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Review This Story || Author: Will Cane

The Prisoner

Chapter 58

Chapter 58


Before Stewart could hear the rest of Slaters account the prisoner was called away to other duties so he wandered back to the Wardresses lounge to read the daily papers. As he sipped his coffee he noticed a folder containing information for staff and inside an article that caught his eye and he commenced to read it:


Policy document M/543 for the attention of staff in charge of male prisoners.


It has been brought to the attention of the Executive Committee that deals with such matters that many staff employed in the Male Correctional Facilities have found a degree of correction applied to the male genitalia to be particularly effective in establishing the authority of female staff. Up until now this has been continuing as an unofficial procedure but the time has now come to regularise the method. After all the area is supremely sensitive and a little discipline will be most efficacious.


This will in no way replace the proper and correct official Genital Punishments that require the presence of a member of the medical staff at all times. It will however, permit wardresses to administer short sharp corrections when they consider it appropriate to maintaining authority.


It is left to the individual wardresses discretion as to the implement used to slap the penis and testicles and the position the prisoner should be in to receive the treatment.

As a guide however it is felt that some personal item of the wardress will be most effective in creating the feeling in the prisoner that this is a one on one punishment specifically designed to create respect for that staff member. Items that may be considered are the leather uniform glove, intimate personal items of underwear such as regulation uniform panties or the straps of a brassiere or whatever is reasonably light, flexible and capable of causing discomfort with no risk of any injury.


The prisoner should be ordered into a position that will enable full access to the penis and scrotum and ensure that the latter will not be trapped between the chosen instrument and the pelvic bone or other hard surface.


Wardresses should bear in mind that single applications should rarely be given as at least two slaps will greatly enhance the fear and anticipation for the prisoner.


Please ensure that this document is shown to the Lady Milkers who attend your centre. As they are required to relieve the prisoners with as little pleasure as possible an application of a slap to the scrotum before during and after release would be guaranteed to ensure that the next event will not be looked forward to.


There will be no requirement for any administrative action or form filling


It was signed by one of the numerous female administrators.


Stewart almost grimaced when he read the note and particularly the last two sentences that would give any irritated wardress the opportunity of being a total bitch to an individual prisoner with no fear of criticism. He could well imagine how enthusiastically some of his colleagues would grasp at the opportunity.

He was aware of somebody looking over his shoulder and realised that it was Miss Jones. For once she was smiling at the thought of trying out the new procedure. She confided that she had yet to select her implement but that the back straps of one of her heavy support bras would fit the bill.


She then told him that Miss Brooks had been looking for him. It seems that she had been taking a female squad for intensive early morning PT and one of them had stepped out of line and required punishments. Unfortunately Miss Brooks had pulled a muscle in her back and was wondering if Stewart would be so kind as to help out.


Because the treatment was to be carried out by a non-centre nurse, it was required that a staff member be there to supervise and ensure that the procedure and punishment were carried out with the required degree of discomfort. Miss Jones related the offences, and certain other information that Miss as they walked over to the room that the Nurse was using. It seems that the girl had been working well doing the strenuous exercises but during a break had failed a panty inspection. When told that she would be on report she made the mistake of complaining, using a rushed use of the toilet as an excuse.


Stewart and Jones strode into a small waiting room adjacent to the room that was being used for medical needs. A tall fair haired girl in her mid-twenties leapt to attention. She was still dressed in her sports kit of thin sleeveless vest, short pleated skirt, ankle socks and trainers. She stared straight ahead and was clearly very concerned at the position she now found herself. A faint odour of sweat hung over her and her face was still flushed form the rigorous exertion that she had been subjected to.


Stewart spoke: “So girl, you have been caught with dirty knickers…why is that?”


The hapless girl, still staring straight ahead and maintaining a rigid attention position replied in a wavering whisper. “No excuse offered… Sir”


“So you admit to deliberate carelessness with your personal hygiene contrary to regulations?”


“Yyy..yes  Sir”.


“I understand that you have been sentenced to a Punishment Enema and Cleansing of the affected area that will be witnessed by Miss Jones and I. Afterwards your further punishment will depend on your efforts during the treatment. Is that understood?”


“Yes…Sir”.


