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Babysitter story
A story, with a lot of real-life basis.

My wife and I were trying a little bit of domestic discipline to give me a relief of sexual fantasies. She would sometimes put me in a chastity device, and keep me locked up for a few days. She would tease me, much to my frustration. She told me to call her my Owner when we were in this mode. One day, she was really pissed off with me for not doing something, and tied me to the bed. She then produced a Kali’s Bracelet that she had kept hidden. This was installed on me in place of the normal chastity device, and she then stripped off her blouse and bra and bobbled and massaged her breasts in front of my face. I tried to never repeat that transgression again.
Then one day, she said that she was going to go out on Friday evenings, to the local pub, but I was to stay at home, in my chastity device. This happened a couple of times, until she came up with a better plan. This is what happened.

It was my Owner’s decision to go out on Friday evenings. She would hire a local schoolgirl, a friend’s daughter, to babysit me. She was studying for her exams, so would often want me to be quiet and not disturb her. When I asked if this meant that the girl’s mother knew of our arrangement, she replied that it did, but would go no further “unless I deserved it”.
On the first Friday, the Babysitter, Stephanie, arrived to meet me. We were introduced, and were both informed that I was to obey her at all times, just as I obeyed my Owner. She also said that she would be doing something new or training me on something new each week. My Owner instructed Stephanie, with my knowledge, that there were certain rules for her. She was discouraged from taking photos, but if she did, they must absolutely not show my face, and must not be uploaded to the internet or shown on social media. They had to be shown to my Owner on request. Stephanie looked at my attire, which was sloppy tracksuit stuff, and stated in no uncertain terms that that would not do for Friday evenings, she would get me a uniform. Stephanie asked if I was kept in chastity, the answer was that I was not always in chastity, but I would be put into the device on Wednesday evenings, to be ready for Friday. Stephanie then measured me for clothing.
She told me to find and put on my old corset, she did a fitting, and instructed me on repairs and enhancements for the following week. She reinforced that she was to be obeyed at all times, and would keep a Black Mark book. She would be buying clothes to make up a uniform, and my Owner would lend her my debit card to pay for them.. I was to be put to bed at 11 pm, dressed in my Baby Doll pyjamas with the matching elastic-edged bloomer shorts. This would be the same every Friday bed-time. We had no intention of ever trying the night-time diaper scene, nor night-time bondage, as I have a real need to use the bathroom at night.
The next Friday, Stephanie arrived with clothing in a bag. First, she told me to face the wall, then standing in front of Owner, opened her coat. My Owner said that that was most suitable, and left for the evening. Then the babysitter told me to face her, and removed her coat. She was wearing a very short skirt, and a crop-top, and my cock hardened in its cage, but it couldn’t go anywhere. I was in pain. Stephanie instructed me to undress, and then to don the corset and new maroon stockings which she had brought. I had plenty of old worn-out underpants and socks to stuff the bra of the corset. She laced it up tight, and then instructed me to put on a pair of grey girl’s school knickers, and a white shirt with school tie. From then on, Stephanie always wore clothing that was designed to excite me, such as a sheer ‘T’ shirt and no bra, and sometimes shortalls, with no shirt or bra, so that when seen from the side, her boobs were clear5ly visible. One week, she had on a Cheerleader uniform, for which she only paid about £15, thankfully. As she out me to bed that night, she said that one of my tasks would be to expand the cheerleader outfit so that I could get into it. Each time, she thanked me for buying the outfit for her, saying that it was fall for my pleasure.
She gave me a maroon gymslip to put on. Then she told me to stand by the wall, and stand up straight. She looked at the hemline, which was well below the stocking tops, and adjusted and pinned the hem so that it only just hid them. She told me to raise my arms up high, and saw that the stocking tops were now visible. Perfect. She told me that it was my homework to make the adjustment permanent using the sewing machine, before the next Friday. When I asked why all the maroon, I was told that she once read a story about a man forced to dress for school in a maroon uniform, and she liked the idea, so was making me do the same.
She gave me a maroon blazer, luckily found at a charity shop. She finished up with a straw boater, complete with elastic band under the chin. The hat was an integral part of the uniform, and I was to wear it at all times that I had the rest of the uniform on.
She told me to be ready for her next week dressed in the corset, stockings, knickers, shirt and tie. I would be practising ironing pleats on the gymslip before I put it on, so I was to have the iron and ironing board ready for use. My weekly homework was to handwash the shirt and knickers, and then iron them. I was to get confirmation each time from my owner that I had done this correctly.
The next Friday, I was ready as instructed, and was told to bring the gymslip to the ironing board. There, I was instructed in ironing pleats, which are luckily quite large on a gymslip. I was then told to put the gymslip, blazer and hat on. Stephanie told me that I would soon be ironing small pleats when I got a narrow-pleated separate skirt, which would take a long time to iron properly. She mentioned in passing the idea of making me do “Punishment Ironing”, to keep me busy when there were no other chores for me
