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Her Headmistress - The Return

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Emma is disciplined by the Headmistress, but she isn't alone

This story follows on from the Lush Notorious competition entry, Her Headmistress.

Emma bit her lip and was more than a little worried when she saw the note from Miss Jackson, the headmistress at the sixth form college. It was her first day back at sixth form college after her holiday when she had attended the S&M fair and, first of all, caned Miss Jackson, and was then caned by her. Emma remembered the promise that Miss Jackson made to her which was to give her a caning every week for the whole term, so reckoned this was the reason she had to attend her study.

All the students were wary of Miss Jackson and it was a reputation Miss Jackson loved to have. She was very strict and had a typically dominant personality for a headmistress, insisted on respect and hard work, and readily punished anyone who fell below her exacting standards. It was well known and students from other sixth form colleges said they were just happy they didn’t have to suffer the same strict regime.

Emma was more than a just little wary of Miss Jackson, She had never met anyone so scary before, and couldn’t understand why she had the equivalent of a schoolgirl crush on her headmistress, but she did. She remembered being so shocked to see Miss Jackson at the S&M fair, and almost wet her knickers thinking she would be in trouble. She went to the fair in the hope of caning someone else thinking it would be more of a turn on for her than getting caned, albeit she used to masturbate after being caned by Miss Jackson at college but assumed that was because it was Miss Jackson rather than the caning. In the event, though, she was even more shocked to be able to cane Miss Jackson, and giving her fantasy girlfriend finger sex afterwards was a joy in itself, although she didn’t get aroused herself. However, she then found being caned really erotic and loved the finger sex Miss Jackson had given her, and her love for Miss Jackson suddenly increased in leaps and bounds, although she never stopped being scared of her.

Now they were back home, Miss Jackson was again the feared headmistress, just as she was before seeing her at the S&M fair. What was more pointed for Emma, was that it was the start of the lunch break and she was now sitting outside the headmistresses study, on one of the three chairs in the corridor, and anyone who passed by knew that she was due to go in and see the headmistress, and everyone knew that that invariably meant being disciplined by her.

No one actually found it strange seeing Emma there, because she had a habit of getting into trouble so that she could be caned. Previously, there would have been a several week gap between each incident, and during that time Emma would have fantasised about being caned once again. The reason she enjoyed being caned by Miss Jackson, was that it turned her on. What she hadn’t realised, was that Miss Jackson saw her sex juice dripping onto her hair mound and glistening in the light. However, now that that was public knowledge, at least for Miss Jackson, Emma knew that she would be sexually aroused on a more regular basis by being caned by her every week.

Emma was in the summer uniform of a blue and white check short-sleeved dress with a white belt, and so bare legs were allowed. She had been sitting outside the headmistresses study for about five minutes, before Lily came up to her and asked, “Are you really in trouble on the first day back at college, Emma?“

Emma didn’t want to admit to Lily why she was there, and said, “Miss Jackson has asked to see me about one of the projects I did last term. She hasn’t said anything else, yet.“

Lily seemed happy with that explanation and said, with a supportive smile, “Well good luck then, Emma.“ She then walked away down the corridor.

Just a few moments later the study door opened and the school secretary, Miss Foster said, “Please come in Emma. Miss Jackson will see you now.“

Emma went and stood by Miss Foster’s desk, and looked nervous. The secretary sat down and gave the instruction, “You can go straight in, Emma. I’m going for my lunch now so let yourself out when you have finished.“

Emma gave a weak smile and said, “Thank you, Miss Foster,” and watched her leave the office. She then turned and went and knocked on the door to the study.

Emma heard, “Come in,” opened the door and walked in, carefully closing the door behind her. She walked up to the headmistresses desk, and as always, was daunted by Miss Jackson’s demeanour. She stayed standing and looked down at Miss Jackson who was still studying some papers and did so for a few more seconds, before putting her pen down and looking up. Emma thought Miss Jackson looked so attractive in her short-sleeved white blouse and as she looked down could see her cleavage and ample breasts which sent quivers flying around her pussy. As much as she was wary of Miss Jackson’s strict manner, she was just so turned on by her.

Miss Jackson looked up said in a stern tone, “Thank you for coming Emma. I need to make a few points clear before we continue. Firstly, I trust that you have not told anyone about our meeting when on holiday?”

Emma remembered quite clearly Miss Jackson’s very firm instruction not to tell anyone about the fact that they had caned each other and fingered each other to an orgasm. Emma was able to reply honestly, “No, Miss Jackson. I have not told anyone.”

