Six of the Best Ch. 02

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The Headmaster and the habitually-wayward 'Justine'.
2.3k words
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Part 2 of the 2 part series

Updated 09/23/2022
Created 09/26/2012
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KinoKe
KinoKe
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It was a little after seven in the evening. The Headmaster was in his study, hunting and pecking at the keyboard that sat atop his large oak desk with its dark forest green inlaid leather top. Tap, tap, tap. Tap, tap, tap. And then, from the door opposite, almost an echo: Tap, tap, tap.

'Come!' The Headmaster called.

The study door opened and Matron -- fiftyish, upright, looking neat and tidy and authoritative in her sensible white-collared navy blue dress with her spotless white over-apron -- stepped from the dark of the antechamber and into the light.

'Ah! Matron! What word from the dorms?'

'I have asked Mr Hermans to move Hodgkin and Pilkington Minor to the sick bay, Headmaster. We don't want this influenza spreading any further than necessary.'

'No. Very wise, Matron. Thank you.'

Matron acknowledged The Headmaster's thanks with a slight-but-gracious nod.

'Is there anything else of which I need to be aware this evening, Matron?'

For a moment or two, Matron said nothing. But then she said, almost apologetically: 'Well ... it is the second Thursday, Headmaster.'

The Headmaster frowned slightly and glanced at the small brass and glass digital calendar on his desk. 'Is it? Hmm. Oh yes, so it is. My apologies, Matron. I had quite lost track of the days.'

'If it's not convenient ....'

'What? Oh, no. No, it's just that ... umm ... you know ... the days fly by. One moment it is Monday, and the next it is ... well, Thursday. And the second Thursday at that. But now that you bring the matter to my attention ....'

'Well, only if you have time, Headmaster.'

'Time? But of course I have time, Matron. Looking forward to it. Yes.'

'In that case, shall we say five minutes?' Matron suggested.

A faint frown formed on The Headmaster's brow. 'Five minutes?' But then the frown passed. 'Yes ... yes, perfect. That will give me just enough time to finish this report for The Governors.'

Matron nodded. 'I will go and prepare Justine,' she said.

'Thank you, Matron. Thank you.' The Headmaster returned -- albeit briefly -- to the report on which he was working. But it was no good. He had lost his train of thought. His mind had moved on. He was already preparing himself for his chat with the habitually-wayward Justine. A difficult girl. Ah well, the report would just have to wait until later.

The Headmaster gathered his papers into a neat pile, got up from behind his desk, and walked across to the antique umbrella stand in which he kept a neatly furled black umbrella, a larger golf umbrella in the school colours, and a selection of hand chosen canes. After taking out and trying four or five of the trusted chastising rods, he settled on a medium-weight length of bamboo which, he recalled, had originally been purchased to stake a tomato plant. 'Yes,' he said to himself. 'Yes.' And he placed the cane -- conspicuously -- on the top of his desk.

A minute or so later, there was another tap at the door.

'Come!' The Headmaster called. And then: 'Ah, Justine. Come in, girl. And turn the key in the door behind you.'

To the casual observer, Justine may have seemed to bear more than just a passing resemblance to Matron -- except that Justine was wearing a white cotton shirt (a shirt that appeared to be a size or two too small for her well-developed breasts). She was also wearing a short plaid skirt, white ankle socks, and black shoes with non-regulation pink shoelaces.

'Matron said that you wanted to see me, Headmaster.'

The Headmaster looked her up and down, wincing slightly when he reached the non-regulation pink shoelaces. 'Did she now?' he said.

'Yes, Headmaster.'

'And why do you think that might be, Justine?'

'Don't know, Headmaster.' (It was difficult to tell whether the wretched girl was being appropriately contrite and respectful or simply cocky.)

'Don't know, eh?'

'Not really, Headmaster.'

'I'm sure that Matron must have had some reason in mind.'

Justine nodded. 'I suppose so, Headmaster.'

The Headmaster picked up the cane from its resting place on his desk and slowly ran the fingers of his right hand along its length. 'Why does Matron usually send you to see me, Justine?'

'Because she thinks I've done something wrong?' Justine suggested.

'Indeed. Because she believes that you have done something wrong.' The Headmaster replaced the cane on the desktop. 'And can you think of something that you may have done wrong in the past day or so, Justine?'

'Not really, Headmaster.'

'Not really? Are you sure?'

Justine shuffled her feet and muttered something about the cricket pavilion.

'The cricket pavilion? What about the cricket pavilion? Is there something that you have done with or in the cricket pavilion that may have caused Matron to believe that you needed to visit my study?'

