Breaking in a Head Girl

From Uniform Girls 51

Eric Crossley Hanfield glanced round his study and sniffed the smell of fresh furniture polish. The school had been empty during the summer recess but that was now almost over and the cleaners had been in and it seemed done a good job. Yes just a week to the start of the new autumn term and there was inevitably a lot to be done, much of it routine and boring — but not all.

This morning for instance he had the most stimulating task of caning a girl.

Eric Hanfield walked over to look out of the mullioned window. St Margaret’s Private School for Girls was situated on the edge of the town in an acre of mature ornamental trees and shrubs, many of which across the immaculate lawn were now resplendent in their autumn reds and golds. The school had been owned and founded by Eric’s father, Dr James Crossley Hanfield, who had bought the property and named his school for his mother, adding the “Saint” with his tongue in his cheek.

Dr James Hanfield was now retired leaving Eric as sole owner and headmaster. Wishing to be his own man he had made some changes, especially where it was necessary to conform with modern ideas and practice, but one tradition of his father’s which he had certainly not wished to change had been the old man’s custom of caning his Head Girl.

Each year as a new Head Girl had been appointed he had caned her. A private but ceremonious caning before the start of school. It was to impress on the new incumbent the responsibility and discipline required of this most honoured school appointment, Dr Hanfield had informed Eric when he had joined the staff as a new graduate from Oxford. But Eric had always taken this with a pinch of salt as the girls selected to be Head of School were always good-looking and shapely 17- or 18-year-olds. There was no doubt in his mind that his father had taken great pleasure in requiring them to take their knickers down and offer their bare bottoms for the cane. Especially as he came to realise that the ceremonious caning at the start of school was not the only caning the Head Girl received. The practice it seemed was usually repeated, again in private, throughout the year, for whatever excuses Eric’s father could find.

When the canings had started of course, back in the ‘30s, caning of schoolgirls was reasonably common practice and did not raise an eyebrow. Now in the 1980s public acceptance was somewhat different, but the custom had nonetheless continued.

The reason for this was that the girl’s parents were informed and their permission obtained. Dr Hanfield had from the beginning robustly informed the prospective Head Girl’s parents of his intentions, and stated that if there was a problem in Clare or Elizabeth or whoever being caned then the school’s most prestigious honour would be given to a girl whose parents had more understanding of discipline at an elite girls school. He had never had any problems in those earlier perhaps more sensible days. But perhaps more surprisingly Eric, seeking to follow his father in this enlightened and most satisfying of traditions, had had no problems either.

No, although he was always a little hesitant in the initial broaching of the matter as he was in some ways a shy man, Eric had experienced no problems. Usually a cosy cup of tea with the girl’s parents at her home and then, in as natural a voice as he could muster, introducing the subject. Trying not to sound either embarrassed or of course excited. Nice and calm. Suave. Grave. Headmasterly in fact. Well he had done it for some years now so he had had some practise. It was always a bit nerve-racking, but it always in the event went alright. For one thing of course he would have got to know girls’ parents by the time they were in the Sixth Form and so could gauge likely reactions. Yet in the event it was always alright. The parents once they realised what was being said were usually more embarrassed than he was. The mother frequently blushing. That was always nice, especially with a good-looking mother. With the thought in her head of course that she instead of her daughter could be getting it. Taking down her own knickers for his cane.

Pamela’s mother had blushed. Sylvia Maidment and mother of 17-year-old Pamela. Who was to be this year’s Head Girl and so, later this morning, in about half-an-hour now, would be the recipient of that office’s ceremonious induction. Pamela’s rather ripe bottom…

Yes, Sylvia Maidment had blushed, and her husband Charles had pursed his lips as he took in this no doubt somewhat shocking information. It had been one afternoon after school towards the end of last term, when the new girl had to be chosen. Yes a shock coming right after the other surprise, though of course a much more pleasant one, as he announced that he thought Pamela would be ideal as next year’s Head Girl. Sylvia Maidment had blushed and nervously shifted her rather attractive legs. She was a very good-looking woman, a brunette like the delectable Pamela.

He had seen Sylvia Maidment again this summer, at the vicarage fete and, catching her alone had, with his eyes smiling, put the question: ‘Were you by any chance caned as a girl, Mrs Maidment?’ He had been rewarded with another blush as she vigorously shook her head. And he had said, ‘Well…’ And the thought had been there: well, it’s never too late…

But it was of course daughter Pam who was the focus of his attention. Delectable Pam who would shortly be appearing up the school driveway in full school uniform.

