The Prisoner

Chapter 56.

Stewart was down to breakfast early the next morning. Two of his female prisoners were on serving duty and rushed to prepare his breakfast to his requirements. A rueful Miss Jones sat opposite and he noted that she frequently squirmed on the hard dining chair as she tried to retain her composure.

Outside it looked a bitterly cold day with a fine drizzle. In the distance he could see the rest of his squad on a work detail removing weeds from the long gravel drive. He was surprised to see that they were lightly dressed in their thin T shirts, short skirts and work boots. No doubt Mr Turman had ordered their lightweight clothes so that they would feel the full effects of the morning chill. As he nibbled his freshly made toast he saw, through the double glazing panes of the Manor that Mr Turman, warmly dressed in his uniform greatcoat, hat and gloves had lined the ten females up for some perceived error on someone’s part. With some difficulty he undid his heavy coat and unclipped his strap. The squad, clearly shivering from the damp and biting wind, held out their right hands. He slowly moved down the line laying a powerful stroke of the strap across the freezing and wet palms.

It was too far away to hear any sound or see the expression of pain on their faces but from the wavering of the hands after the strap had landed, it had hurt like hell. When he had struck the last hand he went down the line again laying a second stroke on the same, now throbbing, palm before stowing the strap, fastening his coat and ordering them back on their knees for more weeding.

Stewart made a mental note to congratulate the young officer on his choice of target and the fact he laid on two strokes to the same hand. No doubt their buttocks would be similarly chilled but nothing could beat a well laid on strap across freezing cold hands even though, to any onlookers, it would appear a very minor punishment. I truth, any male onlooker would have been more absorbed by the way that the females panties, had, with the constant bending and squatting, worked their way into a wedge in their anal clefts. This could. If Turman so chose, be classified as a uniform discrepancy but perhaps he felt that they were already under sufficient discomfort.

Excusing herself, Miss Jones left the table leaving Stewart to his thoughts.

He smiled to himself as he recalled what had happened to her just a few hours previous. He had started by ordering her to lower her stockings and mount the knee board once more. Naturally, her knees had already been sensitised but he kept her there for the same time as before to make her realise that they were starting afresh. It took a fair amount of her self control to hold out, especially as Stewart was even more insistent on her maintaining a straight backed position the maximise the weight on her already bruised knees.

He than told her to replace the stockings into the suspender clips and take up the present.

Standing to one side he slowly looked her up and down. She was certainly far from pretty and carrying a goodly amount of puppy fat around her hips and breasts. He knew that she would be self conscious about this and planned to exploit this as the evening progressed. Moving round to her front he gently rubbed the palm of his hands over the breasts feeling a degree of firmness that impressed him. Despite the thickness of the shirt and her underwear the nipples rapidly became turgid and he could feel them flexing against the breasts. Already a blush of embarrassment was spreading up her face from her neck.

“  I intend to treat you as I would any prisoner who was up before me for a uniform inspection , body search or whatever. I will make this evening as humiliating as possible and you may rest assured that the slightest infringement of any rule or instruction will be dealt with in the same way that a prisoner would be punished, and that means by inflicting corporal punishment to the degree that you will find rather painful. Do I make myself clear girl?”

Jones muttered her agreement.

“Remove your tie and blouse the resume the present position” ordered Stewart.

Her brassiere was one of the type denied to the larger breasted prisoners, it was one that offered maximum support which she clearly needed to contain the large assets. Back at the present she displayed some considerable embarrassment as much of the upper breasts were exposed and the nipples showed prominently in both shape and light pink colour through the white material. Her waist bulged a little over the skirt waist band.

“Before continuing with your examination I am going to show you just how much a harsh application of the cane can hurt. If I waited until your buttocks had been hand slapped or even strapped the effect of laying a cane across cold unmarked flesh would have been reduced and therefore less effective. I will be giving you ten strokes, five with the buttocks tight and five with them relaxed, again so that you can appreciate the difference as do the prisoners. We don’t have the facilities to secure you so you will just have to accept the punishment without that benefit. Should you attempt to stop the application by either standing up or putting your hands in the way…it will be increased…considerably… if necessary, in the punishment barn. Do you understand?”