Next time, I was ready fully dressed. Stephanie inspected me and was happy, but told me to drop my gymslip, then lifted my shirt up and tightened the corset laces. I pulled up the gymslip. Stephanie said that now my training would begin in earnest. From now on, every time I said something, anything, to her, I had to precede it with “Mistress Stephanie”. They must be the first words of the sentence, for example: “Yes, Mistress Stephanie” would be no good. A black mark would be awarded for each time I got it wrong. By the end of the evening, I had several black marks.
The following Friday, the training consisted of instruction in curtseying. By the end of it, I could curtsey properly, holding the edge of my skirt with my fingertips, and keeping my head very level. I asked about curtseying while carrying something, and it was agreed that circumstances could modify the curtsey as appropriate. I now had to curtsey when entering or leaving a room where Mistress Stephanie was present, or when she entered the one I was in. Black marks were awarded for failure to curtsey when I should have done. Along with the “Mistress Stephanie” mantra, it was real progress, and hard work for me. Towards the end of the evening, Mistress Stephanie announced that I had amassed more than enough black marks for my first punishment, and she would carry this out on the next visit. She said nothing about what the punishment would be.
The next Friday, after a week of worrying about the punishment, I was dressed and ready for Mistress Stephanie. My Owner had helped me to get dressed, and asked Mistress Stephanie about the punishment. It was to be six of the best, as appropriate for a naughty schoolgirl, with a slipper (trainer), administered through my knickers. My Owner would watch, to ensure fair play, before going out for the evening. I was told to bend over a chair arm, and grip the back of the chair. I was then instructed in the procedure: I was to ask to be punished, then I was to count each stroke, and beg for another, until they were complete. My Owner was still there, watching. When all was ready, ”Mistress Stephanie, please give me my punishment as is due”, I dutifully said. My gymslip skirt was raised and held up, and the first swipe with the slipper came down. “Mistress Stephanie, thank you for the first slipper. Please may I have another?”. And so on, until the last. I was told that I could not rub my behind, and from now on, whenever I sat down, I was to lift my skirt away, so that I did not sit on it. This made my bottom closer to the chair, and any rough surface that Mistress Stephanie might decide to make me sit on.
She said that she would remove the six spanks from the black mark book, but there were still plenty in there, the account was not clear yet. I never saw the actual list of marks in the book, that was kept from me.
The next Friday, Mistress Stephanie instructed me to bring down my old French Maid outfit, which is a black leotard, a black faux-satin skirt, a full white petticoat just longer than the skirt, and a pair of white frilly tennis knickers. The knickers are clearly visible due to a V shape cut in the back of the skirt and petticoat. There is also a small white apron. I was instructed to change into this outfit, keeping the corset and stockings on. Mistress Stephanie said that it was ok, and would need some work, especially to the top, but would be alright to go on with. She added a mobcap. The evening was spent getting used to the outfit, and ironing the gymslip again.
The next time, Mistress Stephanie brought out a wooden board, with some attachments. She said it was a serving tray, and that I would get very familiar with it. It consisted of a flat wooden board, with one rounded concave side. This was padded, and had a belt attached, so that the buckle was in the middle of my back. Chains connected ring hooks on the board to ‘D’ rings inserted in a dog collar, which was put round my neck, and buckled behind me. This kept the board in place on my stomach, and the collar was adjusted to be a safe fit. Once this was in place, Mistress Stephanie adjusted the chains so that, with me in a normal pose, the board just leaned forward beyond level. There were two cat collars under each side of the board, with bells attached. Mistress Stephanie made sure that all was safe and comfortable, then put small padlocks in rings in the neck collar and the waist belt. I was now locked in. Also, when I put my arms under the board, Mistress Stephanie was able to fasten the cat collars around each wrist and arm near the elbows, further reducing my movements, and making my arms support the tray. On the top of the board at the front was a little bi-directional spirit level, which showed how far off level in both side-to-side and front-to back directions the board was. I was told to keep the board level at all times, and if ever the bells rang, that would be another black mark. Finally, under the front of the board was a small hook, from which the key for the two padlocks was hung, tantalisingly out of reach. For two hours, I had to practice walking up and down, while keeping the spirit levels level, and trying to keep the bells silent. I was instructed to perform curtseys as much as possible while wearing the board. And so far, this was with no added weight on the tray, that pleasure was yet to come.
Mistress Stephanie informed me at one point that she had some new padlocks for the tray collar and belt, and that when she brought them, I would appreciate why they were better than the first ones. When she did bring them, they were huge and heavy, and really added weight to the outfit. Appreciative is not the word I would have used.
Soon, I was informed that the list of black marks was growing, not shrinking, and so my punishment would go up a notch. The following Friday, Mistress Stephanie produced a proper school cane, and this was used instead of the slipper. But I was told that each cut with the cane counted for two black marks, so it not too bad. My Owner approved of this escalation, so there was no escaping it. As the weeks went on, weight was added to the tray, making it harder and harder to keep it level for more than a few minutes. Mistress Stephanie gave me a black mark amnesty for a while while getting used to each new weight, which was appreciated.

