It was a normal work day for Jessica. The eighteen-year-old was a trainee prison guard who loved wearing her prison guards uniform of a white short sleeved blouse and dark blue skirt with a wide black leather belt and the authority over the prisoners that went with it.  

Jessica had really taken to the job which seemed a natural follow through to her being a prefect at school. Jessica had been one of the youngest prefects when appointed at sixteen-years-old and had learned the benefit of being strict and of pedantically enforcing the rules. During her time as a prefect she handed out detentions freely giving doubles to the worst offenders even though it meant them going to the Headmistress to be caned. However, she quickly noted how most of the girls she gave the detentions to were increasingly well behaved in her presence and she took that experience with her when training to be a prison guard. 

Jessica had always been a confident young lady and relished controlling the prisoners and when they got out of hand reporting them to the Governor to be disciplined.  

The law had also changed as attitudes had hardened with society reacting to increasingly violent crimes and prison guards were now able to dispense corporal punishments to misbehaving prisoners. Jessica amongst others was quick to use the cane in the same way as she had handed out detentions and generally saw a speedy improvement in the prisoners’ behaviour. 

When Jessica came across a prisoner who was obstructive or who aimed to control the guards she manoeuvred the prisoner to break the rules and earn strokes of the cane which she happily gave them to enforce her control over them. She always reconciled her strict approach with the logic that prisoners were there to improve and become better citizens rather than to have a holiday.

Today, Jessica was signing in one such prisoner, Lisa Cox, and was in a reception office when she was shown in. Jessica ordered, "Sit down, Cox, and answer my questions please." Jessica was firm and officious but knew that worked best with the older prisoners, like Lisa, who she knew from the form was fifty-five-years-old.

Lisa had been sentenced to her second prison term. She always saw herself as sophisticated and certainly superior to almost everyone she came across and that arrogance had led her to expect people to follow her orders and in the main they did. So, when she was in prison the first time she soon became top dog and had prisoners and several guards at her beck and call. 

This time Lisa was allocated to the block where Jessica was a guard and as soon as she saw her and realised that she was still a teenager she was confident she would have no problem making her do her bidding and her time at the prison as comfortable as possible.

Lisa heard the instruction to sit down but decided to start straight away to make Jessica fear her so she stayed standing and gave her a disdainful superior look and said, "The chair is dusty. Do you have a duster you could use on it for me?"

Jessica could tell that Lisa was as arrogant as they come and knew from the prison records from her first custodial sentence she would talk down to the guards and look on them as her personal servants. Well Jessica had other ideas about that and was going to show this pompous and condescending prisoner just which one of the two of them was in charge. She replied to the question with, "I'll make a note for the cleaning staff but it won't hurt you as much as other things do in here." 

Jessica allowed the last few words to hang in the air although wondered if Lisa had deliberately ignored them as she took out her handkerchief and flicked the seat of the chair a few times before sitting down and crossing her arms looked bored. However, Jessica knew it was one of the ruses Lisa used to usurp the guards’ authority.

Lisa had dealt with guards Jessica’s age before and had them eating out of her hand so she said assertively. "You don't look old enough to be a guard."

Jessica remained cool as she replied, "Well I am, Cox, and you need to respect that." She did think that Lisa had a particularly haughty voice and was no doubt used to brow-beating other women, but was confident that this prisoner had met her match today.

Lisa scoffed a reply saying in a sarcastic openly disrespectful tone aiming to make Jessica a little scared of her, "Respect? Sure, I'll respect you, though you should respect your elders’ as well."

Jessica wasn’t having any of it and looked sternly at Lisa knowing that she had to exercise her authority over the insolent and self-important attitude that even she was blatantly showing, and said sternly, "Silence please and answer the questions. You will also refer to me as 'Miss.' or 'Miss Masters.' Understood Cox?"

Lisa didn't give the retort she wanted to regarding Jessica's surname as she realised that was probably too direct and as awkward and rude as she might be the guards had so much more power now. So, she said a more submissive, "Yes, Miss." Still, she also knew several of the guards were open to sexual favours in return for cigarettes or the like and remained confident that someone as young as this guard could be manipulated more than most.

Jessica was happy that Lisa had at last shown the respect she expected to get from the prisoners. Still conscious of the fact that Lisa simply could not be trusted she then ran through the list of questions and told her the basic rules of the prison, although both knew that Lisa had been locked up before in this very prison and knew the rules well enough.

After asking the last question Lisa ordered, "Right, I need you to change in to your prison uniform. Please undress and put your clothes on the chair. I must give you a body search before you get dressed again though and don’t forget you will earn strokes of the cane if you disobey my orders.”

Lisa pulled an, ‘If I must,’ face as she stood up. 

