Private Lessons

by Wintermist

Rating: mature
Tags: Sex, Anthro, Profanity, Cheerilee, My Little Pony: Friendship is Magic, Romance, Princess Luna, Porn, Fetish
Length: 8455

Ignorant of a thousand years of history and culture, Luna needed a teacher. She wanted somepony to take her gently by the hand, and teach her what she'd missed. Then, with time, she found she wanted somepony to just take her.

Ignorant of a thousand years of history and culture, too embarrassed to seek instruction at the hands of Twilight or her own sister, Luna needed a teacher. She wanted somepony to take her gently by the hand, and guide her through everything she'd missed.

That was how it started.

Then, with time... she found that she wanted somepony to just take her.

-
This is a commission for DbzOrDie! Also entered into Dirty Little Secret's Dirty Little Contest.

Content warnings: anthro, bdsm, bondage, teasing, orgasm denial, dirty language, blowjob, strap-on, dildo, sex

Published 2020-04-22 18:10:02 UTC
Last updated 2020-04-22 18:10:02 UTC

Giving Your Student Motivation

Ponyville, despite its upswing in importance since the creation of Twilight's castle, remained a small, provincial place. The distance from the railway station to the schoolhouse was a mere trifle; a brisk five minute walk covered the ground easily.

For Princess Luna, however, every step made her heart beat faster in her chest. Shrouded in the depths of a hooded, all-encompassing cloak, she hunched her shoulders and tried not to let the outline of her wings show beneath the soft fabric. Each gust of wind sent a spike of adrenaline through her, sweat prickling across her forehead as she pictured, over and over again, what would happen if her cloak blew open in the middle of town.

She could always fly back to Canterlot and go into hiding, she supposed. A couple of centuries might be sufficient.

A small voice piped up behind her. "Oh hey! Hey! Poppa, look! Look! It's Princess Lu-mmffh!"

Luna stumbled; she nearly twisted around, only catching herself at the last moment. Over the muffled sounds of a hand being firmly clamped over a foal's mouth, a male voice called out with boisterous, determined cheer, "Don't you mind her, mysterious hooded stranger! You have a good day now!"

She nodded mutely, tugging her hood forward a little further, her ears burning with embarrassment. They all know. All of them.

Or at least, they all thought they knew.

Cheerilee was waiting for her, outside the quiet, empty schoolhouse. The schoolteacher wore a black waistcoat, buttoned tightly under her chest in a way that subtly echoed a corset. A dark maroon blouse, a deeper shade of wine than her own skin, was buttoned to the neck. An immaculate black skirt over dark tights completed the look; neat, formal, and if a little stern, still utterly professional.

Luna shivered as she came to a stop, a thrill of arousal tingling through her. Wordless, she nodded once at the shorter mare.

"Good afternoon. I presume you are here for the supplementary lessons?"

Luna nodded again. Her voice low, she agreed, "I am. May I come in?"

"Of course, please do." Cheerilee stepped back into the schoolhouse and Luna followed, pulling her cloak tighter around her and bending her head to duck under the lintel. The last school bell had rung an hour before; the place was deserted. And still, it would not do to get careless… Luna stepped past Cheerilee into the foyer, then turned to watch as the smaller mare slipped a heavy key into the door lock, turning it firmly.

The click-thud of bolts shooting home sounded unnaturally loud in Luna's ears.

Cheerilee looked up. There was something different in her expression now, a hardness that her faux-meek greeting had thinly masked. "Apply the seal, please."

"…of course," Luna murmured, casting her eyes down. Her horn flared in the depths of her hood, and all over the school, energy flickered over the windows. Now, no matter whose enquiring eyes peered in, all they would see were empty rooms, and all they'd hear was silence.

A Princess needed her privacy whilst catching up on a thousand years of missed history, after all.

It was the worst kept secret in Ponyville; Luna had met Cheerilee on a visit there, and - too embarrassed to ask it of Twilight, or her sister - had sought elementary instruction in the long centuries that had passed in her absence. History, courses on modern manners, updates to social mores, and contemporary common knowledge. Luna didn't want anypony to know, and so everypony in town carefully didn't know, or at least, didn't know out loud and in public.

