ASSTR 46 Boy Pranked Girl Spanked

A Sally Trubshawe Henderson in Retirement Story 

In the year 2000, after more than 30 years as a teacher at St. Ursula’s Ladies Academy in the southern counties of England, I retired. By then my husband Dave and myself were comfortably off. Dave had a fairly generous pension as a retired police officer and, in addition, both of us had separately inherited valuable properties and assets. As the third millennium dawned we were living in a large farmhouse that had been bequeathed to us by Dave’s uncle Tom, who had recently died a bachelor.
The farmhouse came with a sizeable holding of agricultural land, and Dave busied himself in the management of the estate and of our tenant farmers. As for me, I, among other activities, worked in the garden, taught for the local branch of the University of the Third Age, and supported our four children, who by then were in the later stages of education and the early stages of acquiring partners and offspring.

On a fine May morning in 2001 I was sitting in our conservatory. I had just finished breakfast and was checking emails on my laptop. When I opened one of them this is what I read.

“Dear Mrs. Trubshawe Henderson,

Greetings!

Do you, I wonder, remember me? In the 1990s, when you were the headmistress of St. Ursula’s, you hired me as a part time supply teacher, and for several years I did my best, with some success, to improve the girls’ GCSE and A Level grades in mathematics and physics. Also, do you recall Jennifer Harland? She studied double maths and physics A levels with us and we managed to get her into Cambridge. Well late last year I met Jenny again at a Physics Society conference and we got on so well that we are now dating regularly and have decided to get married. However, before we tie the knot there is something that we would like to discuss with you. If you are prepared to meet with us please reply to this email.

Yours with all best wishes, and with many happy memories,

Jake Westland.”

Well yes! I remembered Jake all right. He came to us with a first class honours degree from Oxford and he worked tirelessly on our behalf. His effect on the Sixth Form A level science grades was dramatic. I also remembered Jenny. She was very bright, very lively, and very likeable, but sometimes rather flippant and offhand, until, that is, Jake took her under his wing. I always thought that she was sweet on him, and now I wondered whether their rendezvous at the conference was purely coincidental, or whether the scheming young minx had fitted Jake up.

But, of course, there was only one reply that could be made to Jake’s email. I wrote back straight away that he and Jenny would be most welcome to come and see me at the farmhouse, and on the following Saturday they both arrived for lunch.

The meal went very well. Dave was on top form with his anecdotes of life as a policeman and a magistrate, and Jenny, although now into her late twenties, seemed just as vivacious, playful and kittenish as when she was a schoolgirl.

I realised, however, that the two lovebirds had something to say to me, so after lunch Dave, at a signal from me, made himself scarce and Jake and Jenny followed me into the room that I used as my study.

“OK Jake. What is this all about then?”

At which there was an embarrassed silence.


“Come on. Whatever it is it cannot be that bad.”

“No, it’s not that it’s bad,” replied Jake. “It’s just that it’s embarrassing.”

“OK. Take your time. We have all afternoon, and into the evening if you like.”

“Mrs. Henderson, do you remember the summer term of 1993?”

“Vividly. That was just before you went up to Cambridge wasn’t it, Jenny?”

“Yes, that’s right.”

“Well,” continued Jake,” It was the last Friday of term and I was down to take the sixth form science girls for their last ever physics lesson.”

“Hang on, Jake,” I interposed. “It all comes flooding back to me. Your entry into the classroom didn’t quite go to plan, did it?”

“No. Someone, with a thin rope, had attached a plastic bucket to a ceiling rafter, and then balanced the bucket on top of the door, which they had left ajar. It was all done with great skill and with a very shrewd insight into the principles of physics, because when I opened the door to enter the classroom the bucket was dislodged. It upended itself and poured over me the best part of a gallon of whitewash.”

“That’s right. The girls all knew who had done it, of course, but I must say that I admired the way that they steadfastly refused to grass up the culprit. In the end, as the Headmistress and Dean of Discipline, I had no option but to drop the matter. Light hearted pranks are understandable at the end of the school year, and I did not want to come down heavy on anyone. But whoever the joker was, I thought that she had somewhat overstepped the mark with that particular jape.” 

“Mrs. Henderson, it was me who did it,” said Jenny.

