Chapter 3

Three people slept badly that night.

Arthur Ash, headmaster, widower in his mid 50s, couldn't get the image of Allison Wilson's deliciously plump bottom out of his mind, remembering how it had shuddered under each of a barrage of twelve hard cane strokes. But he was worried that she might have had second thoughts and could have already reported him to the authorities for what was undoubtedly most inappropriate conduct with a member of his teaching staff. After her caning, she had been the most incredibly delicious fuck, but how could he explain having fucked her to the board of controllers? Had that one fuck been worth the loss of his entire future as a teacher, and above all his position as a headmaster who still had caning privileges?

He knew he should be worrying more about the decision he had to make in the morning about how to deal with young Brian Ross, the boy accused of fighting and causing damage in a local shop. He didn't worry about whether Brian actually deserved the cane, boys often got undeserved canings, it was all part of growing up, but he should be wrestling with the rights and wrongs of the charges against the boy. But instead his mind kept wandering back to Allison's soft voice asking timorously if she could have what she had just seen the Sharon girl get, 'six of the best with the number six cane'! Would Miss Wilson want to be caned again? Poor Brian's coming ordeal didn't rank highly in Arthur's dreams that night.

Allison also spent the night worrying. She kept remembering the excitement of her caning. and the wonderful fuck that followed it. She wasn't worried about the headmaster demanding more of that. But she was worrying about what he expected her to do in the morning with the boy. The head had said that he wanted her to participate in caning some boy, and had said he would only give her back her panties if she "did well with the boy", whatever that might mean.

The third fitful sleeper that night was the young man involved, Brian Ross. He was having difficulty sleeping knowing that tomorrow in the morning break he was due to attend the headmaster's office for a decision on his punishment, and he was pretty certain that it was going to mean he would get another dose of the cane. He knew he didn't deserved the threatened punishment, he had explained to the headmaster how other boys had started the fight, he just happened to be in the shop when the damage was done. Yet when the shopkeeper had reported him to the school he had implied that Brian had been the ringleader. The reality was that Brian had been in school uniform whereas the other boys were in street clothes, so Mr Cooper, the shopkeeper, had just gone to the school and demanded to see all the senior boys at assembly, and had picked Brian out of the gathering. Determined to stop the rampant violence in the town, he insisted that the only boy he could identify as being involved should receive "a sound flogging".

When brought to the headmaster's office and confronted with the angry merchant, Brian had admitted to being present, but had denied fighting or causing damage. The shopkeeper shrugged and insisted that the boy must be punished. Arthur had told Brian to go away and return in a week, when he would announce his decision. And that week was up in the morning. Brian was pretty certain that the man would have his way, in his experience adults always did, and Brian would get his third caning, probably more than the four strokes he had received each previous time.

Brian had another concern. He could not explain it, but the idea of being caned by the headmaster again excited him!

He had been caned twice before, once for what a teacher deemed to be insolence, though he hadn't meant it, and the other was for running in the corridor, when he had been late for class. On both occasions when he dropped his trousers, his cock had been erect! Nothing had been said, the headmaster just coldly told him to bend and touch his toes. On both occasions he was awarded four strokes, and the pain had caused his erection to wilt. But it had returned as soon as he was outside the headmaster's office and Brian had gone straight to the boy's toilet and masturbated desperately.

It didn't make sense, how could that excite him so much? He didn't think he was particularly kinky, like the other boys he lusted after the girls in his school, watching them prancing around in their short skirts and sometimes giving him glimpses of their knickers, whereas he felt no sexual attraction for any of the boys at school. So why did he get so excited when about to be caned by Mr Ash, and when thinking about it afterwards? Worried about his younger brother hearing him, he didn't masturbate before going to sleep, and didn't have time in the morning, so by the time he was due to go to see the headmaster his cock was rock hard again. Life was so difficult for a boy as he passed through his teenage years.

Allison attended the head's office as instructed, thirty minutes before the morning break. She was secretly hoping Mr Ash would cane her again, or even fuck her. But no, he was totally professional, making her sit opposite him while he discussed Brian's case. As she sat pretending to listen to him, she kept thinking, "I'm not wearing any panties, and he must know that I'm not!" He hadn't yet asked her to show him that she was obeying his instructions of the afternoon before, and was tempted just to let her legs fall apart so he could see! It was frustrating sitting so nearly exposed yet not being made to expose herself to him and not daring to expose herself!

She did pay enough attention to what the head was saying, taking in how Brian's angry accuser had stormed into Mr Ash's office the week before demanding immediate justice. When Brian had pleaded innocence of the serious offences, Arthur had been tempted just to give the boy six of the best anyway, to satisfy the shopkeeper, but instead had sent Mr Cooper away with a firm promise that justice would be done. Now, he explained to his pretty young history teacher and discipline trainee, he needed to decide what to do with the boy.

"If he really wasn't involved, you can't cane him just to satisfy that horrible shop owner, surely?" Allison said indignantly.

Arthur admired her simplistic view of life, and tried to explain that Mr Cooper was an important man in the local business and social communities, and Arthur couldn't afford to offend him by letting the boy off just because he was innocent. "I think I will have to cane him, I just can't see any alternative. Anyway he will be here in a few minutes, I suggest you hear his side of the story then you can tell me what you think."

So it was that young Brian was brought into the head's office and was shocked to see the very sexy Miss Wilson sitting in a lounge chair near the back of the office. Brian was made to stand squarely in front of Mr Ash's large desk, over which he remembered only too well how he had on two previous occasions been caned. As he stood facing Mr Ash, he was very aware of the young woman behind him, and of his own erection, already throbbing inside his pants. Surely the head wouldn't make him remove his trousers with a woman present?

"Brian, I have asked Miss Wilson to attend today so she can give me an independent view of your situation. I have told her what Mr Cooper said last week, and now I want you to tell her your side of the story. But first, let's get you ready for the caning that you and I both expect you will shortly be receiving. Please remove your trousers and your underpants and hang them on the hook by the door."

Brian panted, wondering why he couldn't just drop them to his ankles as he had done previously, but didn't dare question the headmaster. Mr Ash and Miss Wilson watched pretending indifference as Brian struggled with trembling fingers to drop his lower clothing. He knew he already had an erection, and Arthur was amused to see it, and to see how the boy tried to prevent Allison from seeing it as he held his clothes in front of himself as he went over to the hook. That was when Allison first noticed that her red and black panties were back on one of the hooks! She gasped as Brian looked at them, then glanced sideways to where she was sitting! He turned away from her and walked back to the headmaster's desk and stood with his hands covering his crotch.