It had even been true, for a while. But then…

With slow ceremony, holding Luna's gaze, Cheerilee unfastened the top button of her blouse. Reaching within, she drew out a short, flat ruler that had lain hidden against her body. "Today, there will be a surprise uniform inspection. You are sure your uniform complies with the rules, aren't you?"

This is utterly beneath the dignity of a Princess. The thought was never far away, during her lessons. Part of Luna could never stop urging her to be more gracious, more poised, like her sister. To maintain the honour of their long stewardship of the Realm. And she knew, without question, that all it would take was a single word, and all this would all stop. Lessons would be strictly business, or cease entirely, as she preferred.

Utterly beneath the dignity of my position, Luna thought again, and a fresh shudder of arousal ran through her. In a soft, compliant tone, she murmured, "Yes, Miss Cheerilee."

In a haze of blue magic, her cloak unfastened, pulling back and folding itself neatly onto a shelf beside the door. Beneath...

...beneath she wore almost nothing. A white blouse clung to her body with fanatical dedication, clearly several sizes too small, baring her toned, concave stomach and straining near to bursting over the full, round curves of her breasts. A neat little tie added a splash of darker blue on top, with a small crescent moon at the end. Her skirt was ludicrously short, exposing flashes of her innocent white panties every time she moved and showing off the gorgeously firm curves of her ass for all to see. Knee-high socks with little blue bows coated her long legs, leading down to sweet, highly polished school shoes on her feet. There were ribbons in her hair, tying her ethereal, flowing mane into twin bunches. Rouge added pink to her cheeks, and mascara lengthened her lashes.

She looked as though she had stepped out of a fetishised fantasy, and she knew it. Knew that if she was seen by anyone but Cheerilee, she'd still be hearing about it in another thousand years.

Her pussy clenched.

Cheerilee circled her slowly, the teacher's green gaze moving shamelessly over her exposed body. "Very good, Luna. I can tell you've studied the regulations carefully. However.Is your skirt under regulation length?"

Luna's breathing quickened at the cruel tinge to Cheerilee's words, despite knowing for a fact that her skirt was more than short enough. Skirt length not to exceed four inches. She knew Cheerilee's regulations by heart, even though they changed often. She wouldn't want to fail a surprise quiz on the rules, either. "...yes, it is."

Crouching, Cheerilee held the ruler against Luna's thigh. Luna didn't dare look down, holding herself in the presentation position, hands clasped behind her. The straight, flat strip of wood was cool against her heated skin.

Then she felt a sudden jerk as Cheerilee tugged the little skirt down a few inches, exposing the upper curves of her ass. Luna gasped in surprise, protesting before she could stop herself, "But-!"

"No buts, Luna. The bottom of your skirt is clearly more than four inches below your waist," Cheerilee told her, with pleasant malice.

"But the top of the skirt is no longer on my waist!" wailed Luna. This simply wasn't fair!

"That was a second 'but', Luna," countered Cheerilee sternly. "Another, and I will ensure you are too sore to sit. Stand here, at once. Hands flat against the wall."

Another wave of prickling heat rolled through the Lunar Princess, her nipples tightening into achingly stiff points beneath her pretty little blouse. No pony ever spoke back to her, no pony would dare. The idea of punishing her was as remote to the ponies of Canterlot as the surface of the moon.

...no pony except Cheerilee would dream of punishing her. Cheerilee found an excuse every single time.

Licking her lips, Luna nodded once, breathing, "Yes, of course." Planting her feet where Cheerilee had indicated, she slowly bent forward, reaching for the wall. Tall as she was, Luna could barely reach it; a fresh blush of crimson humiliation heated her cheeks, feeling her tiny skirt slide up as she bent over, legs wide apart. Cool air caressed her ass, inadequately covered by sweet little white cotton panties with embroidered edges. Panties that were already soaked into translucency, clinging to her pussy where it peeked between her legs.

The ruler smacked down, igniting a line of fire along her tender skin.

"Ahhh!" yelped Luna, her back arching and forcing out her tits. The sudden additional strain on her blouse was too much, and a small button pinged free. "O-one!"

"Why are you counting the strokes, Luna?" asked Cheerilee from behind her.

"B-because all spankings must be counted aloud! School regulations!"