There will be more, if anyone is interested in this.

Hugh Edwin.

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This is an excellent story. Please continue it.
Excellent, please write more.
Excellent, more please
Longing to serve women
Always interested in more. If this is based on reality it sounds like someone has had an interesting role playing session.  Big Grin
(06-05-2021, 10:47 AM)Girlygirl Wrote: Always interested in more. If this is based on reality it sounds like someone has had an interesting role playing session.  Big Grin
It is a mixture of fact and fantasy. I will leave it up to the reader to guess how much of each.
(06-05-2021, 10:47 AM)Girlygirl Wrote: Always interested in more. If this is based on reality it sounds like someone has had an interesting role playing session.  Big Grin

Here is the second half.

The second chapter.

One Friday, Mistress Stephanie told me that, as I was obviously comfortable with the “Mistress Stephanie” requirement, it was going to be extended. It would now be “Worshipful Mistress Stephanie”. And she hinted that it might change at a later date with the addition of ”Most ...”. I was not overjoyed at either of these developments. In fact, the second change was made only a couple of weeks later, so my mantra at the beginning of everything I said to her was now: “Most Worshipful Mistress Stephanie”.

By now, my punishment, dressed as a schoolgirl, was the first event every week after inspection when Mistress Stephanie arrived. The inspection always included my dropping the top of the gymslip, so that Mistress Stephanie could tighten the corset laces. I was told that the list of black marks was still growing instead of shrinking, but she had not decided what to do about it yet.

Mistress Stephanie decided that, as a schoolgirl, I needed some weekly homework. She bought me a diary, and I was to record the events, in full detail, of each visit. To do this, I was to be dressed in my schoolgirl uniform, and my Owner would tighten the laces for me. When I finished, she would read it, and sign to it confirm that I had been dressed correctly, including wearing the hat all the time. My Owner would decide when to let me change out of the uniform, sometimes it was only before bed. On Mistress Stephanie’s next visit, she would read and correct the diary log. Any mistakes or omissions gained a black mark in the book.

One Friday evening, I was told to dress in the maid outfit and don the serving tray, which was locked on me, with the huge padlocks. Only my left arm was fastened into the cat collars underneath. I was then ordered to make a mug of tea and deliver it to Mistress Stephanie on the tray. I had to put it on the tray, then move my right arm underneath to support it. This was really difficult, especially keeping the tray absolutely level while carrying it out to her. I was supposed to not cause any of the bells to chime, and I got another black mark for forgetting to curtsey.

I was told at one point that I would be ironing Mistress Stephanie’s clean knickers and bras every week. She liked the results, so started bringing them over while still dirty, and making me hand-wash them. I was allowed to use the dryer, and then had to iron them as before.

One of my homework chores was to modify the cheerleader uniform that she had bought earlier so that it would fit me. This took a lot of work, but eventually was successful. Occasionally I was then made to wear it for an evening.

Once, she had me wear the serving tray whilst doing the ironing, but it made it too uncertain that I wouldn’t mess it up, and it didn’t happen again.

She bought me a pair of bunny ears and a large bunny tail. She said that they only cost £5, she had looked at a remote control fox tail for £95, but decided it was too much money, my Owner would not have approved it. It would have been good fun, though. I dressed in the maid outfit, Mistress Stephanie added the white bunny ears and pinned the tail onto my frilly knickers. After the fitting, I was told to sew the tail onto the knickers during the week. She said that she had been looking at a butt-plug bunny tail, but wasn’t sure if my Owner would agree. It was not mentioned again, although it had sounded interesting.

I was taught to bunny dip, although I could not keep the tray level whilst doing this. Then I was again kept standing in front of Mistress Stephanie while she drank a cup of tea, using the tray to put the cup on. The bells had to remain silent, and the tray had to stay level at all times. When she had finished, I curtsied and went into the kitchen to wash the mug up. My right arm was still free to work with. This became a regular occurrence.

