Educating Sandra

Story from Blushes Supplement 01.

Educating Sandra

Louise Bracknell, Headmistress of Southwood Comprehensive, smiled al the girl standing in front of her. 'It is a great honour, of course, Sandra. For you and also for this school; and I'm sure it's going to be a marvellous experience. But don't imagine it'll be a path strewn with roses all the way. There will be problems, but problems in life are there for us to overcome, aren't they?'

These suitably headmistress-like utterances were directed at Sandra Clayton who was 16 and about to become the first girl taken on at Southwood College, the local boys public school. She would join the Lower Sixth for the coming summer term. Naturally the prospect was very exciting.

'I'm sure I can cope, Miss Bracknell.'

Sandra was a very pretty girl with shoulder-length blonde hair and big blue eyes and a nice shapely figure of about average height. She was also very bright and level-headed and sensible. Louise Bracknell was sure Sandra would make a success of this, and then if all went well she would be joined by two other girls next year.

'Generally speaking you will find the staff there very nice,' she told Sandra. 'But as in any little community it does have its reactionary elements; those individuals who are reluctant to move with the times and who need convincing that a change is for the better.'

'Anyway it has been decided that the best way to deal with this is for you to visit these particular gentlemen individually during the vacation. Just an afternoon visit so they can get a look at you and see that there's nothing to be frightened about.'

Miss Bracknell smiled at her little joke and Sandra flushed slightly. The Headmistress handed Sandra a strip of paper.

'These are the gentlemen concerned. You can ring them up and make the arrangements yourself. I have also put the Headmaster on the list – not that he's one of the awkward ones. But see him first, Sandra.'

Miss Bracknell wished Sandra good luck and said that they would naturally keep in touch. Sandra turned to go. She had reached the door when Miss Bracknell remembered something else.

'One thing, Sandra. As I expect you know they do use corporal punishment at Southwood College. I don't actually know what Mr Newberry is planning for you in that regard but whatever is decided clearly the best thing is for you to simply accept it. Of course it may well not come up, if you don't get into any scrapes etc.'

* * *

Sandra saw Mr Newberry a week later when she cycled over to his house in the afternoon. By this time she had got her uniform and was wearing it: a girl's version of the regular Southwood College outfit. The blazer was the same – grey with the red Southwood crest – but under this was a white long-sleeved blouse and a full pleated knee-length grey skirt.

To complete all this Sandra had on light brown nylons fastened at mid-thigh with a white suspender belt, plus brown medium heel shoes. The nylons were Mr Newberry's idea. As he had said to his secretary, girls always used to wear them and wasn't it true that they were coming into fashion again?

Sandra found Mr Newberry's red brick house without any trouble; about two miles from her house and a similar distance from the College which was just outside the town boundary. The door at Mr Newberry's was opened by a pleasant-looking middle-aged lady who said she was Mrs Newberry, She ushered Sandra into her husband's study and said she would bring in some tea later, then went out.

Mr Newberry was tall and silver-haired, fiftyish like his wife, and seemed very friendly. He said Sandra would be very welcome at Southwood College and it would be a big thing for the school to start having girls. Mr Newberry also said the uniform looked very attractive, the school outfitter had done a good job, and in addition Sandra was a very attractive girl as well.

Yes he seemed very friendly. As he stood next to her by his desk Mr Newberry's hand came round and palled Sandra's bottom in a friendly way. And then gave it a squeeze.

Sandra flushed, but Mr Newberry's hand let go as he went to sit on his settee. He asked if she had the nylons on. Sandra said yes Sir.

'Good. I rather like nylons. Takes me back to when I was a lad. Come here, m'dear, and let me have a look.'

Sandra was made to stand in front of him and then lift up the front of the grey pleated skirt. Exposed to Mr Newberry's keen gaze were the sleek brown nylons with their darker welts, and the slim while suspender straps crossing softly rounded thighs. Sandra gave a start as Mr Newberry's hand reached out. His fingers stroked her thighs, and fiddled with the suspenders.

As he fiddled about he started telling her about Southwood College's code of conduct which they were very proud of. If anyone had a problem it was sorted out in the school, no one ever took their problems home or to anyone outside. You went to your form teacher or to Matron or to him, the Head. Everyone would naturally be watching to see that the first girl at the school was able to conform to this code of conduct.

