near a toilet, Jimmy. And stop that squirming or you´ll get another spanking!"

"Yes, Mistress!" As I remained in position facing the wall.

Sweating bullets as I tried to hold that enema and with my ass on fire from the spanking, I felt very contrite and I thought I had certainly learned my lesson. I promised myself that I would do my utmost not to cum unless given permission and truly strive to obey my wife and mistress' instructions to the letter.

But that fateful day also had major consequences for me at my firm which was to increase my embarrassment and public humiliation dramatically.

While I continued to do corner time, Ms. Sandra called Ms. Joyce, on a speaker phone making sure that I could hear every word of the conversation.

My heart skipped a beat when I heard my loving wife say, "Joyce, honey, I am so sorry to be calling so late in the evening but I need you to arrange closer supervision for Jimmy at the firm. I caught him jerking off in the shower the other day and today at bath time he exploded without permission. Honestly, he is not to be trusted and needs to be accompanied into the boy´s bathroom and closely supervised. I am certain that he would masturbate if given the chance."

Ms. Joyce replied, "Really, darling, the boys are already very closely supervised and you know that as a contractual agreement they all had to accept video cameras in the boy's work area and in the boy's bathroom. There are several cameras in both areas to make sure they are not slacking off or playing with themselves."

I held a feint glimmer of hope that maybe, just maybe, Ms. Joyce was going to let me off the hook, but my heart sank when I heard her say, "Nonetheless dear, Jimmy´s actions are unforgiveable. The boy is incorrigible, ungrateful for all you are doing for him, and he richly deserves the embarrassment and humiliation from very close bathroom supervision. Moreover, dear, I have just the right person to administer these treatments."

As I was to learn, Ms. Joyce asked Ms. Jennifer, a plump middle-aged spinster to be my chaperone whenever I needed to use the toilet. Her function at the firm is to supply water, coffee, tea, and sandwiches to the employees from her trolley. She was thrilled to take on this new responsibility and could not wait to begin.

Every time I need to use the bathroom at the firm, I must raise my hand while seated in the boys´ work station and hope to catch Ms. Jennifer´s eye.

I must wait patiently for Ms. Jennifer, irrespective of my need. All the other ladies of the firm have been informed to ignore me when I raise my hand. When Ms. Jennifer finally decides to let me out, she accompanies me into the john.

My male colleagues can raise their hand and any lady in the office that is passing by can let them out to go to the john by themselves. My fellow colleagues may be in female led relationships, but unlike me, they have no restrictions as far as the bathroom is concerned.

Ms. Jennifer is a bit of a sadist and enjoys my plight. She has found ways to make it worse. At 9:30 am with all of us "boys" busy at work in our fishbowl office, she unlocks the door and brings in her trolley.

"Hello lads! My but it certainly is warm in here!" she says. The boy's work area and the boy´s bathroom is kept purposely warm at 80 degrees and has us perspiring before long from our intense effort to complete our daily work.

"I´ve brought you some cold water to keep you nicely hydrated while you focus on your work, lads. Here is a nice bottle of water for you, Bob, and one for you, Tim. As for you, Jimmy, I´ve brought you three this morning."

Saucer eyed at the three bottles in front of me, Bob and Tim couldn´t help but snicker at my predicament.

Standing at attention while she placed the bottles on our small circular desk, Ms. Jennifer drives the final nail in the coffin, "You two boys can take your time drinking these bottles since I won´t be back to replenish them until 11:30 am with your lunch sandwiches. But you, Jimmy, have to have those three bottles finished within five minutes. Do you understand me, boy?"