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Six of the Best Ch. 02

By: KinoKe



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.'

Six of the Best Ch. 03



'NO RUNNING IN THE CORRIDOOR.'

The Headmaster's voice rang out loud and clear. For a brief moment the three miscreants halted in their tracks and cast a guilty glance in the direction from which the edict had come.

'How many times do you boys need to be told?'

The ringleader muttered something appropriately apologetic, and then all three walked, cautiously, almost on tiptoe, towards the nearest exit.

'Humph!' The Headmaster waited until the door had closed behind them before resuming his sedate, unhurried progression towards the large panelled door that bore the one-word inscription: MATRON. Once outside the door, he straightened his tie and his grizzled grey hair, and knocked sharply three times.

From the other side of the door there came a brisk-but-muffled response. 'Come.'

The Headmaster turned the large brass door knob, pushed open the door, and stepped into Matron's office.

'Ah! Headmaster! An unexpected pleasure.' Matron – fiftyish, upright, neat and tidy and authoritative (as always) in her sensible white-collared navy blue dress with her spotless white over-apron – rose from behind her desk. 'I thought that you might have retired for the evening by now. Nothing wrong, I hope.'

The Headmaster looked vaguely uneasy. 'Wrong? Umm ... well ... probably not, Matron. Probably nothing really. But ... umm ... well ... you know.'

Matron did not appear to know, but she waited patiently.

'A bit of a ... umm ... an anomaly, I suppose you could say. Probably nothing to worry about.'

'An anomaly?'

'Yes. A slight ... well, reddening, I suppose. And an itch. As I say, probably nothing to worry about, but I thought that perhaps you could ... well ... take a look? Give me the benefit of your clinical opinion?'

'But of course, Headmaster. And where exactly is this ... umm ... anomaly.'

The Headmaster made a sort of circular movement with his hand just in front of his crotch.

'Oh.' Matron nodded. 'I see,' she said. 'Well, as you say, probably nothing. But, still, I'm always more than happy to take a look at these things. Perhaps if you could just remove your trousers. There's a screen over there if you would prefer a little privacy.'

The Headmaster looked briefly in the direction of the screen and then shook his head. 'You're going to be ... well ... you know,' he said. 'The screen seems rather pointless.' And he sat down on the chair in front of Matron's desk and began to remove his shoes.

While he did this, Matron quietly locked the door and drew a heavy blue velvet drape across it. She also checked the heavy drapes that covered the window behind her desk.

Once The Headmaster had removed his highly-polished black Church's half brogues and placed them neatly next to each other, he rose back to his feet and removed his trousers. Finally he lowered his pale blue and white striped boxers and revealed 'the affected area'.

Matron adjusted her desk lamp to throw more light on the subject. 'Yes,' she said. 'I see what you mean. There is a slight ... well, colouration. Have you been doing anything different? Anything unusual? Using a different soap perhaps – or anything like that?'

The Headmaster shook his head.

'I think ...' Matron said. But then she didn't say what she thought. Instead, she donned a pair of latex surgical gloves and began a closer inspection of The Headmaster's penis and scrotum, lifting the penis, retracting the foreskin, inspecting the pinkish purple head. 'Hmm,' she said. 'Hmm.'

'Hmm?' The Headmaster enquired.

'Hmm,' Matron confirmed.

With all the attention and ministrations, The Headmaster's penis was beginning to fatten and extend somewhat.

'Naughty,' Matron said sternly, and rapped the Headmaster's growing member with her gloved finger. 'Now, if you'll just pop up on the examination table, I think we'll get rid of some of that excess pubic hair. I don't think that's helping matters for a start.'

'Is that necessary?' The Headmaster asked.

Matron glared at him with a look that clearly said: Would I be doing this if it were not necessary? 'Come on. Chop, chop, Headmaster,' she said. 'No pun intended.'

Reluctantly, The Headmaster climbed up onto the table and lay back while Matron began to trim away his pubic hair with a small pair of scissors. With the longer strands out of the way, it was then just a matter of finishing off with some shaving cream and a disposable plastic safety razor. 'There,' Matron said, wiping off the remaining cream with a towel and standing back to admire her handy work. 'That should reduce the possibility of any further chaffing – for the time being at least.'

'Is that it?' The Headmaster said.

'Not quite. Just onto your hands and knees, please – if you will.'

The Headmaster rolled over and got to his hands and knees.

'Just a little trim around your anus,' Matron said. 'And then we can apply some soothing lotion.'

'Are you sure this is necessary?' The Headmaster asked. 'All this deforestation, I mean.'

'Oh, absolutely,' Matron said, and, parting The Headmaster's buttocks, she cleared an area around his pink and puckered arsehole. 'Yes,' she said, standing back once more to admire her handy work. 'Yes, that's much better. Much tidier.'

'Are we finished?' The Headmaster asked.

'Umm ... no. No. While I have you in this position, I think we will see if we can do something about your circulation, see if we can stimulate it a little. It will help to speed up the healing process.'

'Well, if you think so.'

'I do,' Matron said. 'I most certainly do.' Matron opened a shallow drawer in a nearby cabinet and, after a few seconds careful consideration, selected a burgundy-coloured leather riding crop. 'I think this should do the trick,' she said.

Matron trailed the flat leather keeper at the business end of the crop across The Headmaster's naked buttocks – once, twice, three times. 'Did you know that the standard riding crop is perhaps the fastest and most responsive of all whips?' she asked. And, before The Headmaster had a chance to answer, she gave the crop a little flick. Whirr-lap! It was really more of a sharp tap than a crack – but it left a small red mark. And then she repeated the process – once, twice, three times. Whirr-lap! Whirr-lap! Whirr-lap! And each time the keeper left its distinctive mark.