"Good girl. Then you can count to ten."

Luna gasped, bracing herself as best she could. Lowering her head, her fingernails clawing into the wooden schoolhouse wall, she closed her eyes and counted aloud through the brisk, stinging cracks. "Two! Three, four, five -ah! Six! Seven, eight- nine ten! That's ten!" she gasped, forcing the words out.

"That's ten," agreed Cheerilee approvingly. "Go take your seat."

Stumbling slightly, tugging her tiny skirt back into place, Luna straightened up and hurried into the classroom. Her ass was burning, her body was on fire, and she felt...

...she felt so, so good.

She was addicted to it. Needed it. When she hadn't been able to make a couple of sessions with Cheerilee in a row, she'd begun to find herself acting out in Canterlot, in the subconscious hope that somepony would spank her for misbehaving. Of course, that would never happen. Couldn't. This was her only release, and more and more, she couldn't live without it.

The classroom wasn't terribly cluttered. Most of the desks had been pushed back against the walls, leaving just one in the centre of the room, seat tucked neatly under it. Gripping the back of the chair, heart hammering in her chest, Luna pulled it out and went to sit down.

She couldn't. Strapped firmly to the chair frame, in the very centre of the seat, was a thick, realistically sculpted dildo. The obscene toy jutted upwards, dark purple, glistening with lubricant, almost threateningly sexual.

"Is there a problem with your seat, Luna?" Cheerilee asked pleasantly from behind her, the teacher so close that her breath tickled Luna's skin.

"I... no. No, Miss Cheerilee."

"Then sit. Class is about to start."

"...yes, of course."

Cheerilee walked over to her desk and seated herself on the corner, smiling cruelly as she gazed at the princess.

Luna's breathing quickened, her cheeks crimson as she looked down at the sex toy again. It was too humiliating! Stretching out one leg, she lifted it over the chair, then hesitated. Clothes were to stay on or be removed solely at the direction of the teacher, and Cheerilee hadn't given her permission to remove her panties. Biting her full lower lip, she reached beneath her legs and hooked her fingers under the edge of her soft cotton underwear, tugging it aside to expose her dripping pussy.

Skies above, she was so wet!

Feeling the heat of her teacher's gaze on every inch of exposed skin, Luna slowly lowered herself. She gasped as the slick hardness of the toy pressed against her entrance, hesitating for a second, then shook her head and kept going. Her chest tightened, breath locked within her as she felt the unyielding shaft fill her, inch by inch. Then smooth, polished wood touched her thighs, and she gasped for air as she let the chair take her full weight, opening her eyes again.

She was unbearably full, the shaft thicker than any Cheerilee had inflicted on her before. It felt so good! Her hips kept shifting back and forth despite herself, pushing her up and down the rigid shaft; she was blatantly fucking herself in the middle of the classroom, and she couldn't hide it, and she couldn't stop. "I - I'm ready for my lessons," Luna panted, near melting from shame and arousal.

"I'm pleased to hear it," responded Cheerilee brightly. "Today, we're going to study the fourth century of the Imperial era, then we're going to cover the political upheaval caused by agricultural innovations in the early fifth century. There will be homework for you to submit on how this period shaped the landscape we know today. First, however, I'm going to give a special demonstration. Please pay close attention."

Cheerilee pushed herself off the desk, and stepped behind it. There was the click of a key, then the long wooden sound of a drawer sliding out, and she straightened with a very familiar bag in her hands. A bag that Luna knew, very well, contained ropes, cuffs, chains... everything needed to make a pony absolutely helpless.

"Escapology," said Cheerilee, with the air of somepony laying down an ace.

Luna's grip tightened on the edge of the desk as the other mare approached. "I - I volunteer for the demonstration!" she managed, barely able to think clearly enough to get the words out as she shamefully found herself grinding up and down the thick shaft that was buried so deliciously within her.

"Good girl, Luna," praised Cheerilee. "You're just the pony I had in mind."

Nodding jerkily as the other pony crouched by her side, Luna found herself with a perfect view down her teacher's blouse. Cheerilee had undone another button, and the slopes of her breasts were tantalisingly visible. Every breath drew the scent of the other mare's body into Luna's lungs. She wanted - needed - to touch, and be touched. She needed to be used!