Miss Jackson nodded her head in satisfaction and smiled briefly. She then asked, again with a serious look on her face, “I take it you still want to be subjected to discipline on a weekly basis?”

Emma had certainly given that some thought on her way home. Up until now, she had been quite happy being caned every five or six weeks. However, she had spent each night since the S&M fair masturbating as she fantasised about being caned on a more regular basis by the dominant Miss Jackson. She licked her lips and replied, “Yes, please Miss Jackson.”

Miss Jackson was quietly happy about this because, of all the girls, she really did enjoy caning Emma. She loved the way that her hair mound glistened with her sex juice, and was pretty sure that she went to the toilets afterwards and masturbated. Indeed, she usually went to her private toilet afterwards and masturbated as well as just soon as Emma had left her study. 

Miss Jackson did think about how it was fortuitous that she had met Emma at the S&M party. Miss Foster had originally suggested she go to understand what it was like to be caned as until then she had only caned the students and needed to understand the pain herself. Miss Jackson hadn’t told Miss Foster that she actually liked the idea of being disciplined herself and so willingly accepted her secretary’s suggestion. That was three years ago and she had been each year since.

Seeing Emma at the S&M party was, of course, a shock, but it worked out well. She got the caning she wanted, from Emma of all people, and discovered she had a real liking for it. Emma got to cane her but discovered she wasn’t turned on by giving her the cane, but was when being caned herself, which made it easier when they got back to college.

What was even better, was that Miss Jackson rather fancied Emma as being a young lady who was usually very hard working and got good marks, with a strong personality like herself, although every few weeks let herself down by being naughty. Of course, that led to her making the discovery that Emma was turned on by being caned. 

Miss Jackson thought these thoughts momentarily and then continued, “Well, we will need an excuse for you coming to see me every week. We will tell everyone that I am going to tutor you and that should satisfy their curiosity. We will do it during lunchtime so Miss Foster will not be in the outer office.”

Emma felt more relaxed that Miss Jackson had clearly thought through how they would deal with a weekly discipline session, and said, “That sounds very good, then, Miss Jackson.”

Miss Jackson continued, “Of course, normally I have given you three or four strokes of the cane. Now, however, the minimum number will be six strokes and it will normally be more than that. Don’t worry though, you will have plenty of time to recover because you will be using my private toilet to sort yourself out afterwards.”

Emma wasn’t so sure that she wanted so many strokes of the cane, but, again, she had agreed to be subjected to Miss Jackson’s discipline and so did not argue. 

Miss Jackson then said, “Okay, Emma, let’s get started. First of all, go and sit at the other desk and write out one-hundred times, ‘Please will you cane me, Miss.’ As you are being disciplined, you will need to take your knickers off now and roll your dress up above your waist so you are sitting on the hard cold wooden seat bare-bottomed.”

Emma didn’t like that idea at all because she hated doing lines. She just found it so boring. However, she realised that this was Miss Jackson asserting her authority over her, and, as she had agreed to the discipline session, she knew she had to do whatever she was told to do. She, therefore, went to the table and rolled her hem up and tucked it into her belt, and then quickly pushed her knickers down to her ankles, stepped out of them, and put them on the table in front of her. She then sat down, opened the exercise book, picked up the pen, and started to write her lines.

Miss Jackson kept an eye on Emma as she wrote her lines, although did manage to get on with her own work at the same time. Fifteen-minutes later, she saw that Emma had put the pen down and was obediently sitting at the table, waiting for Miss Jackson to notice.

With a smile, which Emma didn’t see, Miss Jackson ordered, “Right, girl, stand up and bring the exercise book to me.”

Emma obediently stood up and realised that as she had been writing she was getting more and more tense regarding the caning that was due to happen, but that had actually turned her on. She still found that so strange, but it was the same when she used to sit in the corridor outside the study waiting to be called in to be caned.

Miss Jackson had deliberately set Emma doing lines. She was pretty sure that as Emma got aroused by being caned, doing lines beforehand would make her anxious and aroused at the same time. She wanted Emma to be aroused as she also got turned on seeing Emma’s sex juice on her hair mound as she was bent over with her legs apart. If it worked, then doing lines would be a useful tool for future caning sessions as well as it would arouse them both.

Miss Jackson took the exercise book and opened it up and started to review the lines. She knew that Emma would be increasingly tense with the show of focusing on the lines, and she would assume that they really were being checked. In fact, Miss Jackson did not bother to either count the lines or check the spelling, but looked up and said in a stern tone, “You have done the correct number of lines, but I have found three mistakes. I will therefore add three strokes to the tally I had previously set, which was six strokes. Therefore, go to the caning table, bend over, stretch your arms as far forward as usual, with your legs apart, and get ready to accept your caning.” 