Just then, the nurse who Stewart had previously met at the local hospital arrived. She walked briskly into the room next door and informed them that she would call them through with the prisoner when she was ready. They would obviously have the opportunity to work on the girl for a few minutes. Stewart decided to start with an inspection of the reported panties.


“Take up the panty inspection position” he ordered. Without hesitation the girl reached down to lower the small tight panties to her knees, spread her thighs in a semi-squat position and clasped her hands behind her head.


Miss Jones and Stewart moved in close to examine the crotch and immediately saw the slight brown stain the was the subject of the complaint.. The rigorous exercise had created the usual amount of sweat in the anal cleft and the panties had been worked up into a wedge that caused the contact with the less than spotless orifice.


Both staff members muttered their words of disgust that brought a blush to the girls face and neck as she displayed for them. “Are you as casual in obeying the other rules of the centre?” demanded Miss Jones.


The prisoner stuttered her negative reply as the wardress reached out, caught the bottom of the vest and pulled it up to her armpits revealing a small white half-cup brassiere.


“Unbelievable!” snorted Miss Jones. As well as disgusting knickers you also flout the rule banning any form of breast support when undergoing PT. How dare you girl !!”


“Please Miss…I put the bra on after the PT had ended as my breasts are rather large and felt sore from all the bouncing…I honestly didnt wear it during exercise”.


Kirsty would later admit to Stewart that she knew full well that this was true, Miss Brooks had seen her slip it on but figured that if Kirsty knew…she could force a Breast Related Demerit on the girl. Which she now proceeded to do.


Miss Jones glanced at the girls file laying on a table. The name on the front was “Harding”.


“The rules are perfectly clear Harding. No breast support is to be worn when exercising unless approved by the Governor. Am I correct in assuming that you have no such permission?”


“Nnno Miss …but I didnt wear any support…” The girls words were drowned by a curt order to be silent from Stewart who was now joining  the game.


“I will therefore impose one BRD on your record. Have you collected any others Harding?”


“Yes Miss…just one…for being found with a shoulder strap twisted on a uniform inspection”.


“Good…now remove the vest and the offending item for a closer check”


The prisoner, now trembling with fear slipped the damp vest over her head and unclipped the supports rear fastening and handed it to the wardress hoping against hope that no more demerits would be awarded. A forlorn hope as that was the intention. She was indeed a large girl, which was why she had been singled out. It seems that Lessing would also collect BRDs and Mrs Cheeseman didnt want that woman to appear picked upon hence the plan to have two females up for breast punishment that night.


To Stewarts surprise Miss Jones didnt find fault with the cleanliness of the garment. Instead she stood in front of the prisoner, reached out with both hands and grasped the girls large pink puffy nipples. She suddenly squeezed them both between her thumbs and fingers before the girl had time to brace. Instinctively her hand flew from behind her head and grasped the wardresses wrists.


She immediately snatched her hands back into the correct position, but Miss Jones had achieved her aim. Without releasing any pressure and with the girl screwing up her face against the pain she spoke.


“Attempting to resist inspection is a punishable offence as is touching a member of staff without permission. As your breasts were involved you have caused yourself another BRD my girl making three in total!” With a final extra squeeze she released the reddened nipples.


“Consider yourself on report for a breast punishment!”


Just then the Nurse re-appeared carrying a large rubber bag that had obviously been filled with some liquid. She complained about the lack of equipment for a really thorough cleansing but assured the staff that she would do her best. Harding was ordered to remove her panties, socks and trainers and kneel on all fours on a sturdy table in the centre of the room. Her offending anus was fully displayed as she assumed the knees apart position required by the nurse. There was an almost invisible staining to the area that was the source of her problems today and as expected, that would be the nurses first task.


From her equipment bag she located a large rough cotton swab and a bottle of medicinal alcohol that she poured on to the swab. She then proceeded to vigorously rub the anal area ignoring the girls gasps and flinches. The liquid and the rather coarse material seemed to freeze and scrub heat into the area at the same time. The procedure was entirely in keeping with the policy of making the entire treatment as unpleasant and as memorable as possible. Stewart immediately appreciated how sore and tender the scrubbing would make the anus and hardly encourage the girl to thoroughly clean the area on her next visit to the toilet…but that was hardly his concern.


