The Prisoner

Chapter 55

Stewart brushed past the young wardress with a curt “Follow me!” as he carried the equipment into his apartment. Closing the door behind them he slid a lock into position that emphasised the position of vulnerability that Jones was now in. She sensibly stood again at attention in the centre of the lounge as Stewart arranged the items on a side table.

He then stood in front of the girl looking her up and down.

“You now know that Mrs Cheeseman has approved your request and ordered me to ensure that you really appreciate how the female prisoners here are dealt with. That means that you will obey every order without question and do exactly what I require. As corporal punishment is an essential part of the training process you may also expect to be subjected to some painful examples of that method. Do I make myself clear girl?”

Jones half muttered her reply as she stared at the floor.

Stewart picked up a wooden board around 8 inches by 18 inches and an inch thick. The underside was polished wood and Jones was immediately puzzled as to its use. It was placed on the floor in front of her and she could see that the top surface was covered in ball bearings the size of garden peas that had been firmly glued to the wood. She was ordered to undo her stockings and slip them down beneath her knees.

Blushing, for the first time that evening she reached up under her skirt and unclipped the four suspender studs that held each of the regulation uniform stockings high on her thighs and rolled the nylon material downwards.

“I intend to start with this simple device that seems to give the prisoners some discomfort. It is often used at the start of a session to place them in the right frame of mind. When I say now, you will kneel on the block with your knees together, hands on your head and body straight. You will not attempt move off it until I tell you”.

….now!”

Jones knelt on the carpet and lifted each knee in turn to place it on the device, then knelt upright placing her hands as directed. She was surprised just how painfully the small balls were as her plump knees were compressed against their surface. She soon found that her lips were pulled back her small white teeth were exposed as she absorbed the pain.

It was only a minute into the demonstration that she leant forward in an attempt to relieve the pressure and was told harshly to keep her back straight. She had no idea how long she would be left there and realised that her plumpness at least gave her knees some cushioning even though her weight increased the overall pressure.

Stewart sat in an easy chair watching the girl dispassionately. With prisoners he had seen them compelled to take ten minutes of knee pain and he certainly wasn’t disposed to letting Jones off with much less.

Five minutes slipped slowly by and he needed to snap out several orders to correct her position as she underwent the ordeal. Eight minutes passed and she started to tremble under the pain and stress of her position and had here eyes closed but still with bared teeth in a grimace of pain. Finally, as a tear escaped one of her closed eyes he ordered her to resume the attention position then watched the mixture of relief and pain as she struggled to her feet.

Both knees were reddened and indented with the shape of the ball bearings but her formal position prevented any thought of her soothing the area with and massage. He again addressed her.

“That was merely the first treatment that you will receive this evening. You may think that it was hurting, but believe me, you will even offer to mount the kneeling board to avoid some of the events that I have in mind. I will now move on to the subject of humiliating prisoners”.

Jones’s breath was almost returning to normal but the last remark caused a sharp intake that was only contained by her tight uniform jacket.

He continued:

“Humiliation can often be achieved by the simple removal of clothing in the presence of a staff member of either sex. Some females find a male staff member more embarrassing, others one of their own sex. A difference in age can also have its benefits. My guess is that having you strip in the presence of a senior female would be the most embarrassing and perhaps we will arrange for that later in the evening but for now, it will be just me who examines you…and remember…there is no restriction on staff members handling prisoners to carry out a full inspection”.

He let his words sink in and was about to order her to remove her jacket when the internal ‘phone rang. He had forgotten that he was the duty officer for the night and that any staff member requiring an “unofficial” would be calling on him.

It was young Turman. It would seem that Lessing was causing problems as she deeply resented being under the control of a highly hormonal young lad and was simply not obeying his orders. Would Mr Stewart attend to the problem please?

He was told to send the prisoner to Mr Stewart’s room and she would be returned when her attitude had been dealt with. Miss Jones just had time to re-attach her stockings and regain her wardress composure when a nervous knock at the door announced the offender’s arrival. She was soon ordered into the room to take up the place that Miss Jones had only just vacated

Lessing was as indignant as she was dishevelled. Her flushed face and sweaty appearance gave some clues as to the activities that Mr Turman had been partaking in before he finally realised that she needed further training. He had really enjoyed having a much older snooty bitch at his disposal but to her the humiliation of having to obey the orders of what seemed to be a spotty faced schoolboy was too much to bear. The way her nipples protruded though the uniform shirt showed where his attentions had been partly directed but it would seem her total refusal to agree to provide whatever service Mr Turman required proved her downfall.

