Philippa Courtenay, who preferred to be known as Pippa, was the eighteen year old daughter of Robert Courtenay, the headmaster of Radley Court Preparatory School. She was studying History at college, but stayed at the school during her holidays. Since colleges are more generous with their vacations than prep schools Pippa was often at the school during term time.
Pippa was a good looking girl with a soft, delicate prettiness. She had light brown hair tied back in a neat pony-tail and blue eyes that often sparkled with mischief. Many girls of her age would have found life at as boys’ prep school quite boring, but Pippa was prepared to find enjoyment in anything at all.
She knew that the eldest boys, thirteen and fourteen year olds, were quite old enough to find her attractive and she deliberately teased them by smiling seductively at them or wiggling her pretty bottom in their direction. Once or twice she had even favoured some senior boys with a kiss – ‘a proper kiss with the tongue and everything’ – but she would not have dreamed of going any further.
Although the boys found her irresistibly attractive – she had no competition after all except for the middle-aged teacher Mrs Mills and her own mother – they knew she was just teasing them and was not to be trusted.
Once a boy called Robert Barker had been caught with her out of bounds – she had asked him out for a walk saying she would give him a kiss. When they had been caught Pippa said that she had only just met him. Gallantly Barker didn’t deny it and said that he’d broken bounds by himself to go to the shops. He received six of the best from Mr Courtenay’s cane and was no longer so attracted to Pippa.
This incident revived some speculation amongst the boys. Why had Pippa lied if not to avoid punishment herself? Would Mr Courtenay have caned her as well if he’d known the truth?
There was a tradition, passed down from one year to the next, that Pippa was caned by her father in her bedroom. But although they would have liked to believe it, it seemed unlikely to the boys in the senior dormitory. Pippa’s room was immediately above theirs and none of them had ever heard her being caned.
The truth of the matter was as follows. Pippa had never been caned but up until she had been twelve or thirteen she had been slippered by her father when she’d been particularly naughty. Five or six years is a long time in prep school life, the most senior boys had just been completely new then, and the story of her slipperings had been corrupted by transmission into canings.
One evening Pippa, dressed provocatively in a figure-hugging T-shirt and tight faded-denim jeans, came into the senior dorm as the boys were washing and getting ready for bed. One of the boys, Barry Cronin, had visited Mr Courtenay’s study earlier that day and as he lowered his shorts some boys gathered to inspect the marks left by the headmaster’s cane. Pippa joined the group and drew a deep breath.
“Gosh! Did my dad do that? I bet it hurts! Come on, I’ll give you a kiss if you’ll let me feel the marks!”
As she made these remarks some of the boys noticed her father standing in the doorway. Pippa hadn’t noticed him however and she was dumbfounded to hear him say, in a voice the boys recognised as ominous, “Philippa. You shouldn’t be in here. Don’t answer now. Just go and wait for me in your bedroom. I shall be up to see you in a moment.”
She left and Mr Courtenay proceeded to lecture the members of the dorm for making too much noise. He threatened to bring his cane up straight away if there was a further outbreak. Then he stormed out.
In her bedroom Pippa was wondering what was going to happen. She felt that the best that she could expect would be another taste of the slipper she’d thought she’d grown too old for five years earlier. But it could be even worse – he might cane her! “Surely he can’t,” she thought, “I’m a grown woman.” But she didn’t think, somehow, that he was going to let her off with just a slippering.
When her father entered her bedroom her worst fears were exceeded. He was carrying not one cane but two! One was the ordinary cane, about two feet six long, which Cronin had felt earlier that day, and the other was a good six inches longer and slightly thicker. It was a senior school cane retained by Mr Courtenay from his days as a public school housemaster.
“Right, my girl! Let’s get this over!” said Mr Courtenay. “We both know what you’ve done. Perhaps I haven’t been strict enough with you in the past, but I won’t make that mistake again! Take those jeans down!”
Pippa did not dare to argue with her father in this mood. With trembling fingers she unzipped the jeans and eased them off over her shapely thighs. She slipped off her shoes and removed her jeans, folding them neatly and placing them on her bed.