Sandra, still holding her skirt up and sweating slightly, said yes she understood. While talking Mr Newberry had continued his fiddling about. He had unfastened one suspender clasp and then done it up again. Sandra wondered vaguely what you did if you had problems with the Headmaster.

He finally took his hands away and Sandra was told she could drop her skirt. Then she had to take off her blazer. Mr Newberry, standing now, looked Sandra up and down, in particular casting his gaze over those firm quite full breasts which were bulging out the front of Sandra's crisp while blouse. He told her to turn around, gave her bottom a slap, and then said turn again. Then Mr Newberry said that if Sandra had any problems with boys at school she was to come to him or Matron.

'You know what I mean,' he said. 'Boys with grabby hands and that sort of thing. Because naturally they won't be used to having a pretty girl in their midst.'

As if to illustrate what he meant Mr Newberry turned Sandra once more, so that she was facing away from him. And his two hands calmly slid under her arms to come round and lake hold of her two breasts, in that nice new thin blouse which had only a thin while bra underneath. Sandra gave a shocked gasp and her own hands automatically shot up to Mr Newberry's. He didn't take them away, though, just squeezed...

Fortuitously at this point the door abruptly opened and Mr Newberry did take his hands away. It was Mrs Newberry with a tray of tea. She smiled sweetly as she put the tray down.

'How d'you think your going to like it, Sandra?'

Sandra, hot-faced, said something but she wasn't quite sure what. Mrs Newberry went out and Mr Newberry and Sandra had tea. She didn't really feel like eating though, because this really was turning into something of an ordeal.

There was, perhaps inevitably, more to come.

'The subject of punishment,' said Mr Newberry portentously, draining his cup and putting it down. 'That is something that we have to be clear on. It is in that area that some senior members of my staff have expressed misgivings.'

These would be the masters Miss Bracknell had referred to, the others on Sandra's list. According to the Headmaster they were concerned that, if they had to have girls at Southwood, there might be a slackening of disciplinary standards. Mr Newberry said he could see their point on this. The school's reputation had to be maintained.

He leaned across to Sandra as she sat opposite him and put his hand on one nyloned knee.

'So, Sandra, I have agreed that they can use the cane on you, if and when necessary. I want you to agree that you'll accept this and I also want you to agree that no mention of this will be made outside the school. Remember the school's code of conduct.'

The hand on Sandra's knee squeezed. 'Caning a girl is of course quite legal but it is something which in certain quarters would cause raised eyebrows, and worse. Is that understood and accepted?'

Sandra was sweating again. The hand on her knee made her feel uncomfortable but what Mr Newberry was saying made her feel a lot worse. Miss Bracknell hadn't actually mentioned the cane.

'Of course we may well not get into a caning situation,' Mr Newberry went on. 'But I want a solemn undertaking that if necessary you will accept it, without argument, and you will then maintain silence as to what has happened.'

Somehow Sandra heard herself agreeing.

'Good!' said Mr Newberry in a hearty voice. 'That's settled then. As for myself, Sandra, I can say that I do not intend to use the cane on you – although of course I do use it on boys if necessary. My own feeling is that caning a girl's bare bottom is not the best way of dealing with her – while nonetheless accepting that others have their own views on this. No, Sandra, what I intend, if we get into a situation where some form of corporal punishment seems desirable, is to give you a spanking. A good spanked bottom.'

As he said this the hand which was still on Sandra's knee gave a firm squeeze. Eyes shining, Mr Newberry asked if she had had her bottom spanked recently. Sandra unhappily shook her head.

'Well I must admit that I don't get to spank many girls myself at present. There was my niece a few years ago but she's now married and moved away. Very unfortunate! So perhaps it might be an idea to try things out – just to see there're no snags.'

Sandra gave him a bewildered look. At least the hand had now left her knee. The Headmaster spelled out what he meant.

'Come here and get over my lap, Sandra. Let's have a look at that pretty bottom of yours.'

Sandra's look was now one of disbelief but he clearly meant it all right. Desperately she glanced over at the door in the hope that it could open and admit Mrs Newberry. But the door remained closed.