Jones was really looking frightened as she nodded her acceptance. He ordered her to the centre of the room, told her to place her feet well apart and bend over from the waist. He moved behind her and pulled the uniform skirt up over her back exposing the tightly spread  target. He pulled the panties high into the cleft and walked over to the table on which he had placed the equipment to select a medium sized flexible cane with a rubber handle grip. He swished it experimentally through the air a few times, stood to her left and corrected her position to his satisfaction so that she was fully “tight” even down her thigh backs.

He tapped the left cheek with the cane tip to get his aim correctly, raised the rattan over his shoulder and brought it whistling down to strike both cheeks evenly.

It was, by any standards, a harsh stroke. That was what had been promised and he had no intention of going easy on this girl anymore than he would one of the female prisoners. Jones jumped and squealed with both the surprising force of the stroke and the rapid searing pain that followed it. The next was deliberately laid across the junction of thigh and buttock that was scarcely discernable on account of her tightly bent position.

Her muffled cry indicated how much it had hurt her, but she stayed in position even as the three stokes to the meatier buttocks whistled home. She was then told to stand back at the present.

“The next five will be across the relaxed buttocks Jones, so we will have you standing at the present. My advice is not to clench and remain in position so that your skirt does not fall down and impede my efforts.”

It was always difficult laying on full power strokes with the victim standing but following three that sank well into the semi-relaxed buttocks Stewart laid two firm strokes into the crease at the top of the plump thighs. Jones managed to remain in position but tears ran down each cheek as she was told to adjust her panties lower her skirt and sit on a stool opposite Stewart’s armchair.

She was still absorbing the pain of the strokes and not thinking as clearly as she should. She saw Stewart looking down at her and suddenly realised her mistake and spread her knees the regulation forty five degrees that required her to ease the uniform skirt back up her thighs. She then placed her hands behind her back.

In almost a whisper Stewart told her that he would decide what a suitable punishment would be for that basic error in due time, Right now he required the answer to some questions.

He looked the young wardress up and down taking in the tight brassiere and spread thighs revealing her white panty crotch. When he looked her in the eyes she was blushing furiously. That flush didn’t leave her face as he asked questions that he knew, from previous sessions with female prisoners would cause her maximum embarrassment. Firstly ones about her sexual life, when she last had intercourse, ( a week),whether she had any experience with other females (several experiments when she was in school) when she had last bathed and how often she masturbated. The previous questions were bad enough but this resulted in a look of horror and silence.

Stewart told her that he needed an answer and was perfectly prepared to thrash one out of her. Hesitatingly, and with her face turning an even deeper shade of red she muttered that she did this most nights when she went to bed. He picked up the nearby cane and leaning forward stroked the tip up and down the crease that defined the girl’s vulva under the white material.

“ I may well require a demonstration of that later tonight Jones, but first I need to deal with that error with your knees. I think that a strap applied to your inner thighs should act as a reminder every time you sit down in my presence. Stand up, pull your skirt well up to your waist, put your left foot on the top of the stool at ninety degrees to your other leg. Then undo the suspender straps and roll your stockings down to your knees”.

Jones was beginning to show signs of not only pain but also some real fear of what was to happen next. She stood as directed with her left plump inner thigh parallel to the floor and exposed to whatever Stewart decided. He chose a short thick strap, stood to her front, and applied three hard strokes at the mid point on the thigh, one on top of the other. They left a two inch wide red patch that was almost visibly throbbing. He repeated the exercise on her other thigh, told her to removed her stockings, suspender belt and shoes and resume the present.

Despite her rigid position her face showed marked signs of the pain that her soft and tender thighs were transmitting. He now thought that the time had come to inflict a little humiliation on her and told her to remove her skirt and resume the position.

The young girl now stood in just her heavy bra and regulation panties with her face screwed up as she continued to absorb the pain.

“I see that you wear a heavy support brassiere unlike the female prisoners with large breasts. It must feel very supportive when you are watching my girls exercise in just their lightweight regulation versions. How do you think your breast will feel if we exercise them a little?”

Without waiting for an answer, Stewart ordered her to remove the bra and resume the present. Blushing furiously, Jones reached behind her and struggled to unclip the broad strap, she then leant forward so that the items slipped off her breasts, placed it into Stewart’s outstretched hand and snapped back into the position.

