Boarding School Encounter 05 Henrietta Buggered by the Headmistress
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One Foolish Mistake By The Headmistress free porn video
Miss Hargreaves realised it had been one of her silliest decisions ever. She was forty-five-years-old and the headmistress at the local sixth form college for girls where discipline was strict, and she regularly had to cane the students. She saw caning girls, both for earning double detentions and for individual acts of misbehaviour, as very much part of her responsibility, and knew that the regime led to the girls being better behaved than in other colleges where the cane was not used.
However, she had never been caned herself and had often wondered what it might be like. So much so, in fact, that over the years she had often fingered herself to some amazing orgasms as she pictured herself bent over, just like the girls at her sixth form college, except whilst the girls had their dresses covering their bottoms when caned, she had her dress raised above her waist and her knickers were down to her knees and she pictured her bare bottom being caned.
Then, three weeks ago, she saw a complaint on the local social website about a party that had been held in a restaurant, but there had been lots of shouting, and it was discovered that it was a spanking party where lots of visitors were spanked and caned. Miss Hargreaves had never known such parties existed, and, thinking about her long-held fantasy, it led her to investigate and she discovered details of another forthcoming ladies only party where they were looking for adult women to come dressed as college girls. The location was at a country house fifteen miles away so she thought that would be far enough away that she wouldn’t know anyone at the party, and it would be a good way to satisfy her fantasy of being caned, just the once, and so she applied and was accepted. Details were sent to her which the email said had to be kept strictly confidential.
The day of the party was one day after a detention class at college. As usual, a number of the girls needed to be caned which Miss Hargreaves carried out professionally and without any feelings of arousal as that was her job.
However, today she felt rather different. She was certainly tense as she knew the cane hurt from the way the girl’s she caned yelped with each stroke and hobbled out of her study clutching their bottoms. She also dressed very differently from her normal headmistress' white blouse and dark blue skirt and dark blue tights. Today she dressed as an adult sixth form college girl in the standard college dress which was a short-sleeved green and white checked gingham dress, with a hem just above the knee and with white ankle socks, and she had tied her hair in a bun. When she looked at herself in the mirror she felt herself getting aroused, and as she drove towards the country house she was getting even more aroused, and whilst certainly concerned about being caned it was still something that she wanted to experience in order to satisfy her fantasy.
Miss Hargreaves was still wondering whether the pain would get her aroused or whether it would be so painful it would get the whole wondering about being caned out of her head when she realised just how much, in reality, it did hurt.
Miss Hargreaves parked the car in the car park and there were already lots of cars there. She suddenly realised that it wasn’t going to be just one woman role-playing being a teacher and her role-playing being a student, but there were clearly going to be lots of people there. There was even a sudden panic of what would happen if there was anyone there that she knew. Would anyone recognise her? Should she drive off and accept it wasn’t the best thought out plan she had ever had because so many people knew her including parents of the girls at the college and there were over a hundred girls there. However, as she was having all of these questioning thoughts there was a knock on the car window and a woman who looked about twenty-three or twenty-four-years-old was smiling at her and asked, “Are you coming in?”
The woman looked so friendly it settled Miss Hargreaves down and she smiled back and replied, “Yes I am,” and quickly got out of the car and locked it and turned again and looked at the woman who was still smiling, and Miss Hargreaves asked, “Have you been here before?”
The woman replied, “Oh yes, I’m one of the teachers. I see you’re going to be a student so you had better call me Miss Watson, as it is best to get into the role as quickly as you can.”
Miss Hargreaves was happy with that and replied, “Yes, Miss Watson.”
Miss Watson then asked as they walked towards the building, “So what is your name?”
Miss Hargreaves had already settled on a name and replied, “Helen Smith, Miss Watson.”
Miss Watson kept on walking and although smiling replied in a stern tone, “Well, Smith, welcome to our college. Be on good behaviour at all times because we are very strict with you girls, and any and every misdemeanour is dealt with as it should be, which is very firmly.”
Miss Hargreaves knew that she felt relaxed talking to Miss Watson, and when they got to the building, she pointed to a reception desk and said, “Sign in there, Smith. You will then be directed to the detention classroom.”
Miss Hargreaves went up to the reception desk and the receptionist, clearly dressed as a teacher, said, looking at the computer screen, “I see your wish is to be caned. Good choice, Smith. The detention classroom is over there so go and find yourself a desk, and don’t forget to be a good girl.“
Miss Hargreaves smiled at the receptionist and, not knowing her name, replied, “Thank you, Miss,” realising how easy it was to be respectful to any teacher she came across and smiled at the thought. She walked into the detention classroom and saw about a dozen women all dressed in different uniforms but certainly of a similar type to her own, and all, like her, with her hair tied in a bun. She found a desk at the front of the class and sat down, and did look around and smiled at some of the women although just then was again nervous about whether she recognised anyone, and thankfully she didn’t.
