Keeping a Watchful Eye on Jimmy

"Yes, Ms. Jennifer!" I say quickly lest I displease her in any way, blushing beet red.

The moment she left the glass encased work space, the howls of laughter from the Bob and Tim could be heard all over the firm as they saw me frantically chugging down one bottle and then a second. I usually have a very hard time drinking the last bottle, but I managed to finish it within four minutes hoping to please Ms. Jennifer.

Bob, who takes special delight in my predicaments, often gets me into trouble. Picking up his bottle he said, "Jimmy, I had a big breakfast at home this morning, and I don´t need any more water. But I see that you are perspiring heavily. You are sweating a lot, aren´t you?"

I respond truthfully, "Yes, Bob. I am sweating profusely."

Thinking to myself that I am sweating due to the stress of chugging all that water down in an overly heated room. Hoping that my sweating does not stain my panties because that too is a spanking offense as far as Mistress Sandra is concerned.

"Well, Jimmy, that probably means that you are dehydrating and that is not good at all. No, sir. You won´t be able to do your work properly if you are dehydrated. You need another bottle of water. Here have mine," as he handed it to me with a vicious gleam in his eye and a Cheshire cat smile.

With a fourth bottle of water in my hand, I was about to say that I really couldn´t drink another drop, when Ms. Jennifer walked back into the room. The three of us rose to attention and before I could say another word, she said,

"Why you sweet man, Bob! I heard your kind offer to Jimmy." Turning to me she added, "Jimmy, thank Bob for his kindness and generosity in looking after your wellbeing, and drink down that bottle, boy!"

With resignation and knowing that if I disobeyed Ms. Jennifer I would get a fierce spanking at home, I said, "Thank you, Bob, for your kindness and for looking after my health and wellbeing."

"Anytime, Jimmy-boy, any time."

I just stared at the bottle in my hand, hesitating, wondering how I was going to drink down another bottle of water. It had been bad enough this morning since Mistress Sandra had served me a huge breakfast replete with several glasses of milk and juice. Ms. Sandra makes sure that I have a very nutritious meal before I go to work and, of course, supervises me while I brush my teeth after breakfast.

But whenever I ask if I may use the toilet before leaving for work, especially on the days when she decides not to let me use the toilet after I wake up in the morning, she says, "Silly boy, you will be late if you dawdle and besides you have a perfectly good boy´s bathroom at work. So, off you go," giving me a swat on the ass to get me going.

"Now, boy! Or do you want me to report you?" said Ms. Jennifer.

"No, Maam!"

And popping open the lid, I force myself to chug down another bottle of water in front of her. Two full liters of water and my belly was distended. The thin white shirt becoming transparent with my profuse sweating. Sweat marks also appeared on the chinos especially along the crack of my bottom.

"That´s a good boy, Jimmy. I´ll be back with your lunches at 11:30," she said as she walked out of the work area.

Predictably, I was squirming in my seat all morning long with a very full bladder and bowel and sweating buckets. I tried concentrating on my work, as I knew from experience that I would be ignored by Ms. Jennifer until after she served us lunch.

Finally, she saw my raised hand and escorted me to the boy´s bathroom at 1 pm, locking the door behind us.

The bathroom is very well lit with wall-to-wall mirrors and is quite large, more than twice the size of our fish bowl work space. It does not have any stalls because it is meant for only one occupant at a time. There is a sink, a toilet and a bidet, just like in the ladies' bathroom.

"Let's get this over with quickly, Jimmy, I don´t have all day. You know the drill."

"Yes, Ms. Jennifer."

Removing my shoes and socks, hanging my chinos on a hook on the wall and then slipping off my pink satin panties, which always brings a chuckle to Ms. Jennifer, I am about to hang them when she says, "Let me have the panties, boy. I want to make sure that you haven´t stained them while you've been at your desk."

"Yes, Ms. Jennifer."

Inspecting the panties she said, "Bob was right. You were dehydrating dangerously, boy. Just look at these very heavy sweat stains on the back of the panties, right along the crack of your fanny. This has to be reported."

I am mortified at the revelation and that I will be reported.

The short button-down shirt which is also heavily drenched in sweat, doesn´t get in the way of my doing my business because it is so short. Putting my hands on my head I squat down on the toilet with both the lid and the seat raised. I am not allowed to rest my thighs or bottom cheeks on the toilet bowl rim. I have to stay an inch above it in an uncomfortable squat. And I must wait for Ms. Jennifer to give me the go ahead, before I can begin.

