Danny was seventeen and in the first year at the sixth form college. It was a boarding school. He was sitting outside the door to the headmistress's study waiting to be told to go in.

Danny was one of the more conscientious students and was always well-behaved. That compared to his best friends who worked hard, but misbehaved and were regularly in detention, sometimes getting a double detention which meant the cane. They joked with Danny that he was the only one amongst them who had never experienced the cane and pointed out that unless he was caned when at college, he would never get the chance to experience it.

His friends wound him up about it by even explaining that every time they were caned, they would have a real throbbing hard-on and go straight to the toilets and squirt masses of cum. They even said it was far better than masturbating in bed, although after cumming after the cane they always masturbated multiple times when in bed that night as well.

Danny never enjoyed being wound up, but he did start to wonder more and more about the cane. Two weeks ago, Tom came over and after a couple of drinks Danny asked, "Tell me, Tom, you've been caned a couple of times. How did you feel about it?"

Tom looked up with a smile and asked, "Are you thinking of getting the cane? Is it because you don't want to be the subject of any more jokes about it?"

Danny replied seriously although blushing, "No it's not that. It's just that I've been on a few websites recently and they do suggest that although it's painful, it is erotic. It got me thinking because I don't want to kick myself in years to come that I didn't get caned when I had the opportunity."

Tom took the reply at face value and nodded his head in agreement and replied, "That's dead right, Danny. That's what I thought, and whilst it was painful, afterwards it was just great. Of course, now that we have Mrs Marsh as the headmistress, it's even sexy thinking about her caning me again."

Danny also fantasied about Mrs Marsh who was his mum's age and was particularly authoritative. She often dressed at college in a short-sleeved blouse so he could see her well-toned bare arms and could make out that she had very full breasts. Since going on to the spanking websites he always came when in bed picturing her caning him wearing that same blouse. Not wanting to admit to that, though, Danny still picked up at one point and asked, "So how much did it hurt?"

Tom looked serious as he replied, "I had to see Mrs Marsh this week for six strokes. She's also introduced the rule that when being caned it has to be on the bare bottom rather than over trousers. To be fair, it wasn't much difference, except she did get to see everything." Tom pointed to his penis as he made that comment.

Danny had heard that the caning was now given on the bare and that was confirmed.

Tom was still looking serious as he said, "You should know, Danny, that the pain is really awful. Don't think for one second that you will enjoy being caned. At least not the caning itself and not even the build-up to it."

Danny asked inquisitively, "What do you mean by that?"

Tom explained, "Well it's not as bad as before. It used to be that you would sit in detention and then towards the end get called in to see the headmaster. Mrs Marsh changed that and gave everyone the choice of doing that or going straight to her study and just getting the cane and there was no need to attend detention. That meant less time to worry about the cane. However, it would mean three extra strokes of the cane. We all think the same, I can tell you, which is why bother with detention when we could miss it by just taking three extra strokes. So, I actually got nine strokes the other day."

Danny was still tense about the discussion and just to make sure he was clear about it he said, "So now you just go straight to her study to be caned?"

Tom explained, "Not quite. There is the punishment room where the cane is given. The buildup is that you have to go and sit outside her study in her secretary's office. You can't hear the caning of the previous student, although you know it's happening. You do feel tense though as you know it's going to happen to you just as soon as the intercom goes, and you are told to go through."

Danny said, wincing, "I suppose that I must be such a goody-goody as I didn't even know there was a punishment room."

Tom explained, "You only get to it by going through Mrs Marsh's study."

Danny replied, "Oh, right."

Tom then continued with the explanation. "Once you are called into Mrs Marshall's study she points towards the punishment room and tells you to go in and take off your trousers and underpants and stand looking towards the door with your hands on your head. You have to walk straight through and get ready before she follows you in. She obviously sees making you get undressed as an added embarrassment, and encouragement to behave. The problem is, she walks through the door and immediately sees that your shirt is raised up to above your waist because you have put your hands on your head, and that means that she's looking straight at your penis."

Danny exclaimed, "Crikey, that's embarrassing."

Tom smiled as he replied, noticeably blushing as he did so, "Yes, but also if you fantasise about Mrs Marsh caning you, as we all do, you will have an erection by then."

Danny was shocked as he replied, "No way."

Tom kept smiling and blushing as he said, "Yes you will. After all, if you are turned on, like we all are, by authoritative women then, by golly, you are going to be turned on by Mrs Marsh. More so when you see close-up her stern looking face and blazing eyes as she walks into the punishment room."

On the one hand, Danny felt that he never wanted to be in that position but then realised he had already got an erection as he listened to Tom's explanation. That was crazy, he told himself, because it was happening when he was only having this discussion because he really wanted to know what it was like to be caned. However, given his erection, he was now edging towards getting himself a double detention and the cane.

Thinking those thoughts, Danny asked, "Then what happens?"