Full uniform was generally not required for girls once they were in the Sixth Form, except on special occasions. But what could be more special than this? And so it would be the navy sweater over the pale blue blouse and the pleated grey skirt. Blue-striped St Margaret’s tie and the matching band round the flat-brimmed straw hat, which the older girls generally hated to wear. Plus little-girl white knee-socks worn with black strap-over shoes which they certainly hated. Yes, delicious Pam would be wearing all that. And under it… plain neat white knickers tightly hugging the full cheeks of her bottom. Plain neat white knickers which of course would have to come down.

Eric moved away from the window. He had a definite tightness in the front of his smart trousers. Yes, he had an erection.

----//----

‘Mother, I think I’m going to be sick!’ wailed Pam Maidment. ‘I just can’t go through with this.’

‘Don’t be a silly. Of course you can. Just keep telling yourself it’s only a school tradition and of course no one else is going to know about it. And remember it does mean you are Head Girl. Now come on, you don’t want to be late.’

Mother and daughter were up in Pam’s room where she was forcing herself to get ready for this awful ordeal. Standing in front of her full-length mirror now in the uniform which she and her friends had thankfully abandoned a year ago when they entered the Sixth Form. Pam had grown a bit since then, her boobs especially were bigger and the blouse was very tight over them. Also under the grey skirt her hips and bottom were fuller. Her bottom… No, she couldn’t do this!

‘Come on Pam! If you’re late — well, he might just do it harder!’

Pam turned with a desperate moan from the mirror. Behind her Sylvia flipped up her daughter’s skirt to check her knickers. Mr Hanfield had stressed full uniform which included regulation knickers and he wouldn’t want to find she had thoughtlessly put on something perhaps more racy: those sexy black ones or the see-through pink. But it was alright, Pam had put a pair of the required white ones on.

‘I’ll go and start the car,’ she said. ‘Come right down. You mustn’t be late.’

Sylvia herself was feeling agitated. Anxious for poor Pam but also excited. There was the thought of getting it herself. If for instance Pam really was sick and had to cry off. And she would have to go and tell him. And perhaps say: well if you like you can do it to me instead? And Mr Hanfield with that eager look in his eyes would say, ‘Yes alright Mrs Maidment. Or shall we say Sylvia? Take your knickers down then. And lift your skirt up round your waist and bend over my desk.’

It was such a scary but exciting thought. Perhaps she should say to Pam, ‘Look if you really are feeling ill you’d better not go. I’ll go and explain to him.’

In the garage Sylvia couldn’t help giving her pussy a brief rub. She was feeling hot and twitchy down there. In spite of the fact that two hours earlier she and husband Charles had had intercourse. They almost never did it in the mornings with Charles having to get up and go to the office, but this morning he had definitely wanted it and she had been more than willing to accommodate him. The truth was they were both affected by what was going to happen this morning.

Charles, on top of Sylvia, had said jerkily in her ear, ‘I suppose that dirty bugger’s going to feel her up? When he’s got her bottom bare. Sort of extra perks…

She had told Charles not to be so awful. But would Mr Hanfield do that sort of thing? His hand accidentally on purpose feeling Pam’s pussy… Surely not. But men could be awful and no doubt Mr Hanfield was going to enjoy this caning, tradition or not.

Sylvia started up the Mercedes. She thought briefly of Mr Sinley, Adrian Sinley who a few months earlier had moved into the house next door. Sylvia rather thought Mr Sinley, who was fiftyish, fancied her. Not that she would have any interest in that direction of course. But if she happened to see him in the garden after taking Pam to school… well she just might invite him in for a cup of coffee.

----//----

I am going to be sick, Pam told herself. Walking now up the familiar gravelled driveway with the high leafy shrubs on either side. Her mother had dropped her and had driven off so it was just Pam and Mr Hanfield. He would be in there waiting.

Maybe watching for her from his study window. Maybe… flexing his cane.

She had spoken to Amanda Morling who had been Head Girl last year. After Mr Hanfield came round to her house with the news. Before that of course Pam had had no idea that Amanda had been caned. Perhaps it would have been better if she hadn’t spoken to Amanda, because she had told Pam just what she didn’t want to hear:

‘Does it hurt? Oh Pam, it feels like it’s cut you in two! You think you’ll never be able to sit down ever again!’

Had Amanda been laying it on a bit thick? With her bottom flinching in the regulation school knickers, Pam knew she was about to find out.

----//----

‘Ah there you are, Pam dear! Come in! Mmm… I had almost forgotten how fetching you look in the school uniform. Sometimes I think it’s a mistake to let Sixth Formers wear their own things. I mean the uniform is most becoming isn’t it? Anyway congratulations, Head Girl!’

Mr Hanfield was leading her on as he spoke, across the hallway to his study. And there on his wide polished desk was the cane! The sight of it really did make Pam feel sick. He was going to cane her here. Bending over that desk.

‘So, our little ritual, eh? Take your hat off. And the sweater. I don’t suppose you’re really looking forward to this.’