She usually keeps me like that for several minutes, depending on her mood, smiling at me as my face grimaces from the strain of holding back everything that urgently needs to come out in an increasingly uncomfortable squatting position.

Once I am finished, regardless of whether it has been number one or number two, and it is almost always both, I must then straddle the bidet. Again, I am not allowed to rest on the rim. Ms. Jennifer washes me thoroughly with soap and water. My face is usually beet red since I am so embarrassed and humiliated by this routine. But only she decides when I have been cleaned sufficiently.

Diligent and very thorough, I have a difficult time willing myself not to get hard. I can usually manage this because she is not a particularly attractive woman. But when Ms. Sandra keeps me chaste for more than two weeks, I have a real challenge and more than once have gotten into a predicament in front of her as I squat over the bidet being washed by her nimble fingers.

"How dare you! You dirty little boy! No wonder your wife wants you supervised. You have no control, boy," she scolds me.

"Oh, apologies Ms. Jennifer. I really am sorry, Maam! I did not mean to get hard!" I plead.

"Well, boy, this is also going to be reported to your wife," which has me trembling at the thought. Two strikes in one day.

Part 3

A third major consequence of having been caught masturbating in the shower, is that every time Ms. Sandra goes out for an evening with her friends, or if she has a business trip, she must find someone to supervise and monitor me at home, since I can´t be trusted to be by myself.

Since my wife is an active person and goes out frequently, this presented a dilemma. Unfortunately for me, Ms. Joyce came up with a solution. One of her friends runs an adult babysitter service called Strict Babysitters. This company offers disciplinary nannies for incorrigible adults. The nannies, I came to learn, are both female and male.

Ms. Rita was my first adult babysitter. A no-nonsense lady, she is a good four inches taller than I am and very muscular for a woman. For the record, I am 5'7" tall and weigh 170 pounds. She must be at least 40 pounds heavier than me. Buxom with a curvy and very full figure, she was the opposite of my petite and feminine wife Mistress Sandra. Her disdain for men was apparent from the very first day that we met.

Right before Ms. Sandra left for the evening at 4 pm she told me, "Jimmy, Ms. Rita is here to supervise you. She has been given full parental authority. You will obey her to the letter. Should you displease her in any way, she is authorized to punish you as she sees fit. Do you understand me, boy?"

Saucer eyed and incredulous, thinking how on earth can someone be given full parental authority over an adult, but at the same time fearful of retribution, I said, "Yes, Mistress, I understand."

The moment Ms. Sandra left, Ms. Rita grabbed a fistful of my hair and slapped me hard saying, "Listen, Jimmy! I am going to feed you dinner, give you a nice hot bath and then strap you down for the night. I don´t want any trouble from you, boy, so you are going to bed early."

"But Ms. Rita", I argued foolishly, "it´s only 4 o'clock in the afternoon, Maam!" The next slap was much harder than the first and I only remained standing because she still held on to my hair with a vice like grip.

"Boy, I don't want any lip from you. That little outburst has just earned you a spanking before I tuck you in for the night, with any luck before 5."

I was then stripped naked to avoid staining my shorts and T-shirt and strapped into my "dinner chair", an adult baby chair which Ms. Sandra keeps in the kitchen as a possible baby regression punishment option for me.

With my hands and arms immobilized, Ms. Rita produced an enormous bowl of porridge, which looked very thick, and a large tumbler of milk. She fed me the very bland tasting porridge which became a real chore to swallow and she made me eat every last morsel.

"The porridge thick, huh, baby?" She would coo as she stuffed oversized spoonsful of porridge into my wide-open mouth.

"Yes, Maam," I would say between mouthfuls. My face getting very messy given the speed at which she fed me. Ms. Rita seemed to enjoy getting my face dirty.

"Let me help you with that porridge, boy. Here, drink down this little glass of milk," purposely spilling some on my face and chest which made her laugh.

The glass of milk was anything but little and must have contained at least a half-liter of milk. She wound up making me drink three glasses of milk in addition to the porridge.

