I felt that my recent retirement as Headmaster at a very exclusive girls’ boarding school was unlikely to be as quiet and restful as I had hoped if it was to be overshadowed by the horrors of war, of which I had had the most terrible personal experience in the Flanders trenches. My lapse into a disturbed rêverie was mercifully interrupted by the sound of the bell which hung by my front door.
When I opened the door I was surprised to see one of my former pupils, Emma Barton, whom I recognized instantly despite the passing of what must have been ten years since she left to go up to Girton College, Cambridge.
Emma had been a lovely girl and was now a beautiful woman, still slim and with the long, light brown hair which had so often brushed the floor in my study as she went over my lap for a spanking, or touched her toes for the cane. But despite her tendency to get into scrapes far too often, she had been an outstanding pupil and a credit to the school.
“Emma,” I said, “What a pleasant surprise! Do come in. Let me take your coat.”
As I took her coat she put a linen shopping bag down on the floor by the front door. I was surprised to see that she was wearing her old school skirt and blouse.
“Would you like some tea, or perhaps something a little stronger?” I asked.
“Thank you, Sir,” she replied, “that would be very nice. Could I perhaps have a dry sherry?”
“Of course,” I said, and poured her a glass from the decanter on the sideboard together with another for myself.
“Now sit down and make yourself comfortable, and tell me why you’ve paid me this unexpected but most welcome visit.”
Her hand trembled slightly as she took the glass from me, and she seemed a little nervous.
“Well, Sir,” she said, “I’ve been wanting, in fact needing, to see you for such a long time – it’s about the punishments you used to give me when I was at school.”
“Emma,” I said, “I’m sorry if you felt that they were unjustified or too severe, but that’s how I chose to run the school, and I think the results spoke for themselves.”
“Oh no, Sir,” she said quite forcefully, “on the contrary they were very well deserved and rightly severe – it’s just that…”
She hesitated for a moment and then went on in a rush with her eyes downcast, “…they gave me the most enormous pleasure. I’ve never been able to forget them, they’re always in my mind. Since I left school I have persuaded some of my boyfriends to spank me, but it just hasn’t worked in the same way that it did when you spanked me. And the canings were just sublime. I’ve been agonizing over this, but I just felt that I had to come and see you and ask you to punish me again just as you used to. I just need so much to have you spank me and cane me on my bare bottom again. I can’t explain, it’s just a need I have which must be satisfied. I’ve got to the stage where I can’t sleep at night just thinking about it.”
She stopped and looked up at me with the light, bright green eyes which I remembered so well.
“I’m so sorry, Sir, I hope I haven’t shocked or upset you, I just needed to tell you about it. I’ll quite understand if you think what I’m asking you to do is inappropriate.”
The pleading look which she gave me melted my heart.
I am quite a well-read man, and was familiar with the work of Freud and Kraft-Ebbing. In fact I had had reasons to seek out their work, because my own reactions to spanking and caning the bare bottoms of my pupils had included intense sexual arousal. The arousal was caused not only by seeing their delectable bare bottoms, their anuses and their labia, but by the act of inflicting pain by reddening those same bottoms with my hand and raising red welts on them with one of my large selection of canes.
It was of some comfort to me to learn that I was not alone in experiencing this arousal. I knew, of course, that I had to keep my arousal concealed from the girls– the professional consequences of not doing so would have been disastrous (although they may, of course, have felt my erect penis against their hip when they were being spanked). But I must admit that the temptation to reveal the other aspects of my arousal was little short of overwhelming when punishing girls like Emma: her pleasure in the punishment was impossible for her to conceal as she squirmed herself into my groin while being spanked, and while being caned made sounds which were as close to pleasure as to pain. And her bottom: as she stood upright before bending over for her punishment it clung like a white peach, rounded to perfection, on her slim frame; the cleft was long and deep; the sulci at the bottom of each cheek were deliciously defined, and then disappeared as she went across my knees for a spanking or touched her toes for a caning.
After a long pause I replied, “Emma, if it’s so important to you then I’m happy to help.”