Pulling off the navy sweater Pam woefully shook her head. ‘N… No… oo… No I’m not sir.’

‘It’s natural. No one likes the cane, not on the bare bottom especially. And most girls don’t like the fact of taking their knickers down either. But it is our tradition. And also I think it rather cements the close relationship I like to have with my Head Girl.’

Pam had the sweater off now and was standing unhappily with her hands at her sides. Conscious of her quite big tits in the tight blue blouse. Mr Hanfield’s eyes were on them too.

‘I see you’ve grown a bit since you wore this in the Fifth. Mmm? Yes quite a big girl now…’

Pam gave an involuntary little yelp. The Head’s hands had come up and he was lightly holding them. Gently squeezing her tits through the thin blouse.

‘Don’t be nervous my dear. As I said I like to have a close relationship with my Head Girl.’

He let go and stood back. ‘And now before I actually cane you, which I’ll do out on the stairway as I usually do, there is a preliminary little ritual. I’d like you to take your knickers down for me. And lift your skirt up round your waist.’

Mr Hanfield’s words rolled around in Pam’s head.

‘Come on. It’s a little test of discipline in a way. And also part of the getting-to-know process. That close relationship I was talking about. Working together. Being on intimate terms. And when you’re on intimate terms — well, a girl doesn’t mind showing what she’s got. So come on, young lady.’

With her face bright red, Pam made herself do it. Made her hands go up under her skirt. Her fingers in the waistband of her knickers. To slide them down.

‘Right down. To your knees. Then the skirt right up.’

Somehow Pam did it. To stand in front of the Head showing her pussy. The quite thick tuft of dark brown curling hair. Her knees felt as if they were going to collapse at any moment.

Mr Hanfield was looking. Keen eyes focused right there of course. Her pale, softly swelling bare thighs. Her nude rounded belly. With the hair-covered bulge of her pussy right at the centre. He was looking. Gazing intently. And then stepping forward. With his hand.

She shuddered. As his hand cupped her. Cupped round that warm, hair-covered bulge.

----//----

Mr Hanfield did the caning out on the wide oak stairway, as he had said he would. He said he always caned Head Girls there, it was the tradition and Dr Hanfield the founder had done it there too. At the first bend of the stairs. Pam had to kneel on one broad oak tread with her hands on the next one.

‘Just try to relax. And keep still. I know it’s going to hurt but it’s easier for me if you can keep your bottom nice and still.’

As Mr Hanfield spoke he was folding Pam’s skirt up over her back. And then tugging her knickers down. He had let her pull them back up after that business in his study. That awful, awful ordeal. Standing with her skirt up and her knickers down… and Mr Hanfield’s hand fondling her pussy. As he asked softly: ‘Are you doing it yet Pam? Sex. Sexual intercourse. I like to know, with my Head Girl.’

His hand cupping her bulge. And his fingers then sliding in between her thighs. One finger easing in between the moist lips.

She couldn’t think to deny it and, forcing herself to stand still, her answer came stammering out: yes, she had… Just started… Mr Hanfield wanted to know who, and so Pam had to tell him that too. Robert Enwin… Robert of course had been Pam’s regular boyfriend for over a year now.

Yes that particular dreadful ordeal was at least now over. An ordeal no one had told her about. Because presumably it was something no one ever mentioned. Something Mr Hanfield just did when he had you in for the caning because he wanted to, and not bothering with any excuse that it was a tradition or anything. But now there was the ordeal Pam had been expecting. The cane. On her nude nates.

Mr Hanfield had her knickers down now. And his hand was on the bare warm flesh. Caressing. It briefly slid in between her legs, then came away.

‘Are you ready Pam? Try to keep your bottom relaxed. Don’t clench the cheeks.’

The space of a second or two… and then it hit her. Squarely across those ripely quivering nates. Pam let out a desperate yell. The pain was all she had been fearing — and more! It was like being cut in two, like Amanda Morling had said. Her shocked bottom-cheeks writhed and clenched in an attempt to cope with that fierce sting.

‘Don’t clench!’ Mr Hanfield’s quite curt voice. ‘Keep it loose.’

Pam let out another shriek as the second stroke whipped in, almost on top of the now reddening line of the first. She couldn’t take this! No more!!

The third cut into her and she jerked involuntarily forward, her body collapsing against the polished stair treads. Mr Hanfield’s hand hauled her back into position. He bent over her, the cane transferred for the moment to his left hand.

‘Finding it difficult, are you dear? It’s meant to hurt of course…’ His hand was fondling the glowing heat of Pam’s stricken bottom. ‘We could take a little break if that would help.’ The hand had slid down between Pam’s slack thighs. She gave a whimper as it cupped her pussy.

