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Wishful Thinking

"Jack fantasised about being spanked and caned by the headmistress and a friend"

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Jack didn't know why he was told to go to the headmistress's study straight after the final bell at the end of college for that day. Jack was eighteen and in his final year at college, clearly on his way to university, and was one of the better students both in connection with the work that he did and his behaviour.

When he arrived at the outer office, Miss Mason checked her computer and Jack could see she was forcing herself not to smirk as she said to him, "Go and sit on the chair by the door to Miss Robson's study and you will be called in."

As Jack sat there, he did realise that whilst he was certainly very tense, he also found sitting there exciting. Although one of the best-behaved students, several of his friends, both boys and girls, did misbehave and got double detentions, and were sent to the headmistress for the cane. They had spoken to him afterwards and said just how much the cane hurt, but that was obvious from the way their eyes were filled with tears and, the girls in particular, were rubbing their bottoms.

Jack knew that he had fantasised about being caned himself. More than that, he had regularly logged onto his computer at home and watched films of men being caned. For him, it was always a woman who was the one who gave the cane and the man was the one who received it. He was always very careful when looking at those films because he didn't want to be caught doing so. After all, as well as being one of the better students and one who behaved so well at college, he was pretty much an alpha boy, and so many of his classmates looked up to him.

As he sat there thinking those thoughts, all of a sudden he heard a swishing sound coming from inside the study, followed by a loud thwack, and then a gasp. He was quite shocked as he looked at Miss Mason, but she was looking studiously at papers on her desk. He thought that she was on the verge of another smirk, but he wasn't sure.

Jack heard the swishing sound again followed by a thwack and a gasp, and just then the door to the outer office opened, and in walked Laura, a classmate and friend, also eighteen, and she was one of the girls that he often thought about as he masturbated as he lay in bed. In fact, he often pictured her in her skimpy out-of-college clothes which normally during the summer was a tight-fitting vest and either shorts or a very miniskirt.

He imagined her dressed like that as she put him across her lap, rubbed his bottom in circles as he looked at her bare legs, and then spanked his bare bottom. It was such a hot fantasy for him. So, when she walked into the room, he was surprised to find her wearing those clothes rather than her summer uniform of a short-sleeved skirt with ankle socks. Of course, that meant she had bare arms and bare legs and he immediately thought how sexy she was.

His normal fantasy for being caned was by Miss Robson, but he had given also himself some huge orgasms imagining Laura caning him.

Laura seemed to be blushing as she went up to Miss Mason and was told to sit in the chair adjacent to Jack. As she did so, Miss Mason said sternly, "No talking."

Both Jack and Laura obeyed Miss Mason but did look at each other, wincing. However, it did mean that they could not exchange reasons why they might both be there as college had ended for the day.

As they sat there, they heard four more swishes, loud thwacks, and gasps, coming from inside the study. They again glanced at each other with questioning looks, but still only knew that someone was inside the study being caned.

Jack was wondering if he was going to be caned and as he thought that he couldn't stop himself from getting an erection that was causing his trousers to bulge. What if Laura and Miss Mason saw it, he wondered in a panic, but it didn't stop the erection.

Two or three minutes later, the door to the study opened. Jack and Laura both looked up and saw a boy in college uniform but not someone Jack recognised. Jack and Laura again looked at each other and shrugged shoulders, that told Jack that Laura didn't recognise him either.

The boy went up to Miss Mason's desk, rubbing his bottom, and said, "Six strokes, Miss."

Miss Mason entered something onto the computer which Jack assumed was the number of strokes because his friends who had been caned said they had to give the number of strokes to Miss Mason, and she entered that into the computer.

Miss Mason then looked up and said, "Okay, you can go home now."

The boy replied, "Thank you, Miss," and then walked towards the door still rubbing his bottom.

There was an uneasy silence for a short while before the phone rang and Miss Mason answered it, listened to what was being said to her, then looked at Jack and said, "Right, you can both go in now."

Jack was really surprised to discover that Laura was coming in at the same time, and when he looked at her she shrugged her shoulders and nodded towards the door. Jack took that as being told to go first, which he did, opening the door to the study, walking through and holding it open, watching Laura follow him in, and then walk past him and go towards the headmistress's desk. Jack closed the door and then followed Laura and stood next to her looking down at the headmistress who was seated on the far side of the desk.

Miss Robson seemed to be studying some papers on her desk and Jack saw that she was wearing her headmistress' gown, so dressed just how he had so often pictured himself being punished by her.