Emma wasn’t so sure about getting so many more strokes than she had ever received before. However, she did realise that she was aroused by being scolded by Miss Jackson and, just hoped that the additional strokes would give her a more intensely stinging bottom that would make it even easier to masturbate. So, obediently, she went and bent over the desk, stretched her arms up and clasped the table on both sides, made sure her legs were well apart knowing her pussy lips would be clearly seen by the dominant headmistress, and, with her nose just an inch from the tabletop, waited. As she looked at the table top she told herself if she found the caning too much then she could always refuse to continue with the regime. However, she was now so turned on she wanted to see what nine strokes felt like.

Miss Jackson went and stood behind Emma, swishing the cane as she walked from her desk to the caning table. She rubbed the cane from side to side across Emma’s bare bottom and took the said in a demanding tone, “You will need to say that you agree to come back here every week for a further caning with as many strokes as I decide to give. If you do not agree, then I will not cane you today. What is your answer, Emma?“

Emma hadn’t expected to have to make that decision today but was now far too aroused to do anything other than agree to Miss Jackson’s terms and kept hold of the table but managed to turn her head, and said, “I agree I will come back whenever you demand, Miss Jackson, and take however many strokes you decide.” She then looked back at the tabletop and waited, but got even more tense but also even more aroused by submitting to the new regime

Miss Jackson smiled as she was quite sure that Emma would want to come back, but it was far better to make sure, for both of their sakes. Miss Jackson then focused on Emma’s very kissable bare bottom. Of course, it was a bottom that she had caned several times before, but she now had the added benefit of being able to do this on a weekly basis. So, focusing, she pulled her arm back, aimed, and then brought the cane down with a loud thwack so it landed about halfway down Emma’s bottom. Emma was a slim girl and so there wasn’t so much flesh on her bottom, and it was pulled tight because of the way she was stretching, and so the cane did not bite very far into the flesh. However, the red welt did appear fairly quickly and, of course, Emma let out a gasp and an “Oww.”

Miss Jackson saw that Emma struggled with the stroke but stayed in place and kept hold of the sides of the table and her pained gasp told her she felt the impact of the stroke. Miss Jackson hadn't mentioned it, but knew she was going to land each stroke rather harder than she would for a normal caning because Emma was going to enjoy it. Of course, Miss Jackson knew from her own experience of getting caned at the S&M parties that the actual caning wasn't so enjoyable, but the stinging afterwards was. She also reckoned that Emma saw submission as a sexually erotic way of forgoing control and handing it to someone else. Certainly, Miss Jackson had found it erotic when Emma had caned her. Hence, she caned harder than usual as that emphasised the lack of control Emma had and, she reckoned, the more turned-on she would get.

Emma was, indeed, feeling turned on. She never really understood why being caned was so erotic because, when she looked in the mirror afterwards, what she saw were raised red welts that hurt crazily and had reduced her to tears. However, what she also knew, was that, as much as her bottom stung, her clit was always taut, as were her nipples, and she managed orgasm after orgasm once the caning was over.

Miss Jackson focused again and landed the second stroke on Emma’s bottom and watched the second red welt develop just below the first. Moments later she landed the third and then the fourth, knowing it was more difficult for Emma to deal with the strokes when given in quick succession, and also that it was going to sting far more and give her a better orgasm. In fact, Miss Jackson could see that Emma’s hair mound was already glistening with her leaking sex juice and so was more sure than ever that she was aroused by the harder strokes as well. 

Emma cried out again with the fourth stroke and was still saying ‘Owwww,’ as the fifth stroke landed and again with the sixth. 

Miss Jackson really wanted to set the scene for future canings which was why she added three strokes and landed the seventh quickly after the sixth. When she landed the eighth stroke she told herself that Emma would be hating her right now, but knew that she would have to accept all her punishments and, once in the toilet, she would forget the pain anyway and savour the orgasm. So, when she landed the ninth stroke and heard the elongated ‘ Owwwww,’ she knew the turned-on feelings Emma had because she had them herself and was sure that her own knickers were wet.

Miss Jackson waited only a few moments after landing the ninth stroke before ordering, “You can get up at Emma.” and then watched with her quickly beating heart as the gorgeous young Emma eased herself up and started to rub her bottom whilst stepping foot to foot. Whereas with most of the students she had no sympathy for them, she knew that she had given Emma a harder caning than usual and was turned on herself by seeing her bare bottom and legs and stretched pussy lips.

