Chapter 24

Anna’s ‘dressing lesson’ had continued for another hour before finally Miss Jackie had tired of making her change from pyjamas to school uniform and back again, each time having to neatly fold the garments she had taken off. And each time Anna failed to complete the process within the sixty seconds time limit allowed – which was almost every time – she was made to bend over in her pyjamas and receive two more strokes of the warden’s paddle across her backside.

Anna lost count of the number of times she had dressed and undressed out of her hated schoolgirl uniform: rough cotton blouse with rigid starched collar and tie, bottle green wool stockings held up by a stiff, deep suspender belt, all securely encased in thick elasticated-leg navy bloomers worn under a dark green serge gymslip. The clumpy school shoes and a grey felt hat worn with elastic behind the ears and under the chin that completed the humiliating outfit. After a while she no longer cared how ridiculous she looked as she struggled in and out of her clothes, trembling fingers fumbling to fasten the buttons of her blouse and tie her tie. The faster she tried to dress, the more awkward and ungainly she became as she attempted to pull on her bloomer-style knickers, all the time being urged by Miss Jackie to go faster.

“I can’t go any faster,” Anna protested, begging to be allowed to stop. After a while, she had been reduced to a state of pleading, weeping exhaustion, longing for her ordeal to end. “No more, please, I can’t go any faster,” she implored again and again, but to no avail. Again and again she was made to change from uniform to pyjamas and then back again into uniform, stepping into and out of her knickers and pyjama bottoms, pulling on and taking off her blouse and pyjama jacket, each time buttoning and unbuttoning each garment with trembling hands.

To add to her misery, each time she failed to complete the process in time, she was ordered to bend over in her pyjamas and receive two or three strokes of Miss Jackie’s paddle. When at last the dressing lesson came to an end, Anna was left slumped on her knees, red-eyed and sobbing with fatigue, her bottom red raw and stinging. It was a lesson she did not want to repeat.

****

After her ordeal Anna made her way along to the classroom block, dressed in her schoolgirl uniform, for afternoon class was due shortly. Miss Cleo was the Form Mistress, a pretty, bright-eyed girl several years younger than Anna. Someone who had happily made Anna suffer, day in, day out, for months. The more attractive a prisoner was, the more Miss Cleo liked making them suffer. And Anna was very attractive.

That was something of which she had once been proud but, since coming to Redesdale, she bitterly regretted.

Miss Cleo came striding cheerfully into the classroom. As usual, she was wearing a full-length dress of powder blue satin. In her hand was a cane which flickered whippily up and down. She removed the one which hung by the easel and put the new one in its place.

‘You may sit down,’ she said. ‘Well, girls ... I see we have a new member of our class today!’

Miss Cleo was referring to Virginia Bradley-Jones, the ex-MP who had arrived at Redesdale that morning having been sentenced to six months for fraudulently claiming expenses. Her arrival had caused quite a stir among the other inmates, not least because at 39-years-old she was several years older than everyone else and her fall from grace as a former politician was more acute than anyone else.

The class settled itself in silence. The silence of resignation. And of dread. Several hours of each day were spent in the classroom of Miss Cleo. She was much to be feared ... even if the instruments she was empowered to use were lighter than those used during the evening Punishment Detail.

'Right,’ said Miss Cleo. ‘Classical History. Get your text books out.’

Many hearts sank in that room, but none more than Anna’s. It was a difficult subject for all, but perhaps Anna’s worst.

Although Miss Cleo would have been the first to admit she enjoyed punishing anyone at any time, she would also have admitted she liked punishing women like Anna most of all. The shapely ones. The sexy looking ones. The ones she felt possibly more attractive than herself.

Accordingly, it would amuse her to see to it that Anna was the first one to experience the new cane. Needless to say, that was not something too difficult to arrange!

Towards the end of the class, with six errors in her test on Classical history, Anna found herself kneeling on the trestle stool in front of Miss Cleo’s desk, bending over that desk ... pulling up her gym slip skirt high .. and pulling her knickers down to her knees.

‘Six errors, Anna,’ said Miss Cleo, flexing the new cane and running her fingers over its smooth hard end,’ what do you think that merits?’