Jessica stayed seated as she watched Lisa stand up and kept a straight face as she watched her undress. She knew that most of the prisoners felt awkward undressing in front of a fully clothed guard but also knew they had no choice. However, Jessica wanted Lisa to earn a few strokes of the cane so she could enforce her control over her and hoped she would resist.

In fact, Lisa didn't object as she slipped the straps of her sleeveless dress down her arms and pushed it down to the floor, stepping out of it and putting it on the chair. Then, putting her hands behind her back unclipped her bra and let the straps slide down her arms catching it and putting it with her dress. It left only her knickers and she put her thumbs in the elastic and pushed them down to her ankles stepping out of them and putting them with her other clothes.

When Lisa stood back up facing Jessica she saw the teenager put a plastic glove on her hand and this time winced knowing what was going to happen next.

"Open your mouth," Jessica ordered.

Lisa gave a haughty "Hhmmph" as she opened her mouth.

Jessica eased her fingers into Lisa's mouth and felt around before ordering, "Tongue out, please."

As Lisa stuck her tongue out Lisa grasped it between her thumb and forefinger and lifted it up so she could see underneath and intentionally pulled Lisa's tongue harder than she needed to and when Lisa reacted by pulling her head backwards she snarled, "One stroke."

Lisa knew how some guards were intentionally rough to rile the prisoners and although she wasn't happy with being awarded a stroke of the cane she wasn't going to cow-tail to the upstart teenage guard. "You were too rough," she snarled.

"No I wasn't and that is another stroke," Jessica said sharply

Lisa wasn't used to a guard being quite so quick to award strokes of the cane.

Jessica could see she had caused Lisa some concern and decided to move things along to throw her off guard. "Bend over, Cox," Jessica ordered as she stood up.

Lisa was already unsettled as she could tell that Jessica wouldn’t be easily as controlled as she had hoped and decided she would try for another guard to carry out the internal search and asked, "Please, Miss, but you must be too young to do this. Could I have someone my own age please? That is fair, I think."

Jessica ignored the prisoners discomfort. "I've done this loads of times, Cox. Anyway, I told you not to argue and must tell you if you argue or resist again I will start to notch up some more cane strokes, so do as I ask please."

Lisa winced again. She knew the guards could punish the prisoners for disrespect or blatant misbehaving and supposed that Jessica would do as she threatened quickly enough. So, to avoid any further strokes of the cane she didn't resist and turning bent down and grabbed the seat of the chair and parted her legs ready for Jessica to search her anal passage.

Jessica stood behind Lisa and making sure the glove was pulled tightly over her hand she eased her hand between Lisa's legs and along her pussy lips.

Lisa wasn't expecting a search there but then hadn't read the information booklet she was given earlier in the waiting room. If she had read it she would have known that following several incidents of drugs found in the vagina rather than the anus the additional search was now common practice. However, as she wasn't expecting it she stood up and turned to object and accidentally struck Jessica with her elbow.

"Ow," Jessica gasped as Lisa's elbow caught her. She was livid and immediately said, "Two strokes."

Lisa gasped as she hadn't intended to strike Jessica but saw the look of anger on her face and as she heard the penalty she had earned she knew she could not really object.

"Bend over again and this time stay down, "Jessica ordered.

Lisa wasn't feeling anywhere near as confident as she had felt when she first walked in and saw the young guard, and so submissively she turned and bent down again spreading her legs apart.

Jessica pulled the glove tight again and eased her hand between Lisa's legs and pressed her fingers into her pussy. She edged her fingers deeper inside and felt around until she was satisfied there was no contraband inside her.

Lisa felt so degraded as Jessica felt around her vagina like a young man who had no idea the feelings it usually generated in a woman. She still reckoned it was unreasonable to search her vagina as it was so undignified and was becoming ever more unsettled and as Jessica eased her fingers out she said rudely, "Enjoy yourself?"

Jessica said wearily, "No, but your comment has earned you two more strokes."

Lisa groaned. She was thrown off balance by the intrusive inspection but knew it wasn't over yet. 

Jessica eased her hand along Lisa's bottom crack and finding the hole eased her finger inside and pushed inside wiggling her finger around.

Lisa had expected this inspection but even so knew her anus was particularly sensitive and whilst she tried not to react the continually wiggling finger caused her to groan erotically. 

Jessica knew from some of her colleagues that prisoners normally couldn't help but feel aroused when their anus was fingered and Jessica used it to make Lisa groan so she could increase the number of strokes and she kept a straight face as she said sternly, "Two more strokes."

Lisa was aggrieved because she wasn't messing about and retorted, "That isn't fair as I couldn't stop myself."

Jessica almost laughed as she knew she was now winding Lisa up on purpose to increase the number of strokes she would be able to give her. It was what several of the guards did as caning the prisoners was good fun and got them nicely aroused themselves and quite often the guards made out after caning some prisoners. Mind you, they also knew that some of the prisoners got aroused by being caned and made out with other prisoners after the caning.