Stewart was about to start with a lecture when again he was interrupted by the ‘phone.

This time it was the shy retiring Miss Horne to complain about her charge Barnett. It took some effort by Stewart to extract from the shy wardress what her complaint was about. She had found him most reluctant to provide the service that she required and, like Turman, requested that Stewart carry out some attitude training on him.

In just minutes Stewart had both Lessing and Barnett side by side at attention . Slowly ideas formed in his mind as to how this situation could be used to give Miss Jones an evening to remember. Clearly he would need to maintain her authority over the prisoners but she would have no option other than to join in various disciplines that she would realise would later be applied to her. He decided to start by addressing the two wretches that had been sent to him.

“Both of you are in here because of your total lack of respect to the staff members who were in charge of you this evening. I intend that you will be returned to them in a more contrite and obedient frame of mind to the extent that you will obey any…and I mean any…order that they choose to give you. It seems that you have both refused to carry out a duty of a rather personal nature that the staff members required and so you only have yourselves to blame for what will now happen to you. I will start by administering a dozen hard strokes of the cane so that you will understand how I deal with any refusals to obey orders. You, Lessing, will be first…step forward and remove your skirt”.

Nervously the woman unclipped the short uniform skirt, removed it and placed it on a nearby chair. She was taller than Stewart had first thought and must be approaching six feet tall with her uniform shoes on. Her shirt only partly covered her regulation tight white panties that dug into her plump thighs. Her small white suspender belt held up her stockings with several descending clips. The weals from her punishment earlier in the evening stood out against the pink flesh of her lower buttocks and must still have been hurting her. Stewart ordered her to the “present” and rubbed his hands over the ridges. She flinched at the light contact but held her position.

“Your buttocks seem to be rather sensitive” smiled Stewart,” It would seem to be rather harsh if I were to lay on another set of strokes over the same area so I will be kind and find other areas to accept the cane...”

He picked up a straight thin three foot cane with a rubber grip from the collection, swished it a few times watching the prisoner twitch at even the sound… and continued.

“How about if I gave you three across the front of each thigh”, he stroked the cane up and down each leg lifting the shirt tail up…”then three across the back…” and stroked the now shaking thick legs between the buttock crease and the back of each knee.  I would then let you have three on each inner thigh?  I realise that would add up to more than twelve and that you might be limping for a few minutes, but it would spread the bruising around a little. What do you say to that Lessing?”

She stuttered a hesitant “Yes Sir”.

“Just one more thing” he continued, “…and this applies to both of you, since we have no means of securing you in this room you will be expected to accept the punishments without unnecessary movement, otherwise…we will have to add more strokes for your lack of control.

Lessing…remove your tie, shirt, suspender belt and stockings”.

With a last desperate look around the room she slipped off the tie and undid the shirt sliding it down her arms. Before she could place it with her skirt Miss Jones grabbed it and carefully examined the material checking for cleanliness. The areas under the armpits were damp and she felt obliged to comment.

“Been sweating have we girl? Believe me, when Mr Stewart has finished you will be more than a little damp”.

Having unclipped the stockings The prisoner then had to balance on each leg and slide them down and off her feet finally unclipping and removing the belt itself. Miss Jones pointedly took each item from her, handling and inspecting them with distaste.

Stewart took two large books from a shelf, and placing them on the carpet in front of Lessing indicated that she should stand on them at the present. Both he and Miss Jones took in the sight of the mature woman awaiting their punishment. She had on just the thin white prisoners bra that was clearly a size too small and gave hardly any support to the bulging breasts that sagged slightly under their own weight. The shoulder straps dug into the flesh as did the rear straps. Both nipples protruded forming sizeable nubs under the material. Her underarm stubble again reminded Stewart that he yet to decide on the body hair style for his squad and knew that to a fastidious woman like this, even having this little underarm hair would be irritating. Her entire body had a sheen of light sweat that was becoming more apparent as she stood there. A combination of the over warm room and her embarrassment were both contributing to this.

