Keeping a Watchful Eye on Jimmy

"Yes, Sir", I said tearfully. But it proved difficult to wrap my lips around his crown because it really is enormous. I was also concerned that given the angle I was in over the horse, I might spill some of his cum unintentionally when he came, which I did.

"You clumsy, oaf! Can´t you get any of the rules straight!" He untied me from the horse and had me lick the floor spotless.

As we were climbing back upstairs to the kitchen for dinner, I said, "Sir, my bottom is on fire both inside and out. Could I please be rinsed?"

"No, boy, you were disobedient and you have to learn what happens when you aren't a good boy and follow the rules. Besides if you don´t rinse, the stinging sensation goes away by itself in about three hours and it is perfectly harmless."

He got dressed, but he kept me naked that night and served me dinner telling me to sit down on a hard wooden chair which simply added to my tribulations given my blazing hot bottom.

Mr. Ralph had a steak, salad and several glasses of wine. I got an oversized bowl of salad and a glass of milk.

After dinner, we retreated to the TV room where he watched a movie sitting in the middle of the couch. He told me to lie over his lap with my bottom facing up. Since the movie was for adults, he made me turn my face to the couch.

He did take pity on me though, and rubbed ointment on my blazing hot bottom from the spanking and the relief was immediate. He also inserted a well-coated finger with the ointment into my bottom and miraculously the stinging sensation disappeared.

"Jimmy, I like buggering a boy while I watch a good movie and you do have a very attractive ass. You are free to get hard of you want, but don't you dare cum."

**

That night when we went to bed, he let me use the toilet, and I found out that he had taken over Mistress Sandra´s bedroom and bed. She almost always locked me up in my tiny Spartan bedroom. But unlike my Mistress, Mr. Ralph preferred to keep my bedroom door open, to be at his beck and call.

He woke me after I had just fallen asleep and bringing me to his master bed told me to lie face down on top of three pillows and then he fucked me.

He was gentle at the beginning but soon turned into a piston. As he kissed my ear he said, "You can get as hard as you like while I fuck you, Jimmy, but not a drop of precum. Got it, boy?"

"Yes Sir, Mr. Ralph," I said as I gritted my teeth and endured the pounding.

Part 5

Mr. Ralph woke me up at 7 am on Saturday morning and told me to suck him off and swallow every last drop. He then had me wash my face and brush my teeth, but when I asked if I could please go potty, the term that he wanted me to use when I needed to use the toilet, he said, "You will be allowed to use the potty, after you finish your breakfast and complete all your homework assignments for today. Now go put on your home uniform."

Dressed in my tiny girlie pink short pants and the equally small and tight T-shirt, Mr. Ralph made me eat a large breakfast and drink down a glass of milk and another of orange juice. He then escorted me to my punishment school room office and I began to work as efficiently as I could, grateful that this weekend's homework was much less than usual.

My home office is kept even warmer than the firm´s work area for boys. The thermometer on the wall read 90 degrees.

"It sure is hot in here, Jimmy." Opening a small refrigerator filled with water bottles which Ms. Sandra had thoughtfully placed in my office, he said, "Here are four bottles, Jimmy. I´d like you to drink two of them now in front of me and you had better finish the other two before I come back from the bathroom. I don't want you dehydrating as you do your homework.

"That large breakfast that we just had will give us plenty of energy for a thorough workout at the Club, but right now," he said smiling broadly at me and my evident discomfort, "I really need to use the toilet."

Bloated from the breakfast and not having been allowed to use the bathroom this morning, I really needed to go "potty" badly but knew that if I complained it would only make matters worse, so minding my manners I said, "Thank you, Sir, for taking such good care of me and keeping me hydrated."

"You´re welcome, Jimmy," he said pleasantly. "Remember, boy, that my iPhone is connected to the cameras in this room, so I will be watching you."

"Yes, Sir," I said as I chugged down first one bottle of water, followed by a second.

"Good boy! Now those other two had better be finished when I return from the john," as he hurried up the stairs. There were no bathrooms in the basement. I heard him lock the door to my office at the top of the basement stairs.

Squirming in my seat from a bloated bladder and bowel, I concentrated on my homework assignment and managed to drink the other two bottles before Mr. Ralph came back.

**

After my homework was completed, and Mr. Ralph checked to make sure I had done a satisfactory job, I was allowed to go potty while he put some fresh clothing on my bed.