Tom was still being serious as he explained, "Mrs Marsh walks into the punishment room and you will know that she will look at your penis. After that, she goes to the cupboard and picks out a cane. Having got it, she turns back and glares at you. She points to the caning table and tells you to bend over and grab hold of the far end of the table, making sure that your shirt is well up above your waist."

Danny asked, "What are you thinking as you bend over the caning table?"

Tom blushed again as he replied, "All you're thinking about is the pain. The first time I thought I'd be able to deal with the cane, but after just two of the strokes I knew that I wasn't going to be able to. You can't imagine how much pain there is involved until you get the reality of it. After all, it is supposed to be a punishment and an incentive not to misbehave again, and don't expect any sympathy from Mrs Marsh. If you are one of the boys who has an erection then I can tell you she will cane you even harder. It's obvious really because she reckons that you're turned on by being caned and she wants to make sure that you don't feel that way."

Danny was still wondering if he should get the double detention so he would experience the cane or think that the amount of pain wasn't worth it.

Tom saw Danny thinking, and added, "Don't forget if you get the cane then the dorm mistress also spanks you at bedtime, so the others will hear you crying."

Danny did know that as he had heard others in the dorm crying after being spanked.

Danny asked, "What if I find any of it easy to deal with?"

Tom replied firmly, "Make no mistake, Danny, there is no part of it that you will enjoy because the pain will overtake all your other thoughts and feelings. Not to mention the fact that you will almost certainly be crying before the end."

Danny scoffed, "Crying? No way. I know they supposedly cry on the websites, but they are actors and actresses."

Tom was shaking his head as he replied, "Good luck with that. It's certainly no easy ride and all of us think the same."

Danny couldn't avoid asking the question, "Sorry, but if it hurt so much why would you misbehave again?"

Tom was still blushing as he replied, "Two very good reasons. The first is the personal attention you are receiving from Mrs Marsh. Don't get me wrong, it isn't sexy touching because she is simply giving you the cane. However, you are in the room alone with her, and that gives you a lasting memory to play over in your mind when in bed masturbating. The second is the sheer delight afterwards of masturbating because you are so turned on by being caned. The pain you feel, right then, changes into something so spectacular by the time you've got to the toilets. None of us can explain why, but it does, time and again."

Right now, Danny was sitting in the chair next to the door to the headmistress's study playing over the discussion with Tom as he waited. The headmistress's secretary, Miss Rice, was making a point of not looking at him even as she buzzed through to Mrs Marsh and told her that he was here. All in all, he was feeling more and more worried, but he was here now and there was no turning back.

The intercom sounded and Danny heard the instruction, "Send him in, please"

Danny looked up at Miss Rice who just nodded towards the door to the study. He immediately got up and knocked on the door, heard the command to come in, opened the door, walked into the study, closed the door behind himself, and walked up and stood in front of Mrs Marsh's desk.

As Danny waited to be told what to do, he told himself that at least he didn't have an erection.

Mrs Marsh instructed, "I know this is the first time for you to be caned." She pointed as she said sternly, "Go through the door into the punishment room, take off your trousers and underpants, and stand by the caning table looking at the door with your hands on your head. Do it now."

Danny remembered that was what Tom told him he had to do and so was prepared for that. He went into the punishment room and undid his trousers and pushed them down towards the floor, catching his underpants on the way. He stepped out of both and put them on the table by the wall. He then went over to the caning table, looked towards the door, and put his hands on his head. Just before he did that, he glanced down and saw that he still didn't have an erection.

Danny then stood very still but couldn't help but think about what Tom told him about the pain he was about to get. He could also hear Mrs Marsh moving papers around, presumably at her desk, and he was thinking about her, particularly her pretty face, well-toned arms, and her full breasts.

Less than a minute later Mrs Marsh walked into the room. He noticed that she immediately looked down towards his penis and she gave a knowing look.

Danny was surprised and glanced down and was horrified when he saw that he now had an erection. Of course, he had been thinking about Mrs Marsh, picturing her as he so often did when in bed masturbating. That was so stupid, he told himself.

Mrs Marsh went to the cupboard and took out a hook-ended cane and walked back towards Danny. As she did, she instructed firmly, "Turn around and bend over the caning table, grab the far end, and make sure your shirt is well up above your waist."

Danny again knew that was going to be the instruction and as he turned, he realised that his erection was getting even stiffer. How could that be, bearing in mind he was about to suffer the most horrific pain, at least according to Tom? Still, he did have the erection, and Mrs Marsh did see it, so he supposed the caning would now be harder than it would otherwise have been.

Danny made sure that his shirt was well above his waist as he bent down onto the caning table and stretched his arms clasping hold of the far end. He knew that his bare bottom was now totally unprotected and ready to be caned. So, now he was faced with the reality of the fantasy that he had had so many times and he certainly hoped that Tom was exaggerating in terms of the pain.

Danny felt the cane being rubbed from side to side across his bottom and Mrs Marshall announced, "Seven strokes. Four for the double detention and three extras for not having to sit the detention."