Chains wound around Luna's ankles under Cheerilee's expert hands, binding her to the legs of the chair. The huge sextoy rammed all the way into her as Cheerilee forced Luna down against the chair, further loops of chain sliding around her thighs and anchoring her rigidly in place. "Arms behind you," Cheerilee coaxed, and Luna obeyed with a whimper of compliance, crossing her wrists behind the chair back as the other mare secured her wings with thick restraint bands. Her blouse, already missing a button, was barely holding together now; the position forced out her chest, leaving her too-small top straining desperately to stay closed. Taking shallow little breaths, Luna closed her eyes as a slender collar wrapped around her throat, a rope connecting the back of her neck to her wrists to keep her sitting rigidly upright.

And then her eyes snapped open again as a slim ring slid down her horn.

"Wait!" Luna gasped, a shiver running through her as she tugged carefully at her bonds. Every little instinctual movement of her body came up against the unyielding grip of the ropes and cuffs. Oh stars above, why did it make her feel so obedient?

Cheerilee circled around to the front of Luna's desk and leant forward, green eyes smouldering. She radiated a hot, hungry desire, a savage lust that the delicate disarray of her strict teacher's outfit only emphasised.

"Yes, Luna? Is there a problem?"

Luna swallowed, unable to look away from the other mare's body, her mouth dry. "How will I take notes?" she asked hoarsely.

Cheerilee smiled, casually ruffling Luna's ethereal mane. "It seems you're just going to have to concentrate really hard. Or you could escape. Then there wouldn't be a problem, would there? Consider the rule about damaging classroom property to be suspended for now."

Luna was a warrior, a princess, a creature of ancient powers; no shackles could hold her unless she willingly submitted to them. The rules that forbade her from breaking Cheerliee's bonds were the true restraint that kept her bound by the schoolteacher's whim. But with those now suspended, there was something new in Cheerilee's expression, some secret delight that stirred a trace of alarm in the alicorn. Hesitantly, unsure of herself at first, Luna tensed her arms and tried to pull free. Then harder. Then harder still.

Her eyes widened as the rending snap of rope and wood giving up under the strain simply didn't happen, and she began to struggle, yanking against her bonds as violently as she could. The chair bounced and rocked, and yet remained utterly unharmed by the alicorn's brutal strength. There was no element of choice left; she couldn't escape.

Cheerilee laughed softly, covering her mouth with one hand. "I asked Princess Twilight to demonstrate every strengthening charm she knew on a few items I had around the classroom. Then, after class, I challenged her to do it again blindfolded. She was very helpful."

"I - I see. That was... very prepared of you," Luna managed shakily, her breaths shuddering in and out of her chest. She was trapped. No way to save herself. All her power, all her magic, lost to her so simply. She couldn't escape the massive dildo that was splitting her divine cunt open, filling her completely, no matter how she struggled. She was pinned to the spot, like a doll, helpless to move. Her heart hammered within her, and a flush of heat tingled through the alicorn, a surge of arousal that absolutely nothing in Equestria could have made her confess to feeling.

Tracing her fingers down Luna's cheek, Cheerilee murmured, "Do you see? You're already learning. You've learned that you are not in control. Not at all." Her fingers softly parted Luna's lips, gathering a little dampness on her fingertips, then withdrew.

Straightening up, Cheerilee strolled back to her desk and perched casually on the corner of it once more. Her short skirt slid up her thighs, and as she slowly, deliberately crossed her legs, Luna caught just a glimpse of the other mare's barely-concealed pussy, a soaked mesh of white lace outlining her lower lips in intimate detail. "Now listen closely, Luna, and don't get distracted. We have a lot of ground to cover today."

A low whine escaped the captive pony. "I - I will do my best to learn," she managed, dragging her gaze up to where it should be, on Cheerilee's face.

"Very good! I'm sure that you'll learn all sorts of things during today's lecture." Cheerilee picked up the chalk, and began, "At the turn of the fourth century, what would later become known as the city of Vanhoover was merely a depot for the maintenance of-"

Cheerilee was playing with her tits. It was almost as though she was watching a mare possessed, a mare that continued to lecture in her pleasant, mild tones without knowing that her hands had abandoned the chalk and were caressing and kneading her chest through her blouse. Luna watched, shivering with need, as the schoolteacher unfastened another button.

