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The Chaperone's Apprentice

by Charlotte Arabella Graham

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© Copyright 2016 - Charlotte Arabella Graham - Used by permission

Storycodes: Solo-M; advert; job; maid; F/m; cd; ts; latex; boots; toys; insert; inflate; hood; mitts; bond; outdoors; catsuit; ball; encase; play; susp; cons; X

Well, here it is, The Chaperone’s Apprentice, the sequel to Ms Westbury's Niece. Enjoy

Part 1

Cecilia lay on the bed looking up at the ceiling. This last twelve months. Was it all a dream? Would he wake up and find he was still in the old hum-drum World. He pinched himself hard.

“Ouch, that hurt.” Cecilia wasn’t sure that one couldn’t dream of pinches but it seemed real enough. But what a year. Twelve months ago all had seemed rosy then, without any warning, he had been summoned to the boss’s office and told that his services were no longer wanted. Going home and wondering what might now become of him, he had picked up a piece of newspaper littering the sidewalk, pavement, he corrected himself, ‘You’re in England now!’ About to drop it in a bin he realised that it was not a local one; rather it was English. He had taken the foreign paper home as something to read and found the advert.

Successful businesswoman seeks a live-in maid and occasional travelling companion. The successful candidate will be disciplined, intelligent, resourceful, but willing to be totally obedient. Employment will be on an, ‘all found’, basis and will be subject at all times to strict, flat extra, dress code.

Having read and re-read it a couple of times, the wording still seeming a bit strange. Clearing up the next day, doing his maid’s chores as he thought of them, he had suddenly realised what was so odd. It was the, ‘flat extra’, that appeared, seemingly out of place, in the middle of the bit about dress code. It was, as he now knew, latex, lightly disguised! The maid was going to have to wear latex uniforms; perhaps even when acting as travelling companion. It was all too tempting, especially in his present circumstances. He typed-out a letter; the CV suitably doctored to be ambiguous about matters of gender, and sent it off not really expecting to hear anything further.

Then, ten days later, a letter from England dropped into the box containing a one-way air ticket and a request to attend for interview the following week.

His mind went back to the first meeting with Ms Westbury. Gosh, she was formidable. So upright and precise. And he had had to appear in front of her as a girl. He’d come as a man on the ‘plane and only changed in the hotel where he had stayed for the night. But she’d seen straight though. He could hear her saying it now, “There can, of course, be no concessions as to gender.”

The first few weeks had been hard, very hard. “If there is something that you are unable to do, you will be trained. After which there will be no excuse”, Ms Westbury had said. He smiled to himself as he remembered some of the training. It seemed so easy to carry glasses on a tray now; but then, on the tread-mill? And the corsets; were they really that tight? And his near dismissal. That must have been very close!

His mind wandered again.

‘Poor old Joseph’, he thought, ‘I wonder if the Contessa has found the key yet. I bet she hasn’t’.

Then there was Ms Westbury herself. He still found it strange to say, ‘Aunty’, when talking to Ms Westbury, even more difficult to say, ‘Aunt Lavinia’, saying that she was going to start her special chaperoning agency again and wanted to call it, ‘Westbury and Niece’.

‘Actually’, he thought, ‘it probably ought to be Dr Westbury’.

He knew that she was an orphan who had, somehow, managed to go to university then, stayed on to do research, paying her way by becoming a top-flight society mistress, which turned out to be a much the most lucrative occupation.

‘’spec she got her PhD as well’.

He had always had a rather androgynous appearance and now he was unsure whether he was a girl or a boy. After taking 25mg dose of Cyproterone acetate twice a day for months now he was at best a bit of both. He was now dressing like a girl – a rather sexy one at Ms Westbury or rather Aunt Lavinia he corrected himself, insistence. Sometime he thought that he was thinking more like a girl, though how could he be sure. Certainly body-hair was very much less, almost non-existent in fact with what was left, downy and easily removed. Then there were now breast-like mounds where none had been before while the continuous wearing of tight corsets had had a very visible effect on waist-size. No looking back, though. From now on it would, perhaps best to be a, ‘she’.

And so as to avoid confusion, so shall we.

Anyway, it was time to get up. Whatever may have become of Cecilia, now Ms Westbury’s adopted niece, the urge to act as maid and to make breakfast was by this time so deeply engrained that the thought of doing anything else was impossible.


Even still a little embarrassed Cecilia turned to Ms Westbury and admitted, “I’ve been looking in the toy cupboard”.

That was name they had unconsciously adopted for the room in which Ms Westbury kept all the many things she had held for clients when she was in practice as a professional Mistress.