'I was just trying to be helpful, Headmaster.'

'Helpful? I think it is very unlikely -- very unlikely indeed -- that Matron would send you to my study for trying to be helpful, Justine.'

'Yes, Headmaster.'

'In what way were you trying to be helpful?'

'I was trying to help Mr Pennyman to relax before the annual Masters-Pupils cricket match, Headmaster. That's all. He said that he would play better if he was relaxed.'

The Headmaster nodded. 'And precisely what form did this help take, Justine?'

'I just rubbed his stiffy for him, Headmaster.'

The Headmaster frowned slightly. 'Mr Pennyman had a stiff muscle?'

'Not a muscle, Headmaster. A stiff cock.'

The Headmaster's frown deepened. 'I see. So when you say you "rubbed his stiffy", you are really telling me that you manually stimulated Mr Pennyman's erect penis. It that correct? Is that what you are telling me?'

'I suppose so, Headmaster.'

The Headmaster shook his head in disbelief. But then, after a moment or two, he asked: 'And did this ... umm ... stimulation have the desired effect? Did it help him to relax?'

'Well Mr Pennyman spunked, Headmaster, so, yes, I suppose it must have.'

The Headmaster raised his eyebrows. 'So he spunked, did he?'

Justine nodded.

'And was Mr Pennyman the only waiting batsman you helped to relax in this way, Justine?'

'And Mr Wentwhistle.'

Again The Headmaster shook his head. 'And Mr Wentwhistle. I see. And did Mr Wentwhistle spunk too?'

'Not as much as Mr Pennyman, Headmaster. But Mr Pennyman had a bigger stiffy so I suppose that he had more spunk.'

The Headmaster casually rearranged the position his own growing stiffy within his trousers. 'I see,' he said.

'I was only trying to help, Headmaster,' Justine said again. 'I told Matron that. I said that I was only trying to help Mr Pennyman to relax.'

'And what did Matron say?'

Justine hesitated.

'Come on, girl' The Headmaster said. 'What did Matron say?'

'She said that I was a lewd and lascivious little tramp, Headmaster.'

'And are you?'

Justine said nothing.

'Well?'

Justine shuffled her feet. 'Perhaps just a little bit, Headmaster. You know ... just sometimes. Not all the time, Headmaster.'

'And did you enjoy stimulating the erect penises of Mr Pennyman and Mr Wentwhistle, young lady?'

'It was OK,' Justine said.

'OK?'

Justine smiled. 'Well, quite nice really ... I suppose. Mr Pennyman's stiffy was really long.'

The Headmaster nodded. 'And tell me ... did stimulating the erect penises of Mr Pennyman and Mr Wentwhistle -- and causing them to spunk, as you say -- have any noticeable effect on your own physiology? Did it cause an increase in your heart rate, a tingling, a certain dampness of your vulva perhaps?'

'A little bit,' Justine said.

'And what about now?' The Headmaster asked.

'I don't know, Headmaster.'

'Don't know? Or just won't say?'

'Don't really know, Headmaster.'

Oh, come here, girl,' The Headmaster said impatiently.

Justine stepped closer to The Headmaster.

'Spread you feet and put your hands on your head,' he instructed her.

Justine did as she was told and The Headmaster reached up under her short plaid skirt and ran a finger along the gusset of her knickers. 'Wet,' he said. 'Wet as a shag on a rock. Matron is quite right: you are a lewd and lascivious little tramp. And you know what happens to lewd and lascivious little tramps, don't you, Justine?'

Justine nodded.

'Assume the position and lift your skirt.'

'I was only trying to help,' Justine protested. But she did as she was instructed anyway.

'Knickers down,' The Headmaster commanded.

Justine lowered her knickers.

The Headmaster took up his cane and began to prepare Justine's exposed buttocks with a series of perfectly judged little stinging flicks, none of them sufficient to inflict any real pain, but, collectively, enough to wake up her circulation and start to turn her pale, almost white, buttocks to a rosy shade of pink.

And then The Headmaster was ready to get about his work proper. His cane swished through the air and landed on Justine's buttocks with a sharp crack. 'That is for being lewd, young lady,' The Headmaster said.

Thwack! 'And that is for being lascivious.'

Thwack! 'And another for being lubricious.'

The Headmaster paused briefly and reached between Justine's parted thighs. His fingers found their way between the swelling outer lips of her vulva. His index finger parted her slippery inner lips and briefly explored the warm wet entrance to her vagina. 'Lubricious in both senses of the word,' he said, slowly withdrawing his juice-covered fingers.