At first he ignored the female and concentrated on a thorough examination of the garment. It was damp under the arm pits and when he glanced at her, noticed how a thin film of sweat had formed over her upper body. It was of a sturdy construction and the label was marked 42EE which did not surprise him. To his delight he found a smudge of dirt on the rear strap where she had obviously slipped the garment on with some dirt on a finger. He casually threw it to one side commenting on the mark letting the implications pass over the girl’s face. Following the requirements of the “present” position her elbows were well back lifting the large breasts so that all but the lower surface was held well from the chest. Her areolas were swollen and light pink with thick stubby nipples that usually indicated above average sensitivity. He would soon find out.

He grasped the enlarged aerola between his thumbs and forefinger ensuring that the nipple was included in the grip. He increased pressure until Jones began to shake slightly, then lifted the breasts up so that their undersides were clear of her chest. Her face was now displaying the pain and discomfort she was feeling so he increased his grip until he could sense her knees beginning to flex.

“Your bra was somewhat soiled and for that you would be awarded a Breast Related Demerit. Do you know what happens when a prisoner has been stupid enough to collect three such BRD’s?”

Gritting her teeth she nodded.

“Then tell me!”

“Please, Sir, they receive a b-breast caning across them.”

“They do indeed Jones, and right now I have it in mind to apply for permission to do just that. On the other hand, I could dispose of the charge with a simple breast spanking…if you agree?”

Realising that Stewart was deadly serious, she nodded a hurried agreement. With a final extra squeeze, he dropped the breasts and stood back.

“I think that a dozen slaps across each breast will be adequate. You will of course remain in position and not attempt to impede my hand in any way”.

Stewart ordered her to lean slightly forward from the waist, but to keep her elbows well back. Her breasts hung slightly away from the chest and were well presented to him. Drawing his right hand back he gave her right breast a hard back handed slap on its outer side feeling it compress and sway inwards. He then gave the same swinging globe a slap on the inner surface. Next he dealt with her left breast in the same manner then gave each a hard downwards slap on the upper surface. He gradually worked his way over the damp swinging breasts until the last two slaps to each one. He flicked his hand even faster and ensured that the back of his finger tips impacted on the nipple area. After the second one on her right breast Jones’s hand flew protectively to cover the tender area.

As a staff member she should have known better.

“Well Jones, you have really blown it now. As you well know that is classed as “Refusal to accept punishment” It means that the whole punishment is now void, even though it was the last slap out of 24. Not only will the original BRD still stand but you have now collected another one. I will have to think very carefully about this, but almost certainly I will have to report you to Mrs Cheeseman for her to decide how it should be dealt with. Back to the present girl!”

As she braced Stewart could see that her eyes were reddened, whether this was from the breast slapping or the thought of what might be to come was anyone’s guess, but he knew that he now had her trapped and realising just how hopeless a prisoner would feel in the situation. He looked down at her white panties and spread thighs. It was time to remove her last vestige of pride.

“Remove your panties, hand them to me and resume the present girl” he ordered in a whisper. Blushing to the roots of her hair she slipped off the wardress knickers and handed them to him. He carefully and pointedly examined them in front of her asking when she had last changed them. It would seem that it had been very early that day, a day in which she seemed to spend the whole day on her feet and more to the point, on which she had either punished several of the males, or witnessed the same act. They were certainly damp in the crotch and slightly stained. It would have been enough to place a female prisoner on report and he was not going to allow this young wardress to get off without experiencing some form of punishment.

Stewart produced a pair of latex gloves from the table behind him and heard Jones emit an audible gasp. He slipped them slowly over both hands allowing the customary “plick” as they were released around his wrist.  He did not have to tell the girl what was to happen next, she knew only too well how the staff were expected to carry out thorough body searches on prisoners. Stewart thought that he would start with the mouth and ordered her to open her jaws wide. He kept her waiting there while he opened a small jar and rubbed the contents over the gloved fingers. He intended that this would be as unpleasant as possible.

It was a jar of particularly pungent English Mustard.

She realised this as the fingers passed under her upturned nose and entered the mouth. He pushed the tips around both upper and lower jaws and then roughly under her tongue. She started to splutter and gasp and this was made worse when two fingers pressed the tongue down and forced themselves to the back of the throat.

He then slowly, in turn, inserted a finger into each nostril knowing that the trace of mustard would have it’s effect. As his finger withdrew from the last nostril her eyes were already red and her nose starting to run.

