Finishing School - Episode 06

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In which Diana pleasures the major and the headmistress.
3.9k words
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Part 6 of the 7 part series

Updated 07/12/2023
Created 12/27/2012
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It's been over a decade since I've contributed a story here! This story is part of a series, but you can enjoy it without having read the others.

Mrs Castlewick sighed, removed her glasses and rubbed her temples. While she enjoyed her position as owner and headmistress of Mrs Castlewick's School for Young Ladies, and felt that she was providing a valuable service to society, it was a lot of work keeping the whole place running while also instructing her charges in the finer points of being a woman. At 45, she was starting to feel as though perhaps an extra pair of hands around the place would allow her to keep on top of the priorities. Such as preparing young English ladies for their lives to come by instructing them in ALL the necessities for gaining and keeping a husband.

As the early evening light began to fade, she rang for a servant to come and light the lamps. A moment later there was a respectful knock at the door. On her command to "Enter", a chambermaid opened the door and bobbed a quick curtsey.

"Ah, Sarah, please be so good as to light the lamps," Mrs Castlewick commanded.

"Yes, ma'am. Also Mrs Wettcat asked me to let you know that Major Harpole has just arrived."

"Splendid, thank you Sarah. Once you've lit the lamps please have the major taken to the Burma room. When he's settled in, bring him along to the drawing room. You might also see to it that a fire is lit there."

"Yes, ma'am," Sarah replied and set about lighting the kerosene lamps that were set about the study.

Once the servant had left, Mrs Castlewick settled back behind her desk to finish reviewing the accounts. She permitted herself a slight smile at the memory of the major. A friend of her late husband, he had remained in contact with her throughout the years since she was widowed. In fact, he had become something of a benefactor to the school, making occasional contributions to the running of the establishment. In recognition of his generosity, Major Harpole enjoyed certain privileges when he chanced to visit.

In due course Mrs Castlewick closed the books and proceeded down the corridor to the drawing room. On entering she was pleased to see the lamps lit and the fire flickering in the hearth. She was even more pleased to see the major standing at the large bay windows taking in the last of the view in the fading daylight. He turned as he heard the door open.

'My dear major, it's simply wonderful to see you again," Mrs Castlewick gushed as she gave him a peck on each of his whiskery cheeks.

'Mrs Castlewick, it's always a pleasure! It is jolly good of you to put me up for the night. The thought of spending time in one of those wretched roadside inns was simply too much."

"But of course, major. You know you are always welcome at our humble school. How has your journey been?"

"Well after two weeks at sea I must say I'm jolly pleased to be back on dry land! It might be alright for those naval types, but an army man's place is firmly on dry land in my opinion. As for the journey from Portsmouth, well the less the said the better!"

"I shall do my best to ensure you have at least one night of ease and comfort, sir," Mrs Castlewisk replied. "May I offer you some refreshment? Tea? Or perhaps something stronger?"

The major's genial, open face broke into a wide grin at the suggestion. Although his full beard and muttonchop whiskers were beginning to go grey in places, his face was only lightly lined and such lines as there were were more of laughter than of sorrow. No mean feat for a professional soldier.

"Why Mrs Castlewick that's most generous of you. I shouldn't mind a whiskey if you have any."

As the headmistress moved to the drinks cabinet and removed the stopper from a cut glass decanter the major added, "It was a devilish long time we were at sea, or at least it felt that way to this landlubber. The captain was awful strict about there being no women on board on account of them bringing bad luck. And so a chap had no real chance to satisfy his manly urges, if you take my meaning. And with the prospect of a sojourn at your fine school I simply couldn't bring myself to go with one of the tuppenny ladies at the docks. And so one was wondering if..."

"Say no more, major. As you know, our girls are expected to avail themselves of every opportunity to practice the skills that they learn here. We have just completed a week's study on the act of intercourse and there are a few students who would benefit from extra tuition. Let me see. I think Miss Appleshaw will be to your liking - a sweet young lady though somewhat lacking in confidence. And her friend Miss Mapleton. The two usually come as a pair. Miss Mapleton is one of our more... enthusiastic students and I'm sure she wouldn't disappoint."

"That sounds capital!" the Major exclaimed. "Jolly good of you, ma'am. One feels simply beastly when one has so much pent up... well, you know. And if I can further the education of one or two fine young ladies at the same time, why then everyone wins dontcha know!"