"Boy, your uniform is soaked from sweating and, while it is fine for you to wear at home, it is not really suitable attire to be worn in public. You can wear what´s in your bedroom," he said after making sure I was whistle clean after using the "potty". He had me squat over the bidet without resting on the rim, just like Ms. Jennifer did at the firm, and then he rinsed the sweat from my body in the shower.

I looked at the clothing on my bed and even though it was more substantial than my home uniform, I knew it would make me look very odd to any passerby in the Street.

It looked like a wrestler's singlet with shoulder straps, baby blue in color. Unlike normal wrestling gear which usually covers half the thigh, this singlet was awfully short and went down about a half an inch below the crotch.

It also appeared to be at least one size too small for me. The seat covered my entire bottom, but I saw that it had a nasty seam that rode all the way from the crotch up the back to fork into the shoulder straps.

Wonderful, I thought to myself, the seam will stick into the crack of my ass, every time I take a step. I knew better than to dawdle or complain which would only earn me another spanking and so I put on the singlet.

Looking at myself in the mirror, I saw that the spandex material fit me like a glove and traced my cock and balls clearly since there was no interior lining. The fabric was also very tight against my chest which raised my nipples that stood on end.

"Don't you look cute, boy!" Said Mr. Ralph as he escorted me out into the driveway locking the front door behind us.

Mr. Roberts was standing by the car and he smiled the minute he saw me. As he buckled me into the back seat of the car with my hands on my head, he said, "Don't let me catch you playing with yourself, sonny!"

"No, Mr. Roberts, I wouldn't dream of it, Sir."

Mr. Ralph sat in the front passenger seat and told him that we would be doing some shopping before heading out to the Lotus Club. My heart sank.

It was clear from their familiarity that they knew each other quite well. Since Mr. Ralph had heard Mr. Roberts berating me, he steered the conversation to my getting spanked last night over the vaulting horse.

After a vivid description of the scene and why I had earned the punishment, a clearly very agitated Mr. Roberts said, "You know, Ralphy, even though I´ve caught Jimmy doing corner time and once saw him over Ms. Sandra´s knee, I have never seen him receive a full punishment session," said Mr. Roberts.

"Well, that can be fixed easily enough, Justin," using Mr. Roberts' first name which he never let me use. "Why don´t you come over for dinner tonight. It´s more than likely that Jimmy will do something naughty in the next several hours and then you can watch him getting his well-deserved spanking. He can also serve us dinner. Are you free tonight?"

"Thanks, Ralphy. Yes, I would love to have dinner with you tonight in the mansion. I really would like that," he said as he looked into my eyes in the rearview mirror and licked his lips.

**

Mr. Roberts drove us to an adult emporium on the outskirts of town. Fortunately, there weren´t many people on the Street and we entered the store without causing any commotion over my costume. It was different inside the store, however, where a couple openly stared at me and she laughed. I felt so embarrassed.

My humiliation increased when I realized what Mr. Ralph had in mind for me.

"Let´s try on this belt, boy", he said as he fit a shiny black four-inch leather belt around my waist. It fastened at the back and he secured it snugly. I noticed that it had d-rings both in the front and on the back. And against the baby blue singlet, it really stood out.

He chose a black six-foot leash which he attached to the back of the belt. Holding on to the other end of the leash, he said, "With this leash you won´t get lost in public, Jimmy. Doesn't that make you feel nicely safe and secure, boy?"

My mind was reeling from the embarrassment and humiliation that I would have to endure dressed in this fetish singlet and now leashed just like an unruly little boy. But rather than risk the ire of saying what I truly felt, I said, "Thank you, Mr. Ralph, for keeping me so closely supervised and safe, Sir."

As we left the store, we spotted Mr. Roberts parked on the next block and I noticed that the Streets had suddenly begun to fill with pedestrians. They would openly stare at me and Mr. Roberts, who walked two steps behind me, told me to keep walking straight ahead.

I was mortified when a group of teenage girls turned the corner and saw me. Mr. Ralph spotted a fresh opportunity to embarrass me and pulling on the leash to make me stop he ordered me to put my hands on my head.

The girls burst out laughing and pointed at me. Mr. Roberts explained that I was a very naughty and unruly boy who needed to be kept on a short leash, which made them hysterical.

We finally reached the car and Mr. Roberts buckled me in.