When the swab had been discarded the nurse produced a nozzle that made even Miss Jones flinch in anticipation. Rather than the expected thin rubber probe this was longer and thicker, some two inches in diameter at its widest point. The outside of the white device was heavily ridged along its length to greatly increase the discomfort of its passage into the rectum. A detent reducing the diameter at a point six inches from the nozzle would assist in the retention of this cruel piece of prison medical equipment.


Having connected it to the tube that leg to the bag the nurse made a point of showing it to her victim who looked horrified as to what was to be forced into her.


“Its my job to give you a thorough clean girl and the last thought on my mind is your personal comfort…but I will lubricate this nozzle if you would prefer it” intoned the nurse. Not surprisingly the nervous female agreed. What she forgot to ask was what  the lubricant would contain.


With a conspiratorial wink at Jones and Stewart the nurse produced a tube of some grease. Whatever it was, it wouldnt normally be used on a sensitive area as the nurse demonstrated by slipping on latex gloves before applying it liberally to the probe. She then rubbed a large dollop around the anus itself resulting in a surprised gasp then some hip and knee flexing by the prisoner.


The nurse indicated to Stewart that she needed some help and he quickly leant over the naked prisoner, grasped each buttock in a hand and pulled them way apart to fully expose the area. The nozzle was introduced to the puckered anus and with much flexing it around the central opening was slowly pushed into the girl. From the gasps it was larger than any other probe, male or clinical that the girls had experienced into that secret place.


Eventually the tube was imbedded up to the detent and Stewart relaxed his grip allowing the anus to grip the device even more uncomfortably. The nurse reached up and opened the valve. A clear piece of pipe showed how the liquid was flowing at a fast rate and the girl was soon fidgeting slightly as she felt her stomach take in what was to be a large volume of fluid.


“I normally use an additive of my own creation” the nurse murmured “It is just enough of an irritant that it really increases the cramping effect and therefore the deeper cleansing. Believe me the girl will be delighted to empty herself when the time comes!”


Miss Jones then mentioned that prison rules required at least a ten minute retention and although that didnt take into account any liquid other than pure water, this time would still have to be adhered to. According to the briefing given by Miss Brooks one stroke of the cane was traditionally inflicted for every minute that the enema was released early and that was why Mr Stewart had been asked to help. A deep gurgling sound could be heard from the prisoners stomach and the nurse reached between the splayed legs and started to massage the now distended area to assist in the passage to the higher areas of the girls bowels.


Eventually the bag was empty and the large probe was unceremoniously snatched from the bottom. The girls yelped and slammed her knees together as the dilated anus sensed the presence of the irritating liquid. With the nurse on one arm and Miss Jones on the other the girl was led down a short corridor to a simple toilet. The seat was raised and the girl ordered to stand astride the pan in the present position facing the staff members.


Miss Jones made a big play of holding out her left arm with the wrist watch. “The timing will start from…..NOW!. I will call out every minute and that will mean one less stroke if you release prematurely. If you do release it had better all go in the pan or you will qualify for further treatments!”


The toilet room was not particularly warm, but the prisoner under cleansing was soon sweating profusely as the internal liquid surged around inside her. She managed to hold the present position, albeit with a screwed up face and a degree of doubling over as the cramps gripped as she fought the overwhelming requirement to sit and release. Stewart admired the girls stamina, particularly knowing that Miss Jones was extending the minutes by a goodly percent to ensure that his cane would be needed.


It was just after Miss Jones intoned the fourth minute that the prisoner could no longer hold on any more. She half collapsed on to the toilet seat and released the contents in a gurgling roaring rush into the pan. She then had to sit there trying, in front of the nurse and two staff members to squeeze out the remaining stained fluids from the upper reaches of her intestine which added noisily to her shame. It didnt relieve her sweating humiliation when, with a handkerchief over her nose, Miss Jones loudly remarked on the disgusting events that the staff were obliged to witness.