Emma had never had so many strokes and as each one landed in quick succession her bottom stung like never before. She wondered how she could possibly have wanted to be caned, but as she stood back up and the tears rolled down her face as she rubbed her bottom and stepped from foot to foot, she looked at the dominant Miss Jackson and, once again, fell in love with her. As the stinging subsided, although Emma continued to step from foot to foot and rub her stinging bottom cheeks, she couldn’t wait to go to the toilet and play with herself.

Emma was looking towards the door to the toilet and, thankfully, Miss Jackson told her she can go. So, she quickly went to the toilet, opened the door, walked in and closed the door behind her, lifted the toilet seat cover, and sat down. She quickly spread her legs apart and ran her fingers up and down her already very wet pussy lips, easing inside whilst also making sure that her tort clit was flicked, which, together, quickly brought her to a sensational orgasm.

As Emma sat on the toilet and recovered, she still couldn’t understand why the pain got her so aroused but supposed it was also linked to the fact that it was almost a loving relationship with Miss Jackson. She knew that she would masturbate in bed tonight, no doubt several times, and would be thinking of her throughout each day and always hoped to walk passed her and glance at her sexy figure.

Miss Jackson stood close to the toilet door and listened, with a smile on her face, as she heard the growing intense gasps coming from inside. She couldn’t resist slipping her own fingers inside her knickers and playing with her own very wet pussy lips and tort clit, although walked across the room before bringing herself to an equally intense orgasm. She never felt this way with the other students, but told herself how that really meant she fancied Emma so much.

Miss Jackson was sitting at her desk by the time Emma came out of the toilet. She reverted to her strict headmistress persona and looked up and ordered, “Stand in front of the desk with your hands on your head, Emma.“

Emma had thought the punishment was over but did as she was told, so she still felt like a naughty girl, but enjoyed being submissive to Miss Jackson.

Miss Jackson had always intended using these, so called, tutorials to ensure Emma got even better marks on her tests and exams, and, now Emma was committed to them, explained, “I know that getting low marks in an exam would normally get you a punishment. However, what I am proposing, is that to make you work even harder, high marks will earn you additional punishments. I know that you currently get about seventy percent in your tests and exams. From now on, if you get seventy-five percent then I will give you additional strokes but if you get under sixty-five percent you will get less strokes. However, if you do get lower marks, you will be put into lower sets and given detentions which, I rather suspect, you don’t want, whilst, on the other hand, I think that you will enjoy even more strokes of the cane.”

Emma was getting more and more aroused as Miss Jackson was explaining the new regime. She certainly did hate detentions, but, she now knew that she would enjoy getting the extra strokes of the cane, particularly when given to her by Miss Jackson. She remained in awe of her and, bearing in mind she fully intended getting higher marks so that she could get to the University of her choice, it would be an excellent bonus to be given those extra strokes of the cane for getting those higher marks she wanted. 

Emma happily said, “Agreed, Miss Jackson.”

Miss Jackson smiled knowing she was going to have so many orgasms herself after caning Emma. “Good, that is settled then.” After a moment, and seeing the time, she said a stern, “You had better get back to your classroom as lunch is almost over.”

Five minutes later, Miss Foster came back from her lunch break. She had seen Emma outside and therefore knew that Miss Jackson was alone, and so, without knocking, she entered the study and saw the suddenly contrite look on Miss Jackson‘s face. Miss Foster was sixty-years-old and wearing a short-sleeved white blouse and dark blue skirt, with dark blue tights.

Miss Foster ordered, “Get up, Jackson, and stand in front of your desk.“ 

Things were reverting to their now normal structure in the headmistresses study and Miss Jackson knew what that command meant. She quickly got up and walked around the desk and stood in front of it, looking down at her chair and desk. She watched as Miss Foster went and sat in her chair and looked up at her with a glare and demanded, “Did Emma go with my idea of additional strokes for better marks?”

Miss Jackson replied, “Yes she did, Miss. It was very good of you to suggest it. I suppose I should’ve thought about it, but I didn’t.”

Miss Foster smiled. She remembered how she used to think that Miss Jackson was so special and intimidating, but then she saw her make more and more mistakes and she realised that although having a tough-woman reputation, she actually suffered from a lack of self-confidence and was risking losing her job. It was only when she started making the decisions for Miss Jackson that she started to get on top of her job, still taking the credit for everything. However, the reality was that the secretary was in charge of the boss lady, which only the two of them knew, for now anyway.