She was then ordered to lay on the table with her knees apart and drawn well up.She had dense dark pubic hair. His gloves were still moist from the mouth inspection and his next examination was never intended to be anything less than uncomfortable. Jones now realised to the full how the male prisoners must feel when she used her authority to casually examine their intimate areas. She was blushing profusely and unable to look Stewart in the eyes as he parted her labia with his left fingers and forcefully inserted the fingers of his right hand into her cavity.

She felt tighter than most of the female prisoners that he had body searched and it took some effort on his part to thoroughly explore her cavity. But searched it was with Jones struggling to maintain the humiliating position that she had been ordered into.

Next she was ordered onto her front with head well down, knees drawn up and spread wide. She could feel his breath on her anal cleft as he examined her and then the insistent touch of his finger as it stroked he up and down finally resting on the puckered brown opening. He had re-lubricated the finger with some mustard and when he pushed, despite the viginal tightness the combination of her position and the added lubricant resulted in the finger sliding immediately up to the second knuckle.

She gasped at the shock of the intrusion but then started to squirm as the mustard took effect. A sharp order to remain still somehow gave her the strength to do just that. She even remained in position as the second finger was inserted and that secret cavity probed and pressed. He was in no hurry, sensing that of all the indignities he had subjected her to, this seemed to be the worst.

He walked away slipping the gloves off and dropping them into a basket. He returned to the table with one of the female centre’s most unpleasant devices. It would be an ideal way of starting to wrap up her experience of being treated as a prisoner.

He ordered her to squat on the table and held the device in front of her.

“This is what we call an understrap Jones. It is used for a variety of reasons and tonight it is going to be applied to remind you that the standard of panty hygiene you displayed earlier is not acceptable.”

He reached round to fasten the waist strap pulling it tight into her soft waist then reached between the legs to pull the crotch strap up to the tight position. It took his some time to adjust the anal knot and, without the gloves, noted how warm the area felt, no doubt thanks to his unofficial lubricant. The other larger knots were manoeuvred into position filling the vaginal cleft in what he thought would be a stimulating but uncomfortable manner.

She climbed down from the table, with some expressions of discomfort, to stand in front of him.

“I did mention earlier that we should give those breasts of yours a work-out so that you will appreciate the support that your regulation wardress bra normally gives you…but we got distracted by the condition of the garment. Now is the time to combine that exercise with ones that will give you an appreciation of the disciplinary benefits of the crotch strap. We will start with running on the spot…and I want to see those knees high”.

Jones began running and initially raised her knees to the high position. Soon the effects of the understrap caused her to slow down and lower her knees a little. Ignoring the grimace of pain on her face Stewart stood behind her and used a flexible crop with a thick leather tab to slap the backs of her legs as they moved upwards. He kept her at the exercise for a full five minutes watching the unco-ordinated flopping of her unrestrained breasts.

After just a brief pause he started her on the astride jumping with arms out at shoulder level and an extra bounce as the legs closed and then spread wide. With naked females this was the exercise guaranteed to make the firmest of breasts move and Jones’s  started bouncing in unison but soon developed their own rhythm and indeed sound as the slapped upwards then downwards against the sweat moist chest.

After another five minutes of that exercise he ordered her to the present and allowed another brief rest. She was sweating profusely and her skin was shiny and dripping in places. He ran his hands over the now still globes and then down to her crotch checking on the tightness of the leather strap. It was certainly fitted well and must be causing some considerable discomfort.

Which,… after all,… was its purpose.

He raised his fingers to his nose and sniffed them looking straight at the girl..

“Mmm. It seems your personal hygiene standards are already slipping Jones. Let’s hope I don’t give you another personal inspection when you finish exercising.”

Time, he thought to bring the proceedings to an end. He pondered the possibilities for a few seconds then made his decision. First, it would be necessary to give her a beating that she would remember. He selected a hard wooden paddle 6 inches by a foot long and spoke:

“When you have a male prisoner up before you for training I presume that you end the session with a beating that will leave him in no doubt as to your authority. What do you do to get him to demonstrate that respect after the beating Jones?”

She thought for a moment, shaking slightly from the results of her exercise.

“He would be required to carry out a personal service for me Sir”. She replied.