“So as to know what’s there it case it should be wanted”, she added, rather too quickly. She hurried on, “… and came across these”, holding out a pair of inflatable latex bondage mittens and a ball hood. “I’ve always wondered how it would feel to wear them, being sort of cut-off from everything, but could never afford them. And, in any case, you would have to have someone to help put on the mitts and to blow them up and I didn’t.”

All this came out in a bit of a rush.

Ms Westbury smiled. Cecilia didn’t notice. If she had she might have wondered if it was in remembrance of occasions past or anticipation of what was to come.

“They can be quite fun”, she agreed. “Or not, depending on what happens to the wearer afterwards”, adding with a smile. “I will put them on for you but you need to wear something suitable. Go and change into one of your latex parlour-maids’ outfits; the hood and mitts will go well with that.”

Cecilia scurried off, up the stairs and along the passage, almost running to the Apprentice Room, as it was now called, across the passage opposite to Ms Westbury’s suite.

In fact, Cecilia had found many more inflatables in the toy cupboard than she had admitted. These included a gag but, more intimidatingly, a butt-bung. There were, in face, a range of sizes of these. She had chosen what seemed to be a medium one; even though that seemed pretty large. But now it was preying on her mind.

She had anticipated what her Mistress would say regarding a suitable dress but, in any case, wanted to try the new Victorian parlour-maids’ dress and apron she had ordered. They had arrived by post some days before and she was impatiently waiting for an opportunity to wear it. Superficially the dress was much like the previous one, though the skirt was even tighter and more hobbling, while its stiffened neck was longer, extending upwards as a posture collar, even a neck corset, so as to hold the wearers head up and very nearly immobile. And, yes, the black latex was much heavier, the thickest that the maker could handle in fact. What was really different, however, was the skirt. At the back it had a large heart-shaped opening, edged with the same white ruffled latex trim of the rest of the dress so as to reveal the wearer’s bottom in all its glory.

Cecilia worked herself into the dress.

‘My, it is tight and stiff, did I actually order it quite like this? I suppose some of the sizing was a bit optimistic’, she thought. ‘…and heavy too’.

She had already decided that the dress deserved ballet-boots. At one time, was it really only a few months ago, they were something she had only dreamed of? Now they were almost ‘every day’. Well, may be not quite; but with gel pads in the toes she could walk fairly well for short distances. Now she was going to force herself to keep them on for a long time; just how long she didn’t know. Perhaps it was as well.

Then there was the butt-plug. She decided against it.

‘Can have too much of a good thing’, she thought. But there it was, on the bed, glaring at her as she got changed. She even got to the door to go down stairs again only for it to call her back again.

“Oh well”, she said, addressing it and picking it up. “I suppose I shouldn’t miss the opportunity of showing you off. It’s only like an enema, after all”.

Of course pushing it in was easier said than done. At first her sphincter clamped up tight. Three tries and a lot of lubricant later it slid in. Once the widest part was passed the sphincter the plug was rapidly draw-in until brought to rest by the big end-stop, the outside closing up again so as to hold it firmly in place.

Cecilia gave the bulb an experimental squeeze. The plug inside her swelled and pressed slightly.

‘Not exactly comfortable’, she said to herself, wiggling to try and get it in a better position, ‘but certainly different’.

This time she did make it to the door and down the stairs; conscious that, with ballet-boots and the thing inside her, walking was a whole new experience.

Cecilia returned and showed off what she was now wearing to Ms Westbury.

“Ballet boots, just the thing, locked-on of course. Good. Give me the keys. And a tail too, excellent”, she said. “All right, let us finish dressing you.”

“It is an interesting procedural point”, said Ms Westbury as she worked the first mitt on to Cecilia’s right hand and buckled the strap round her wrist, “whether it is more interesting to first fit the mittens or the hood. On the whole I think the former is preferable.” She said, fastening the other mitten and blowing both up into hard balls squashing her already clenched fists even tighter. “Mittens render the wearer incapable of doing anything while waiting for the hood or whatever else may be in store”.

“That”, she went on, “can be rather interesting.”

Cecilia tried moving her hands. No, she really couldn’t move her fingers or feel anything.

“I could leave you like this but I’m sure that you want to try the hood. But ear-plugs, we have to have ear-plugs. I think that I know where some are. I will go and fetch a pair. You will not let your wandering hands do anything naughty while I’m gone, will you?”

Cecilia flapped her now useless hands or at least what used to be, by her side. How could she now they were reduced to little more than rubber spheres!

Ms Westbury disappeared. She was gone for a long time, or so it seemed to the helpless Cecilia. Eventually she returned brandishing the biggest ear-plugs imaginable.

“For use in very noisy environments”, Cecilia was told.

Ms Westbury inserted the plugs; then turned her attention to the hood.