‘I’ll give you one more… and then you can take a little break… Before I continue…’

Mr Hanfield’s fingers were in her. One finger stroking Pam’s clitoris. As the awful pain continued to throb in her bottom.

‘Does this make it feel a bit better?’ he softly asked.

Mr Hanfield gave her one more of those dreadful strokes. His hand coming away from Pam’s pussy as he told her to try to keep still this time and then the cane whipping in. After that he said she could have five minutes break. She was to sit on the stairs with her knickers still down and her skirt up. Mr Hanfield said she would get some relief from the pain with her bare bottom in direct contact with the wooden stairs. He was going to his study to look at some papers for a few minutes, and then he would resume the caning. The caning wasn’t finished.

----//----

‘OK Pam? Ready to resume?’

Pam shook her head. there were tears in her eyes now, because she hadn’t been able to prevent herself weeping as she sat there with her bare bottom on the cool polished stairs. That fondling of her pussy had got her into an even more emotional state of course. Mr Hanfield shouldn’t have done that, he wasn’t allowed to do it, even if he could cane her because her parents had given permission. She should have told him to stop.

She thought of Amanda. Mr Hanfield doing it to Amanda. Probably he had… and would she have told him to stop? Probably not. Amanda was quite a sexy-looking girl, with sometimes a flirty way with men teachers. And then Pam had a further thought. Of Amanda telling Mr Hanfield she didn’t mind him doing that — playing with her — if he would not give her any more of the cane. Amanda saying that and even saying Mr Hanfield could do something else… if it was instead of the cane.

That thought was still in Pam’s head when Mr Hanfield came back out of his study. Carrying the cane in his left hand.

‘OK? Are you ready for some more then Pam?’

Getting to her feet Pam shook her head, blinking because her eyes were still wet. No, she definitely wasn’t ready for more.

‘Oh I’m sure you are,’ Mr Hanfield said. ‘Lift the skirt again. Up round your waist…’

Biting her lip, Pam did it. Mr Hanfield’s hand came out, to take hold of her pussy. Fondling it…

----//----

‘Well, young lady, it’s all over then,’ Pam’s dad said. ‘And probably it wasn’t that bad after all.’

‘It was!’ Pam blurted. ‘it was just… devastating.’

Charles Maidment was just home from the office and had come up to Pam who was in her room. Sylvia was downstairs preparing the evening meal. He hadn’t been able to get the thought of it out of his head all day. The thought of what Eric Hanfield was doing to his daughter. Caning her. And anything else?

He slid his hand round his daughter’s waist, then slipped it down to lightly cup her bottom. Pam winced, squirming away. ‘It’s still really sore.’

Charles couldn’t resist it. ‘Let me see. Let’s see the damage.’

Pam tried to refuse but her father insisted, sitting down on her bed and pulling her down over his lap. She had changed from her uniform into a summer dress but because her bottom was still sore hadn’t put any knickers on. She struggled to hold the blue dress down but her father got it up — and there was Pam’s squirming bare bottom. The stripes from the cane had darkened but were plainly visible. Mr Hanfield had, it seemed, hit her five time across the full meat of the cheeks.

Charles made sympathetic noises. Well it must have been painful receiving that lot. His fingers touched the warm flesh. Then he pushed her further over. Pam was still protesting at being over her father’s lap and having him see her bare bottom. She was squirming about and as her thighs parted Charles was presented with a full view of Pam’s cunt. He felt a guilty surge of excitement. No doubt Hanfield had made sure he got a good look at it too. But was that all?

He let go of Pam and she struggled to her feet, red-faced and grabbing her skirt down. He questioned her further. At first she said no, Mr Hanfield had done nothing except cane her. But then as he pressed her she admitted the Head had fondled her cunt, and quite extensively it seemed. But she insisted that was all, he had done nothing else.

Had Mr Hanfield done anything else? No doubt Charles would have pressed his daughter further had he known the sequence of the caning. Pam had received four before the break — but the five stripes on her bottom indicated she had been given only five in total. So after that break there had been only one more. Why was that? One would have expected the Head to give her several in the second period, three or more. So why only one? Unless Pam had agreed to something else. Agreed perhaps to let Mr Hanfield fuck her instead of any more caning? Because maybe that was what he really meant with his talk of a close relationship. He meant he wanted to fuck Pam.

And maybe there would be no more caning in her year as Head Girl. Or at least only the very minimum. Instead there would be this close relationship that the head had stressed he wanted. Regular fucking.

Pam certainly wasn’t saying. Not to her father or mother. Not to her boyfriend Robert either who, as Pam had admitted to the Head, she had started fucking though it had only been recently and she didn’t let him do it very often. Robert didn’t even know about the caning. The fact that Mr Hanfield caned his Head Girls. But then most people didn’t know that either, it was something everyone was happy to keep quiet about.