After dinner, I felt bloated and completely stuffed but before I could say or do anything Ms. Rita unstrapped me from the chair and grabbing me by the ear, led me straight to the master bathroom. She bathed me in Mistress' large circular tub. This was a no-nonsense affair and she lathered every inch of my body paying special attention to my cock, balls and ass.

"I know your wife lets you get hard when she bathes you, boy, so feel free but don't you dare cum!"

Embarrassed yet erect, I was grateful that the bath finished in record time and then holding me by the ear again led me to my bedroom.

Ms. Sandra no longer lets me sleep with her. I have to be invited into the marital bed. My bedroom, however, does connect straight into Ms. Sandra´s very large bedroom. Mine is tiny without any windows and locks from the outside where all the light switches for the room are to be found.

The room is in fact a large closet that was converted into my bedroom. It´s Spartan with only a spanking chair and a cot bed. The door is also a full-length one-way mirror; mirror on my side and a window to my soul on the other.

Ms. Rita sat on the chair and spanked me hard for my foolish tirade. I was then laid belly up on my cot bed with my hands and feet strapped down. My bottom was on fire from the spanking and rubbing the bedsheet really stung.

In all the commotion, however, I had forgotten to ask to go to the bathroom and I really needed to pee badly. So, as Ms. Rita was about to lock me in for the night I pleaded, "Oh, Ms. Rita I really need to use the bathroom, Maam."

"Silly boy, why didn´t you think of that while I was bathing you?"

Stunned silence on my part, eyes saucer wide looking miserable on the cot.

"Ok, little boy, tell you what, I will let you pee if you do me a little favor first." She hiked her skirt up and I could see she wasn't wearing any panties and that her pussy was very hairy and wet. Her feminine scent was also very strong. She straddled my face with her thick thighs on either side of my head.

"Lick and get me off, boy, if you want to use the john."

**

There were other strict nannies that came to babysit me. Each lady was different and their supervision styles varied but the experiences were invariably embarrassing, humiliating and painful.

They also involved very intimate sexual contact, without any sexual release on my part, of course. But having that sexual intimacy troubled me as I was after all a married man. I finally broached the subject with Sandra and regret to this day that I did.

Slapping me hard she said, "You ungrateful, incorrigible boy! How dare you question what your nannies decide is good for you! They have all been carefully selected to help you improve your self-mastery and to expand your horizons as my toy boy.

"Do you understand me, Jimmy? You are my toy boy and I have told you repeatedly that you are to follow all their requests to the letter. What part of that is unclear to you? Now, do you want to receive a thrashing over the vaulting horse with the cane, or do you get it?"

"I do understand, Maam! I am your toy boy and I must obey the nannies completely and do everything they say. I am so sorry, Mistress Sandra! Please don´t punish me with the cane, Maam!"

"Very well, Jimmy. Never bring this subject up again."

**

A week later Ms. Sandra decided to test my resolve. It was 3:30 pm and I was being driven back home from work by Mr. Roberts. He knows how I am treated at home and whenever he sees me, he snickers and asks if I have been a good boy.

"You touching yourself again, sonny?" He asked with a twinkle in his eye.

"No, Sir! I have been good."

To avoid any mischief on my part, he orders me to keep my hands on the top of my head as he buckles me in the car, tightly, in the center of the back seat. He frequently looks at me during the drive home in the rearview mirror and often aims it at my crotch to see if I have gotten an erection which he would gladly report to Ms. Sandra.

Safely home, I rang the doorbell. Mistress Sandra does not allow me to have keys to my own home and I must be let in.

"Hello there, Jimmy. You know the drill, boy."

"Yes, Maam," as I strip off my work clothing and hand over my panties for inspection. Satisfied that they are dry and unstained she dropped a bombshell on me.

"Jimmy, I am leaving on a business trip in a few minutes and will be gone for at least a week.

"Strict Babysitter´s had to search long and hard to find the right person who could be available to supervise you for an extended period of time and, fortunately for you, they have found the perfect nanny."

I gulped and I saw that she was serious as there were two packed bags in the foyer. Oh no, I thought, not another nanny! And for a full week! I had never had a babysitter stay longer than 24 hours.

"Now scoot upstairs and get dressed quickly into your new home uniform, your nanny is about to arrive!"

I did as I was told concerned about living with the nanny for a full week. I found my clothing on top of my bed and was taken aback by the new "shorts". They were much smaller than the ones I normally wore, more like tiny speedos, but without an inner lining.