I got up and went into the dining room, returning with one of the armless chairs from the dining table. I sat down on it and beckoned her to me.
“Get over my lap, Emma.”
She complied, and I lifted the short, pleated school skirt to reveal the delicious bottom I remembered so well, though the passage of time had made it a little plumper than it had been ten years ago. I took down her knickers and stroked her bare bottom, which was a little softer than when I had last spanked her.
“Right, Emma,” I said, “tell me what you want.”
“Please, Sir, I want you to give me a good, hard spanking on my bare bottom.”
“Very well.”
I began to spank her hard and slowly, eliciting a squeal every time my hand landed on one of her sweet cheeks. Each spank resulted in the familiar flattening and then wobbling of each cheek in turn, giving me fleeting, tantalising glimpses of her tight, puckered little anus. The first few spanks each left the red outline of my palm, fingers and thumb clearly imprinted on each cheek, and then as the spanking continued the whole of her bottom turned bright crimson. She wriggled and squirmed in my lap, hardening the erection which had begun as soon as I had inserted my fingers into the waistband of her knickers and pulled them to her knees. After a hundred spanks I stopped.
“How was that, Emma?” I asked.
“It was wonderful, Sir,” she replied, “just as I remembered, except even better. Please give me another spanking, a harder one.”
I gave her another hundred spanks, even harder, and after that my palm felt hot and blistered. But as for her bottom: it was deep, deep crimson and blazing hot to the touch. I rubbed it for her, gently kneading each cheek in turn, and as I did so her squirming in my lap continued ever more strongly. My erection was now rock hard.
“Right, Emma,” I said, “I think it’s time for you to be caned. Get up please, and take your knickers right off.”
She got up and stepped out of her knickers, rubbing and squeezing her bottom continuously.
“In the cupboard under the stairs, Emma, you will find two canes both of which I think you will remember well.”
When I retired I had taken my two favourite canes with me: one a thickish kooboo which I used when caning sixth-formers for less serious offences, the other a slender yet incredibly dense and flexible dragon which I used for more serious offences. Emma returned carrying both canes.
“Sir,” she said, “what about the pre-caning examination which Matron used to give me?”
“What pre-caning examination?” I asked.
“Well, Sir, she said it was something you required her to do. She used to put on a rubber glove and then smear some stuff on her finger and in the hole in my bottom and then stick her finger right up my bottom and sort of wiggle it about. She said it was to make sure that we were fit to be caned.”
Well, this was news to me, and revealed a side of Matron which I had always suspected, but of which I had never had proof until now. What possible reason could there be for a rectal examination before a girl was caned? Absolutely none. It was certainly standard practice for a girl to visit Matron before a caning to make sure that she was fit enough to be caned, but as for the more intimate procedure which Emma had described, well that was news to me.
“Actually I got to quite like it, Sir,” she said. “Would you do it for me?”
“Well, I would if I could, Emma,” I replied, “but I’m afraid I have neither the ‘stuff’ you refer to nor a rubber glove.”
“I thought that might be the case, Sir,” she said, “so I’ve brought both of them with me.”
With that she put down the two canes, picked up the bag she had brought with her and produced from it a tube of something called K-Y Jelly and a surgical rubber glove.
“Very well, Emma,” I said, “give them to me and get over my lap again.”
She handed me the tube and the glove and got over my lap. I put on the glove and smeared some of the contents of the tube onto the middle finger of my right hand.
“Pull the cheeks of your bottom apart please, Emma.”
She reached back with her right hand and did so, pulling her right cheek to the side to reveal her anus and perineum. I put my middle finger a little way into her bottom to partially lubricate her anus, and then put another large blob of the jelly onto my finger and gently inserted it fully into her bottom. She groaned with pleasure as I moved my finger gently to and fro. She alternately gripped and then released the base of my finger with her tight little anus as I carefully explored and stroked her anal canal and her rectum. After a minute or so I withdrew my finger.
“Right, Emma, get up please.”