A thickly waisted stomach spread around a recessed naval that was just above the white, tight regulation panties. He estimated her weight at around 160 lbs and pondered how fit she would prove to be when the prisoners were subjected to forced PT under Miss Horne She would certainly be one of those who would suffer from a lack of breast support during movement.  He instinctive knew that her chances of avoiding early breast punishment was almost zero once the effects of Lady Halliday’s dislike of her was acted upon.

He stood to her right, flexed the cane between both hands with her looking nervously at it and then rested the tip across the front of her right thigh just below her panty crotch. He then brought the cane back and struck the target with the cane tip whistling along parallel to the floor.

Lessing gasped slightly but held her position.

The following two strokes were just as hard and an inch below the preceding one. From the increasing look of fear in the mature woman’s eyes Stewart knew that the strokes, though only leaving a six inch or so weal, were causing a very real level of pain and that Lessing was fully aware that this was only the start.

Slowly, Stewart moved to her left and administered the three across her left thigh front. All of which Lessing accepted with an increasing stoicism. The next two sets across her rear thighs would be more difficult as Stewart kept her in the legs wide position by ordered her to bend over to grasp her knees.

The skin was visibly tightened by this position and the weals from the earlier punishment were even more apparent. Unfortunately for the woman, the lower strokes had cut into the upper thighs so the first stroke was, of necessity be laid across them despite Stewart’s early promise.  He took up position for the right thigh and dragged the cane up and down the small area that he intended to hurt making sure that she realised the tender area would be involved. The first landed about six inches from the buttock crease, was laid on with force and had Lessing gasping and her legs buckling slightly. The next was three inches higher but the last was high into the bruised area extracted a short yelp and a hand brought round to rub the impact area.

“Keep still girl!” he snapped “I will deal with that error later and if you move again I will regard it as a serious offence”.

His warning achieved the required effect and the three on the back of her other thigh were received with scarcely a grunt. But now would come the six on the softer more vulnerable area of the inner thighs. Stewart knew that her positioning could add greatly to the effectiveness of the strokes. He decided that she should stand with one foot out to the side resting on a two foot high stool. This presented her left inner thigh completely as her panty crotch was pulled embarrassingly tight revealing her pubic hair either side of the material. He pressed the cane tip into the panty covered vaginal cleft firmly sawing it back and forth as he ordered her exact position, hands clasped behind her head, left foot at right ankles to her right with the thigh just above the parallel with the ground. He withdrew the cane from it’s moist contact and brought it whistling down across the pale plump inner thigh midway between the crotch and the knee.

The pain came as a surprise to Lessing. The chosen area was clearly more tender than even the bruised upper thighs and it would take considerable effort on her part to accept the strokes without movement that would displease Stewart. But she knew that she had no alternative.

He waited for a minute so that the first weal had partly formed before he gave her leg the next one between the first and her crotch and then surprised her by giving a third to the very top of the thigh. She whimpered and struggled to keep her feet in position as the pain hit her. Changing position to present the other thigh was difficult as she felt the flesh tighten around the top of her leg in protest at the strokes.

Somehow she managed to accept the next three with her teeth bared and her entire body shaking. She then fell to her knees with her hands clutching each upper thigh protectively and tears running down her face. Stewart indicted to Miss Jones that it was her turn to deal with the prisoner. He pondered, as she walked over to the woman how well she would cope with this as all her experience to date had been with male prisoners. Would she turn out to be too sympathetic with this much older woman and would she be prepared to carry out the necessary handling to ensure that she was truly humiliated?

He need not have worried.

Jones walked quietly over to the kneeling prisoner and stood over her. In almost a whisper she gave the order:

“Present!”

With a struggle Lessing forced herself to her feet and took up the braced present position looking far more dishevelled than when she first came into the room. She towered over the wardress who stood close enough with her hands clasped behind her back to almost make contact with her eyes on a level with the woman’s breasts.

“You seem to be wallowing in self pity girl” she murmured. “Believe me, Mr Stewart has been more than kind to you so far so don’t try to pull the tearful sympathy stunt on me as it won’t work. I will now take a very close look at you. I have to say that I have been very unimpressed so far with your general standard of cleanliness so I hope to find an improvement as I examine you in detail”.