'Come on, my dear; snap to it!' urged Mr Newberry in sterner tones. 'At Southwood College we learn to respond immediately.'

Sandra got up. Not looking at him she moved to Mr Newberry's side. He pulled her down across his lap. Immediately she felt her skirt being lifted and then the Headmaster's hand was stroking the backs of Sandra's thighs above the stocking tops, and her tightly knickered bottom. Her knickers were quite skimpy, blushing pink, and they were also, she thought hotly, partially transparent.

But transparent or not didn't really matter because Mr Newberry simply inserted his fingers in the waistband and pulled them down. Two firm tugs and Sandra's bottom was bare!

He proceeded to give that ripe 16 year old rear a number of firm but not hard smacks – and then Mr Newberry's hand was running caressingly over the silky smooth flesh.

His voice said, 'Yes, I think we shall manage, Sandra. Don't you?'

Sandra couldn't think of answering; it was so desperately awful. There was some more fondling and a few more smacks and then she was told she could get up. Her face was crimson as she scrabbled her knickers back up under her skirt.

'No need to be embarrassed,' Mr Newberry assured her. 'I've seen girl's bottoms before, you know.'

The interview went on for a while longer but Sandra didn't really take anything in, her mind was still centred on the enormity of being over Mr Newberry's lap with her knickers down. He checked the list Miss Bracknell had given her and agreed that those were the masters to see. And that was it.

Mr Newberry helped Sandra on with her blazer. As he did so his hands quite deliberately felt her breasts again. If he wasn't Headmaster of Southwood College you could be excused for thinking he was just a Dirty Old Man, Sandra thought. Cycling back home she had plenty to think about. And she hadn't met the 'problem' masters yet!

* * *

The first of these was Mr Wilmot, Senior History Master, who was a bachelor and had a flat in the College itself. Sandra arranged to see him three days later. Mr Wilmot certainly sounded somewhat curt on the phone and after that traumatic visit to the Head she was feeling decidedly apprehensive as she cycled the four miles to the College.

It was very impressive, old grey stone buildings, ivy-covered in parts. At the moment naturally it was deserted and it was kind of eerie with all those blank windows seemingly watching you. Yes, it was impressive but scary – especially when you thought of that now central mind-boggling fact: the cane. Sandra found herself half hoping that perhaps Mr Wilmot might have forgotten her appointment and not be in. And then somehow she could forget the whole thing and go back to Southwood Comprehensive next term.

But that was not to be as a caretaker-looking man came up and enquired if she was Miss Clayton, and then told her where to go.

Mr Wilmot was a tall man, like the Head, and also about his age, but with gold-rimmed glasses and a thin dour face. He said, 'Hello; so you are the famous Miss Clayton, eh?'

He didn't sound very welcoming but he led her into his room which had leather armchairs and a settee and books covering a good part of the walls. He indicated an armchair that Sandra was to sit on and he himself stood opposite, leaning against his desk. Sandra perched tensely on the edge of the leather seat as Mr Wilmot fixed an unblinking stare on her.

'Ever had the cane, young Miss?' he queried in precise tones.

Sandra experienced a hot flush. Mr Wilmot wasn't even going to lead gradually up to it. She shook her head.

'Every pupil at Southwood is liable to the cane, Miss Clayton, and I have the Headmaster's word that you are not to be excluded from this. You are aware of that, I presume?'

Sandra nodded dumbly.

'First caning with knickers retained but all subsequent ones with your knickers off. The cane on your bare bottom, Miss Clayton, that is what we are talking about.'

Sandra sensed he was trying to scare her – and he was certainly succeeding. She felt sick in her stomach.

'And at Southwood College, Miss, no one goes home crying to mother. You keep the matter to yourself. Has the Head told you that?'

Once more Sandra nodded. She could now feel tears in her eyes. Mr Wilmot suddenly left his desk to go over to a cupboard. He came back with a wicked-looking cane in his hand. In front of Sandra's eyes he bent it almost into a circle, then let it spring back. She shuddered.

'So, Miss Clayton, shall we carry out a little lest? Shall we have those knickers down – or I should say right off.'

Sandra could scarcely believe it. She stuttered, 'I... I haven't done anything.'