**

When we reached the Lotus Club, I was led out of the car by Mr. Ralph with the leash. I was deeply embarrassed when we entered the hallway and Mr. Ralph paged Ms. Valerie and Mr. Luis. We didn´t have long to wait. They had normally seen me dressed from work at the Club or in normal street shorts that Mistress had me wear on Saturdays when going out.

"Hi Val!"

"Ralphy, what a surprise!" She said as they kissed.

"Hey Luis! Long time no see, compadre!"

Mr. Luis also kissed Mr. Ralph and they gave each other a warm embrace.

They all turned to look at me with evident glee. Mr. Ralph explained that we only had three hours available today and that he had booked me for a two hour stretch massage with Mr. Luis, so Ms. Valerie agreed to shorten my swim class as an exception. Turning to me, she said, "Don't think that I will go any easier on you, boy. And I now know who to call to give you a well-deserved spanking if you don´t put in enough effort!" She said sternly.

"And that will be me, boy," said Mr. Ralph who handed the leash to Ms. Valerie, as he and Mr. Luis left arm in arm for the men´s locker room.

Pulling on the leash, Ms. Valerie said, "Let´s get you suited up, boy," as she pulled on the leash to quicken my step.

**

It was a very intense swim class dressed only in a tiny white thong which, I realized to my dismay, became transparent as soon as I hit the water.

After class she berated me for not having done my best, although I had put in as much effort as I could, and would report me to Mr. Ralph. I was crestfallen as I knew exactly what that meant.

Walking me to the massage room straight from the pool, Mr. Luis took charge of me, thanking her again for agreeing to cut the class short.

"You're welcome, Luis, but have a care. This lazy boy is going to be reported to Ralphy for not having done his best. As for you, boy, make sure to do everything that Luis asks, or that too will get reported and you will be spanked twice tonight," she said in a loud and threatening voice.

Closing and locking the door to the massage room which was larger than a normal office at the Lotus Club with a shower, sink and toilet, as well as a massage table, Mr. Luis said,

"Hang your panties on the hook on the wall, boy. Do you need to use the toilet?"

As I stripped off, I said that I did, and he let me use it. He then made me shower, and as he stared at me, he asked, "Have you ever received a massage, boy?"

"Yes, Sir, I have but not very frequently, Sir," in fact, I hadn't had a massage since I married Ms. Sandra. She thought her toy boy should be giving her massages, not receiving them.

"Well, young man," he said, "this massage is a little different since it will stretch all your muscles and joints. It may be a bit painful, but it will do you good. There is also one muscle that we will work on especially hard and long today, your boy pussy," he said.

Dry gulp.

Suffice to say that he did give me a very energetic and strenuous massage, almost verging on brutal. Having done my back and front telling me that it was ok to get hard, but warning me that I was not authorized to cum, he asked me to bring my knees up to my chest and hold them with my hands. He placed a rolled-up towel underneath my lower back which raised my bottom further.

"I´m going to start thumbing your ass, boy, and when you start to gape, I'm going to stick both my thumbs in your boy pussy and stretch your opening. I will repeat this exercise for the next 20 minutes. I don´t want to see you cumming, boy, not even a drop of precum. Got it?"

"Yes, Sir, Mr. Luis!"

The thumbing and even the stretching wasn´t half as bad as it sounded, nor as stressful as the massage I had just received. Moreover, after a while, his stretching actually began to feel really good, which is when I got into trouble.

"Oh, Sir, please, I think I am very near to cumming, Mr. Luis," I shouted.

He stopped what he was doing and peered at the tip of my penis. Sure enough, he spotted a pearl drop of precum and scolded me. He said that my lack of control would be reported. Fetching a bag of ice, he placed it on my still very near to exploding cock and balls. I soon became flaccid and he continued thumbing me.

**

Leaving the Lotus Club dressed again in the singlet and belt, Mr. Ralph walked me to the car. He waited until he was within earshot of Mr. Roberts to say, "Well, boy, I had a wonderful afternoon work-out and a great steam bath. But it was marred by the reports I have just received about your performance, Jimmy. Both Val and Luis told me that you were badly behaved, so, boy you will definitely get spanked tonight, a double spanking after you serve our dinner tonight."

I was crestfallen but knew I had it coming. Mr. Roberts, however, was beaming at the prospect of my punishment as he drove us back to the house at 6 pm.