She got up slowly, and then looked into my eyes again - hers were shining and she was smiling with an expression of the most intense pleasure. I took off the glove and put it in the rubbish bin in my kitchen. I left the tube of jelly where I had put it, on a little side table next to the sofa.
“Will you cane me now please, Sir?” she asked.
“With the greatest of pleasure, Emma,” I replied. "How many strokes would you like with each of those canes?”
She picked them up and smiled.
“Can I have six of the best with each, please, Sir?” she said.
“You may, Emma,” I replied. “Give me both canes, please, and then bend over and touch your toes in the centre of the room.”
She handed me the canes, smiled again, and then bent over and touched her toes as instructed. I put the canes down and then lifted her skirt and draped it over her back. I picked up the standard sixth form kooboo, stood to her left and then placed it on her bottom exactly parallel to both cheeks with the tip about two inches to the right of the centre of her right cheek. I then stepped half a pace to my left so that the cane was at a slight diagonal.
I had learned from many years’ experience that if you cane a girl with the cane parallel to her cheeks and the tip in the centre of the right cheek (as so many caners do), then the tip bites viciously into the right cheek when it lands: the speed of the tip is greater than that of the rest of the cane because of the flex in it. This can, after many canings from a right-handed caner like myself, cause what I call “weak spots” in the girl’s right cheek, which tend to bleed all too readily. For a left-handed caner it was, of course, the left cheek which was at risk. My technique avoids this problem because on impact with the girl’s bottom the tip wraps round slightly to the right of the centre of the right cheek, with its speed slowed by the prior impact of the rest of the cane.
“You remember what to do and what not to do, don’t you, Emma?”
“Yes, Sir. I have to count each stroke and thank you for it. And I mustn’t stand up or rub my bottom after a stroke. If I do, the stroke will be repeated.”
“Quite right, Emma. Very well, brace yourself, my girl!”
I raised the cane, aimed at the level of her anus and whipped it down, cutting viciously into both cheeks. The familiar white tramlines appeared immediately but briefly before being transformed into a raised, red welt.
“Owwwh … mmm, one, thank you, Sir.”
She clenched and unclenched her buttocks once or twice, then relaxed for the next stroke which I delivered just above the first.
“Owwwh … mmm, two, thank you, Sir.”
I delivered the next three one above the other, regularly spaced, so that after the fifth stroke her bottom, from the anus almost but not quite to the top of the cleft, was covered with a symmetrical pattern of raised, red weals. She was by now sobbing with pain, but at the same time moaning with pleasure. Now for the last stroke with the kooboo. This would be on the sit spot, between the anus and the sulci.
“What do we know about the final stroke of a caning, Emma?” I asked.
“It’s always the hardest, Sir,” she replied.
“Very well, Emma, bend slightly at the knees and stick your bottom right out for me.”
She complied: her cheeks parted a little further and I stroked them softly. Her bottom was quite firm to the touch in this position.
I raised the cane for the sixth stroke and delivered it with a vicious flick of my wrist right on target, just below the first. It bit deep into her bottom, buried into the flesh before bouncing out as her bottom reciprocated with a delicious bounce of its own.
“Owwwh … mmm, six, thank you, Sir.”
“Stand up and give yourself a rub, Emma,” I said and she did so, giving me the most enormous smile.”
“You know, Sir,” she said, “whenever you spanked me I could feel your erection on my left hip, through your trousers ..... and I certainly felt it again today. Is there anything you would like me to do with it? I have an idea.”
With that she knelt down in front of me and gently unbuttoned my fly to reveal my erect penis. She stroked it gently.
“My goodness, Sir,” she said, “that’s a thick one.” She put it into her mouth and sucked on it, moving her head slowly backwards and forwards. After a minute or so I asked her to stop, since I had further plans for my erection which I felt sure she would enjoy. And at my age, the chances of another similar erection within half an hour or so were not good.
“Up you get, Emma, time for your six of the best with the dragon.”
She got up slowly, then bent over and touched her toes again. I picked up the dragon and inspected the proferred bottom. I planned to use the dragon to fill in neatly the spaces between the existing weals, starting with the one between the first and second strokes. I took up my caning position and raised the dragon high.