Mr Wilmot gave a dry little laugh. 'A test, Miss Clayton, does not require you to have done anything. I merely want to be assured that you can take a caning like a sensible disciplined 16-year-old, that's all. I understood the Head had explained this to you.'

Mr Newberry hadn't, there had been no mention of being caned for nothing. It was quite impossible. Two fat tears rolled down the pretty cheeks.

'Do I actually see tears before the cane has even been raised, Miss Clayton? That indeed says very little for discipline!'

His mocking voice became suddenly hard. 'Stand up, Miss, and take those knickers off, and be sharp about it!'

Silently weeping, Sandra obeyed. Standing, she reached up under the grey skirt. A pair of white nylon knickers eventually appeared and were slid on down shapely nylon-clad legs. She stepped out of the knickers and, as directed by a pointing finger, put them on Mr Wilmot's desk.

'That's better,' he told her, whipping the cane sharply through the air. 'And now please bend over the arm of that chair. Head right down on its seat and bottom up.'

Still weeping, Sandra got over the arm of the chair. Mr Wilmot pushed back her blazer, then flipped the grey pleated skirt up over Sandra's back. He gazed – and licked thin dry lips. The girl's ripely rounded bottom seemed to gleam in its sudden nakedness. A decidedly stirring sight, even for a confirmed bachelor. Perhaps especially for a confirmed bachelor. The cane twitched in James Wilmot's hand and he felt something else, the front of his tweed trousers, twitching as well.

Boys were not caned bare-bottomed at Southwood College, they were allowed the considerable protection of underpants and trousers; but James Wilmot and the three other masters who had objected to the presence of a girl in the College's hallowed halls had forced the Head to agree that with a girl it could be different. If she was coming she was very much on trial and had to be tested thoroughly. If she couldn't take it then they would be rid of her. If she could, her acceptance of the school's code would ensure it was kept quiet. And wasn't caning a girl's bare bottom much more stimulating then with her knickers on?

Yes indeed! Mr Wilmot savoured that rare tightness in his trousers and gave the cane a couple of anticipatory cuts through the air.

'Legs straight, Miss; and try and keep it nice and still.' He aimed the cane and without ceremony whipped it down.

THWACK!...

Squarely across the ripest curve of the round cheeks. There was a gurgling gasping yelp from the seat of the chair. The stricken bottom did a frantic dance.

James Wilmot waited, letting her feel the pain, then: THWACK! The cane landed once more, two centimetres above its first line. This time the yelp from the depths of the chair was louder, more urgent, and the bottom's writhings more frenzied.

At the third THWACK! Sandra's hand came desperately back to clutch at her red-hot rear. Only to have the clutching hand immediately feel the sting of Mr Wilmot's precisely aimed cane.

'No hands, Miss Clayton! That is not the way we do things at this school. I want your bare bottom quite unencumbered.'

The smarting hand retreated to the chair seat. And after a suitable period Mr Wilmot's cane whipped down once more across Sandra's clenching bottom.

THWACK!... To leave a fourth double red line.

He gave her eight in all. By the end of this time Sandra was clearly in some distress and Mr Wilmot had no wish to overdo it. He placed his cane on the desk and observed his handiwork. The red-striped bottom was twitching and trembling and there was the sound of uncontrolled sobbing. As for James Wilmot himself, his whole body was glowing, with the exercise and also with a quite intense excitement. In particular he had a very stiff erection.

Sandra struggled to her feet. The pretty face was rather a mess, red and blotchy and tear-stained, and she was still sobbing.

'Sting a bit, did it?' enquired Mr Wilmot.

Sandra tried to say something but all that came out was a 'Nnggghh' sound.

Mr Wilmot moved close and took hold of Sandra's arm. 'Going home with a sad tale to mummy now, are we?'

Eyes blinking to try to stop the tears, Sandra glanced up at him, then looked down. She hesitated. Then she shook her head.

James Wilmot experienced a tingle of relief. An awkward parent could cause trouble and in spite of his obtuseness at times he would rather avoid that. He put a reassuring arm round the unhappy girl.

'Good! That's what I like to hear. No one will be more pleased than I if you do prove able to accept our rather strict regime. But you can see that you must be properly tested. Now then, perhaps I can find some biscuits, and a cup of tea. You may put your knickers back on.'