Anna had been positioned often enough before where she was. She had even learnt to take both strap and cane with no more than clenched teeth gasps. Something which, at one time, she had never thought it possible for her to do. Now she was facing something new ... different ... more painful. Her lushly rounded buttocks gave an involuntary twitch .. for all to see.

‘Six ... I suppose, Miss,’ answered Anna.

‘You suppose correctly,’ said Miss Cleo.

The arm rose and fell. The cane whistled and hit. The bright weal leapt up across the twin curves.

‘Agghh ... owww ... aagghh!’

Anna’s cry was uninhibited and she jerked violently. The stinging, burning pain of the cane seemed twice as bad as usual.

Sssswweee ... craacckkk!

‘Owww ... oowww ... aahhh ...’

Anna’s shapely bottom squirmed frantically. Round and round, as well as juddering up and down. Miss Cleo observed it with evident relish.

‘Hurts more, eh Anna?’

‘Y-Yer .. esss ... y-yes ... Miss ...’

‘Good!’

Sswwweee ... craacckkk!

Another series of breathless yelps from Anna. More convulsive contortions of her bottom. The class looked on in shocked dismay. All were aware that Anna could take the normal cane with relatively silent stoicism. What must this new one be like!

Anna’s yelps and writhings continued unabated until she had received her ration of six. Then, with a smug smile on her lips, Miss Cleo ordered the tall blonde to pull up her knickers and return to her place in class. The new cane was replaced on its hook.

There was a strangled gasp from Anna as she resumed her seat.

Miss Cleo smiled even more smugly. ‘I think it was evident to all,’ she said, ‘that Anna found those six rather more painful than usual. Yet I gave them to her no harder than usual. All of you, if you don’t watch your step, will soon be finding the same. Now let’s get on with the next lesson. Get out your Mathematics books.’

Within minutes the class had settled down to another couple of hours of slogging mental grind.

Yet every mind was keen and alert to its task. Putting in maximum effort.

Perhaps Anna, with six brand new, throbbing weals across her bottom, was the most keen and alert of all!

Chapter 23

Another cold grey early morning with a sharp little breeze out of the east and a hint of drizzle in the air. The three women in detention are once more awakened by the yells of the wardens.

"Waaake up! Get out of bed, NOW!"

Two of the three fall groaning out of bed. Catherine has to wait for release. Once Melanie and Anna are able to get up all three are lined up at the foot of their beds. Pyjamas are unclipped and they are ready to be inspected. They stand there shivering in the early morning chill; Melanie is aware of Miss Jackie’s eyes running her over. “What’s Matron going to find in your plastic panties this morning?"

Melanie stares sullenly back at her.

"Cat got your tongue? Well let's make sure you're nice and warm for Matron. Get running!"

Melanie is made to jog up and down the dorm, waddling awkwardly from the thick padding between her legs, the binding around the legs of the plastic pants scraping at her sore skin where it has been digging into her all night. Her present discomfiture is brought to an end by the arrival of Matron.

She starts with the naked and shivering Catherine, but once again a minute examination of her pyjamas produces no evidence of morally debilitating activity.

Anna groans as her pants are pulled down and the padding falls to the floor, revealing the hessian pad, dark with sweat, running between her legs. As Matron releases the bindings and removes the belt the others can see the red and irritated patch that the scraping of the hessian has produced. Anna groans with relief as it is removed.

"I trust that this will be a reminder to you to restrain yourself in future, Dobson?"

Anna can only groan in reply.

Matron turns her attention to the remaining two. She indicates Melanie to the wardens: "Get her pants down, while I check this one."

Miss Jackie moves forward and starts to ease down Melanie's pants, her thumbs deep inside the waistband.

Anna winces as Matron yanks down her plastic pants and pulls out the pad. Inspection over, the wardens unclip the last of the mittens and bonnets and send the women scattering for the showers, with a few slaps over their aching bruises.

The showers are as icy as ever, but this morning they are provided with shower caps which do a little to mitigate the head aching impact of the deluge.