Thwack! 'That is for wanking off Mr Pennyman and pretending that you were only doing it to be helpful. It is quite clear to me that you were doing it for your own depraved self-pleasure.'

Thwack! 'And another for wanking off Mr Wentwhistle.'

The Headmaster adjusted his stance for one more blow. 'And for not having the courtesy to first tend to my own stiffy ... let this be a lesson you will not forget.' Thwack!

'There.' The Headmaster returned the cane to the umbrella stand, took out a clean white handkerchief from his pocket, and dabbed his brow.

'As much as the red stripes become you, I must say that this is all very disappointing,' The Headmaster said. 'It is happening far too often, young lady. Unless I am very mistaken, it seems that I am being called upon to beat you at least once a month. Indeed, if it wasn't such a perverse idea, I would suggest that you actually enjoy being beaten.' The Headmaster again reached between Justine's thighs. 'The state of your pudendum certainly suggests that you enjoy being beaten.'

'Perhaps I do, Headmaster,' Justine said quietly.

'Hmm.' The headmaster unbuttoned his fly and allowed his erect penis to take the air. 'And tell me, young lady, how does Mr Pennyman's stiffy compare with this?'

Justine carefully studied The Headmaster's now rampantly-erect penis. 'Difficult to say, Headmaster -- you know, without actually feeling it -- yours, I mean.'

'Well, touch it then, girl. It won't bite.' The Headmaster seemed annoyed that Justine had not instantly chosen his erection as the clearly-superior erection.

'Well ... I think your stiffy is probably thicker,' Justine said, after she had carefully weighed it in her hand for a few moments.

The Headmaster suddenly seemed happier. 'Hmm,' he said, nodding. 'Yes. Yes I'm sure it is. Not that I have seen Mr Pennyman's penis, you understand. Not in its erect state, anyway. But, yes, I'm sure that mine would be more ... well ... more substantial.'

Justine started to gently stroke The Headmaster's upstanding member.

'And I think thickness is what women most appreciate,' The Headmaster said. 'Length is much over-rated. Yes, thickness -- that's what most women prefer. I'm sure that you are someone who appreciates a bit of girth, Justine, a bit of heft. Perhaps you would like to feel my substantial member in your ... well ... you know.'

'If you think that would be alright, Headmaster,' Justine said. 'Although I wouldn't want to get into trouble with Matron again.'

'No. Of course not. But I'm sure that Matron would understand. You know ... just in the interests of ... well ... science, I suppose. Just for future reference. That sort of thing.'

'Perhaps if I was to bend over your desk, Headmaster.'

'Yes. A good idea,' The Headmaster said.

Justine bent over The Headmaster's desk and raised herself slightly on her toes so that her womanly arse was almost perfectly positioned. Helpfully, she reached back and parted her reddened buttocks to further expose her already slick vulva. 'There. How is that?' she asked. The Headmaster aligned the head of his erect penis with the entrance to Justine's wet-as-a-shag vagina and pushed.

'Oh, gosh, yes,' she squealed. 'That feels perfect. Just perfect.'

The Headmaster was inclined to agree. 'Perhaps just a few exploratory thrusts?' he suggested. 'Just to give you the full effect.'

Unfortunately, it was 'just a few'. Maybe ten. Twelve or thirteen at the most. And then it was The Headmaster's turn to spunk.

'Oh, yes! Oh, fucking yes!' The Headmaster shouted. 'Take it! Take it! Take my magic seed, you wanton cum bucket! Let my divine essence fill your greedy wanton cunt!'

For three or four minutes afterwards, Justine continued to lean across the Headmaster's desk while he gently, absent-mindedly -- almost lovingly -- smeared his 'magic seed' across Justine's red-striped buttocks. But all things must come to an end and, eventually, he announced that he needed to get back to work on his report for The Governors.

Justine retrieved her discarded knickers. 'Yes. And I really should get going too, Headmaster. I still have a couple of things that I need to do this evening.'

The Headmaster nodded. 'Yes. Yes, of course, Matron.' And then he added hastily: 'I mean ... Justine.'

KinoKe
KinoKe
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CockSparrowCockSparrowover 1 year ago

A delightful little gem. These things are only perverted if they are done properly. And it was.

AnonymousAnonymousover 11 years ago
Nicely bizarre

A nice bit of erotic theatre. I liked it a lot.

mel_pomenemel_pomeneover 11 years ago
Very nice!

I like a good hot-bottom story - thank you for writing this one for us!

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