Eventually the three decided that the girl was effectively empty and she was led back into the room and on to her knees on the table for the final cleaning of her anal cleft. As the nurse vigorously scrubbed the alcohol based spirits around the anus and entire crotch area ensuring that the soft folds of the girls vagina were pulled to one side and themselves subjected to the stinging attention of the fluid. She remarked that as she was now due a thrashing for failing to retain the liquid, she had better swab down her buttocks. She added with a grin that she used to just swab just the buttocks but then learnt how many of the disciplinary staff liked to include the soft tender upper thighs that she now did that as well.


Miss Jones temporarily left the room and soon returned with a cane that she had left in another part of the building. It was an unusually slim but very flexible plastic rod around two feet long with a rubber handle grip. The rod had small lumps along every inch of the shaft with a larger hard ball at the tip. Not the harshest implement that could be used and one that gave the prisoner some hope that the caning would be relatively mild.


“You were warned Harding that any failure to retain the enema would be punished. As you released after just four minutes you will now have to receive six strokes of this cane across the offending area. Stand over here, legs wide apart and bent over gripping your ankles. I will warn you that failure to remain in place will attract extra strokes!”


The naked, sweating and shaking prisoner took up the position as ordered. She did her best to spread her feet well apart and gripped her ankles with some effort. The recent application of surgical spirit seemed to make the skin on her buttocks appear even tighter and pulled apart to expose the anal area fully and would certainly feel the cane to the maximum. Miss Jones handed Stewart the cane and he flexed it and gave a few practice swishes to cause the girl even more apprehension.


Stewart then moved a chair to position it directly behind the girl and took a seat with his legs and feet protruding through her splayed thighs. Leaning forward he gently rested the cane vertically down the anal cleft. Harding flinched in shock: It was to be a cleft punishment.


“Thought that you would be getting away with a few strokes over your bum did you girl? We did warn you that this punishment would be one that discouraged any lack of hygiene in that area. Im sure that Mr Stewart is an expert with the anal cane and will make every stroke count!”


Stewart wasnt so confident. He had seen the technique in a training film so had some idea. He held the cane handle in his left hand, positioned the tip of the implement against the sore and tender anus, pulled back the rod to almost ninety degrees with his right fingers and let fly. Without the previous tenderisation of the area it would have been painful but for the girl it was like an electric shock.


She jumped almost a foot in the air but rapidly regained her exposed position.


Stewart held the rod upside down, pulled back and released.


This time the tip struck into the vaginal cleft and from the girls shriek must have impacted on her most sensitive nub. The flexibility of the rod also ensured that a trail of red spots were left on the perineum.


More out of a sense of decoration rather than kindness he spread the next three flicks over the entire cleft but saved the last one to aim at the reddened and sore rosebud.


Harding yelled aloud, stood up and reached behind her with her hands to protect the area.  Realising the error, she immediately apologised and went back to the correct position…but she knew that her reaction would result in more pain from the wretched anal cane.


“Big mistake girl!” said Stewart. “I am not without some feeling so I will give you a choice as to what will happen next. You can take one more like that…without this ridiculous jumping around or you can take two on your other orifice. I think you realise where the tip will land!”


Harding realised only too well but decided that anything was less sensitive than her poor anus. Following Stewarts orders she turned to face him, spread her legs and gripped each lip of her vagina with her finger tips, pulled them apart to expose the inner lips and clitoral hood.


Miss Jones added to the girls apprehension by producing the offending soiled panties and rolling them into a tube, used it to force her jaws apart as a form of a gag.


The girl was trembling. She knew, only too well, that she would have to take what was coming. Repeat punishments were always made as hard as possible.


Stewart was in no hurry. He touched the shamefully exposed clitoral hood with the cruel tip then started a scratching circular motion to irritate the area. It took only a couple of minutes before the girl, despite the pain from her rear, started to gasp gently and flex her hips slightly. The clitoris swelled appreciatively becoming more displayed and vulnerable.


Holding the implement in his left hand he touched the nub with the hard tip, then pulled the flexible shaft back fully with his right fingers…..and let fly.


A muffled yelp, a lurch of the hips but no attempt to avoid the punishment or cover herself after the pain bit. She knew that if you could repeat that self control, it should all be over.


Stewart waited a couple of nerve straining minutes for the clitoris to swell and then repeated the positioning of the device. This time the girl was visibly shaking in fear as the unbelievably sore and sensitive nub of girl flesh was hit by the cruel tip.