Mr Courtenay told her to take the books off the bedside table and to move it into the centre of the room. The frightened girl did so, embarrassed at the fact that all she was wearing below her waist was her white cotton panties. When the table was placed to her father’s satisfaction, giving him room for and unrestricted swing of the cane, he told her to bend over and grasp its top. He made her move her legs slightly until he felt that her pantie-clad bottom was perfectly placed.
Then he said “First I’m going to give you exactly what I gave Cronin. Six of the best. I intend it to hurt but I do not advise you to make a fuss unless you want those boys to hear. Their dormitory is directly below this room.” With that he drew back the cane to begin the punishment. Pippa’s whole body tensed as she waited for the first stroke.
The well-used cane bit its way deeply into the tender flesh of its first-ever female victim, across the narrow V of the girl’s panties. Pippa inhaled urgently. It was bad, but it might have been worse.
She rode the second stroke quite well, choking back a cry and wriggling her backside. But she still had four of the best to come and she knew that on this occasion her father would deliver only the very best.
Somewhat surprised at how well his daughter was coping with the early part of her punishment, Mr Courtenay applied even more force to his third stroke.
“Oh . . . ow . . . oh!” cried Pippa. She raised first one foot and then the other. It seemed as if white hot flames were searing her entire bottom.
The fourth cut brought forth a resounding screech and a furious writhing of the teenager’s haunches. That vicious stroke sent vibrations to every nerve and fibre of her body. She had tried very hard not to cry but now the floodgates burst and her slender body heaved with sobs. She was on the point of leaping up and clutching her rear, but a stern rebuke and the threat of additional strokes made her slump back over the table.
Pippa flexed her bottom-muscles, anticipating the next slash of pain. It wasn’t her bottom that got it, however. The cane dug deeply into the firm flesh at the top of her thighs.
The girl’s agony was acute. Despite her firm intentions she screamed and stamped her bare feet hard on the floor.
Only one stroke of the six remained. The angry father was determined it would be a good one. The cane scythed through the air.
SWISH! . . . WHACKK!!!
“Oh . . . ooh . . . ah . . . oo . . . agh!” cried out Pippa, her body jerking upright. She must have leaped a foot in the air before her feet landed back on the floor. Her hands stuck to her wealed bottom as though they had been magnetised.
Mr Courtenay grasped his sobbing daughter by her shoulders and addressed her: “Well, you wanted to know what Cronin’s marks felt like. Now you know – from the inside! Now I propose to deal with you for you disgraceful and indecent behaviour.” And he put down the smaller cane and picked up the longer.
Pippa tried to protest that she had already been punished, but her father insisted that he had not started yet. He told her that she had wanted to know what Cronin had got and now she did know, but she had not yet been punished for her own misbehaviour. He told her to take off her panties.
The chastened girl obeyed, but very slowly as if hoping every moment for a reprieve. Her buttocks were now fully revealed, the pale flesh bruising and clearly marked with raised crimson welts. With a dismal sigh she draped herself over the table again.
Mr Courtenay had intended to give his naughty daughter another six with the senior cane, but seeing her state he decided that a lesser punishment should be enough to make his point. “Right, Philippa. Two strokes,” he said.
The headmaster was not so used to using the longer cane and he found it difficult to aim accurately. Nevertheless the first stroke dug into one of her earlier weals. Pippa yelped like a scalded cat and her feet danced up and down on the floor. She lifted her head and it thrashed to and fro in line with her tortured bottom.
Her father did not give her any time to recover before he delivered the final stroke. It crashed into her anguished bottom and she nearly went berserk. Then he back arched and she squealed softly for a long few seconds. Mr Courtenay told her she could get up.
He delivered a few well-chosen words and then left his daughter alone to her pain and her shame.
Downstairs in the senior dormitory much of the canings had been audible. There was now no doubt that Pippa did get the cane! The boys did not dare to talk much with Mr Courtenay in his present mood, but several of them masturbated while thinking of what had happened to the pretty teenager.
Next morning all eyes were on Pippa during Assembly. She wore a long, loose skirt and it was noted that she stood stiffly throughout, even while everyone else was sitting.
By hopeful sissy.