Once more it's the naked run back to the dormitory, showing off their lividly bruised bottoms to the world, not that there's anybody about to see them at that still early hour. Upstairs in the dormitory their uniforms have been laid out on their beds. The same scratchy woollen stockings and vests, the same baggy knickers and navy bloomers with the thigh-pinching elastic. Rough cotton blouses and tight collars, heavy serge gymslips and clumpy shoes.

At last they are dressed and ready for Miss Jackie Frayn's inspection.

"Arms by your sides!"

Miss Jackie adjusts Anna's tie, straightens the bodice of her gymslip, giving her breasts a little squeeze; pulls down the legs of her knickers and presses her hand against Anna's crotch. All the while Anna fights to stand still and keep her arms by her sides. Miss Jackie tears Anna off a strip for the untidiness of her uniform; she is particularly annoyed at her failure to have her hat elastic running in the prescribed fashion behind the ears and under the chin, where the extra distance makes it much tighter and uncomfortable.

“Since you don’t seem to be able to get dressed correctly, Dobson, I think we had better give you a dressing lesson. You can begin by getting back into your pyjamas and be quick about it. You have exactly one minute!”

While Miss Jackie looked at her wristwatch, Anna hesitates momentarily then hurriedly pulls her gymslip over her head, undoes her tie and begins unbuttoning her blouse, kicking off her shoes as she does so. The other women prisoners watch in silence as Anna peels the tight-fitting elasticated bloomers down her legs, followed quickly by stockings, suspender belt and knickers. Naked from the waist down, she grabs her pyjamas and pulls on the trousers, removes her vest and finally puts on her pyjama jacket.

“Thirty seconds,” Miss Jackie announces as Anna hastily fastens the buttons and ties. “And don’t forget your bonnet.”

Anna had certainly not forgotten her bonnet. Nor had she overlooked the fact that she would be expected to fold the clothes she had just taken off. Squatting down, she carefully folds each garment, placing them in a neat pile in the prescribed manner, shoes and stockings on top, underclothes, shirt, tie and gymslip underneath. Standing up, she holds them out for inspection.

Miss Jackie glances at her watch again, then studies the pyjama-clad girl standing nervously to attention in front of her.

“Right Dobson… You now have one minute to get dressed again.”

Anna knows this is going to be the hard part, with so many more items of clothing to put on. In a matter of seconds, she has stripped off her pyjamas and is pulling on the woollen vest, baggy grey knickers and rough cotton blouse she has just removed. Putting stockings on while standing proves more difficult, causing her to hop about in an ungainly fashion while pulling them up her legs. Next the suspender belt, its unfamiliar fastenings proving awkward, then on with the navy bloomers.

“Thirty seconds!”

Jackie Frayn’s time check spurs Anna to even great effort to finish dressing within the time limit, but her fingers struggle with the tiny buttons of her blouse and, to make matters worse, she has considerable difficulty knotting her tie. Gymslip and shoes follow, and finally on with her hat just as Miss Jackie announces: “Time’s up!”

Anna makes a face of sullen despair as she stands to attention once more. Her pyjamas lie in an untidy heap at her feet where she has discarded them in her anxiety of beat the clock. Yet she so nearly succeeded.

“Not good enough, Anna,” Miss Jackie says mockingly. “You’ll have to do better than that.” She bends down, picks up the pyjamas and thrusts them at Anna. “These won’t do, will they? They’re supposed to be neatly folded on your bed, not on the floor.”

Anna takes the pyjamas and carefully folds them before placing them on her bed, all too aware that she is probably going to have to put them on again.

Miss Jackie watches her, enjoying the control she had over the young woman in front of her.

“Now let’s see if we can do it properly this time.” Miss Jackie glances at her watch. “Go!”

Without a moment’s hesitation, Anna quickly pulls her hat off, lifts her gymslip over her head, undoes her tie, unbuttons her blouse and removes both it and her vest together. Shoes are kicked off and down come the navy bloomers again, elastic snapping at the flesh of her thighs as she frantically pulls them off, quickly followed by stockings, suspender belt and knickers. Then it’s on with the pyjamas again, jacket buttons and trousers fastened and finally the bonnet just as Miss Jackie calls “Twenty seconds!”