“Then I will now beat you with you being aware of what you will be required to do for me after I have stopped. I am going to give you 20 hard whacks across your buttocks that you will feel for some hours. You will also carry the bruises for several days to remind you of this experience as a prisoner. Bend over that table, legs wide and with your hands gripping the far edge. Remember, any attempt to impede my efforts will result in a noticeable increase in the number of strokes. Brace yourself!”

It was a heavy piece of wood, well polished by all the buttocks that it had previously landed upon. Stewart laid each whack on with suitable force striking both chubby cheeks evenly. As the buttocks bounced he could see the understrap and the redness around the anus that it had caused. Soon the whole area would match.

As the heavy application of the panel progressed it was obvious that the girl was starting to have great difficulty in maintaining her position. By the tenth stroke bruising and white patches were already beginning to appear and she was starting to shake as she desperately absorbed the increasing  pain. At the fifteenth slap she almost grabbed her burning nates with her hands, but managed to resume her grip on the table before Stewart had to issue any reminders as to the increase in punishment that would follow such a slip.

Jones would later admit that she had no idea how she accepted the last five whacks across her burning buttocks. Perhaps it was the potential shame of admitting that she was unable to take the sort of punishment that she handed out on an hourly basis.

But accept them she did and finished up, back at the present shaking with the pain and humiliation. Real tears ran down her plump cheeks as waves of burning pain swept through her thighs.

Stewart picked up a sealed condom from the table and placed it between her teeth then casually slipped his clothes off until he too was naked with his erection all too visible. He knelt down between her spread legs and unclipped the under-strap snatching it from the folds in which parts of it were hidden. He could see that it had done its job from the redness around her labia and the way in which her delicate inner labia remained parted after it’s removal. Still carrying the damp leather device he went over to the large armchair, laid back in it with his feet outstretched and pointing to his penis, ordered her to fit the condom.

She knelt between his legs and tearing the packet with her teeth, extracted what seemed to her to be a strange latex device. It was one of a set that a male colleague of Stewarts had specially ordered. It had hard ridges around the shaft that would make the organ feel exceptionally thick in girth, but more to the point if worn for penetration following a females wearing of an understrap, it would continue the chafing of soft tissue so that the normal pleasurable sensations would be denied her.

All this possibility was written on her sweating face as she forced the condom down over the hard organ in front of her. With a frightened glance at Stewart and without any further orders she dutifully climbed up onto the chair with her legs spread and, facing him, mounted the penis with a gasp of pain as she slid her hot and well lubricated  sex  over the hard latex shape.

“This is not intended to be pleasant for you girl, just me, so I want you to start lifting yourself up and down until I tell you that you can stop”.

With her face screwed up in response to the stinging chafing of the condom she raised and lowered herself rhythmically with the sweat covered inner thighs contracting and expanding to raise the crotch. Each time she tried to slow, Stewart reacted by firmly gripping both the tender nipples and squeezing until the rhythm had been restored.

Despite the pain and discomfort Jones worked away riding Stewart’s penis until after just a couple of minutes the expression on his face and a long shudder told her that she had achieved his aim. If she thought that her ordeal as a prisoner was now over, she was mistaken. She remained kneeling over Stewart.

“Just one more thing before you get dressed Jones. I am sure that you were not able to climax yourself and knowing the Centre policies regarding not allowing prisoners to spend too long between sessions of sexual relief…I have decided that you will be allowed to take yourself to a climax using this rather damp understrap. How long this takes will be up to you.”

Swallowing back what remained of her pride, Jones grasped the cruel knotted length of leather and, opening her intimate divide with one hand, gently started to rub the device against her reddened clitoris seemingly enjoying the sensation of pain mixed with pleasure. The way in which Stewart looked into her face watching every twitch of her expression seemed to spur her on and in just seconds she began to shudder, moan and rub frantically to her peak.

Allowing no time for rest, Stewart ordered her to her feet and then to dress in the clothes she had stripped off on his earlier orders. She soon stood in front of him, dishevelled and registering the humility of what she had been through.

“I have yet to decide on what measures to recommend to Mrs Cheeseman regarding your breast offences, but I would prepare yourself for the worst as she is not a lady to let standards slip”.

“Dismiss!”.

…and a now humbler young wardress left for her own accommodation and a period of self-pity.