“I don’t find that surprising, Jenny. In fact, I suspected as much at the time. But there was very little that I could have done anyway. Sixth form girls were exempt from the slipper. I suppose I could have banned you from attendance at the next Speech Day, but, hey, you were our star pupil, the winner of both the Maths and the Physics prizes. The school would have been cutting off its nose to spite its face. And in any case, I myself was secretly amused at the prank. It was quite brilliantly executed. Jenny, consider yourself forgiven—by me, at any rate; but how do you see it, Jake? What an amused onlooker smiles at may not seem as funny to the victim.”

“Oh, Jake’s a good sport,” cut in Jenny. “He is quite prepared to forgive and forget. But there is something that I have found out about him. He is a secret spankophile. He has admitted to me that he used to get sexual stimulation from the disciplinary regime at St. Ursula’s, especially from the way you used to slipper all of those big, nubile, sexy fifth formers. And he was really miffed, and he still harbours a resentment, over his whitewashing. I think that, if you could see your way to giving me the spanking that I so richly deserve, it would provide closure for both of us and strengthen our relationship. I don’t want to become Jake’s wife until this matter has been resolved.”

“I see. What do you think, Jake?”

“Well Jenny is right about the resentment that I felt at the time. I was livid. I suspected that she was the culprit, and I would cheerfully have tossed her across my knee and spanked her hard. But that was not on the cards and, well, it was all a long time ago now so perhaps it is time to forgive and forget.”

“I tell you what. I need to think about this. Jake, could you leave us girls to ourselves? I would like to discuss things privately with your fiancée?”

“Oh! OK. Of course.”

Upon which I shouted to my husband and, when he appeared, asked him to entertain Jake in the garden. Soon the menfolk were sitting in the sunshine drinking cold beers and talking about football (or soccer as you Americans call it) and other masculine topics.

“Come on, Jenny, what is all this about? For me this incident is closed, and Jake shows no great desire to pursue it. What is going on in that devious little mind of yours?”

Well at first Jenny was very embarrassed and I could get nothing out of her; but I patiently plied her with questions and slowly the narrative became clearer. Jenny told me that Jake was, indeed, turned on by spanking, and she had hopes that if he witnessed her getting her bottom smacked it might turn him on to her. Jake, she added, was a dear man but he was an only child and he had attended an all male academy throughout his secondary education. He was very shy, gauche and awkward with ladies, even with her.

“Do you know, Mrs. Henderson, that Jake has never seen me naked, and he has never viewed my bare bottom? Which is, I think, a pity, because in my view it is very shapely. He kisses and cuddles me of course, but so far that is all. He says he loves me but he has never taken me to bed. It is driving me to distraction and I think that it is about time to make him an offer that he cannot refuse.”

Well, Jenny and I discussed these matters in depth and for a long time, and we developed some plans and strategies; after which I called Jake back into my study.

“What are you two folks doing next weekend?”

“Nothing much, are we Jenny?”

“Well come back here next Friday and stay for the weekend. I think that this issue might take two or three days to sort itself out.”
Over the next few days I talked things through with my husband, Dave, and acquainted him with the plans and strategies that I had agreed with Jenny. I explained that I owed Jake. What he had done for me and for St. Ursula’s was worth many times the value of the paltry salary we had paid him. Indeed, Jake was a major reason that, when I left my job, my reputation was high and the school was at the top of its game. The academic successes that we had achieved as the result of his efforts had left me and the school deeply in his debt. I considered it my duty, I told Dave, to help Jake in any way that I could.

“Well you seem to have worked out how you are going to play this.”

“Yes.”

“And you are going to smack young Jenny’s bottom?”

“Yes.”

“Wow! That I would like to see!”

“No way, you dirty old man. You will have to make do with the usual report from me after it is all over.”

“Oh, OK. That’s not too bad. You do have quite a racy and vivid descriptive style.”
On the following Friday Jake and Jenny arrived at around 11 a.m. and the four of us shared an early lunch. Then Dave made himself scarce and I conducted Jake and Jenny into my study.

“Now look,” I explained to them, “This is not about me. It is about you two. My perception, Jake, is that you still harbour a resentment against Jenny for drenching you with whitewash all those years ago. As for you, Jenny, as I read it you feel guilty about your schoolgirl peccadillo, and you would feel better if you received a schoolgirl’s chastisement to atone for it.”

