📚 finishing-school-episode Part 9 of 7
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Finishing School Episode 09

Finishing School Episode 09

by the_inspector_and_the_fish
20 min read
4.6 (8700 views)
adultfiction

Clara Pennywhistle dithered in front of her wardrobe. What should she wear to her meeting with the headmistress? And what could Mrs Castlewick want with her? Although she supposed that since earlier that day she had sucked the stablehand's semen off Mrs Castlewick's breasts, it probably wasn't to discuss her needlework.

In the end she decided on her red silk underwear (a present from her papa after a trip to Italy) with a simple pale green dress over the usual assortment of petticoats and slips. Satisfied, she hurried down to join the girls at supper. Mrs Castlewick had required her presence after the evening meal.

Sitting with the other young women in the dining hall and listening to their excited chatter about the day's lesson, she felt a pang of jealousy. She really did wish that she could enjoy the lessons as much as they seemed to, but the thought of congress with a man was something she just couldn't get excited about. Perhaps Mrs Castlewick would have some answers.

Once supper was over, Clara hurried along the corridor and up a short flight of stairs to the solid wooden door that marked the entrance to the headmistress's drawing room. She was a little nervous - Mrs Castlewick could be an intimidating character, especially with girls with whom she was displeased - and Clara knew that she was not the most diligent student. She drew in a breath and rapped on the door.

"Enter," came a stern voice from within the room, and Clara turned the handle. The hinges creaked as she pushed the door open and stepped into the room. The drawing room was large and well appointed. Heavy curtains covered the windows, and a fire crackled and snapped in the hearth.

"Ah, Miss Pennywhistle. Please sit. I shall just be a moment." Mrs Castlewick was seated in an armchair, working at her needlepoint. Clara sat in a simple chair facing the headmistress and regarded the older woman.

Mrs Castlewick had her greying hair pulled back into her usual rather severe bun. She wore a slightly old-fashioned black dress, but even with its unflattering cut it couldn't hide the size of the breasts that lay beneath it. Clara had a momentary flashback to that morning, when she had licked them clean of Fletcher's man milk. Her heart caught a beat and she felt a small throb between her legs.

"Thank you for your patience, Miss Pennywhistle," said Mrs Castlewick putting her work onto a side table and fixing Clara with an appraising gaze from over the top of her spectacles. "I shall come straight to the point. I have noticed since your arrival that you are less than enthusiastic at your lessons. You seem to take no great pleasure in learning new skills. Your attempts at felatio last week were, I must say, nothing short of woeful. You appear to have no interest in learning the skills that you must know are crucial if you are to acquire a husband of sufficient standing to allow you to live a happy life."

Cara began to speak, but Mrs Castlewick cut her off. "Shush, girl. I know what I have seen. But I have not called you here to chastise you. I aim only to help you. It is not only your reputation as a young woman skilled in all the ways of marital life that is at stake here. It is the reputation of this school as a place where parents can be confident that their daughters will be given the best chance of securing for themselves a life of ease and plenty."

She continued, "Yours is a problem that I have encountered from time to time in the past. All women are capable of enjoying sexual congress, and it is my firm belief that it is our God-given right to partake of all the pleasure that the carnal world has to offer. For many of us, that pleasure is derived through the caresses, the fingers, the tongues and the penises of men. But there are also women whose path to sexual release lies down a different way, and for whom the attractions of their own sex are paramount. You, Miss Pennywhistle, are of that persuasion. A follower of Sappho, a resident of Lesbos, one who drinks from the furry cup."

"I say it is a problem, but do not mistake me. There is no problem in seeking to take your pleasure with another woman. One must be discrete, of course, but as long as you give no cause for scandal you will find an ample array of willing partners. No, the problem comes because this world is unkind to women who do not marry, and marriage is unkind to women who do not satisfy all of their husband's base desires. But to this problem, there is a solution."

Clara squirmed uncomfortably. She had thought that no-one knew, that no-one could tell that in their lessons it was not the sight of the men, with their bare chests and engorged members that caused a warming glow between her legs. It was her fellow students, and yes even her headmistress and instructor, that left her with damp panties at the end of class. But the promise of a solution, of something that could help her be the good young woman she wanted to be, to take some pleasure in the intimate company of a man - that promise tempered her discomfort and she leaned forward to listen attentively.