When Sarah re-entered the room in response to Mrs Castlewick's ringing of the bell she was instructed to fetch Miss Appleshaw and Miss Mapleton to the drawing room.She was to convey to the students that their attendance was required forthwith. If not sooner.

The major and the headmistress had been making small-talk over the chances of the new steam locomotives reaching the county when the door opened and the young ladies in question bustled into the room. They each gave a brief curtsey to Mrs Castlewick and then looked wide-eyed at the major.

Diana Mapleton was the taller of the two, and at 20 the older by two years. A generous bosom swelled over the top of her tightly laced bodice and her skirt was daringly cut to just above the ankle. Her dark hair fell in langorously curling ringlets to a little past her shoulders. Her friend, Fanny Appleshaw, was somewhat less endowed in the cleavage department, but had the straight blonde hair that many gentlemen preferred. Today it was pulled back in a tight bun. The usually creamy pale skin of both girls was flushed a delicate pink, suggesting that they had taken the urgency of their summons seriously. It never paid to keep Mrs Castlewick waiting.

"Major," said Mrs Castlewick. "May I present Miss Diana Mapleton and Miss Fanny Appleshaw. Girls, may I present Major Harpole of Her Majesty's 15th Light Horsemen."

As the girls bobbed again, this time to their visitor, the major strode towards them with hand outstretched. "Delighted to meet you, Miss Mapleton. Miss Appleshaw," he boomed shaking them forcefully by the hand. "I must say, Mrs Castlewick, every time I visit you your students are ever more pretty than before and these fine young ladies are no exception!"

The girls blushed deeply at the compliment as Mrs Castlewisk addressed them. "Girls, the major here is an old friend of mine and a generous patron of our school. Now, as you know, students here are expected to take every opportunity to practice and refine the skills that you learn. Major Harpole has generously offered to assist you in revising what you have learned so far. Good students though you both are, I think few would disagree when I say that you both have areas on which you could work."

The young ladies were certainly well aware of the expectations and rarely shirked them. Diana in particular actively sought out opportunities. Just this morning she had spent an educational half an hour with Johnson the gardener. She was the first to speak.

"Why thank you, Major! That's extremely generous of you. And thank you, Mrs Castlewick, for thinking of us. We'd both be very grateful for the opportunity to show you just how much we've learnt in the last three weeks and of course any pointers that may help us improve would be most welcome. Don't you agree, Fanny?"

"Yes of course," her companion said in a softer voice than Diana's. Casting a sideways glance at her friend, Fanny had to confess to herself that while she enjoyed the school's activities, the chance to see her friend in intimate positions was its own reward. Many was the time after lights out in their dormitory that she replayed in her mind images of Diana in the throes of passion. She felt a heat rising between her legs at the very thought.

"Capital, capital!" exclaimed the major. That's the spirit, what? Does my heart good to see young ladies so passionate about their education."

Diana stepped up to the major. "Now, sir," she said speaking more quietly and making her voice a little husky. "May I perform an inspection? I have heard that military men are expected to stand to attention on a moment's notice. Shall we see if that's true?"

She kept her eyes fixed on the major's as she fumbled with the buttons of his trousers. As she did so, Mrs Castlewick settled into an armchair and said "Major if you don't mind I shall remain in the room. It is always instructive to see first hand how one's students are getting on."

"Of course not, my dear," replied her guest. "And pray don't be afraid to offer pointers or whatnot as you feel necessary. These girls are here to learn, after all."

The headmistress perched herself on a wingback chair and watched as Diana finished undoing the major's flies and reached into his trousers. She brought forth an average sized member that was indeed standing fully to attention. She dropped her gaze and admired the way the head already glistened, a bead of moisture just visible in the lamplight. Beginning to stroke with her right hand, with her left Diana unclasped the suspenders allowing the trousers to fall to the floor.

Returning her gaze to the major she cooed, "Mrs Castlewick has taught us that the preliminaries are as important as the main event. I believe this is called 'wanking'." Diana's hand kept a slow, steady rhythm. When she reached the bulbous end, she rolled her palm over it, luxuriating in the slick feel as the pre-cum lubricated her skin.

"Am I doing it right?"

"Ye.. yes. Oh dear lord. Oh yes, my dear. You're doing it very well. Very well indeed, if I may say. Ohhhh....."