As at Mr Newberry's Sandra didn't feel like eating anything, all she could think of was her dreadfully sore bottom on the hard leather chair. Mr Wilmot, now he'd caned her, was more amenable, talking about the school and asking if Sandra liked history.

Eyes glinting behind those gold-rimmed glasses, he said that perhaps they were going to get on all right after all. Then, after he'd had his tea, he said he thought he had better take a look at her bottom before she went. So once more Sandra was made to bend over the arm of the chair. Mr Wilmot pulled her knickers down himself this time, to the tops of her stockings. His hand went over her still glowing rear like a giant-sized creeping spider.

At home her mother enquired brightly how she had got on. Sandra managed a normal-sounding 'OK' and went quickly up to her room. She took off her knickers and looked at her bottom in the mirror. For the first time Sandra saw the bright red stripes and it was all she could do not to burst into tears again.

What she wanted to do was go to her mother and to Miss Bracknell and tell them she had decided to call the whole thing off. She didn't want to go to dreadful Southwood College with its horrid caning and horrid masters like Mr Wilmot. But if she backed out Sandra knew she would be letting everyone down and would simply be seen as inadequate. She didn't know what to do. Changing into T-shirt and jeans she decided that maybe the best thing was to go and see Miss Bracknell.

Sandra didn't mention the Headmaster and the fact that he had taken her knickers down, but she did say that Mr Wilmot had caned her on her bare bottom and for no reason at all.

Louise Bracknell bit her lip. She had been expecting something like this and had tried to give Sandra some general warning.

'Well, it wasn't exactly for no reason, was it, Sandra? He was testing you, as he told you. We may consider it was a very unfair and unpleasant test, but that is what it was. And if you can't take the test then he will be quite happy because he's silly enough not to want girls there.'

'What if he keeps on testing me?' asked Sandra miserably.

Miss Bracknell put her arm round Sandra. 'Let's look on the bright side, dear. I can't believe Mr Wilmot is a complete sadist; and by being brave you show these few obstinate characters just how wrong-headed they are.'

Sandra wiped away some tears that had started to come. Miss Bracknell said some more encouraging things and also said, of course, that if Sandra didn't go through with it she would be letting everyone down.

Then she asked if Sandra had made arrangements to see the other three masters yet.

Sandra saw Mr Cutler, Head of Geography, a week later. He lived in the town and he had a wife but she conveniently went out to do some shopping when Sandra arrived. Mr Cutler didn't look like Mr Wilmot, he was shorter with a black moustache, younger probably, but he sounded very much the same. Brusque and curt and not very welcoming.

'So you've seen Mr Wilmot?' he queried. 'And did he put the cane across your backside? I understand he was planning that to see how a girl could cope with it.'

They were in Mr Cutler's sitting room, standing by the fireplace. As with Mr Wilmot, Mr Cutler was starting right out on the subject of caning. Sandra nodded, feeling that sinking sensation in her stomach.

'Bare bottom?' She nodded again, flushing pinkly.

'And were there tears?' Another unhappy nod of the head.

'You look a bit as if you're about to cry now, Miss. An unhappy memory no doubt. But at least you took the caning?'

'Yes Sir.'

'And you are aware of our code of conduct regarding tales outside? You followed that, I hope?'

Sandra had told Miss Bracknell but that didn't really count. She said 'Yes Sir' again.

Mr Cutler left Sandra to go to the cupboard. He came back with a sardonic look on his face – and a three-foot-long, whippy cane in his hand. He raised it and brought it thwacking down across the arm of a chair.

'So, Miss Clayton, if we are to have you at Southwood I don't see why Mr Wilmot should have all the fun, do you? I'm sure you would agree that I should carry out a little testing of my own.'

Sandra said nothing. What was there to say? She felt her knees trembling.

'Yes Miss. Sandra, isn't it? Well, Sandra, please take off your blazer. And then your skirt. And then your knickers.'

She stood, paralysed, as the words gradually sunk in.

'Come on, Sandra dear. Get them off. That nice Miss Bracknell wouldn't like to hear we were having problems, would she?'