Slowly, throughout the lesson, Cheerilee had been stripping. Her skirt was hiked up around her waist, baring her translucently damp panties to Luna's gaze. Her waistcoat hung open, her blouse parted in a deep 'v' that exposed her smooth cleavage, and every forceful squeeze of her breasts brought the edge of her nipples into view. Low, sighing groans escaped her lips between sentences.

One final squeeze was too much for her parted blouse; Cheerilee's left breast slipped free of its scanty confinement, bared fully, nipple jutting. Smooth, polished fingernails slid around her areola, teasing it harder.

"...and that is the end of today's lecture material." Cheerilee raised her eyebrows. "Oh dear. You seem to still be tied up, Luna. Have the ropes given you trouble? I suppose you haven't been able to make notes after all."

Nodding shakily, Luna dragged her gaze up to Cheerilee's face for a moment, barely able to think through the fog of simmering lust that clouded her mind. The lecture was over already? She'd completely lost track of time; each little involuntary jerk of her hips shifted the thick dildo she was impaled upon, scattering her thoughts all over again. The bonds were tight and expert, the enchanted ropes and chains utterly unyielding, despite all the writhing she'd done to try to escape them. It was impossible to get away.

"...no, no notes," agreed Luna dazedly.

"In that case, there's only one way to be sure that you've been paying attention: a quiz on the topics we've covered. With punishments for every failure. Are you ready to begin?"

Luna blanched. A test? She wracked her mind, trying to remember what Cheerilee had actually been saying. There had been the development of the eastern marches, and... and other things... she was a good student! Usually! She took her studies seriously! But then Cheerilee had begun using her pointer to grind against her pussy, and...

"Failing to answer a question is an automatic demerit, Luna," Cheerilee said sternly. Her hand touched a small, pen-like cylinder lying on her desk.

"I apologise for-" Luna began, then gasped aloud, caught utterly off-guard as the shaft buried in her suddenly hummed into life, shuddering and vibrating. The curved, shaped base of the toy pressed up against her clit as she struggled, teasing and torturing her, stealing the breath from her lungs, her chest constricting. "This is not fair!" she gasped, a purple flush of heat darkening her cheeks as a fresh wave of quivering shame overcame her.

"I decide which punishments are proportionate, Luna," replied Cheerilee firmly. Bending forward, her other breast slipping free of her barely-fastened blouse, she cradled her tits in both hands. "Question one. Who oversaw the treaty between Griffonstone and the Eastern District Collective?"

"...it was Hatterton the Diplomatic," Luna answered after a second's hesitation, trying desperately to remember the actual lesson as the vibrations against her clit obliterated her every attempt to think straight.

"Very good, Luna! Question two..."

Luna struggled through the next few questions correctly. Then, however...

"It was - it was Bridlestone," Luna forced out, just about managing to keep herself from panting in the middle of her answer. Her cunt was so full, her juices spreading over the chair seat and slicking the underside of her thighs, but no matter how she struggled, she couldn't even rock against the faux cock, she couldn't move! Please, please just fuck me, begged a part of her that only her iron discipline kept back from being voiced.

A Princess does not beg! It was an ancient truth, part of the very foundation of her self-image. And, to her mingled lust and despair, she knew that being forced to violate that sacred teaching would only make it hotter.

"I'm afraid the answer is 'Binderhoof'," Cheerilee announced, with a hint of playful regret. "You've earned another demerit." Her hand touched the thing that wasn't a pen once more.

"Ohhfffuck!" Luna gasped, biting her lip as the vibrations grew more powerful, thrumming through her body and drumming against her clit. She found herself struggling against her bonds once more, though whether to get off the toy or to ram it in and out of her drenched pussy as fast as she could was a question that not even she could have answered.

"Luna! Swearing in class! That will be a third demerit," declared Cheerilee with a brightness that verged on the sadistic. Her hand moved again, and the muted humming of the torturous shaft escalated even further.