After a few moments, Miss Robson looked up and seemed to glare at Jack as she said in a very stern tone of voice, "I have you down as having a double detention and so that means you are here for the cane."

Jack was completely thrown by that and replied, "No, Miss, no one has given me a detention."

Miss Robson looked at the computer screen and said, "Miss Thomas and Miss Bonny have both given you a detention. If you insist on questioning it then I will message them now, but, if that is the case, your punishment will double and will go on your record which will have to be disclosed when you apply for university. I really don't think that is necessary. Do you?"

Jack was completely thrown because, not only was he not aware of being given either detention, he was also not aware that incorrectly disputing it would have to be disclosed to any universities he applied to. That really was too much of a risk.

Jack also took into account his desire to know what it was like to be caned. He knew that he was running out of time at college, but now he would be caned by Miss Robson, so that was a plus. He just wasn't sure why Laura was here if this was all about him being caned. He then had the sudden thought that maybe Laura was going to be caned as well.

Jack's thoughts were interrupted by Miss Robson saying, "Anyway, being caned won't do you any harm. You know, there are lots of students who have it in their head that they want to be caned but aren't, and they end up regretting that. I'm not saying that is you, but that is the kind of thing I would bear in mind if I was you."

Jack was surprised by such a direct comment, particularly as it was pretty much what he was thinking. Could the headmistress mind read, he asked himself, knowing, of course, that she couldn't.

Miss Robson continued, "This is also a training session for Laura. She wants to become a teacher and wanted to experience the reality of a student being caned. I did make the assumption that as you were friends, that would not be a problem for you. Am I correct there?"

Jack was about to agree but Laura immediately turned and faced him and, grabbing his arm, she turned him sideways to face her, although, to be fair, he was never going to resist, and she came right in close, her face inches from his, and said, "You're not going to object to me having some training, are you, Jack?"

Jack was quite taken by Laura's face so close to his, feeling her breath on his face, and then she put her bare arms around his neck, and, as she pulled him close to her, he felt her breasts against his chest. He never wanted that moment to end, but Laura released him, keeping her face close to his, and asked, "Well, Jack, What do you say?"

Jack knew that he wanted to agree because Laura was someone whom he had fantasised about spanking and caning him. So, he replied, "Of course I won't complain, Laura."

Miss Robson then said, "As she is taking the role of a teacher, you will address her as Miss Laura."

Jack gasped because when he fantasised about Laura spanking and caning him, that was how he addressed her. So, happy to do so, he said, "I won't be complaining, Miss Laura."

Miss Robson then said, "Right then, Jack, let's discuss your punishment. Two detentions gets you the cane. I also want this to be a training session for Miss Laura, and I am suggesting this. You should first get a bare bottom spanking from Miss Laura, and then the cane from me. Understood, Jack?"

Having said that, Miss Robson then stood up and immediately threw off her headmistress's gown. She was left wearing a sleeveless floral dress, and, now she was standing, Jack could see that she had bare legs. So what with her very sexy looks and authoritative tone of voice, and his fantasy of being disciplined by both Laura, rather Miss Laura, and Miss Robson, this seemed to be several of his dreams coming true at the same time. So he had no difficulty in replying, "Understood, Miss Robson."

Miss Robson then explained, "I know I normally cane boys over their trousers and girls over their dresses, but a spanking needs to be given on your bare bottom. Given that, I am proposing that after Miss Laura has spanked you on your bare bottom, you will get caned on your bare bottom."

Jack wasn't thinking straight as he was looking at two women with bare arms and bare legs, both of whom he found so attractive, and both of whom he had imagined disciplining him. He knew that he was getting excited at the prospect, and eagerly replied, "Of course, Miss Robson."

It was then he noticed that Miss Robson briefly looked down towards the desk, but in fact, he quickly realised she wasn't looking there but was looking at his trousers. He gasped as he also looked down and saw he had an erection which was creating a huge bulge in his trousers.

Miss Robson looked back up directly at Jack and said, "Clearly, none of this is going to be a particular problem for you. Of course, when the IT department told me about the things you were looking at on the school computer, I was pretty sure this would be your reaction."

Jack was completely thrown by that. He hadn't looked at any videos on the school computers but had been on a spanking forum. He now realised that that was where he had exchanged messages with others saying how he had imagined being disciplined by both the headmistress and a girl in his class and had even mentioned both by name. He thought that he had set the computer up so that the history of his usage was immediately deleted, but now it was obvious that that wasn't the case.