Mistress Stephanie bought me a cuddly toy to sleep with, Sweep, the same as I had had as a youngster. I was told to take it to bed every night.

One evening, Mistress Stephanie took some photos of me in my outfits: the school uniform, with my arms low and also held high, so showing my stocking tops and suspenders; the maid outfit with and without the serving tray; and the cheerleader outfit. She said she was leaving my face out of the images, as instructed by my Owner. She showed them to her after she came home, and my Owner ordered a couple of prints for the following week. Of course, I was not allowed to see the images.

My Owner talked about letting her drinking pals know something of this story. She had already shown some of them the photos that Mistress Stephanie had given her. I was not happy!

Another evening on her arrival, Mistress Stephanie told me to go to my room and wait, as she needed to talk to my Owner. After about ten minutes, I was called back in to join them, and resume the normal procedure, ie the weekly punishment. Naturally, I had to remember my curtseying duties at all times. But I was curious about what they had been discussing, it didn’t bode well for me.

After my Owner had left, Mistress Stephanie told me that she also had photos of me which included my face. The ones that she had shown my Owner had been cropped versions. The full-face ones were safe at home, but she wanted to keep them just in case we ever did this again, it was good insurance. She promised to never send them over the internet. I had absolutely no control over this.

A week or so later, Mistress Stephanie told me to dress in the maid uniform, and introduced me to a face-cock, which is a small leather cock to be gripped in a sissy’s mouth with straps tightened behind her head, and which then presents a full-sized dildo to be used by a Mistress. No suggestion was made of if or when this would be used, I carried it around on the tray for the evening and then it just sat in full view on the side table every Friday. When I asked, Mistress Stephanie replied that its purchase had been approved by my Owner, much to my surprise. She decided to call it George.

All good things come to an end, though. This all started soon after the beginning of Mistress Stephanie’s Spring Term, continued though the Easter holiday, and went on into the summer term. But she was doing her exams, and occasionally called to cancel the Friday evening visit, or sometimes change the day, and since my Owner did not go out to the pub on those days, she stayed behind to watch what happened. On those occasions when she cancelled, my Owner would have me dress in the schoolgirl outfit, with the dreaded hat, and leave me alone for the evening to do whatever chores she decided, while she went out to the pub as usual. She made a CCTV recording of me, to make sure that I never took the hat off. I was warned of dire consequences if I ever did. Of course, I was by now kept in chastity almost all the time, so that was not a problem for her.

Mistress Stephanie passed her exams, and was accepted to go to a distant university, so the arrangement had to finish. On the final evening, my owner replaced the normal chastity device with the Kali’s Teeth Bracelet for the ‘Special’ evening. Mistress Stephanie was of course dressed to tease, with a micro-skirt that showed off her red panties when she sat down. Panties that I had hand-washed and ironed the previous Friday. I was in agony the whole time. She kept me up instead of putting me to bed, and my Owner came home a little early, to find me dressed in the maid outfit and locked in the serving tray. We all said our goodbyes, and then I was positioned in front of the full-length mirror in the bedroom, and she made sure that George, who had never been used, was close by. She produced the keys for the tray padlocks and hung them on the little hook underneath the front of the tray. She then took Sweep, my night-time cuddly toy, and put him on top, and propped my debit card up against him. She had me go and get the diary, releasing one hand so I could grab it, and added it to the tray. She produced her ‘phone, and composed a picture which showed me, from the front, with serving tray, keys hanging in full view, Sweep and my debit card and the diary, with my back, complete with padlocks and bunny tail, reflected in the mirror, and George on the side cabinet. She showed the result to me, and it was so, so embarrassing, with the fact that it also showed my face. She promised me that only my Owner would ever see it. Then she said “Oh no, I’ve forgotten something”, and went to get the bunny ears, which she put on my head over the mob cap. She told me to smile this time, and took another photo. Then she took off my cap, and took another picture with me wearing the ears without the cap.

Her final comment was: “I will return when I get my first break from university, and see how you are both doing. I still have your black mark book. If your Owner hasn’t used George on you by then, I will make sure that he doesn’t go to waste. Don’t forget to curtsey as I leave”. I was violently reminded of the Kali’s Bracelet I was wearing. She picked up the diary, and left, saying that she would e-mail me all the pictures she had. She sent me the three taken on that last day, but only sent the cropped versions of the others, not the full-face ones. She must have forgotten...

I hope everyone enjoys this. Hugh Edwin.

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Thanks for continuing your lovely story.
Another great chapter - good to see that some useful domestic tasks were woven into your experience as well.  Big Grin
Brilliant and you got to learn some useful home skills too.

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