"Oh, I am pleased," Diana purred. "But we mustn't forget Fanny. Fanny dearest do come here and kneel down next to me." Diana dropped to her knees.

In a rustle of skirts, Fanny did the same. She might not have the same animal enthusiasm for her studies as her friend, but she was a conscientious student and genuinely enjoyed giving and receiving pleasure, so it was no great hardship for her to join Diana in front of the major's erect cock.

"Shuffle a little forward, won't you, and open wide," Diana instructed. Fanny did as she was asked and Diana guided the major's dick into her companion's mouth. Fanny brought her lips together and used her tongue to caress the end as Diana gently wanked Major Harpole into the warm wetness. Remembering her lessons, Fanny allowed saliva to build up in her mouth and then parted her lips slightly to let the spit flow down the shaft and run over Diana's hand.

"Well done, Miss Appleshaw," said Mrs Castlewick approvingly. "It's little touches like that that gentlemen really do appreciate. Isn't that right, major?"

"I should say! Jolly arousing when - ohhh - a lady gets all messy. No good being all prim and - uhhhh - proper with a todger in one's mouth, eh? And Miss Mapleton you have excellent - mmmm - technique if I may say. I don't suppose I could - yessss - prevail upon you to increase the tempo somewhat?"

Diana gave him a wicked grin. The smell of sex, the warmth of the room, the prospect of more debauchery to come was beginning to induce the almost narcotic effect she experienced from carnal acts. "You'd like me to wank faster, major? Is that right? You'd like me to wank you faster and faster and faster into Fanny's hot, wet mouth." As she spoke, Diana increased her tempo until she was pumping the major vigorously. Fanny struggled to keep her head still as the major's cock was thrust in and out of her mouth.

"How's that, major my dear?" Diana's voice was low and raspy. "I can see you're enjoying it, aren't you, you randy devil? You like having a young lady wanking you into her friend's mouth, don't you? Are you going to shoot your spunk into her? Is Fanny going to have a nice big load to swallow? You'd like that wouldn't you, Fanny dearest?"

Fanny grunted her assent. Her chin was slick with her spit, as was Diana's hand and the major's cock. The major too had been reduced to grunts, which soon became gasps of pleasure and then in an unexpectedly high-pitched gasp, "Oh my dear, don't stop, don't stop, don't stop..."

As Major Harpole reached the edge of his climax Diana grabbed the back of Fanny's head and pulled her forward, releasing her grip on the major so that the whole of his cock was forced into Fanny's mouth. As Fanny sucked as hard as she could while trying not to gag, the major thrust his hips violently into her face. "I say, I'm coming. Oh my god, I'm coming. Yes, yes, yerrsss, ohhhhhhhhh".

His semen gushed to the back of Fanny's throat causing her to gag and pull back. Diana released her grip so that the major's cock emerged from Fanny's mouth just in time to spray her face with a generous gob of cum. Fanny reached for the major's organ and pumped another splodge onto her chin. The cum trickled down and on to her cleavage. She slumped back on the floor. Diana slumped next to her, running a finger down her cheek and licking the creamy, salty deposit.

"Oh, Fanny. Wasn't that wonderful? Wasn't that just... Oh, I'm lost for words. And you were so good, dearest! Taking his manhood like a trooper."

"I must say, I do think I could get a taste for this. Having semen - I mean, cum - on one's face is quite a thrilling thing. And we do make such a good team, don't we, Diana?"

Diana didn't reply, lost in her reverie, until Mrs Castlewick spoke.

"Well, major, I trust that was to your satisfaction?"

"Simply capital, first rate!" the major replied, having recovered some of his composure.

"Wonderful! And I must say girls, that really WAS a fine display of the art of cock sucking. Such a good display, in fact, that I find myself quite aroused and in need of a little relief myself."

For the first time, the girls noticed that Mrs Castlewick's skirts were hitched up above her knees with her legs spread as wide as the arms of the chair would allow. Her plain beige knickers were stained by a large wet patch, just visible in the warm light of the lamps.

"Miss Appleshaw, I should think you may need a little time to recover from your exertions. So Miss Mapleton please open the drawer on that sideboard over there and bring me the object you find inside."

Diana did as she was asked, walking past the major who had settled himself into an armchair with his trousers still around his ankles. Opening the drawer, she found a white cylinder about 8 inches long that looked remarkably like...