Thinking these thoughts meant that all of the erotic thoughts that Jack had had disappeared, as did his erection. That was so disheartening for him, but certainly explained why Laura was there.

Miss Robson and Laura were exchanging glances as they could see the panic on Jack's face. Miss Robson stepped in and said, "It's okay, Jack. We are doing this now because college is finished. Miss Mason has already left so it is just the three of us here. I told you that it wasn't so uncommon for students like you to want to know what it was like to be caned, but weren't, and how they regretted it. I wanted to give you that experience so that you would know what it was like. I asked Miss Laura to get involved because she was a friend of yours, and you did specifically refer to her in the forum. So long as you now accept whatever punishment I decide you should be given, then I can assure you that all the history will be deleted and never spoken about again. Will you now agree to accept the punishment, or do you want it to stay on your record?"

Jack was completely flummoxed by what he was being told. One thing he did remember was the two detentions he had been given and so he asked, "What about the detentions, Miss Robson?"

Miss Robson replied, "I did make that up, Jack, but that was just to get you here and into the mood. Just like the boy you saw wasn't actually caned but was the son of a friend who agreed to role-play. I actually caned a cushion. You can take it, though, that the real reason you are here is because you used the school computers to access the forum you are on."

It was then that Jack remembered that Laura had gone onto the same computer that he had been using straight after him, just a few days ago. She was taking a computer course and so maybe she was the one able to go into his history and find out the things that Miss Robson had just spoken about.

However, as Jack looked from Miss Robson to Laura and back to Miss Robson and back to Laura again, what he saw once again were two women whom he had imagined time and again disciplining him, much in the way that had just been described. So, there was no reason to object, particularly if they were the only ones still at college. Jack also thought again about how this could bring to real life his fantasies, and as he thought that, so he realised he was getting an erection back together with the feeling of excitement.

Moments later, Jack happily said, "Okay, Miss Robson and Miss Laura, I am yours to punish."

Miss Robson exchanged a glance with Laura and then said to Jack in her headmistress's authoritative voice, "Just so we are clear, Jack, you have now passed complete disciplinary control to myself and Miss Laura. You will be both spanked and caned, but it will be for us to decide who does what, for how long, and how hard. Once you have accepted that, then any resistance from you, other than howls of pain, will lead to additional punishments. Is that agreed by you, Jack?"

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Jack listened to what he actually had no desire to do other than to agree. Therefore, knowing that he was about to hand over control, he replied, "Yes, Miss Robson, I agree."

Miss Robson then ordered, "Right, Jack, first of all, you are going to be given a spanking by Miss Laura. For ease, take off your trousers and underpants and socks and shoes right now."

Jack wasn't used to undressing in front of women, but again he reminded himself that these were two women who he particularly fancied and who he imagined punishing him. So, he immediately undid his shoes and stepped out of them, and placed them next to the headmistress's desk. He undid his trousers and pushed them down towards the floor, catching his underpants on the way. He then stepped out of both, screwed them up, and put them on the headmistress's desk. Finally, he bent down and took both of his socks off, and put them with his clothes. He then stood back up and waited for further instructions.

Both Miss Robson and Laura did enjoy watching Jack obediently undress. Miss Robson knew that she had always favoured caning the students, both girls and boys, on their bare bottoms and not over their dresses and trousers. She was, therefore, looking forward to doing that with Jack.

Laura knew that the only reason she was here was because she had told Miss Robson about what she had found on the computer that Jack had used just before her. It wasn't that she was annoyed with Jack, in fact, neither was Miss Robson, but they discussed between themselves how it would help Jack if he was given the experience that he was fantasising about. That was when they also discussed having him undressed.

Knowing it was always intended, Miss Robson looked at Jack's penis and saw he still had an erection. She had hoped it would be there and used it to say in her usual authoritative tone, "Actually, Jack, I think there's a real risk that your shirt will get in the way, particularly given your erection. Therefore, I think you should take your shirt off."

Jack heard the instruction and judged from the tone of voice that Miss Robson was not going to change her mind. He also looked towards Laura who was smirking and he knew that she wouldn't want to say anything to stop him from taking off his shirt and being naked. Anyway, he came to the view that it hardly mattered now that he was naked below his waist, so he quickly undid the buttons of his shirt, slid it down his arms, screwed that up, and put the shirt with his other clothes.

As soon as he was undressed, Laura went and sat on the visitor's chair which was high-backed and armless. She had already turned it into the room which Jack realised as he watched her sit down. There was no mistaking the firm instruction that Laura gave him, similar to the authoritative teacher's, ordering, "Get across my lap."