With a superhuman effort she remained with her hands exposing herself and just a quick lurch of her hips.


“And I should think so girl!” snapped Miss Jones. Had you displayed more self control earlier then these additional strokes wouldnt have been necessary.”


The girl, still shaking but now perhaps from relief that the immediate punishment was over, was allowed to dress and depart. Stewart and Jones bade farewell to the nurse and walked over to their accommodation discussing their plans for the evening.


Following dinner and a social evening with Lady Halliday, Jones and Stewart wandered over to where the male prisoners were no doubt asleep.


Miss Jones strode into the male dormitory slamming the lights on. As the tired and sleepy males raised themselves she shouted out.


“Spot inspection, you know the score boys, at the end of the bed, stark naked, at the present and with those foreskins snapped fully back”


The twelve prisoners, ranging in age from late teens to their early forties rapidly followed the orders. Several of them displayed erections, with Stewart almost feeling sorry for them as he knew that this was something that the young mistress detested and always felt necessary to discourage. She looked at the ones so displayed with contempt and ordered them along one side of the room as there were conveniently just six of them. Total silence reigned apart from the clicking of the wardresses boots as she briefly inspected them.


“I will deal with those who lack any form of self control later” she snapped “In the meantime I am here to inform you about a recent change in the rules that you will allowed to experience earlier than most male prisoners. A new form of correction has just been authorised that will enable the ladies in charge of you to regularly check and update you on their authority. The powers that be have approved the use of a short sharp slap to your testicles that will enable you to demonstrate your total obedience to my authority in the way that you will have to position yourself…exactly as I direct …knowing that I will then be hurting you in what I believe is a very sensitive area. The implement used to do the slapping has been left to the discretion of the wardress. I will be trying three different items…and I am sure that you will be happy to let me know which you feel will best impress my authority on those little balls of yours”.


“It is suggested that using items of a personal nature should reinforce the personal authority of the staff member, so the first item I will try out will be my uniform gloves. They are rather lightweight and the stitching is minimal so they should not be too harsh…but…. we will see.” Stewart, thinking of her usual damp hands wondered if the gloves would really be as light and flimsy as she suggested.


She arranged two wooden seats about three feet apart in the centre of the room. The look of fear and apprehension increased on the faces of the prisoners.


“We will experiment starting with the male over by the door. As he is dismissed the male in the next bed space will come and stand, feet well spread on the chair seats and facing away from me. When I say “prepare” he will bend over and grip his knees so that I have a good view and full access to the rear of his scrotum. I really have no idea of how much this will hurt so it will come as much of a surprise to me as it will …no doubt… to you.”


We will start with those displaying a lack of self control: “First prisoner!”


It was the male in his forties that Miss Jones had charged with having an erection. He still had. His buttocks bore the results of the stringent punishment that had been ordered and duly inflicted. As he followed the order to prepare, the stretching of his heavily bruised and wealed buttocks evoked a gasp of pain.


His scrotal sac hung low and clear of his thighs looking, and no doubt feeling, vulnerable. They were just under face height to the young wardress as she removed and screwed up her leather uniform gloves. She rested the finger tips on the rear of his scrotum, drew her hand back and brought them forward with a loud slap.


The dangling scrotum snapped forward and a deep grunt came from the male.


“It will be the second and more so the third contact that will really give you all a chance to demonstrate that you accept my authority without question.” She said.


The second slap was quickly followed by the third and the male almost brought his hand round as protection but his training helped and he was able to accept this demonstration of authority without question.


One by one the males mounted the chairs and fought against their natural instinct to protect themselves with each meekly accepting Miss Jones slapping their most sensitive area. More than one resumed the bedside present position with tears in their eyes.


She gave the room an about turn order so that the males all had their backs to her. Standing in the middle she calmly removed her tie and undid the buttons on her uniform shirt slipping it down to her waist before unclipping her heavy sport brassiere and slipping off. As it brushed against her still swollen nipples she gave Stewart a wry grin, then quickly slipped the shirt back on leaving most of the button tantalisingly undone. She fastened the rear bra clips and told them all to face inwards.