Miss Hargreaves looked towards the front of the classroom and saw a desk with two chairs behind it, and then several more chairs on both sides of the desk, similar to an assembly where the teachers sat at the front looking out towards the students.
It was only about another five minutes before several teachers walked into the classroom, and Miss Hargreaves was aware that all the other adult college girls stood up and were silent. She quickly followed suit as most of the teachers sat on the chairs facing them and two of them sat behind the desk, and one said sternly, “Good morning, girls, sit down but be quiet.”
All of the girls sat down, and Miss Hargreaves saw that everyone was being an obedient college girl rather than the adult women they actually were.
Miss Hargreaves also realised that whilst pretty much every adult college girl was at least thirty years old, not one of the teachers looked over twenty-five-years old.
One of the teachers at the front explained in a haughty tone, “Girls, I am Miss Jones and this is Miss Welling. We have here your punishment forms and, as well as doing lines, those of you who have earned a caning will be escorted out of the classroom and into one of the punishment rooms. We have a selection of teachers who are responsible for punishing you girls and you will do everything they tell you to do, without question. Is that understood?”
Miss Hargreaves joined in all of the others with an immediate, “Yes Miss.” In fact, Miss Hargreaves was feeling more and more aroused being subject to a similar discipline regime that she imposed at college. Mind you, the big difference here was that here all the women had requested a punishment rather than earned it. Still, it was role-playing after all so she was also feeling very relaxed as she didn’t know anyone and that took a major worry away from her.
Miss Hargreaves was actually quite happy writing the lines they had all been set which simply said, ‘I have been a very naughty girl and deserve being in detention,’ and wasn’t surprised how boring it was sitting there just writing line after line that said the same thing, but then when she held detention at college she knew the intention was to make the girls feel bored which, she hoped, would help them stop earning a detention. Of course, if it was a double detention, like the one she had signed up for today, she was going to get something rather worse than writing lines, and, likewise, an even better incentive not to misbehave.
After several minutes of writing lines, Miss Jones then called out some names of the college girls in detention. They got up and went to the front of the classroom, and each stood next to one of the seated teachers, raised their dresses above their waists and lowered their knickers to their knees, and bent across the teacher’s laps. Miss Hargreaves watched as the girls were then given what were rather long and hard spankings right there at the front of the classroom. The spankings were first given with the teacher’s hand, but that later changed to thick wooden paddles that had each of the college girls yelping in pain and squirming around on the teacher’s laps as the teachers turned every bottom darker and darker shades of red.
Eventually, that first round of spankings was completed and the girls, crying and rubbing and clutching their no doubt stinging bottoms, were sent back to their desks. More names were called out, and Miss Hargreaves was one of them. She got up with the other girls and walked quickly to the front of the classroom and knew to raise her dress and lower her knickers, which she did, and then lowered herself across one of the teacher’s laps.
Certainly, it did feel strange to Miss Hargreaves to find herself across the lap of one of the young teachers bearing in mind that she was forty-five-years-old, and was going to be spanked by a girl who didn’t look more than nineteen years old. However, once the spanking started and she saw the girl’s calf muscles tense and felt the increasingly intense stinging of the hand spanking her bottom she realised that their respective ages really didn’t matter.
Miss Hargreaves struggled even more when the paddle was used on her bottom. She had counted out fifty spanks that the first girls had got and assumed she would get the same but she lost count because she found the spanking just so painful. Eventually, it did stop, though, and she was told to get up and go back to her desk and, like the previous girls, she did so clutching and rubbing her stinging bottom cheeks, and wondering that if the paddle hurt so much just how much more would a caning hurt.
Miss Hargreaves got back to her desk knowing her eyes were blurred, but they soon cleared and she tried to write some more lines but soon realised that there was someone standing next to her, and it was Miss Jones who said in a very stern tone of voice, “Right, Smith, as yours is a double detention you will be taken to one of the punishments rooms where Miss Lewis will deal with you.”
Miss Hargreaves then heard a second voice say sternly, “Right, Smith, up you get and come with me.”
Miss Hargreaves looked up at the second teacher referred to as Miss Lewis and saw immediately that she was actually Emma Peyton, one of the girls at her college who she caned on a regular basis both at double detentions bit also for different acts of misbehaviour that earned her a caning. She panicked when she saw Emma and she stood up and said firmly, “No way can she cane me.”