Jack immediately went and stood next to Laura and looked down and saw her bare thighs and knew that he was going to be lying across them, pressing his stiffening erection onto them. He judged from the smirk that was still on her face that she was very happy about that, particularly as she was staring at his erection at the time.

Jack, therefore, lowered himself down across Laura's lap, pressing his erection down onto her bare thighs, and actually liking the feeling of submission being upside down as he looked at Laura's gorgeous legs so close to his face, and gasped erotically as he felt her hand rubbing his bottom in circles. He also liked the fact that Miss Robson was standing very close to his face so he saw her upside down bare legs as well. As much as he knew that from here on in he was going to suffer more and more pain, he was just happy that things had worked out like this and he was going to be punished by these two fantastic women.

Jack knew that he had always fancied the headmistress given how dominant she was and authoritative. It was natural to want to be disciplined by a woman like that. His desire to be disciplined by Laura was because he would love to have her as his girlfriend, obeying everything she said every time, or suffering whenever he didn't. He knew that didn't fit into his alpha teenage male persona and never understood why he would be so happy to be submissive to Laura, but he just knew that was how it was.

No sooner had he had these thoughts, when Laura landed the first spank on his bottom. He gasped as much in surprise as anything else because he didn't find the spank particularly painful. He did find the continuing spanks more and more uncomfortable, though, and as Laura continued to spank him he found his bottom was stinging more and more and he was actually squirming around on her lap.

Jack had to admit that whilst he fully expected a spanking to hurt, and he had certainly imagined himself crying when fantasising about being spanked, the actual pain was rather different. He found himself gasping with the pain rather than crying because of it and wondered if that would change. He did manage to keep looking at Laura's bare legs and loved how her calf muscles tensed as she landed spank after spank, and liked the close-up view of her painted toenails.

He was a little surprised when Miss Robson said, "I tell you what, Miss Laura, why don't you give him a few spanks with this wooden-backed hairbrush? You will notice the difference in his reaction."

Jack heard Laura reply, "Thank you, Miss Robson, that is certainly a good idea."

The next thing Jack felt was a far firmer spank which hurt rather more, and then as the spanks continued with the paddle hairbrush, so he was struggling to cope. Maybe he had handled the hand spanking too well, he told himself, but he certainly wasn't going to handle being spanked with this hairbrush very well.

It wasn't long before Jack realised that as he was looking at Laura's calf muscles and painted toenails, they became more and more blurred. Well, that told him his eyes were filling with tears, so he knew that his ability to cope was going to disappear very soon. Given how hard the spanks were, he did reckon that Laura wasn't holding back at all. He supposed that she wasn't anyway, because he supposed that as much as he wanted to be spanked by her, she was very happy to spank him.

Jack didn't see Miss Robson indicate to Laura that she could now stop spanking him and go on to the next element of the punishment. Jack did hear the instruction, "Right, Jack, get up and bend over and clasp hold of the chair so you can be caned."

Jack was sniffing back tears as he pushed himself up from Laura's lap, and, once standing, watched as Laura stood up, albeit seeing her blurred image. He then bent over as instructed and clasped hold of the seat of the chair. He looked at the floor behind him but that was also blurred, although he was pretty sure that the legs that he did see were those of Miss Robson. He also heard a swishing sound which he reckoned must be the cane, and that got him momentarily excited at the prospect of being caned, but that was quickly followed by the realisation that the spanking hurt enough, so just how awful was the cane going to be?

Miss Robson positioned herself as she did so often when caning the students, although at least this time she was rubbing the cane from side to side across a bare bottom which was already red from being spanked, thinking that it may not sting as much as a cold caning would, but would still give Jack the experience that he so clearly wanted.

When the first cane stroke bit into his bottom, Jack yelped and told himself that he must have been crazy to want to be caned. He did wonder if it hurt so much more because it was on his bare bottom compared to his friends who were caned over their trousers, or was it any different because he had been spanked first? Either way, he told himself he really was silly as the second stroke bit into his bottom and then even more silly as the third stroke bit into his bottom.

He did hear some talking as he was trying to cope with the increasingly stinging pain. He stopped listening when the fourth stroke bit into his bottom, then the fifth stroke, and then the sixth stroke.

When the talking started again he realised it was Miss Robson talking, and she was telling Laura how she should position herself and use the cane. That shocked Jack because he assumed that Miss Robson would give every stroke, and, after all, he had already received six strokes.