To Lessing, this was a threat from her worst nightmares. Could it possibly be true that this young girl had the authority to have her strip even more and handle her as thoroughly and cruelly as she wished?

“You seem to have remarkably large breasts girl” Miss Jones continued, “Even larger than mine. What size bra do you normally take?”

“42D Miss”

“Your nipples seem to be rather excited, why is that?”

“Please Miss, Mr Turman squeezed them just a short while ago and made them swell up”.

“Then we had better take a look at them. Remove your bra and hand it to me for inspection”.

Blushing, the elder woman unhooked the back of the garment, slipped it of her breasts and handed it to the wardress. Miss Jones ignored the naked flesh in front of her and carefully checked the bra, both inside and out.

“You have of course heard how prisoners are punished on the breasts for any related offence?”

“Yes Miss…”

“…and that cleanliness of underwear is one of the areas in which staff expect the highest standards?”

Lessing mumbled her agreement again, but with decreasing confidence and increased fear.

“I accept that you have worn this item for some hours…but even so…I would not expect it to be so damp and sweaty…it seems that you have just earned yourself a BRD or Breast Related Demerit. Two more errors like that and your breasts will feel as your thighs do now so be warned girl”. She placed the bra with her other clothing and returned to stand in front of her staring at the breasts themselves. She gently reached up and gently stroked the aerolea and nipples with the tips of her fingers until they were fully erect. They were indeed fine examples with the surrounding area pink and swollen and the nipples themselves fully half and inch long.

“These males just don’t realise how sensitive a girl’s nips are do they Lessing? It must have been very painful to have him squeeze and pull them…and they must still feel sore and tender.”

The prisoner nodded her agreement, grateful for the sympathy and gentle rubbing.

Without any warning, the young wardress suddenly grasped each nipple between her fingers and thumbs and squeezed.  Lessing screamed with the surprise of the pain and her knees buckled.  Miss Jones maintained her grip and shouted at her to stand properly pulling upwards on the teats until she was back in position.

Tears were running down the face of the prisoner even after Miss Jones had released her grip. What would this young wardress do next she wondered and was relieved when she stood back from her.

“Take off your panties” was the next simple but humiliating order.

Lessing bent to remove them, aware of the soreness of her nipples as they swung about. She handed them to the wardress and resumed the present position. Miss Jones examined the small white garment thoroughly taking particular care over the crotch. She made a few comments on the general dampness but, much to Lessing’s relief, placed them with the other items and told her to stand back in line with the other prisoner.

She called Barnett forward to stand in front of her at the present. He looked even younger as he stood nervously in front of the junior wardress who was almost his own age. He knew that he had several visits to her scheduled for the following day to receive even more swats with the implement that he was coming to dread. He realised that he was in for even more pain before that would take place.

She soon had him stripped of his prison shirt and shorts and standing, naked at the present. His plastic chastity tube hung between his legs preventing any possibility of him becoming erect or finding relief from his constant frustration.

Miss Jones was slightly shorter than Barnett and certainly plumper. Her right hand went forward and cupped his scrotum resulting in an instinctive flinch from the boy.

“Keep still!” she ordered. “I haven’t begun to hurt you yet. I bet these are really sensitive and swollen now that you have been denied for some weeks. I bet that you would give anything if I were to let you be relieved this evening. What a pity we don’t have a nurse with us so that you could be given a thorough genital discipline while they are so wonderfully sensitive. Just imagine how they would feel when she rolled them together…like this!”

She was almost gentle in the way that she closed her fingers around the bulbs and pressed them together then moved the tips of the fingers so that they would slide against each other. Barnett gasped with his eyes wide and knees bent as he tried to absorb the growing pain. Suddenly she released her grip lowered her fingers to below his scrotum and brought them upwards in a sharp almost inaudible slap.

Barnett yelped in protest and started to pull back from her hand. She immediately ordered him back to the present which he achieved only with some effort and a screwed up face.

She transferred her attentions to the plastic tube gripping it tightly and pulling against the thin chain that went behind the scrotum securing it to his person.

“One of the problems of this type of restraint Mr Stewart, is that it is impossible to clean the penis whist it is fitted. This makes the whole organ rather cheesey and often sore. I could remove the device should you wish to examine his penis”.