"Justin, why don't you go to your cottage and get dressed comfortably," he always wore a suit and a tie when driving us. Would you be ready, say, by 7 pm?"

"Sounds good, Ralphy. I really am looking forward to tonight's dinner," he said, as he looked at me and smiled like a Cheshire cat.

Mr. Ralph led me into the house and taking me straight up to the Master bedroom he removed my belt, and I was told to strip as he went to his closet and fished out my clothing for the evening.

He returned with black thigh high stockings, and a very short French maid white apron which he tied in a bow at my lower back. I saw myself in a mirror and became aware that my nipples were exposed at the top of the apron and it was so short that it just barely covered my flaccid genitals. My backside was to be on display all night long.

Dressed as a fetish maid, I was sent down to the kitchen and prepared a delicious dinner for two. I was served a bland salad and a glass of milk, before the guest arrived.

As I finished setting the dinner table and completing preparations in the kitchen, the doorbell rang. Mr. Ralph called from the living room and said in a booming voice, "Answer the door, Jimmy!"

**

Mr. Roberts laughed when he saw me. He was dressed in blue khaki cutoffs and a short white polo shirt. This was the first time that I saw him without a suit, and I realized that he was a very hairy man. The cutoffs also revealed another feature about Mr. Roberts that I had not known. He packed quite a bulge in his crotch.

"Justin, I am so glad you could make it!", said Mr. Ralph as he embraced him in a warm hug.

I was dumbfounded when they hugged and kissed each other. Not just a friendly peck on the cheek, but a drawn-out mouth to mouth lovers' kiss. I had no idea about Mr. Roberts until that moment.

"Can I kiss the serving wench too, he said?" As they broke off the embrace.

"Be my guest," replied Mr. Ralph.

"And, boy, you better be nice to Justin because he will be administering one of your spankings tonight."

**

After that night Mr. Roberts became another one of my babysitters, whenever Mr. Ralph had to leave me unexpectedly. Mr. Roberts proved to be a very stern taskmaster who would make me clean his garage cottage thoroughly on the weekends and delight in spanking my bare bottom over his knee for any slip-up, real or imagined, on my part.

Part 6

Three months after she had left on a business trip, Mistress Sandra returned. I cried in in her arms and she gently stroked my hair as she asked Mr. Ralph for a full report about my behavior, having me kneel between them.

"Jimmy has been spanked every day since you left except for two days when I allowed him to cum. He has been chaste for the last four weeks. I will say this on his behalf, he has accepted all his punishments stoically and politely.

"In addition, you will be happy to hear, that just like you predicted, Justin Roberts has been recruited and he has gladly accepted the role of being a part time nanny for Jimmy whenever you or I are not around to supervise him. Justin loves supervising the boy and he is a firm believer that the boy needs ultra-strict discipline and control."

"Wonderful!" Said Mistress Sandra, "Have you explained to Justin, that while he can punish the boy at his will, he must never do lasting harm?"

"I showed him myself how to spank the boy without bruising or breaking the skin."

Kneeling between them as they spoke, I thought to myself that all my supervisors were indeed highly skilled and trained spankers since despite having received very painful punishments over the years there was only one incident where I had had a seriously blemished rear end. I still shudder when I remember the day when Ms. Sandra flogged me with a cane. Fortunately, she has only done this once.

When Mr. Ralph took his leave, Ms. Sandra hugged me tightly and leading me by the hand to her bedroom had me make love to her and she let me cum inside her. I was ecstatic and overwhelmed with emotion, but naturally, I also had to eat her cream pie to her satisfaction.

**

My life with Ms. Sandra resumed as it had been before she left. I fell into the comforting routine that I had had before Mr. Ralph had entered the scene. I was grateful to be back in a female led relationship and a female dominated work environment.

Two weeks after her return, Ms. Sandra bathed me right after inspecting my panties from work. This was much earlier than usual. She said, "Jimmy, I have a surprise! To celebrate my return, we are throwing a little dinner party tonight for our friends."

"Oh, Mistress, how nice. Can you tell me who is coming?" I asked incredulously as she walked me to my bedroom where she had told me she had laid out my evening attire.

"Of course, silly!" She said with a sharp slap to my ass. "Joyce your employer is coming over tonight with her husband Bob, and so is Valerie your swim coach with her husband Tim and to round out the table of six, I have asked Jennifer, who looks after you so well at the firm, to dine with us too.