Anyway, Jessica reprimanded Lisa and said, "Two more strokes, Cox."

Lisa winced as she counted out the strokes she had been given.

Jessica made a point of standing in front of Lisa and with her gloved hand pinched Lisa's nipple between her thumb and forefinger and lifted her very full almost drooping breast up as though to check underneath.

Lisa was taken by surprise and took hold of Jessica's wrist and as she did saw the smirk on the teenagers face as she said, "Two more strokes which makes a dozen. Do you want any more, Cox?"

Lisa knew Jessica was rather more experienced than she had given her credit for. She had known all about the guards who wound up prisoners on purpose so they could cane them and she had fallen for it hook line and sinker and now she was going to suffer the punishment.

Jessica could tell from the downcast look on Lisa's face that she now knew that she had taken on the wrong woman and didn't expect her to resist her caning. "Bend over again, Cox, and get ready for your caning."

Lisa was quite worried knowing she had never received twelve strokes before. In fact, six was the most she had taken before and that was awful enough. So, as she went to the chair and bent over she really wasn't looking forward to this caning at all.

Jessica watched as Lisa bent over and grabbed the chair but unhappy with her stance she eased the cane between Lisa's legs and swished it from side to side and ordered, "Spread those legs apart."

Lisa gasped as the cane hit her inner thighs time and again which stung and made her quickly spread her legs as instructed.

Jessica was still unhappy with the way Lisa stood and ordered, "Lower your tummy and stick your bottom right out, woman."

Lisa knew that Jessica had instructed her to stand in a way that caused her the most humiliation as was bottom was stretched and which also led to the most pain.

Jessica was happy enough at the now well-presented bare bottom cheeks as she positioned herself and tapped the cane on Lisa's bottom to make sure the whole cane would cut in to her bottom cheeks. Once satisfied Jessica pulled her arm back and brought the cane down firmly on to the waiting bottom cheeks and smiled as she heard the expected grunt and as the red welt quickly developed. 

Lisa gasped as the cane bit in to her bottom and realised this was very different to the caning she had got from the other guards last time she was in prison. They hadn’t used anywhere near as much strength as Jessica did just then and Lisa realised this was going to be a discipline caning which she was going to find hard to cope with.

Jessica knew that Lisa was going to be in her wing and that she had a reputation for trying to control the guards and knew that this caning was needed to show Lisa who was in charge as she landed the second stroke right on top of the first.

Lisa cried out loud with the second stroke. She had never had a second stroke that hurt so much and was dreading the rest as there were ten more strokes to go.

Jessica smiled as she listened to Lisa's cries of distress. She knew she wanted to show Lisa just who was in charge and so had every intention of making the caning as painful as possible. As she brought the cane down for the third stroke she enjoyed hearing Lisa's agonised cry as she watched the red welt quickly appear just below the first two. She only waited a few moments before landing the fourth stroke and savoured the repeating cry and developing welt.

Lisa was breathing in and out through gritted teeth as the fifth stroke landed and sent streams of pain cascading across her bottom and the pain only increased with the sixth stroke.

Jessica paused as she was halfway through the caning and rubbed the cane to and fro across Lisa's bottom reckoning the tension would increase the feeling of pain.

Lisa felt the cane being rubbed from side to side and supposed the caning was halfway through although she had lost count after the second stroke. Still, her experience of the cane said most guards rested halfway through. 

Jessica listened to Lisa's pained breathing for a few more moments before pulling her arm back again and as she landed the seventh stroke she relished once again what she thought was an even louder despairing cry. As she watched the seventh welt appear so she pulled her arm back and focussing on the very limited space that remained without a welt landed the eighth stroke just below the seventh. 

Lisa could not stop herself sobbing as the pain intensified and bent her legs as the cane bit in to her bottom and when the ninth stroke landed she bent her legs and raised one leg although desperately held on to the chair as she was sure that if she let go it would lead to additional strokes.

Jessica momentarily couldn't decide whether to land the cane higher up Lisa's bottom and hit the same spots as the earlier strokes or to place the cane lower down on her thighs which she knew was particularly tender. She reckoned in that instance to hit higher first and then lower and so the tenth stroke was angled slightly to traverse four of the earlier strokes and she was delighted with the increasingly pained cry from Lisa and the sound of uncontrolled crying.

It left two strokes and Jessica decided a double stroke was called for. She landed the eleventh stroke right across the soft spot where Lisa's bottom cheeks met her thighs and as she heard Lisa shriek she immediately landed the twelfth stroke on the same place and drew an even louder shriek and her continued frenzied crying. 

However, Jessica also recognised that Lisa stayed bent over and had clung on despite the pain. She would have preferred it if Lisa had stood up but had to accept that was probably due more to Lisa’s fear of further strokes rather than anything else. It actually encouraged Jessica who reckoned Lisa would now fear her which would mean the caning was a resounding success.