"The solution is this. We must condition you to associate sexual activity with a man with the same pleasure that you derive from the female form. It is not difficult, in itself, but it does require consistency and repetition. We will begin tonight. Tell me, Miss Pennywhistle, have you ever been intimate with another woman? Have you had another woman's tongue lick delicately at your rosebud? Have you had another woman slide a finger into your love canal? Or done the same to them?"

"No Mrs Castlewick, ma'am. I have not done any of those things, nor had them done to me. Well, except for this morning when you told me to... clean you."

"I see. Well, in addition to addressing your problem I can also instruct you in some techniques that I think may serve you well in any extra-marital dalliances that you may have. But for now, to work. Please disrobe. Turn around and I shall help you with the stays and buttons."

Clara rose from the chair and turned her back as Mrs Castlewick came towards her, her stiff black dress swishing and rustling as she crossed an Oriental rug that covered the parquet flooring. In a moment the fastenings of her dress had been undone and she removed it, laying it over the back of a brocaded armchair. She had removed her shoes and petticoats when Mrs Castlewick commanded her to turn around which she dutifully did, standing before the headmistress in her vibrant red brassiere and underpants. Her breasts amply filled the cups of the brassiere, spilling over the top. The dark flesh of her aureoles was visible above the lace edging. The silk of the panties stretched taughtly over her mound. Stray wisps of dark hair peeked out here and there. Her buttocks and thighs had some substance to them, framed by the black suspenders that held up her stockings. Clara clasped her hands demurely in front of her as Mrs Castlewick inspected her.

"Hmm. Yes, very fine. You certainly have the looks to secure yourself a good match, Miss Pennywhistle. I should say that you are far from a lost cause. Tell me, do you find me attractive?"

Clara blushed hard at this unexpected question. She certainly found the female form, with its curves and softness and its familiarity preferable to the male body with its hardness and angles and covering of hair. And there was something undeniably enticing about the older woman. Her physique was bearing the years well, and she had admired her breasts when they were exposed in the lesson that morning. Her face was handsome, and the grey hairs if anything added to the allure. And sucking and licking Fletcher's sticky load from her chest had very much aroused her.

"Yes ma'am," Clara replied in a quiet voice. "I do find you attractive."

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"Capital. I ask not for my sake of course, but for yours as you shall understand shortly. For now, please unbutton my dress for me."

Mrs Castlewick now turned away from Clara who undid the buttons for her. She watched as the teacher undressed, feeling a flutter in her stomach. She was sure she knew

what

was going to happen, but was not at all sure

how

it would occur. Soon Mrs Castlewick was also standing in her underwear. Her enormous breasts - truly, none of the students at the school were possessed of such huge tits - were barely contained in a plain black brassiere. Her arse was larger than Clara's, and time and gravity had caused a little sag to set in. Plain beige panties topped thighs that were lightly dimpled.

"The trick, Miss Pennywhistle, is to have you associate the experience of being taken by a man with the pleasure you desire to have from having congress with a woman. To that end, we shall be using these." Mrs Castlewick walked to a dresser against the far wall and opened a drawer. She produced a tangle of black leather straps and metal rings, and a long thick object that seemed to bend slightly in her hand. "These articles will allow me to assume the role of the gentleman. All will become clear soon. For the moment, remove your knickers."

Clara had become used to being naked in the presence of others. The lessons at the school required it, and nakedness did not hold the same shame for her that it used to. Even so, there was something more intimate about this occasion, and she blushed once again as she removed the undergarments, exposing a generous thatch of curly dark hair.

"Sit on that chaise, and spread your legs Miss Pennywhistle. You do have a pretty little cunny, don't you? Spread your lips for me. No not your mouth, you silly girl, your nether lips. Very nice. And already a little aroused, if my eyes do not mistake me."

Mrs Castlewick regarded her pupil. She was not a lesbian, not by a long chalk. But what purpose was there in having a position of respect and authority if one did not take its benefits from time to time. Of course she had required Miss Pennywhistle to see her because she was duty bound to see her education to a successful outcome (school fees were not cheap, and parents expected their investment to be repaid by their daughters marrying well). But why should she not make the most of the abundance of firm young flesh that passed through her doors, when the fancy took her. And the way that Clara had cleaned her up after Fletcher sprayed his load on her - that mix of desire and reluctance combined with her warm, nimble tongue - had led her to decide to give a special lesson tonight.