Miss Jones was clearly not having any arguments and instructed, “No, Smith, you will be disciplined by whoever I decide you will be disciplined by, and I will not have you arguing so hold your left hand out, palm up, now.”
Miss Hargreaves was in shock but probably because of that she did as she was told. Once she had held her palm out, she saw the cane resting across it, and she knew that if one of the students at college took her hand away before the cane landed that would add to the number of strokes she would get on her bottom. It was that thought going through her mind as she watched the cane raised and then brought down with the swishing sound she was so used to hearing at college as it bit into her hand. It stung so much and she yelped and was ordered to hold out her other hand, which she did, palm upwards, and moments later the cane swished down onto that palm and she yelped once again.
Miss Jones then instructed in a very firm tone of voice given that she looked like she was only twenty-one-years-old, “Now go with Miss Lewis to the punishment room. You were going to get twelve strokes but it will now be fifteen for arguing.”
Miss Hargreaves’ mind was all over the place. Her hands stung and she told herself she hadn’t realised just how good a way of punishing the students at college it was. Then, when told the twelve strokes she had put on the form as the number she wanted was now going to be fifteen, she thought that was far too many but on the other hand, she was here so that she could experience being caned, and did an extra three strokes really matter? Equally, having just been spanked in front of the whole class of adult college girls was so humiliating, and so being caned privately was less so and more acceptable. However, none of that helped knowing that Miss Lewis was one of her students and she now realised just how foolish she had been to apply to come here.
However, she didn’t want her hands caned again, and, still not being able to think quite straight, she replied, “Yes Miss Jones, I will go with Miss Lewis and obey her instructions.”
So, Miss Hargreaves found herself being led through the other desks and out of the classroom, along a corridor and then into another room and heard Emma, or rather Miss Lewis, close the door and then order, “Go and stand in front of the caning table, Smith.”
Miss Hargreaves saw the table and did exactly as she was told, trying to forget the fact that she was about to be caned by one of the students who was just seventeen years old, and the fact that her desire to be caned might very soon be public knowledge with all the trauma that would cause her.”
Once Miss Hargreaves was standing in front of the desk, Miss Lewis ordered, “Raise your dress above your waist and lower your knickers to your knees and then bend over and stretch your arms to the far end of the table, Smith.”
Miss Hargreaves continued to do as she was told realising that even a seventeen-year-old could sound like an authoritative teacher. Moments later she bent over the table knowing her bottom was bare, and then, once she had stretched her arms to the far end of the table, she felt Miss Lewis tying her wrists into leather clasps.
As Miss Hargreaves gently tugged at the wrist clasps and realised she was immobilised she thought how unlucky she was to be allocated to Emma. It was at that precise moment that she worked out, though, that Emma must have seen her in the classroom and asked Miss Jones to allocate her to her and it all made sense in a lightbulb moment that she should not have agreed to any of this. As soon as she saw Emma she should have walked out there and then because no one would have stopped her. Instead, she meekly followed Emma’s orders and not just came to the punishment room, but was bent over a caning table with her bare bottom ready to be caned by a college student of hers.
She was the headmistress of the college and she knew Emma was a trouble maker and would be bound to tell all the other students how she had caned the headmistress and that would be far worse than just telling everyone she had seen her being spanked because that was by someone else. What really worried her now was that being caned by one of the naughtier students of hers could be the end of her career. How could she have been so foolish, solely to experience for herself what it felt like to be caned? How really really foolish, she told herself time and again.
Miss Hargreaves thoughts of despair were interrupted with what was probably the most painful thing that had ever happened to her as she yelped as the cane bit into her bottom. My goodness, she thought, no way did she think that the cane would hurt as much as it did, but, as the second stroke landed she yelped again and the pain seemed to be even greater, as it did with the third stroke.
Miss Hargreaves knew that she was yelping again every few seconds as yet another stroke of the cane landed on her bottom, and the pain got worse and worse. She was well aware that she never gave more than six strokes at college but now she knew exactly why the girls were crying and clutching and rubbing their bottoms as they walked uneasily out of her study, and they had been caned over their dresses and not on their bare bottoms. Miss Hargreaves was crying after the first few strokes just like the college girls and wasn’t able to count the number of strokes she received and had to assume she got the fifteen strokes because the caning suddenly stopped, and wondered what her bottom would look like with the raised welts painted across it.
Miss Hargreaves was still not thinking straight as she felt her wrists set free from the clasps and she managed to push herself up, and her hands rushed to her bottom cheeks which she rubbed and clutched but realised none of it was helping quell the stinging. Still sobbing she looked at a blurred Miss Peyton and said a respectful, “Thank you for caning me, Miss,” and it suddenly struck her that anyone who was responsible for caning students at college should first experience being caned themselves to fully understand just what it felt like. It wasn’t going to put her off caning the girls in future, and she would probably cane them just as hard as she already did, but this had been so educational for her.