"Yes, it looks like a penis doesn't it?" Mrs Castlewick said. "And not just any penis. It is said to have been modeled on one of England's greatest heroes, none other than Lord Nelson himself! It's made from the finest ivory. I've nicknamed it 'The Admiral'. Now stop gawping at it, girl, and come over here."

As Diana approached the headmistress, Mrs Castlewick leant forward and said "First, be so good as to loosen the ties on my bodice. Ah, thank you. That's much better." As the garment was loosened, Mrs Castlewick pulled the front of the bodice down and slid her breasts free of the clothing. "It's rather warm in here, don't you think? Allowing one's body to breathe in these conditions is so much more comfortable. May I suggest you do the same, Miss Mapleton? I think if you were to remove all but your undergarments you would find the room rather less close."

Diana hesitated. Although she had just forced a stranger's cock into the mouth of her friend and licked his cum off her fingers, disrobing in front of the headmistress felt like crossing a line. But her hesitation lasted only a moment. She understood her duty, and if she were to get a favourable reference from the school then she must respect Mrs Castlewick's authority. She had to call Fanny over to help with some of the stays and ties, but shortly Diana stood in front of the school's owner in her bottle green knickers and her camisole. Despite the warmth, Diana could feel her erect nipples pressing into the fabric of the camisole.

Mrs Castlewick cast an appraising gaze over her student. Generous breasts that only slightly diminished when released from the confines of the bodice. Fairly flat stomach. Hips that swelled enticingly and a derriere that could best be described as voluptuous. And yes, Mrs Castlewick could see, Diana was also in a state of some arousal. Her knickers were a darker green where they stretched across the mound of her pussy.

Diana too was sizing up the woman in front of her. Her teacher's breasts were, she thought, frankly enormous with large aureolas and prominent nipples. Her thighs were dimpled here and there, and curls of dark hair escaped at the edges of her knickers.

Neither of them would describe themselves as lesbians, but Mrs Castlewick did enjoy a little variety on the odd occasion when she did engage her carnal desires. And Diana was simply keen to try any and all new experiences connected to the sexual world.

Mrs Castlewick began to massage her left breast, squeezing and rolling the nipple between her fingers. "Come closer, Miss Mapleton, and kneel down between my legs. That's right. Now pull my knickers to one side. Yes, good. Do you feel how wet they are? That is a testament to your performance, dear. As you were the instigator of that fine display I think it is only right that you assist me in joining the major in having an orgasm. Do you like my hairy bush? I dare say it's a good deal hairier than yours, is it not? I understand it is the fashion amongst the younger set to trim yourselves closely down there. I frankly can never be bothered, not at my age. Show me yours, Miss Mapleton."

Still holding the ivory dildo in one hand, Diana stood up and pulled her knickers aside. As the headmistress had expected, Diana had a simple strip of hair perhaps two inches wide.

"Thank you. As I thought. I don't see the attraction myself, but I suppose each generation has its own foibles.Now please get back on your knees. You still have The Admiral? Good. Press the tip against my pussy and rub gently back and forth. All the way up until you touch my clitoris. Then back down. Then up. Then down. Oh yes. That's the way. It feels so slick. You didn't even need to spit on it, I'm so wet it just slides up and down so easily. Good. Good."

As Mrs Castlewick moaned softly in pleasure, Diana noticed the musky sweet smell of her pussy. The warmth of the room seemed to amplify the scent. She began to feel light-headed. She shifted her weight slightly on her knees as the headmistress spoke again.

"Good girl. Very good girl. You may pause for a moment and remove your camisole. I do enjoy seeing a young pair of breasts. I think when we study titty fucking next week I may call on you for the class demonstration. I think your breasts would look very fine with a cock pistoning between them. Would you like that, Miss Mapleton? Would you like to have one of the stable boys titty fucking you? Yes, you would. Now take The Admiral and put it in me. One strong thrust. Oh YES. Like that. Perfect. Now fuck me with it, girl. Slowly at first. That's it. Ohhhh. Devine."

Doing as she was told, Diana slowly slid the dildo until the hand holding it nudged against Mrs Castlewick's pussy. Then she withdrew it until just the tip nestled at the entrance to the hot wet tunnel. Repeating the motion again and again, Diana noticed that the headmistress was kneading her breast with greater and greater force, pinching the nipple so hard Diana thought surely it must hurt.

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