"Slide a finger in there. Good. You have done this to yourself before, have you not?"

Clara nodded, sliding the pointer finger of her right hand slowly in and out. "Yes, ma'am."

"Of course you have. Despite what the ignorant may say, there is no shame in a woman pleasuring herself. In my youth, I would bring myself to climax three or four times a day if there was no man on hand to do it for me. How many fingers do you use?"

"Two mostly, sometimes three."

"Show me."

The headmistress watched as Clara slipped her middle finger in as well and continued to move them in and out. She gazed admiringly at Clara's cleavage, the red lace of her brassiere framing the perfect white globes of her breasts. She would suck on them before the night was out, before the end of Clara's lesson.

"Stop now, and come here." Clara rose from her seat and approached Mrs Castlewick. The older woman took Clara's right hand in hers and brought it to her mouth. Clara gasped as Mrs Castlewick licked the two fingers she had been using to frig herself and then swallowed them into her mouth, sucking greedily on them as she held Clara's hand firmly in place. Clara experienced a sensation she had never felt before, an electric thrill that travelled from her hand to her pussy.

Mrs Castlewick withdrew Clara's fingers from her mouth. She looked Clara in the eyes as she moved the girl's hand down between her legs. Without letting go, she expertly hooked the gusset of her underwear to one side, opened her legs slightly, and brought Clara's fingers into contact with her pussy.

Clara could feel the wiry pubic hair and then she gasped again as she felt soft flesh yield and two fingers slipped into the hot wetness of Mrs Castlewick's pussy. Her legs felt weak as the headmistress kept her grip on Clara's hand and forced her fingers in and out of her wet snatch. She began to increase the pace, moving the fingers faster and faster.

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Clara was entranced. This was it. This felt right. Her own pussy ached and she hoped it wouldn't be too long before she could satisfy it. In the meantime, she resolved to participate fully in this experience. "I can do it, ma'am, if you please. I can finger your pussy."

Mrs Castlewick released Clara's hand, and the student continued the same pace. Mrs Castlewick let out a small mew of pleasure. She continued to hold Clara's gaze, and was beginning to flush red from the heat of Clara's body and the lewdness of the encounter. She was being fingered by a young woman more than half her age. And more was yet to come.

"You may add a third finger, Miss Pennywhistle, if you please. Sadly when one reaches my age one is no longer as tight as one used to be, and it takes a little more to feel full. Oh yes, that's it, my dear. Faster. Faster. And deeper. Deeper into my pussy. Yes, that's it." The headmistress bent her knees to open herself up and to get herself further down onto Clara's hand.

After a minute she could feel her climax building, and decided to delay the moment. "You may stop, Miss Pennywhistle, and remove your brassiere. Those titties of yours are far to fine to be hidden behind fabric all night."

Clara removed her fingers, and as she reached behind her she caught the scent of Mrs Castlewick's pussy - sweet yet musky at the same time. She unclasped her brassiere and let it fall to the floor. Although not as big as the teacher's (few women's were), her breasts would turn heads in any London ballroom. They sat high on her chest, firm and proud and topped by strainingly erect nipples.

Mrs Castlewick moved to a large daybed near the curtained window and sat down on the edge, her legs spread to expose her pussy. Her pubic hairs were wet with her juices. She motioned Clara to her. "Sit on my lap, facing me. You will continue fingering me, while I suck on your titties. I know you enjoyed sucking on mine this morning, and I am sure you will enjoy the service in return."

"Yes ma'am. But ma'am, beg your pardon, but might you finger my pussy also? I do so ache between my legs and I am desperate for relief."

"Oh you will have plenty between your legs, Miss Pennywhistle, do not worry your pretty head about that. But for now do as you are told and finger my pussy."

Clara did as she was told. The lips of her sopping pussy slid apart as she sat on Mrs Castlewick's thighs. She pressed down to maximise the sensation, then slid three fingers into Mrs Castlewick's pussy and began fucking her again.