These observations of mine were met with silence, so I continued.

“Jenny, I am going to chastise you for your prank. I sentence you to 12 of the best with the slipper. Is that OK?”

At this Jake nodded his agreement and Jenny answered contritely, “Yes Mrs. Henderson.”

“But first, we have some other business. Jake, what do you know about Sir Thomas More and his book Utopia?”

“Not very much, I am afraid, Mrs. Henderson. I am a scientist not an Arts graduate.”

“Well it was Sir Thomas’s view that before a young man married a young lady he should know what he was getting; in other words, he should see her naked. Well, I agree with him. Jenny, please strip off and display yourself to Jake in your birthday suit.”

Well Jenny and I had agreed this in our girl-to-girl chat the previous Friday. She was expecting the instruction, and she responded to it sensually and provocatively with a slow, titillating striptease. Wow, Jenny had clearly been practising this bit and she put on a really professional show for us, at the end of which she stood before her lover completely nude.

Well, understandably and as I had anticipated, the effect of all this on Jake was dramatic. He was mesmerised and stunned by his beloved’s beauty and he ogled her obsessively.

“Come on, Jenny,” I urged. “Don’t stand there like a statue. Continue to display yourself to your fiancée. Throw a few pirouettes. Strike a few poses. Show Jake exactly what he will be getting if he marries you, and exactly what he will be missing if he doesn’t. This is a good marketing opportunity. Make him an offer that he cannot refuse.”

Which, to great effect, Jenny proceeded to do. Oh, wow! She is a stunningly beautiful girl. In ancient Greek mythology the sun god Helios pursued the nymph Daphne; but if Jenny, on that day, had been in the nymph’s grove he would have been sorely tempted to abandon his chase and try to rape her instead. As Jenny stood there on that bright summer’s day, with the sun shining through the windows of my study and the sunlight cascading over her body, she was sumptuous, she was gorgeous, she was irresistible to any lusty, healthy male. I gazed at Jake’s crotch and I observed with satisfaction that his excited cock stood thick and engorged under his thin, tight-fitting trousers. Oh, the potency, the hegemonic force, of a beautiful naked lady, celebrated by artists and poets down the generations and as powerful now as it ever was!

Well, that was my main mission accomplished and I suppose that I could have left it there and abandoned proceedings. But hey! That could never be! As I have explained elsewhere I love spanking and I have a long standing commitment to Dave not to let slip any opportunity to slap young ladies on their bare bottoms. Dave was expecting a full report of that and I was resolved to give him satisfaction.

“OK, Jenny,” I remarked after a few minutes. “That ‘s enough posturing for the time being. In 1993 you were a very naughty girl and now I am going to spank you for it. Stand on the red mat in front of my desk, please. Good, now face the desk and touch your toes keeping your legs straight.”

Then I turned my attention to Jenny’s fiancée. “Jake, please take a look at the whiteboard on the wall behind you..”

On this were three coloured-in circles one above the other. The top circle was red, the middle circle pink and the bottom circle white.

“Note also the pointing stick, similar to a conductor’s baton, on the ledge beneath the white board. Please pick it up. Now, I am going to slap Jenny’s bottom. After each slap, if you want the next slap to be harder point at the red circle with the baton. if you want the next slap to be similar point to the pink circle. If you want the next slap to be less hard point to the white circle. Is that clear?”

“Yes, ma’am.”

“Jenny, you are to count out the slaps, ‘One. Thank you headmistress. May I have another slap, please? Two. Thank you headmistress,’ and so on. Is that clear?”
“Yes, headmistress.”

“The whiteboard, has been deliberately placed behind you so that you cannot see it, or which circle Jake is pointing at. Jake’s pointings, I may add, are merely advisory and I may, or I may not, take his advice. So you will never know, unless he chooses to tell you, whether your spanking was what he wanted me to give you, or what I myself decided you should get. Is that clear?”

“Yes, headmistress.”

“Very well. Let us proceed.”

The first part of my old familiar ritual was the slapping into position. I gave the 
undercarriage of Jenny’s rump a sharp flick with the slipper.
“Come on, girl. You know the drill. Legs straight, fingers on toes.”