Danny realised that Mrs Marsh didn't ask for his agreement so he remained silent. At least he was silent until that first stroke bit into his bottom, and he yelped. There was no doubt in his mind that that was the most pain that he had ever been in. He wondered how he would deal with any more strokes when, the next moment, the cane bit into his bottom for the second stroke and he yelped again. My goodness, Danny thought to himself, Tom really was right about the amount of pain. The third stroke landed, and he yelped once again. Somehow, he managed to keep a hold of the far end of the table and told himself to focus on that for the rest of the caning.

Danny couldn't stop himself sniffing which he was pretty sure meant that he was close to crying. As the fourth stroke bit into his bottom, and he yelped again, he did manage to open his eyes and realised that his vision was blurred. The fifth stroke followed and he yelped again and was pretty sure tears were dribbling down his face. How could they because, at his age, he should be able to cope with something as straightforward as this? However, Tom did tell him that he wasn't going to enjoy any part of the caning and as the sixth landed that was once again confirmed.

Danny knew from what he had seen on the websites he had looked at that the final stroke was always the hardest. When that seventh stroke did bite into his bottom, he knew that was true as he yelped again and hissed in and out through clenched teeth which helped calm himself down. He even kept a hold of the far end of the table which he saw as a triumph. Then, once calmer, on the one hand, he was glad that the punishment was over, but on the other, he realised it was going to be so humiliating for him to stand up and for Mrs Marsh to see him crying.

Danny heard Mrs Marsh say in a still very stern voice, "Okay, Danny, you can get up now. Get dressed and then come out and see me in my study."

Danny heard Mrs Marsh leaving the punishment room as he pushed himself up. He couldn't understand why he was struggling so much and as soon as he did stand up, he couldn't stop himself clutching and rubbing his stinging bottom. This was even worse than crying, he told himself.

Even so, Danny went over to the table where his clothes were, stepped back into his underpants releasing the elastic quite gently just in case it stung his bottom which was something he also learned from the websites. He then stepped back into his trousers and did them up.

Once dressed, Danny went back out to see Mrs Marsh, wiping the tears away with his hand. Once he was standing in front of Mrs Marsh he lowered his hands and then realised that he was actually rubbing his bottom still. His eyes had cleared a little, and he was pretty sure that Mrs Marsh was smiling but couldn't be sure about that. He also couldn't say anything still as he was sniffing back tears,

Mrs Marsh was entering the punishment in the logbook, confirming it had been carried out, and noting that seven strokes had been given. She then looked up and instructed, "Okay, Danny, you can leave now. It's dinner time so go to the dining room. Hopefully, this will be the last time you will have to come here, but, if not, at least you'll know what will happen. However, your dorm mistress will be giving you a spanking before you go to bed tonight, so learn from that as well."

Danny just managed to nod his head in agreement, turned, and walked out of the study, then through the outer office and into the corridor. Once he was there, he calmed down a little bit more as he walked towards the dining room. As he walked, though, he once again had mixed feelings. The pain was still causing his bottom to sting like it hadn't done ever before, but as he got closer to the toilets, he realised his erection had actually come back just as Tom had said it might. Again, he asked himself how this could be, although he did know from the websites that he had looked at there was always the possibility, and he was thrilled that it had happened to him.

So, smiling, he diverted his walk into the toilets, happily finding that there was no one else there. He went into a cubicle, lowered his trousers and underpants, and moments later his cum squirted into the pan.

Feeling really happy he quickly did his trousers back up and left the toilets. He made his way to the dining room thinking how he might well earn himself another double detention in maybe a couple of weeks' time and so get another taste of the cane. He wanted to see whether the feeling lasted until he got to bed, but even by the time he got to the dining room he knew that would be the case,

The first person to come up to him was Tom, who asked, "Well, how was it because I can tell from your eyes that you cried."

Danny admitted, "Yes, Tom, I did cry because, as you said, it really did sting. However, you are also right, and I did go into the toilets on my way here and had the most fabulous orgasm. I know my mind is still buzzing and by the time the dorm mistress has spanked me at bedtime I have no doubt I will have several more orgasms in bed tonight. So, yes, you were absolutely right and I will be earning another double detention before too long."

Tom smiled and said, "Well, Danny, welcome to the club. Don't worry as you can earn double detentions and get the cane and get top marks in the exams as well. Anyway, you have had the experience that you wanted and know that you will get that experience again before you leave the college.

As Danny calmed down, and had his supper, he couldn't talk that much but was already thinking about the spanking he was going to get from his dorm mistress. He had to admit that he had pictured that happening to him as he masturbated in bed, and, just like being caned by Mrs Marsh, he now expected the reality to be far better than the fantasy, even if more painful.

He also knew it would not hold him back from getting top marks in the exams, but at least he could now move forward, and, maybe, seek out a girlfriend who would remind him of Mrs Marsh. Maybe one his mum's age, who would continue to spank him afterwards? Time would tell but he was up for it.