If they didnt have an erection they soon would as she made no attempt to cover her large wobbling breasts with no more than three fastened buttons holding the front of the white shirt together with her nipples firm, hard and visible through the cotton material.


“I now want you to feel and accept a slap or three from my bra straps. Unfortunately some of you will have noticed that I am rather a large girl in that area and so I need a well reinforced support garment with stronger than average back support. Had I been one of the thinner wardresses you would hardly feel the next session…as it is you may find it a little challenging to remain in position. The first prisoner up on the chairs…NOW!”


The previous first victim could not help but briefly touch his aching scrotum as he climbed on to the two chairs. He braced himself as much as he could and waited.


Miss Jones held the large support bra by the cups and as the back support would not flatten with the rear clips done up, undid them so the heavy back straps with the attendant metal clips and wiring lay flat against each other. She took aim and lashed the rear of the dangling bulbs…hard.


It hurt the dangling unprotected testicles. The prisoner began to sweat knowing that the next two lashes would hurt even more. Somehow he managed to contain his protests to a low grunt each time. The whole room was now full of nervous tension as they realised that this young girl meant to really hurt every one of them under the pretext of demonstrating the new policy.


One by one each male climbed on to the chairs, squatted and waited for the gut aching straps to hit. Somehow they all managed to submit to the authority of what was almost a schoolgirl.


When the last prisoner had felt the weight of the bra straps Miss Jones, without a trace of embarrassment reached under her skirt and pulled down her uniform panties stepping out of them to hold them in her hand. They were the uniform standard rather than a thong with plenty of material and a broad elasticated waist band.


These will provide the last intimate article for me to slap your rather tender scrotum boys. Im afraid that I have been wearing them for some time and a certain dampness will add to their weight and therefore effectiveness. She then slowly turned them inside out.


As you can see, the part that was in contact with my sensitive area will be the part that hits yours. She then positioned a third chair between the others and facing them. Sitting in the chair she told the waiting room that there would be a change in the position for the recipient. He would now stand on the chairs but facing her and squat down so that his genitals would hang well below his body and right in front of her eyes.


Again, it was the prisoner that she had arranged to be formally punished earlier in the evening. He was still partially erect and as he squatted as ordered his view of her breast and spread thighs did nothing to help. She then ordered him to hold his penis to his lower stomach to ensure that her selected target area was clear.


In full view of her victim she screwed the panty material into a tight spiral, held it in place with her left hand as she brought the right hand holding the waist band fully back and then, before the panties could unwind, taking careful aim at the hanging, aching and defenceless testes she slapped forward with the bundle.


Being struck in the gonads would be painful, but Miss Jones had achieved what every staff member tried to. She had kept within the guidelines but managed to increase the level of pain by screwing up the panties.


It clearly hurt the prisoner, but more to the point, it had clearly convinced the group that this was now a serious punishment, rather than the nominal one that they had expected. Certainly the first recipient with two slaps still to endure was now shaking as he awaited the second.


He knew that any objection or attempt to avoid the panties would result in even more punishment for his body. He had no alternative other than to totally submit to this young girls punishment…without question. He continued to hold his penis as directed and managed to accept the next two slaps with just a sharp intake of breath.


One by one the frightened group of males did the same. Each trying not to look at their young disciplinarians breasts or thighs as they squatted in front of her and awaited the slaps.


Eventually they had all been slapped and had managed to accept this form of authority without any rebellion standing at the foot of their respective beds. Despite her earlier threat of punishing the ones with erections, Miss Jones made no further reference to their earlier lack of control. Perhaps the total absence of any tumescence was helped by the dull scrotal ache that they all felt and their total humiliation at her handling of them.


She simply collected her underwear and without bothering to put them back on, simply smiled sweetly and bade them all a restful night.


When Miss Jones and Stewart had departed all of the males gratefully climbed into their beds clutching their now aching testicles in a vain hope that this would somehow relieve the pain. Perhaps it did, but nothing would relieve the hopeless frustration of having to submit to the young girls cruelty without any right to complain or protect themselves.


Had they known her plans to correct their unauthorised erections earlier that night, they would have slept even less soundly.


Review This Story || Author: Will Cane
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