Miss Hargreaves was then brought back to the reality of having been caned by one of her students as she was told sternly, “Right, Smith, get back to the classroom,” and her feeling of utter foolishness returned as she heard, “I look forward to seeing you at college, Miss Hargreaves,” and then heard in a very firm almost threatening tone, “Or, should I say, Smith.”
Miss Hargreaves was again anxious as she pulled up her knickers making sure that she eased them onto her stinging bottom, and then straightened out her dress. Still struggling with the stinging effect of the caning she knew she mustn’t argue now because she risked a further caning, so she again did as she was told and walked out of the punishment room and back to the detention classroom, and found herself knocking on the door rather than just walking in. She heard the instruction to enter, which she did and managed to walk albeit still shuffling a bit because of the pain of her stinging bottom, and sat down.
As she did, she yelped because she had sat down too hard, and heard the laughs from the adult college girl sitting close to her. Feeling humiliated she then tried to sit still but wasn’t able to and realised that she was pretty much doing a spanking dance but sitting down. She even found that funny but realised that that was how the students at college must have struggled when they were sent back to the detention room after she had caned them.
Miss Hargreaves sat as still as she could although did squirm around on her seat as the remaining girls were dealt with. Once the session was over everyone seemed to be laughing and joking whether they were young role-playing teachers or the older role-playing college girls. Miss Hargreaves couldn’t quite understand it because her bottom was stinging so much that she couldn’t find anything funny about it, but she stood listening to those who were chatting until it was time to leave.
When Miss Hargreaves got to her car she really couldn’t understand how come she was so aroused, but was. The caning had been so painful, but she knew she was wet and so drove for about a mile and then stopped in a country lane and quickly eased her fingers inside her knickers and along her very wet pussy lips, easing her fingers inside her vagina and also flicking her taut clit until she came with a huge orgasm. It shocked and delighted her, and she wondered if she would have the courage to attend another party, except then she remembered Emma and told herself not to be so foolish again.
That was nearly a week ago, and today was another detention day at college, and, looking at the list of those she was due to cane, she saw that Emma Peyton was on there. Miss Hargreaves had become more confident as the days went by as no one mentioned to her the fact that she had been caned by Emma, so maybe Emma was too embarrassed to tell everybody what she did in her spare time? Well, it was going to be nice to get her revenge, she thought, but felt that the six strokes she was due to give her weren’t nearly enough.
Emma was the third and final girl on the list and Miss Hargreaves stayed professional about the first two, giving each of them four strokes of the cane. She was sitting at her desk, still feeling confident, as she waited for Emma to be sent in, and, suddenly, Emma knocked on the door and Miss Hargreaves called out, “Enter.”
Miss Hargreaves hadn’t seen Emma since the party, but there she was now standing in front of her desk, in her college uniform dress, and probably feeling rather contrite. Miss Hargreaves didn’t refer to the party, though, and made a point of looking at her notes and then looked up at Emma and said, “I see it’s six strokes for you today, Emma.”
Emma wasn’t contrite at all and in fact quite the opposite as she replied, “Actually, Smith, it’s going to be you who gets the cane by me.” She added firmly after a moment, emphasising her position, “Again.”
Miss Hargreaves was shocked as she replied in a far less confident voice than she had used just a moment before, “Now look here, girl.”
However, but before Miss Hargreaves could say anything more Emma snapped back to her in that haughty authoritative tone of voice she had when she was Miss Lewis, “No, Smith, you look here. You will address me as Miss Lewis as you did at the venue, and you will bend over clasping hold of the chair after lifting your dress and lowering your knickers. If you do not, I will be telling the whole college what I did to you. Of course, you may well think you can expel me, but I suspect the governors will take a very different view once they know the truth.”
Miss Hargreaves gasped but realised that all of that made sense and pleaded, “What if I let you off this time?”
Emma snapped, “I said address me as Miss Lewis, Smith.”
Miss Hargreaves surrendered now and replied obediently, “Sorry, Miss Smith. What if I let you off this time, Miss Smith?”
Emma responded firmly, “That’s better, however, that’s not your decision, any more, Smith, but mine. Now get ready and bend over for your six strokes and get used to it as I get sent to you rather often for the cane.”
Miss Hargreaves once again realised just how really foolish she had been to go to the party, and as she slowly stood up and walked around to the front of her desk, raised her dark blue skirt up above her waist and yanked first her dark blue tights and then her dark blue knickers down to her knees and bent over, it now looked very much as though she would be paying the price, time and again.
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