This time Anna doesn’t wait to be told to fold the clothes at her feet. Stockings, underwear, blouse, tie, gymslip, hat and shoes are all folded neatly again and held out for inspection.

“Don’t forget your bonnet, Dobson.”

Anna has certainly not forgotten her bonnet. Nor has she overlooked the fact that she is expected to fold the clothes she had just taken off. Squatting down, the pyjama-clad girl carefully folds each garment, placing them in a neat pile in the prescribed manner, shoes and stockings on top, underclothes, shirt, tie and gymslip underneath. Standing up, she holds them out for inspection.

“Still not quick enough, Dobson. I think it’s time to stimulate that big bottom of yours into action. Now get into position.” Miss Jackie was determined to teach her charge a lesson she would not forget in a hurry.

Anna knew that getting into position meant bending down and presenting her backside for a spanking just as she had done on many previous occasions. Feeling suddenly cold and vulnerable, she stepped into the middle of the room. Bending over, her ample backside was thrust out invitingly as she touched her toes, stretching the pyjama material tight. Anna’s hair fell forward untidily and her buttocks trembled nervously, making ripples in the fabric that betrayed her growing apprehension as she waited.

For a moment Miss Jackie eyed Anna’s pyjama-clad backside and then, taking careful aim with the leather-covered paddle in her right hand, struck the left buttock cheek a resounding blow that dented the thin pyjama material deep into the soft, yielding flesh.

THWACK!

In the stillness of the room, the noise was like a firecracker going off, and Anna’s head shot up, her hair flying out as she gave a sharp intake of breath. Holding her position, she waited for the next, her buttocks clenching convulsively in anticipation.

THWACK!

This time, Miss Jackie struck the woman’s right buttock with as much force as she could muster, almost causing her to topple forward. Unable to see clearly through the tears in her eyes, Anna fought to stay in position as the pain seared into her bottom, determined not to cry out. Worse almost than the pain itself was the awful humiliation of having to submit to a spanking at her age like a naughty child.

Chapter 22

There's a heart-stopping pause before one of the wardens points at Anna. The slow crooked finger beckons, then indicates the horse. Very theatrical. But no sooner has Anna shuffled her leaden legs forward than she's told to stop.

"Take off your pyjamas!" The wardens are grinning again and Miss Jackie makes no move to contradict them.

Anna's hands are shaking as she struggles to unbutton her pyjama jacket and then steps out of the trousers. She goes to undo her bonnet, but no… "You can leave your bonnet on, Anna!" The wardens can’t help laughing at the sight of the chubby young woman standing naked except for a bonnet on her head. "We wouldn't want you to catch cold."

Then they advance on her, marching her over to the horse once more. She's dragged across it, and, like the others, she's strapped down by wrists and ankles but she also gets a broad strap around her middle, this time making sure she can't ride up from her ankle straps and thrash about in an unseemly fashion.

At last she's firmly secured again. The wardens retreat to enjoy the show and Miss Jackie begins to take up the measure of her target. Anna's stomach churns at the faint whistling sounds of the measuring strokes; she flinches at the light touch of the cane as it taps on her. By the time the first stroke lands she's already keyed up to fever pitch. Anna thrashes about, as much as she can, her determination to withhold from the wardens the satisfaction of seeing her struggle lost in an angry wave of memory and resentment. Not that it makes any difference to Miss Jackie. The restrained gyrations of the bare bottom in front of her do little more than induce a degree of divergence in the angry welts she's raising on the flesh.

Her rancour sees Anna through the first four strokes and an incoherent yelling boosts her through the next two, but Miss Jackie is not having any more of it. She pauses while Anna's jerky struggles and noise subside. "Have you finished making an exhibition of yourself, Anna? I would have expected a little more self control from a schoolgirl, even one sufficiently lacking in it to have ended up in detention in the first place."

Anna is drenched in sweat and rigid in her restraints. Her breath is coming in a shallow rapid panting and she would gladly have leapt off the horse and punched the nearest warden on the nose, if she was able.

Miss Jackie is still waiting. "Well, Anna, have you regained some semblance of composure?"