“I am sure that you will have noticed”, she said in her best lecturing mode, raising her voice so that Cecilia could hear, if only faintly, “that the hood has two layers. The rubber on the outside is rather thick so that it expands only a little while the thinner inner layer presses against the head and face. Some hoods are made with a metal cage to further prevent expansion so that the pressure even greater. Shall we proceed?”

Carefully, Ms Westbury pressed the breathing tubes into her niece’s nostrils then, making sure that she could breathe easily, pulled the hood over Cecilia’s head, zipped it up at the back, fastened the buckles round her neck and started to inflate it.

Once started it seem as if Ms Westbury could not get enough. Not content with simply reducing the top of Cecilia’s to a round beach-ball where her head used to be, she turned Cecilia round and gave the hanging bulb several squeezes.

“It would not do for it to work loose, would it?” she said, though Cecilia could no longer hear anything.

In fact, Cecilia was beginning to wish that her aunt had been rather less enthusiastic when seeing the butt-bung. She would also have liked to tell her to stop pumping but she couldn’t. Ms Westbury carried on so that, when finally she did relent, Cecilia was convinced that she was being split in two. Not that she could do anything about it – even if she had wanted too!

Ms Westbury snapped a dog-lead onto one of the D-rings on Cecilia’s collar and, after starting her with a none-too-gentle tug, led her out through the French windows and on to the stone-flagged terrace. Cecilia, cut off from sight and sound, had little idea where she was except that now, under foot, it was hard and a little uneven rather than soft and carpeted. Another tug on the lead was, clearly, a signal to stop. Cecilia guessed that they must be at the top of the shallow steps leading down to the lawn at the rear of the Old Rectory that her aunt had bought on her first retirement.

‘How to get Cecilia down the steps?’

For once Ms Westbury’s impeccable planning deserted her; was she letting herself get too excited? She turned Cecilia round so that her back was to the three steps then, holding her very tight, gingerly eased her down, one tread at a time. At the bottom it was unclear who was the hotter; Cecilia in her rubber dress or the much relieved but panting Lavinia Westbury.

The steps having been negotiated, Cecilia was unclipped from her lead, spun round three times, much like in a children’s game of blind-man’s-buff, so as to disorientate her, not that even before she had much idea of which way she was pointing, and given a smart push from behind to send her on her way.

For a while she blundered about. The only sensation she could feel was that of the heels of her boots sinking a little into the ground as she walked or rather, staggered, along; she decided that she must still be on the lawn though where but, by now completely disorientated, she had no idea.

Suddenly she felt a sharp push from the side. Though Cecilia had no way of knowing it, she had been about to fall into the fish-pond, only to be saved at the last moment.

For the next half-hour Ms Westbury left her adopted niece as alone as possible, only once or twice stopping her from crashing into a tree or tripping over a croquet hoop or, again, from falling into the pond.

At last Cecilia felt the lead being reattached. Going back in the house, she thought. But she was wrong.

She was led across the grass; then stopped. She felt the lead unclipped but something else was happening too. She tried to move but couldn’t. Then she realised what must have occurred. Ms Westbury had fastened her collar to the chain over a branch of one of the trees that usually supported a wicker hanging-chair, and had left her there!

Cecilia’s toes were beginning to hurt. She tried shifting her weight from one foot to the other but it didn’t help, in fact it made it worst as, with each move, the boot heels dug deeper into the lawn putting more tension on the chain that fastened her neck.

Cecilia had no idea how long she stood there. All was black inside the hood and the sound of the church clock chiming, indistinct at the best of times, was completely blocked out by the ear-plugs and hood with what little remained of any sound totally drowned by that of her own breathing.

Then Cecilia felt the dog-lead being reattached to her collar while being released from the chain. For a moment she didn’t realise what was happening. With a tug she was set in motion, staggering at first, as she had been immobilised for such a long time. Ms Westbury led her back to the house; getting up the steps proving to be a lot easier than it was going down them.

Back on the lounge carpet Cecilia was in more familiar territory. Ms Westbury let down and undid the mittens, allowing Cecilia to again flex her hands. Finally she slowly pulled off the hood. Cecilia blinked at the sudden change in the light but blinked again.

What greeted her she could never have imagined, even in her wildest imaginings. Her aunt was dressed from top to toe in a black latex cat-suit; her head covered by a hood with small openings only for nostrils and narrow slit at the mouth. The latter, reinforced round the edge with extra rubber so it could take a breath-through gag, made Ms Westbury’s normally precise diction a little blurred. Even her eyes were covered over with plastic lenses that were already steaming up.