'Are you sure that this is necessary, Matron?' The Headmaster asked yet again.

Matron paused for a moment. 'With all due respect, Headmaster, I do wish that you would stop questioning my judgement in these matters. I think you will find that when it comes to clinical matters I am possessed of a level of expertise far beyond your own.' And, to underline her point, she gave the crop a serious flick. Whirr-lap!

'Aargh! That stings,' The Headmaster said.

'It is supposed to,' Matron assured him. 'It stimulates the circulation.' And she repeated the process yet again. Whirr-lap!

'Aargh!'

And again. Whirr-lap!

After another four or five well-directed strokes, The Headmaster announced that he thought that he had perhaps had enough.

'You will have had enough, Headmaster, when your buttocks are a nice rosy red. And not before.' And she commenced to administer six of the very best. 'Shall we count them?' Whirr-lap! 'That's one.' Whirr-lap! 'Two.' Whirr-lap! 'Three.' Whirr-lap! 'Four.' Whirr-lap! 'Five.' Whirr-lap! 'And one more makes six. There. That's more like it. Although ... perhaps just one more for luck.' Whirr-lap! And she laid the crop on his reddening flesh with her full force.

'Aargh!'

'Yes. I think that should do it.'

Matron placed the crop back into the open drawer and quietly closed it.

'Now ... while I have you this way up,' she said, 'I may as well give you a brief rectal examination. Nothing to do with your present course of treatment, but I think that you might enjoy it anyway.' And, with that, she squirted a generous quantity of lubricant in the region of The Headmaster's anus and entered it with her gloved finger.

The Headmaster tensed a little – but then relaxed.

'There,' Matron said softly. 'That's not so bad, is it?'

The Headmaster grunted slightly.

'And how are things below?' Matron enquired. And with her other hand, the hand that was not probing The Headmaster's rectum, she reached for The Headmaster's rock-hard erect penis and gave it a couple of exploratory pumps. 'Excellent,' she said. 'Most encouraging. The circulation is clearly working. Perhaps we should turn you over. Your knees are probably ready for a bit of a rest.'

The Headmaster's knees were, indeed, ready for a bit of a rest, and he gladly – although somewhat creakily – resumed a recumbent position, being more than a little tentative as he lowered his freshly reddened buttocks onto the examination table.

Matron peeled off her surgical gloves and consigned them to the nearby waste receptacle. She then briefly rubbed her hands on a disposable towel and donned a fresh pair of gloves.

'Are we done?' The Headmaster enquired, more in hope than expectation.

Matron just smiled.

'It's just that ....'

But before The Headmaster could finish what he had started to say, Matron held up an admonishing finger. 'You came here, Headmaster, with the objective of benefitting from my clinical expertise ...'

The Headmaster nodded resignedly.

'... and in my clinical opinion it would be most unwise to leave your unquestionably substantial erection in its present state, As things stand – no pun intended – there is a risk that it will diminish circulation to the surrounding area and delay the healing process. Do you understand?'

Again, The Headmaster nodded.

Matron took a small black container with a pump top from one of the cupboards and handed it to The Headmaster. 'Now ... while I get myself organised, if you could just apply some of this special lubricant to your penis. It contains vitamin E – a useful aid to healing. I'm afraid it might feel a little cold at first, but it soon warms up,' she said cheerily. 'Oh, and you might want to put a little on your scrotum too.'

While The Headmaster did as he was instructed, Matron removed first her white apron and then her white-collared navy blue dress. And, finally, she removed her full-cut navy blue lace-trimmed satin knickers, leaving her wearing just her rather fetching balconette bra, a satin and lace suspender belt, and a pair of dark blue stockings.

'I could put some music on if you wish, Headmaster,' Matron said. 'Entirely up to you.'

The Headmaster, who was now smiling and playing with his cock, shook his head. 'Your voice is music enough for me, Matron,' he said.

Matron smiled an almost-girlish smile. 'It's kind of you to say so, Headmaster. I will, however, turn the lights down slightly.' And she did.

'Right. Are we ready?' Matron climbed up onto the examination table and positioned herself astride the recumbent Headmaster. 'Perhaps if you would do the honours, Headmaster,' she said. And while Matron helpfully parted her fleshy, glistening labia, The Headmaster lined the head of his stiff and lubricated cock up with the entrance to Matron's soft and lubricated cunt.

For the next ten or 15 minutes – maybe longer – Matron rode The Headmaster as if he were a horse that was eager to please but in danger of tiring before the journey was over. Occasionally, she brought him to a brisk canter; but mainly they progressed at a steady trot. Up and down. Up and down. All the way up; and all the way down.

And then, with the journey's end in sight, she let her mount have his head. 'Come on. Come on. That's it,' she said. 'Come on. You can do it.'

'Oh, yes! Oh, yes! Oh, fucking yes!' The headmaster cried out.

Matron jumped from the saddle at precisely the right moment. A split second later and The Headmaster was spurting cum like cheap mayonnaise from squeeze bottle.

Matron left The Headmaster to catch his breath for a few moments while she put her dress and apron back on, and checked her hair and makeup. And then she took a small bowl of warm water and a disposable towel and 'tidied' The Headmaster's nether regions.

'Thank you, Matron,' The Headmaster said.

'The pleasure has been mine,' she assured him. 'I am always happy to help, Headmaster.'

As he slipped back into his trousers, The Headmaster took one last look at 'the anomaly'. 'Possibly just the light,' he said, 'but I sense that it is getting better already.'

Matron nodded. 'Well, if it hasn't cleared up by this time tomorrow,' she said, 'perhaps you should come back and we will try something else.'

'Yes. Yes, I'll keep a very close eye on it,' The Headmaster promised.