Slap! I gave Jenny’s succulent and meaty undercarriage another admonitory flick with the pump.

“No. Not good enough! Push those fingers to your toes.”

Slap! I administered another wicked little flick to exactly the same target: the plump, nubile pussy meat to the rear of Jenny’s perineum.

“Now you are failing to hold your legs sufficiently straight. Come on, girl! Shape up! This can go on all afternoon if you want it to.”

And so on, until Jenny was, in my arbitrary opinion, making a sufficiently serious attempt to bend over as instructed.

“Right. Let the chastisement commence.”

Slap!

“Agh! Aw! Aw! Aw!”

Then, after a few seconds, “One. Thank you headmistress. May I have another slap, please?”

Jenny let out a satisfyingly loud yell as the flat sole of my thin, floppy gym slipper struck the meaty undercarriage of her bum with a sharp, high pitched crack. I aimed a slightly upward blow that hit home just above the thighs across the back of the perineum. I struck hard and, as Jenny later confirmed, the sting was sharp, and the escalating tingling excruciating. Jenny’s shapely, callipygian buttocks wobbled and shuddered alluringly and her pubic hairs were scattered every which way. As the slipper rebounded from the buttock meat it revealed a white imprint that, over the next four seconds or so, blushed to a fetching shade of pink. I waited for this to happen, for the keen initial sting of the pump to be supplemented by that infuriating tingling which is one of the hallmarks of a good, old fashioned slippering. Then, just as the tingling reached its apogee, I delivered the second slap to exactly the same piece of buttock meat, across the back of the area between the bum hole and the cunt.

Crack!!

This second slap was just as sharp and just as wicked as slap number one and the sting, incrementally added to the stinging and tingling from the first slap, elicited from its recipient a loud and lusty yell, followed by a series of involuntary howls.

“Aaagh!! Aw!! Aw!! Aw!!”

This time it took the best part of thirty seconds or more for Jenny to regain sufficient composure to make the required response: “Two. Thank you headmistress. May I have another slap, please?”

I then looked at Jake to see how he was taking all of this. As he later confirmed to me, he was absorbed and fascinated by his fiancée's predicament, and his sexual stimulation was intense. But he was also horrified at how hard I was smacking her. He was pointing vigorously at the white circle on the whiteboard and indicating that he wanted me to abate the ferocity of my onslaught. But no. For the moment that was not to be. By now my hackles were raised. I recalled my initial annoyance at Jenny’s prank way back in 1993, and my frustration at my inability, at that time, to chastise the perpetrator. “Right, madam,” I thought. “The long arm of justice has caught up with you at last. Take that!”

And I inflicted a third slap that was just as hard as slaps one and two, and that landed onto exactly the same piece of arse.

“Aaagh!!! Aw!!! Aw!!! Aw!!!”

I was not timing it, but it seemed to me to be at least a minute before Jenny composed herself sufficiently to be able to enunciate her stipulated response: “Three. Thank you headmistress. May I have another slap, please?”

Thereafter, for the next six slaps, I acceded to Jake’s wishes. I abandoned for the time being my assault on the sexy undercarriage of Jenny’s bottom. I delivered my slaps higher up, trying, as far as possible, to turn the rest of the bum a tasteful and even shade of red. I slapped pretty hard, and certainly hard enough for the smacks to be disciplinary rather than playful. But, to an extent, I abated the venom of my initial assault.

However, it is one of my principles when smacking bottoms that the final smacks should be the hardest of all. I like to build up my spankings to an escalating crescendo, a rousing and memorable finale. I like to make the victim’s rump ring like a bell. I like to give her a little something to remember me by. I like to make her feel sorry for herself. And I like to impress on her the need to improve her future behaviour. “Oh, wow!” I like her to think as she takes her fingers from her toes, rises up straight, and vigorously rubs her stinging and tingling bottom. “I don’t ever want to take another spanking like that! From now on I will be a good girl!” 

So for the final three slaps I returned to the epicentre of my initial assault, the sexy, meaty undercarriage of Jenny’s bum, the sweet spot just above her thighs. And I made sure that slaps ten, eleven and twelve were just slightly harder than slaps one, two and three.

Crack!!!