Thwickkkkk!
“Owwwhowwwh! … mmm, mmm. One, thank you, Sir.”
Perfect. The gap was precisely filled with a new, red weal. I continued with the next four strokes: the weals now covered the whole of her bottom from the level of her anus to just below the top of her cleft. Now for the final stroke, which I planned to place precisely across the site of her sulci.
“Right, stick it out for me, Emma.”
Thwickkkkk!
“Ooowhoowhoowh! Aaaaaah. Mmm…mmm…mmm. Six, thank you, Sir.”
“Up you get, Emma, give yourself a quick rub and then bend over the arm of the sofa.”
She bent over the arm of the sofa and lifted her skirt, presenting her deliciously striped, bare bottom for my inspection. My erection was now amazing.
“What next, Emma?” I asked.
“I want you to fuck me please, Sir,” she said. She pulled the cheeks of her bottom apart. “In my arse, please, Sir.”
I picked up the tube of jelly from the side table, squeezed a large blob onto my finger and fed it gently into her anus which she had relaxed to allow me entry. I followed up with another large blob, and then eased my penis inside her.
She took her right hand away and felt for her clitoris, which she began to massage gently as I slid my penis as far in as I could, and then began to fuck her very slowly. She alternately squeezed and then relaxed her sphincter, and we both began to moan quietly. Then she began to gasp more and more quickly as her climax approached, and we came to orgasm at precisely the same moment. We both groaned in complete ecstasy.
“Gosh, Sir,” she said, “that was the best ever!”
“For me too,” I said, quite truthfully.
She got up and I gave her an enormous hug, gently stroking and squeezing her red hot bottom with my left hand.
“Now, Emma, wait here while I get something from the bathroom for that delicious bottom of yours.”
I came back with a large jar of cold cream.
“Right, Emma, over my lap again, please.”
I sat down on the sofa and she draped herself across my knees. I lifted the short skirt once more and began to gently rub some cream into her bottom.
“Oh, Sir,” she said, “that’s so nice!”
The raised, red welts were, I have to say, quite spectacular and her bottom was still hot to the touch. After a few quiet minutes I stopped, and she got up, found her knickers and eased them up over her bottom. I fetched her coat, helped her on with it and handed her the bag. Then I offered her the tube of jelly.
“Oh no, Sir,” she said, “I don’t think so. Just keep it here for the next time ……”
“All right,” I said, and opened the front door for her.
“By the way, Emma, do you know what ‘figging’ is?”
“No, Sir, I’m afraid I don’t.”
“Well, next time you may find out….Goodbye, Emma, and thank you for a quite exceptional evening.”
“Thank you, Sir,” she said with another enormous smile, “I hope you enjoyed it as much as I did. Goodbye for now, Sir.”
And with that she was gone. Until the next time.
Two weeks after Emma’s first visit I received a very pleasant letter from her, thanking me for giving her the experience which she had been longing for ever since she left school, and asking if she could visit me again in a fortnight. I replied suggesting an evening and a time which would be convenient for me, and shortly after had her confirmation that that date would suit her very well, and that she would arrive promptly at 7:30 pm as suggested. The prospect of her visit quite dispelled the dark cloud of the likely war with Hitler’s Germany which still hung over all of us.
On the morning of the appointed day I went to my local greengrocer where I purchased a hand of ginger, and then to my usual chemist to buy a packet of the London Rubber Company’s Durex condoms. Although I had not needed these on Emma’s first visit, my plans for her second visit made them a prudent purchase. I also bought a tub of Nivea cream.
The doorbell rang at 7:45, and I opened my front door to let Emma in. She apologized profusely for being late, and said that for that she deserved a good, hard spanking on her bare bottom. Taking her coat, underneath which I saw that she was again wearing her old school uniform, I said that I considered that to be an excellent idea, but that perhaps she would care for a sherry first. I invited her to sit on the sofa and poured us both a generous glass of Amontillado.
“Lovely to see you again so soon, Emma,” I said, sitting down beside her.