“I obtained this equipment for one of the last clients in my previous profession. It was never used. It was, however, always my view that it was impossible to know what a client’s sensations might be when using a piece of apparatus unless, subject to any physical differences, one had tried it oneself beforehand. Now, rather belatedly I admit, it is time to try out the ball bag.”

There was a pause while Cecilia, still slightly disorientated from her experience, took all this in.

“Well, are you going to help me in or shall I blow-up your tail a bit harder?”

Cecilia whisked her, ‘tail,’ away as Ms Westbury tried to grab at the inflator bulb, missing it by quite a margin, hampered as she was by hood and its now almost opaque lenses.

“Now hurry up, please, I had quite forgotten how stimulating the bra and panties are that I put on under the catsuit”, she said, kicking off her heels.

Later, her concern became clearer to Cecilia when washing their things before putting them away again; the panties had two solid didoes while both of them had rubber nubs at strategic places on the inside.

The pair went over to the pile of heavy latex on the floor.

The ball was made in two parts that zipped to together. The zips, rather like those of a soft suit-case, had two sliders with rings on them through which a small pad-lock passed so joining them together. Not that someone inside the ball could get at the zips to undo them but locking the zips would clearly be very symbolic. Arrangements for breathing were a little different from those of the hood. Pressure inside could not be relied on to keep tubes in the nostrils so, instead, a full medical mask was provided attached to a short tube, the open end of which terminated in the centre of the short piece the join between the fixed end of the zip.

“Exactly how one is supposed to proceed is unclear and, in practice, the client may already be restrained. For want of any better idea, I suggest that I lie on one half while you zip the two halves together”.

Ms Westbury put on the mask and lay on one side in an otherwise fœtal position, on one half while Cecilia zipped the two parts together, locking them for good measure. Ensuring that her aunt was breathing normally she switched on the pump and began to inflate.

Inflating it took quite a while but, eventually, she was rewarded with a ball, 150cm in diameter, not perfectly spherical because of the zip, but nearly so, her aunt now more or less upright, sandwiched between the two halves.

Now what?

Cecilia tried an experimental press on the top of the ball; it sprang back and bounced a little. With Aunt Lavinia inside it the ball too heavy and too big to lift but it was quite springy. Cecilia tried bouncing it some more. Rather like getting a swing going, after a few presses it was bouncing quite well, turning at random as it did so.

‘Aunty must be getting quite a ride, good job she’s not prone to be seasick’, thought Cecilia, the bouncing ball so that it rolled in the direction of the open French-widow. Out she went onto the terrace; the ball hardly noticing the threshold bar. Cecilia, though, found that the ball had a mind of its own. The wind caught it and it rolled, out of control, along the terrace in the direction of the steps down to the lawn. Cecilia ran after it, wishing that she had not decided to wear locked-on ballet-boots after all.

In vain. The wind caught the ball again. It teetered on the top step then ever so gently, in slow motion it seemed to Cecilia, bounced down them and onto the lawn where it came to rest.

Cecilia tried pulling the ball but the grass offered rather too much resistance.

‘Would be more fun to play push-ball with others,’ she thought, forgetting that inside, in some orientation or another, was her aunt.

Then she had an idea.

The ball had stopped by the tree where, a little while ago, she had been fastened. The patch where the zipper started was at the top and, for the first time, Cecilia noticed that it had a stoutly reinforced, ‘D’, ring. Clearly it was intended to secure the ball – even suspend it.

Pulling down on the end of the branch, Cecilia manages to attach the ring to the chain. The branch sprung back lifting the ball a few centimetres off the ground. The clearance was not great but it was enough; the ball now free of the grass, gently swung to-and-fro in the breeze.

Cecilia sat down on the stone bench, and got up again straight away. She had quite forgotten about the thing in her bottom, until she sat on it, plus the fact that the seat was cold to her bare back-side too!

She looked at the ball, with a surge of temptation to get her own back by leaving it like that for a long time. She took a tour round the lawn, sticking to the hard bits where her boots suck in less. Getting back to the ball she gave it a push that sent it swinging and spinning the same time. Cecilia was about to give the ball an even bigger push when she relented.

‘You can have too much of a good thing’, she thought, ‘even if Ms W did want to try it out’.

Pulling the branch down again, she unfastened the ball from the chain. That presented another problem; how to get it back into the house? Her aunt certainly wouldn’t take very kindly to being undone in the middle of the lawn.

‘Oh well, nothing for it!’, and began to roll the ball back. It seemed to be easier this time, even going up the steps. Once in the lounge, she let down the ball and unzipped it. Ms Westbury was fast asleep, ‘like a baby’, Cecilia thought.

She put cushions under her aunt’s head and tip-toed out (though she could hardly have done otherwise in those boots) at the same time wishing that she know where the keys to the ankle-locks were. It was going to be a long session.



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