“Aiee!!! Oh!!! Oh!!! Oh!!!”

It was a long time before the victim recovered from that one. By now she was a very chastened young lady and her tone was contrite, as if pleading for remission: “Ten. Thank you headmistress. May I have another slap, please?” 

But, of course, remission there was none. The art of administering an effective spanking, as I have intimated above, is to make it a lot sharper than, in the victim’s opinion, it ought to be. As I have written before, it is like with parking and motoring fines. To be effective these have to be much more punitive than the malefactor thinks reasonable. They have to elicit outraged cries at their swingeing severity. They have to make the victims cry “Unjust!” “Unfair!” and feel very, very sorry for themselves. They have to shock the miscreants into submission and jolt them into obedience to the law. “What! Outrageous! Sixty pounds for two minutes on a double yellow line!” “Yes, sucker! And pay it quickly or we’ll double it! That will teach you not to do it again!”
 
Well, in my view, the same is true of spankings. A disciplinary spanking with a flat, light, floppy gym pump is not as serious as a caning. The stinging and tingling are soon over, and they are ended even quicker if you are allowed to rub your bum. But, while it lasts, the stinging and tingling must be excruciating, and the person who administers the slaps should make sure that it is. It was in this frame of mind that I girded up my loins to deliver the two remaining spanks.

Crack!!!

“Aiee!!! Oh!!! Oh!!! Oh!!!”

By now Jenny was in some distress. I was amused at her sexy and stimulating plight but she most certainly did not see the funny side. It was a very contrite and submissive young lady who, after a considerable pause and in a very small voice, mumbled: “Eleven. Thank you headmistress. May I have another slap, please?”
 
Oh, yes, Jenny! You certainly can! And I proceeded to administer a real beauty slightly harder than any of my other spanks, that slapped loud against nubile, naked buttock meat like a report made by rifle fire.

Crack!!!

“Aiee!!! Oh!!! Oh!!! Oh!!! Ouch!!”

This time the delayed, contrite, mumbled response incorporated a plea: “Twelve. Thank you headmistress. Please don’t slap me again!”
 
What we have here, I thought to myself, is a young lady who is very, very sorry for herself. And I smirked with complacent satisfaction at the effectiveness of my disciplinary exploit.

”Now Jenny, listen carefully. I want you to put your hands on your head and stand up straight. Now, stand in the corner of the room with your face to the wall. You will remain there for ten minutes. Jake, could you come here and sit by me. For ten minutes I would like you to study your fiancée's bottom. Then I would like you to decide whether she has now atoned for the wrong that she did to you, or whether you would like me to administer further discipline.”

Well, ten minutes is a long time to stare at a young lady’s bare bum, but for all of that time Jake seemed entranced. He gazed hard and obsessively at his beloved’s red, well smacked derrière, appalled and stunned at what I had done to her, but also fascinated and aroused. Indeed, I was gratified to see that his sexual stimulation was still sharp, that his cock still stood stiff and excited, and that its tumescence was still clearly visible beneath his thin, tight fitting trousers.

“Now, Jake,” I told him when his ten minutes of ogling was up. “Please go to your lady. Jenny, please take your hands off your head and turn to face Jake. Now, Jake. Give your verdict. Has Jenny atoned for your whitewashing, or do I spank her again tomorrow?”

Well Jake was clearly stimulated by my final suggestion and he paused briefly to consider it. The his face broke into a broad grin.

“No, Mrs. Henderson. Jenny is forgiven.”

There followed an embarrassing silence.

“Well, young man. Don’t just stand there. Kiss her! Now, take her by the hand and follow me.”

And I led Jake and his completely nude fiancée out of my study, down the corridor, and into the guest bedroom.

“Now. I want you two to be very nice to each other, and I want you, Jenny, to be especially nice to Jake and to give him full satisfaction and redress for the wrong that you inflicted on him in 1993.”

That evening Jenny told me that Jake was a virgin when he went into that bedroom, but that he most definitely was not a virgin when he came out. She told me later that it took some time to train her lover in the arts of love, but that by the time of their marriage he was giving her complete satisfaction on that score.
It was a year later when Jenny gave birth to her first baby, a little girl. They baptised her Sarah (which is my baptismal name); like me, she is addressed as Sally, and I am her godmother.