Tight-lipped, Sandra took her clothes off. It got increasingly difficult and after removing her skirt it needed a superhuman effort to take off the white nylon knickers in front of Mr Cutler. But she made herself. She stood in front of him in blouse and tie, suspender belt and nylons, and her brown shoes. With one hand covering her blonde bush.

'Both hands at the sides, Sandra. We mustn't be shy with a master, must we?'

Crimson-faced, Sandra dropped the hand.

'Very nice, Miss. Very nice indeed. If we have to have a girl then clearly it is best to have a pretty one, is it not? And one who is indeed pretty all over. Just turn round, would you, dear; so I can see your bottom. That's it. Yes, very nice indeed. And now what we have to do is give that pretty bottom a little touch of the stick, isn't that right?'

The 'little touch of the slick' proved to be six breath-stopping cuts as Sandra bent herself over the back of an upright chair with her head down in its seat. Mr Cutler's thin whippy cane made transverse cuts across the full meat of Sandra's bottom, landing in very much the same area as Mr Wilmot's cane had a week earlier. The pain was absolutely sickening but somehow Sandra managed to hang onto the chair legs and keep in position.

When it was over Mr Cutler said, 'Not bad, Sandra. Yes, you did quite well. Passed the test with flying colours one might say.'

She stood up, sobbing and aching with the smarting pain. Mr Cutler came up behind her and cupped Sandra's red-hot bottom in both hands.

'Not a word to your dear mother, of course; or to anyone else. This has simply been a private test for our new girl.'

* * *

There were two more masters on Sandra's list, Mr Parkinson, Physics, and Mr Morris, English. Somehow she forced herself to visit them. Mr Parkinson caned her on the palms of her hands, two hard cuts to each – before making her take her knickers off and proceeding to give her six equally unpleasant ones on her bare bottom. Mr Morris caned Sandra's bare bottom and upper thighs – after making her lie spread-legged over a stool.

After all this, in some desperation, Sandra went to see Miss Bracknell again.

This time Louise Bracknell had considerable difficulty in persuading Sandra that she should go through with the proposed transfer. The Headmistress had to pull out all the stops, pointing out that Sandra really was in an historic position being the very first girl to be taken in by this noted boys public school. In years to come Sandra would look back on these days with a very proper sense of pride.

'I just can't take those canings,' Sandra wailed tearfully. 'And also h...having to take my knickers off for them. That's just as bad.'

But somehow she was persuaded to be brave and carry on. As Miss Bracknell pointed out they had been testing her and she had taken it, and once she actually started at the College things could well be a lot easier. And she would, she said, have another word with Mr Newberry.

Louise Bracknell did phone Mr Newberry to say that she hoped they weren't being too hard on the poor girl. She could not be too specific because their prized school code meant that Sandra was not supposed to have told her about the canings. But she did say that she hoped Mr Newberry would remember that Sandra was not used to the cane.

In his rather superior manner Mr Newberry merely observed that if Sandra was to have the privilege of becoming a member of a noted public school she must certainly accept the rules and regulations as she found them.

Louise felt like pointing out that Sandra had been caned by four masters on her bare bottom and as far as she knew no boy was caned in that manner; but to say that would certainly lay Sandra open to the charge of talking out of school. So she confined herself to saying that could he please remember that Sandra was a girl, and a sensitive one.

'Of course,' said Mr Newberry. 'But anyway I can now tell you that I have good news to report. By her excellent deportment Sandra has been able to win over those more reluctant members of my staff. They are now quite happy to accept her.'

Happy to put the cane across her bottom, Louise Bracknell thought bleakly.

'Yes, our policy of introducing her individually has been a great success, Miss Bracknell. And with this success we can now look forward to taking more of your girls next year. Two girls I should think.'

Louise said, 'Yes Mr Newberry, of course.'

'Two like Sandra would I think do very nicely. Good brains of course, and well-mannered girls. And also... well, attractive. Yes, attractive young ladies.'

With nice attractive caneable bottoms, thought Louise Bracknell. But what she said was, 'Yes, I'm sure we will find two suitable ones. And naturally it will be a big honour for them.'

So Sandra Clayton duly started at Southwood College. It certainly seemed an excellent school, thought her mother. During the first week Sandra was kept behind four afternoons out of the five, for half an hour or so, for extra tuition from one master or another.