The need to acknowledge her surroundings grounds Anna with a bump and she manages a sullen "Yes, Miss," knowing it will be the permission for her caning to resume.

"Very well." Miss Jackie takes up her stance again, once more measuring her distance, although this time the two or three measuring taps are hard enough to make Anna wince.

One… Anna jerks at the fiery diagonal stroke. Two… she's twitching at the matched burning across the other buttock. Three… she's groaning at the cross hatched bruising. Four… she's giving choking, tearless sobs as the bone deep ache and burn spreads to the other side.

A little rational part of her has watched and counted; she's had fourteen: Melanie had twenty. Catherine had ten. Surely that's her quota done.

She hears Miss Jackie move around from the rear striking zone and out of the corner of her slightly misted over eyes she sees her come just into her restricted view looking back down her left side. Anna groans and slumps in her restraints. At last it's finished.

No it isn't.

Anna gasps at the hiss of the descending cane and squeals like a stuck pig as it carves a line half way down across the back of her left thigh. The strokes aren't nearly as hard as the earlier ones, but they still have a stinging bite, and with less padding over the muscle, raise bruises every bit as livid as those on her backside. Miss Jackie finishes the four on Anna's left thigh and calmly moves around the other side to lay on four matching bruises on the other side.

Anna is wriggling and whimpering and her eyes are tight shut. They open wide when Miss Jackie Duncan another shallow diagonal across her buttocks and re-ignites the fire smouldering there. That, and the final counter diagonal which sets Anna squealing afresh are Miss Jackie's little extras to reward Anna for her earlier exhibition.

"Thank you. You may let her down." Jackie Frayn tosses the cane aside, nods to the wardens and makes to leave. "I'll inform Matron that these girls are ready for bed."

Anna lies panting on the horse, overwhelmed by the agonising pain enveloping her rear, momentarily too exhausted by her fight for control to notice that the wardens aren't exactly rushing over to release her. Her attention is attracted by one of the wardens tweaking her nipple. They are gathering around her.

"You've disappointed us, Anna."

"You didn't cry for us."

They are curling her hair between their fingers, flicking at her breasts. Anna has a sick sinking feeling that the wardens haven't finished with her yet. She feels a cool hand sliding over the burning ridges carved into her buttocks.

"So we'd better see if we can finish the job."

Anna gives a choked cry as the hand on her rear gives her a stinging slap. The other wardens quickly surround Anna and undo the straps restraining her, holding her upright as she is hauled off the horse. Matron and the maids return as the weeping Anna is dumped across the end of her bed.

"Right, time these girls were in bed."

The warden hustle around Melanie, securing her pyjamas and tossing her into bed. She whimpers as the rough flannelette material scrapes her sore skin, but she's glad to be in the security of her bed.

Catherine stands sullenly as the maids pull her up from over the end of the bed and then lie her on her back on the bed. She winces at the feel of the rough woollen blankets on her backside, but makes no sound as a thick pad is placed between her legs and held in place with a pair of tightly fitting briefs.

Next comes a pair of thick plastic pants, stiff until they warm up. Catherine loathes these. She knows only too well the sweating and itching they cause and just hopes it will not be a warm night. They are drawn up until they encase her from her waist to the top of her thighs and her private parts are secure from all reach. Her pyjamas are secured in position and finally her hands are wrapped up in thick padded mittens, clipped and secured like everything else.

Catherine climbs stiffly into bed. Despite the ache in her buttocks she feels she has got off more lightly than on her last visit to the detention dorm. The presence of Anna seems to have drawn the wardens' attention away from her, at least for the moment.

While Anna's still bent over the bed, the thick padding is pushed between her legs and the tight cotton briefs pulled up her legs to hold it. Only then is she pulled to the bed and pushed on to it on her back. Anna groans as her backside impacts on the lumpy old mattress. She cries out as the binding on the leg of her plastic pants scrapes the bruises on her thighs as the trainer pants are drawn up. Soon she, like Catherine, is encased waist to thigh in thick plastic and she is dressed in her heavy flannel pyjamas. Thick padded mittens, firmly secured, reduce her hands to blunt formless appendages.