Lisa had forced herself to cling on to the chair so that she didn't get up because she knew the alternative was going to be extra strokes. She could also tell that although so young Jessica was going to be a force to be reckoned with and she was unlikely to be the queen bee whilst she was there. That was a shame she told herself but better to keep a low profile and show Jessica the respect she knew she had to rather than be caned again just now. Of course, she was now well aware that she would be caned again and again by Jessica and other guards as that was the new regime. 

Jessica listened to Lisa as she continued to cry and saw the tears rolling down her face. Maybe she had caned Lisa too hard, she supposed, but without any sympathy or regret. She knew this was her chance to impose her authority and she felt she had succeeded there. Time would tell of course but as she was the guard and Lisa just a prisoner she held sway in any case.

Jessica remained stern as she ordered, "Get up, Cox, and make sure you behave."

Lisa eased herself up and when she did all she could think of was her stinging bottom which she rubbed feverishly as the tears ran down her face and she stepped from foot to foot.

Jessica explained to the still crying Lisa in a stern tone, "You had better watch it, Cox, as things have changed since your last spell in here. There is a caning table in the canteen and another one in the games room so punishments are given immediately and in front of anyone there at the time. All of the guards have far more leeway to punish you prisoners as it has been found that there is much less trouble than there used to be."

Lisa listened with increasing dismay realising her stay in prison this time would be very different to her first term.

Jessica looked disdainfully at Lisa and knew how to deal with her in future as she ordered, "I am going to fill in the discipline book and then I will be back. If you move then I will be caning you again. Understood, Cox?" 

Lisa was crying too much to speak but nodded her head to signify her acceptance but knew as well how humiliating it was for her, a lady in her fifties being disciplined by a teenager and knowing it was going to happen again and again. 

Jessica turned and walked towards the door knowing she was going to be in control. 

The still naked Lisa only saw a blurred Jessica leave the room as she stayed standing and rubbing her stinging bottom feeling the raised welts on her bottom. She knew that although only twelve strokes they were far harder than she had been given before or maybe there was just less of a gap between strokes. Either way she knew that Jessica was so much tougher than she looked and that she had met her match with her and she wouldn't find it easy at all during her stay this time in prison. In fact, she reckoned she would have a terrible time of it under Jessica's authoritative control. 

However, as Lisa rubbed her bottom she felt other feelings taking over. She ran her fingers along her pussy lips and realised she was damp and that she had flutters flying around her vagina. She ran her fingers up and down her pussy lips and in only a few moments she had an orgasm and knew that the stinging pain had turned her on. She was so amazed as she hadn't had an orgasm like this one for ages and wondered whether another hard caning would turn her on as much. As she wondered she thought ruefully that Jessica was bound to find a reason to cane her again very soon and so she would find out quickly enough. 

In the control room Jessica sat in the chair next to Lauren, her thirty-four-year-old girlfriend. Jessica had her hand lovingly on Lauren's inner thigh. They were in the control room alone and smiled at each other as they watched Lisa masturbate knowing she was totally unaware about the camera in the room broadcasting everything that went on to the control room. 

Jessica looked mercilessly at the screen. "I fully intend making sure the arrogant self-important snob is put in her place for her whole stay here. Maybe it will even make her change her ways and that this will be her last time in prison."

Lauren looked at Jessica and smiling said, "Judging from the way she is masturbating I bet she gives you a reason to cane her again pretty soon."

Jessica leaned across and kissed Lauren on the lips and ran her hand along Lauren's inner thigh. "You as well, my love," she said pulling her hand back and smacking Lauren's inner thigh, adding, "Don't forget I'll be disciplining you tonight as well."

Lauren hadn't forgotten. Although sixteen-years older than Jessica their relationship had Jessica very much in charge and with Lauren disciplined as least once a week. "Yes, Jessica, I know. You will be giving me a long and hard spanking and one-hundred-and-twenty spanks with that wicked hairbrush of yours."

Even though Lauren knew it would hurt dreadfully she was smiling because she also got really turned-on by a hard spanking and as Jessica was turned-on by giving the spanking they made the most fulfilling love-making afterwards.

Jessica kissed Lauren on the lips again and smiling said, "Exactly what you have earned."

Jessica was so turned-on by the caning she had given Lisa and as she edged her fingers inside Lauren's knickers and along her pussy lips she groaned erotically as Lauren's fingers were doing the same to her wet pussy lips. 

Jessica and Lauren continued to kiss each other and eased their fingers inside the others vagina and flicked the others taut clit until they both exploded in their wonderful orgasms.

Jessica and Lauren smiled lovingly at each other and then looked at the screen and saw a still crying Lisa although laughed as they saw she was masturbating again. They looked at each other knowing Jessica would be caning Lisa again for sure just as she would be disciplining Lauren time and again.