Stewart moved towards them.” I think that we could well use this problem of his to ensure that Lessing here has an opportunity to demonstrate her bodily respect skills. I think that we will give her an opportunity to clean up Barnett’s genitalia. She will need to do it thoroughly and this might be somewhat pleasurable for the boy, but should he succumb to releasing his built up load, he will be thoroughly punished.

I think, in the meantime, we should start with him receiving a dozen with the cane across his backside from you Miss Jones, and in view of your inexperience that will be increased by a third to ensure that he feels sufficient pain.

Kirsty needed no further guidance. She ordered her victim to bend over the back of an armchair with his legs wide apart and head well down. His buttocks were somewhat marked from her earlier work with the slapper, but she knew that no account should be taken of existing bruising. She took off her jacket, rolled up her sleeves and gave the same cane that was used on Lessing a few experimental swishes.

“You are really going to feel these Barnett, especially where I lay them over the earlier marks that I made. Just remember that you have to remain in position or you will really be for it. 16 strokes then boy…brace yourself!”

For someone who had little or no experience with the cane Kirsty certainly learned quickly. She took up a stance to the victims left with her feet planted well apart. The cane was brought well over her right shoulder and brought whistling down across the targets. Her spacing lacked the accuracy of an experienced disciplinarian with three landing across the upper thighs and several crossing over each other. Additionally the right flank took much of the punishment as the cane tip spread past the correct impact point. There were few comments from her target who managed to remain more or less in position despite continual struggling against the back of the chair and frequent groans and gasps. Only once did he have to be ordered back in position when the fifteenth stroke landed across the top of his right bruised thigh. Tears were running down the prisoners face as he stood back in the present position as the pain gradually died to a dull aching throb.

Mr Stewart then addressed the naked female prisoner.

“Well Lessing, I am going to give you the opportunity of demonstrating to me how you will show respect for Mr Turman. You will now fellate this boy to ensure that his organ is properly cleaned. As you heard, this will not be a pleasant task as it has been encased in plastic for the last few weeks but that is not my problem. Should you succeed to Miss Jones’s satisfaction…all well and good…but if you lack enthusiasm for the task in any way you will be caned across the thighs…again.”

“You boy may well feel rather sore and sensitive when the tube is removed. Under no circumstances will you refuse the services of this prisoner or…ejaculate. Should you do so I can assure you that the punishment will be severe, unpleasant and appropriate.

Without being told Kirsty slipped on a pair of latex gloves, mentally dismissing from her mind what Mr Stewart had originally decided to do with them, retrieved the chastitiy key from her key chain and unlocked the device. She wrinkled her nose in disgust as she removed the tube and freed Barnett for the first time in weeks. She pulled hard back on his foreskin to expose the red sore glans covered in white creamy deposit. He was told to lay back in the same armchair over which he had just been thrashed with a splayed knee over each arm. Lessing was then ordered to kneel between them and carry out her rather unpleasant duty.

Even before her lips had made the first contact Barnett’s penis had sprung to the fully erect condition. Lessing experience in this particular field was somewhat limited as she had always regarded the act to be demeaning and beneath her. She realised that in this case, she would need to swallow something more than her pride and tentatively started licking the exposed glans, trying to ignore the rather foul smell that the plastic restrainer had caused. Her sore nipples dragged on the rough material of the chair as she moved closer to her target and she was only too aware of the throbbing weals on her legs that sharply reminded her of what she would feel if she failed to overcome her natural instincts.

For his part, the mere touch of her hand, let alone her soft tongue was almost more than the hapless male could bear. He could anticipate the severity of any punishment that the young wardress might order if he allowed himself to climax, but after so long without release it was going to take every ounce of willpower that he could scrape together to prevent being driven over the top.

It took several minutes before the task was completed. Lessing knelt upright with her face screwed up against the taste and smell that she had endured and licked her tongue clean on the back of her hand.

Before Miss Jones could find fault, Stewart, anxious to start work on her own training called a halt to the punishment of the two prisoners and having lectured them on what would happen if any more complaints were received, ordered them to dress and dismissed them back to their original tormentors. As they left he locked the door behind them and turned to the wardress and addressed her:

Well, Jones, an interesting interlude and a good display of how you are prepared to hand out discipline. Now we will see how good you are at taking it”.