When Jack felt the cane being rubbed across his bottom again, he knew it was going to be Laura who was going to give him more strokes of the cane. However, he also realised that he didn't mind Laura caning him. He hadn't minded Miss Robson caning him, but then she was the headmistress. Now Laura was going to cane him, he saw that as almost amounting to lovemaking. He even thought that he was getting an erection back as he pictured a smiling Laura smirking as she looked at his bottom, or maybe was looking at his erection.

When Jack heard the swishing sound and the thwack and felt the cane bite into his bottom, he told himself the stroke was every bit as hard as those given to him by Miss Robson. As the second stroke bit into his bottom just as fiercely, he even hoped that Laura was enjoying herself and not just feeling obliged to cane him. He knew that he wasn't enjoying all of the stinging pain, except he didn't want it to stop because, as much as it was painful, he was also finding pleasure in it.

Jack did find himself sobbing as the cane strokes continued, although they did stop after Laura had given him six strokes. He couldn't believe that he had actually taken twelve strokes in all, double the number that he had heard anybody else receiving. At least, he assumed the caning was over.

Jack heard Miss Robson say sternly, "Okay, Jack, you can get up now. Turn around and face Miss Laura, put your hands on your head, and do not even think about rubbing your bottom."

A relieved Jack pushed himself up and, when he was standing again, he realised that he really did want to rub and clutch his stinging bottom cheeks. However, he knew that he mustn't disobey Miss Robson, or, at least, if he did, he definitely risked receiving maybe another six or even another twelve strokes of the cane. He didn't want that right then.

As Jack turned and put his hands on his head, and felt the stinging and throbbing right across his bottom, he stood looking at the blurred images of Miss Robson and Miss Laura as he now definitely thought of her. He even heard Miss Laura giggle and realised just by slightly swinging his hips that his erection had come back. That told him that he was feeling aroused, and knew both Miss Robson and Miss Laura would see his erection and know the same.

As Jack stood there, feeling aroused whilst also struggling to cope with his stinging bottom, he still found it difficult to fully understand why he wanted to be spanked and caned again. He even thought how wonderful it would be to return here to Miss Robson's study to be spanked and caned by both Miss Robson and Miss Laura again. As he thought those thoughts, he knew that his erection was getting even stiffer.

Miss Robson kept a straight face as she always did when disciplining the students even when they were crying and tears were pouring down their faces. It didn't happen to many, but she liked it when it did happen, in particular to those who were the more disruptive of the students. Of course, she also knew that, albeit occasionally, some of the boys had erections after she was finished with them, so she wasn't at all surprised that Jack had one as well. She also knew that some of the girls went to the toilets afterwards, and orgasms could be heard coming from the cubicles they were sitting in. She supposed those girls already had wet knickers as they walked out of her study and walked towards the toilets as they rubbed their stinging bottoms.

Laura couldn't stop herself smiling as she saw Jack's erection. She had to admit that she did enjoy both spanking and caning Jack, and would be more than happy to do it again. Maybe it would work if he was her boyfriend and agreed to be submissive to her decisions and general authority.

Miss Robson looked from Jack to Laura and thought she knew what they were both thinking. She had discussed this with Laura before they came into the study, and she knew that Laura had a party to go to tonight and was looking for a plus one.

Miss Robson therefore said, "Miss Laura, I think you have found your plus one for tonight's party." She looked towards Jack as she said it and could see he was wide-eyed at the possibility.

Miss Robson then added, "It will, of course, be on the basis that you, Miss Laura, are the one in charge, and you, Jack, will do everything she says when she says it. Any shortcoming and you will have to end up across her lap for another spanking and bent over for another caning. Is that understood?"

Jack looked at the blurred Miss Laura who he could make out nodded at him, and he replied, "Yes, Miss Robson, fully understood."

Miss Robson replied, "Good. Now, get dressed, and then Miss Laura will give you instructions about tonight."

As Jack got dressed he knew that he was so excited and that this had turned out very differently to what he had expected as he sat outside the study and listened to what he had thought was a caning. He certainly wanted to be spanked and caned again, and as much as it hurt he really did hope that Miss Laura would spank and cane him again. Maybe Miss Robson would as well, if he got a double detention, or, maybe, even if he didn't, just like today.

Anyway, the possibilities seemed endless to him, particularly as Miss Laura had nodded to him indicating her agreement. Therefore, he would make sure that he did do everything Miss Laura told him to do, at least until they were on the way home and he could perhaps earn himself another spanking and caning. After that, who knew, but he did hope for the best.

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Written by Peter242
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