No sooner had she done that than the headmistress bent forward to take Clara's right tit into her mouth. She sucked in a mouthful of tit flesh, and Clara again felt a jolt of pleasure. She moaned aloud, and the sound of it almost startled her. "Oh ma'am, Mrs Castlewick, ma'am. Oh god. Oh yes. Oh that feels... Oh god. Oh yes suck it. Ohhhh". This was it. This is what she had been missing. A woman's mouth on her tits. A woman's pussy around her fingers. Clara pressed down still harder onto Mrs Castlewick's thigh and began to grind slowly on to it. Overwhelmed by the sensations from her tit and her pussy, she pistoned her fingers faster and faster into the teacher's pussy, feeling her fingers slick with the juices.

Mrs Castlewick let go of the right breast and let out a stream of saliva on to the left one. Clara moaned again as the hot wet mouth swirled around the breast, one moment tonguing the tip of the nipple, the next swallowing a big mouthful of Clara's tit. Clara's grinding increased, her pussy leaking so much juice that there was barely any friction on the teacher's thigh. With her free hand she grabbed the back of Mrs Castlewick's head and forced it down onto her breast, waves of pleasure washing over her. She felt the older woman tense and her pussy begin to spasm as she moaned into Clara's breast. The moan got louder and louder and joined with Clara's as the waves of pleasure washed over her, washed over her and then finally broke in a shuddering climax that drew a wail of pleasure from Clara and a guttural moan from the headmistress as she forced Clara's hand deep into her pussy and held it there as she rocked and jolted with her own orgasm.

The two women collapsed onto the day bed in a tangle of limbs - sweat, juices and spit all mixing together as the pleasure subsided and their breathing began to slow.

Mrs Castlewick was the first to regain her composure. She sat up, patted her bun to check that it was still in place and adjusted her spectacles. "I trust you enjoyed that experience, Miss Pennywhistle?" She looked down at Clara, still slumped on the day bed with her hair dishevelled and her cheeks and chest flushed. She would enjoy supplementing Clara's education with some personal tuition, she thought to herself.

"Y-yes ma'am. That was... I mean, I am... I mean... Yes, it was... good." Clara's mind was reeling. Had that just happened? Had they really done that? And it had felt so, so good. Her pussy tingled. She sat upright and looked up at the headmistress. One nipple had slipped out of the cup her brassiere and sat tantilisingly in front of her. She longed to feel it in her mouth again.

"Good. Now we shall continue." She took up the leather contraption that she had produced from the drawer earlier. "Observe, Miss Pennywhistle, as I put on this harness."

Clara sat naked, still catching her breath, as Mrs Castlewick removed her knickers. Clara noticed the dark wet patch that covered most of the crotch. Mrs Castlewick slipped the harness around her waist and passed a strap between her legs, fastening it with loops and buckles. She then picked up the long thick object that had also been in the drawer. It was a dull grey colour and shaped very much, Clara thought, like a penis. As Mrs Castlewick placed it through a metal ring at the front of the harness and secured it in place with black silk ribbons, the penny dropped and Clara stared in amazement. There, jutting out from between her headmistress's legs, was a perfect facsimile of a cock. A large, meaty cock at that.

A faint smile played over Mrs Castlewick's otherwise stern face. She reached behind her back and undid the strap on her brassiere. Her breasts spilled out, two large pillows of flesh topped by impressive dark aureolas and magnificently erect nipples. She stroked the phallus slowly while gazing at her pupil. "You see, Miss Pennnywhistle, with a little ingenuity we women wield the same tools as a man. It's made of India rubber, another product of our glorious Empire. You can receive the experience of being taken by a man, while at the same time having the pleasure of being intimate with a woman. I take it from our little coupling that you do take pleasure in being intimate with a woman?"

"Oh yes, Mrs Castlewick. I, I enjoyed it very much."

"Yes you did, didn't you, you dirty minx. Good. It is healthy for a young lady of good breeding - or of no breeding for that matter - to revel in the carnal pleasures. Keeps the mind and body fresh. I shall fuck you shortly. I shall make you cum while you have this dildo deep in your sweet young pussy, and so you will take an important step in being able to secure for yourself a future husband. But first, come here and suck me."

Mrs Castlewick released the dildo and took her right breast in her hand and proffered it towards Clara. Clara stood and crossed over to Mrs Castlewick, leaning down as the headmistress pressed her tit into Clara's mouth. "That's good, my dear. Suck it nice and hard. Yes, very good. Now keep sucking, and take the cock in your hand. Stroke it as you've been shown in your lessons. Up and down, yes that's right."

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