The spandex material clung to every nook and cranny. And it had a very thick seam up the back that felt like a tight thong separating my bottom cheeks. On top of it all, they were pink in color, soft baby girl pink.

The white T-shirt which completed my home uniform felt much tighter and shorter than usual leaving my navel fully exposed and given the tightness and slight scratchiness of the fabric against my chest, it raised my nipples which poked out like pencil eraser ends.

Dressed, I ran back down the stairs just as the doorbell rang. I looked at Ms. Sandra in panic reddening as I was dressed more humiliatingly childish than ever, in point of fact, like a little girl. Sensing my apprehension to answer the door in my new home uniform she saw a fresh opportunity to embarrass me and smiling with a devilish gleam in her eye said, "You silly boy! Go and answer the front door, Jimmy."

"Yes, Maam," I said cheerlessly knowing better than to disobey my Mistress.

Blushing from head to toe, I opened the door. The first thing that I registered was laughter, deep guttural laughter, and then I heard,

"You must be Jimmy. Hi there, boy! My name is Mr. Ralph and I am here to babysit you for the next two weeks. Won´t that be fun!" He said while pinching my right cheek like older ladies sometimes do when they meet little boys or girls. Walking in to greet Mistress Sandra, he also swatted my ass hard.

Two weeks! I thought to myself. And it's going to be with this big burly man! And hadn't I heard Ms. Sandra say distinctly just one week? My doubts were soon dispelled.

Mistress Sandra and Mr. Ralph spoke quietly out of my ear range, but a honk from the driver, had her rushing to the front door with the suitcases in hand. Looking at me she said sharply, "Jimmy, you had better obey Ralph to the letter. He is an experienced nanny and he has full parental authority over you for the next two weeks while I am gone.

"It may actually be a bit longer and I might be gone for a month or two. Remember your promise, boy. This is for your own good."

Gulping and in a cheerless shocked voice I said, "Yes, Mistress Sandra. I will keep my promise. Safe travels, Maam," as she left the house.

Part 4

Watching my Mistress as she climbed into the back seat of the limo, I felt Mr. Ralph put a strong arm around my shoulder as he closed and locked the front door. Turning to me I could see he was a very strong man. At least six feet tall, dark and hairy, I would guess he must have weighed well over 200 lbs. Yet he seemed very fit and athletic. The bulge in his pants was also unmistakable.

"Jimmy, let's give each other a nice welcome hug and kiss before I inspect you", and cupping my head with his powerful left hand he told me, "Part your lips, boy."

"Yes, Sir", as he brought his lips to mine and drove his tongue deep into my mouth. His right hand began to grope my bottom squeezing the left cheek and then the right. He traced the seam along the crack of my ass and kept squeezing and groping me sensuously as he kissed me passionately.

I had never been with a man before and felt terribly embarrassed, awkward and out of place. His kiss was intense and his tight embrace and sensuous groping seemed to go on forever.

I felt his huge erection grow against my belly. But what really concerned me was that I was responding to his advances. I became fully erect.

I rationalized that the reason why I was getting hard with a man was because Mistress Sandra had not let me cum in more than three weeks which had me feeling randy all the time.

Then I panicked as I realized that no one had given me permission to get hard. As he felt my erection, he broke off the embrace and seeing that I was indeed hard, which was easy to spot in the tiny pink shorts I was wearing, he slapped me hard and said, "You haven´t been given permission to get hard, boy! Now I know why you need supervision! You are a disobedient, naughty little boy that can´t control himself!" He scolded me.

"I am here to make sure you obey the rules, boy. So, let´s make sure you are crystal clear about what I expect from you while I am here.

"Rule number 1 : You are not allowed to masturbate, ever.

"Rule number 2 : You are only allowed to get erect if I authorize it.

"Rule number 3 : You are not allowed to cum unless I give you permission.

"But, boy, I most certainly will be cumming, a lot, and you will take pains to swallow every last drop of my semen or take it and store it up your ass."

Dry gulp.

"Rule number 4 : Your bathroom privileges are suspended for the duration of my stay.

"Seeing as you are a bit slow, as well as disobedient, Jimmy, let me explain what Rule Number 4 means. You have to ask me if you can use the toilet, any time that you need to go, while you are within your Mistresses estate or with me in public. Each and every time. And you will always do your business in front of me, never alone."