Miss Jackson was, indeed, wary of Miss Foster who she had come to rely on so much. She knew she had to be thankful that Miss Foster took on the role of her mentor and for sorting out all of the things she missed. It also made sense that Miss Foster treated her more like one of the students and so whenever her work was below par, it was right that Miss Foster should discipline her. That was what Miss Foster had demanded when agreeing to help Miss Jackson. It was also agreed that the punishment couldn’t be as public as a detention and so the cane was the obvious choice. It was quick and easy compared to, say, a spanking, which took far longer to give and had more chance of being discovered.

Miss Jackson stood obediently looking at the dominant Miss Foster. She had a severe attitude and Miss Jackson was as wary of Miss Foster as the students were of her, which was funny as around the college everyone was wary of the headmistress but not of the secretary. If they knew the truth they would no doubt be shocked, though. 

Miss Foster knew that enough things had gone wrong today for Miss Jackson to deserve her next caning, and, ordered, “Take your knickers off, Jackson, and roll your dress up.“ When alone Miss Foster addressed Miss Jackson by her surname only, whilst Miss Jackson addressed Miss Foster as, ‘Miss.’ 

Miss Jackson winced but immediately did as she was told. She raised the hem of her dress and tucked it into her belt so it would stay up above her waist, and of course her hair mound, and slipped her thumbs into the elastic knickers, pushing down to the floor and stepping out of them. She scooped them up and put them on the visitor's chair, knowing that she was not going to be asked to sit down on it. 

Miss Foster kept a stern glare on her face as she watched Miss Jackson step out of her knickers, but thinking how she was the one very much in charge, with Miss Jackson being her submissive. 

The change around had happened quite quickly three years earlier when Miss Jackson realised that she was turned on by being submissive to her own secretary. They were having a coffee in the study, one day when Miss Foster pointed out the mistakes that Miss Jackson was making. Miss Jackson simply blurted out, ‘I think I need you to correct my errors, Miss Foster.”

Miss Foster replied sternly, “I will, but I think I should treat you as one of the students and discipline you when your standards aren’t high enough.”

Miss Jackson had been thinking for a while how she found Miss Foster such a domineering woman and had fantasised about being caned by her, so when she demanded disciplinary rights over her, she quickly replied, “Yes, Miss,” and the roles reversed. That was the last suggestion Miss Jackson made about her own discipline with all subsequent decisions being taken by Miss Foster, which was funny given Miss Jackson’s reputation for being so strict.

Miss Forster studied Miss Jackson who was still naked below her waist, and wondered if her pussy lips were as damp as usual before a caning. She would know soon enough, she told herself and ordered, “Bend over the caning table, Jackson. I thought your report to the Governors was awful and I had to spend my own time correcting it, so you need another lesson.”

Miss Jackson blushed with embarrassment as she went to the end of the caning table and bent over, stretching and clasping the sides of the table as far up as she could. She knew her report was rubbish as she was going out last night and was late, and, rather than cancel, she rushed it and reckoned that Miss Foster would correct it for her. So, getting the cane was definitely right in the circumstances, and as she felt the cane being rubbed back and forth across her bottom she knew she deserved every stroke. 

Miss Foster loved how she had taken disciplinary control over the headmistress. Miss Jackson had a reputation for being strict and using the cane instead of reasoned argument. The students were scared of her, and still were, but then they didn’t know their headmistress got caned by the school secretary. They would chuckle if they knew. On the other hand, the school's reputation improved with Miss Jackson’s strict discipline regime so the governors were happy, but they too didn’t know the role the school secretary played in the effort to improve things. So, as Miss Foster got ready to land the first stroke on Miss Jackson’s bottom and get the usual pained gasp, she knew that after the eighteen strokes she was going to give her, Miss Jackson would give herself multiple orgasms, but her bottom would still sting as she attended the governors meeting in two hours time. Luckily, she was going to be able to present to the governors standing up, as she was bound to still find sitting down very testing. Well, Miss Jackson might be the one with the reputation, but her secretary was the powerhouse behind her, literally, Miss Foster told herself.

Miss Jackson felt the cane rubbed from side to side across her bottom and knew her bottom would be stinging crazily when she was standing to give her presentation to the governors. Still, she would have time for multiple orgasms first, and, after all, she had to thank Miss Foster for correcting the mistakes which would make her look so good at the meeting. Being caned by her secretary was a small price to pay and, anyway, she was thinking of suggesting the same scheme as Emma got, so that improvements she made resulted in more strokes of the cane, and thought Miss Foster would agree to that. She hoped so anyway.

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