"I am - very sorry - for breaking - class rules!" Luna managed, perspiration breaking out on her forehead. The chair creaked and groaned as her sleekly powerful muscles clenched, even the magically-enhanced wood protesting under the strain of containing her. She was so hot, so humiliated! And, oh, by the stars, she needed this... she needed it more than anything she'd ever known! Her hands trembled, clenching and releasing, her nails digging into her palms.

Over the roaring in her ears, she half-heard Cheerilee say something. Forcing herself to open her eyes, Luna looked up at the gloriously depraved figure of her schoolteacher, searching for a clue in the other pony's expression.

"I am waiting for an answer, Luna," scolded Cheerilee, the corner of her lips curled into a cruel smile.

Answer? What answer? Struggling to think of anything but her need to touch her aching nipples, her need to grind her pussy against the huge shaft impaling her, Luna stuttered, "I - I did not hear your - your question!"

"It seems you haven't been paying attention to what I've been saying. What an unbearably lax student you are, Luna." Cheerilee shook her head, tapping her nails on the desk. Uncrossing her legs, reaching down with one finger to tug her panties aside and bare her glistening maroon lips, the prim, proper mare said firmly, "Your next question carries bonus marks. Do you think you should get away with it?"

"No!" gasped Luna, shaking her head convulsively. "I should not be permitted to get away with such lax, disrespectful behaviour! I implore you, impose your discipline upon me!"

"Very good, my prize pupil," Cheerilee praised her. "Whether or not you have learned the history of the 4th century, I can at least teach you a lesson."

Every fibre of Luna's being flared in anticipation, the chains groaning in metallic protest as her muscles tensed. Punish me. A hot breath escaped her lips as she watched Cheerilee approach, pen-remote for the vibrator held loosely between the teacher's fingers. Punish me!

Cheerilee rested her hip against Luna's little desk, hunger in her gaze as she slowly pulled up her skirt. "Please watch this demonstration closely." Kicking off her heels, she unsnapped the straps connecting her garter belt to her stockings. With slow sensuality, she rolled the left stocking down her leg, tugging it free and laying the silky black fabric across Luna's lap. Then, holding Luna's gaze, she slipped her fingertips into the waistband of her panties. Inch by inch, the schoolteacher slid the lacy scrap of white fabric down her legs, until at last they lay pooled around her feet.

"These are for you," said Cheerilee softly. "Something to ensure there will be no more dirty language, language that is unacceptable in this classroom, from my student. Now open."

"Y-yes, Miss Cheerilee!" Nails digging into her palms, heart hammering in her chest, Luna opened her mouth.

Folding her sodden panties neatly, Cheerilee leant forward, bared tits swaying beneath her with each movement of her arms, then pushed them into her student's mouth. Stretching her discarded stocking between both hands, she pressed the band of silken fabric across Luna's mouth, forcing it open wider around the bundle of her panties, then tied it tightly behind the captive mare's head. "I will expect a written description of the taste of my cunt later. Pay attention to it."

An unintelligible sound escaped Luna as she nodded, whimpering deep in her throat. The gently inexorable pressure of the stocking bound around her head pinned Cheerilee's panties in her mouth despite the instinctive pushing of her tongue, and all she could taste was the delicate mixture of fabric and the wetness of the dominant earth pony standing over her. Finally free of the burden of self control, Luna moaned the words she longed to speak into her gag, knowing no pony could understand her now. Fuck me! I beg you, fuck me!

"You've made it harder to test you," scolded Cheerilee, stroking her thumb over Luna's cheek. "However, you did get most of the answers right so far, and I do believe in positive reinforcement. So if you get these last few questions correct, you will earn extra credit. And that means a special treat."

Maintaining her pleasantly professional expression, Cheerilee spread her legs and settled onto Luna's lap. Waistcoat parted, blouse mostly undone, her bare tits pressed up against her student's bound body, the warmth of her skin radiating through Luna's thin, struggling blouse. Below, Cheerilee's skirt was hiked up around her waist to completely expose her glistening pussy. "The following questions will be true or false, okay?"

Luna nodded jerkily, wanton desperation on her face. By all the forgotten spirits of the ancient realms, she needed to get this right! The thought of being unbound and sent home without release was intolerable! But Cheerilee always made her earn it.

"The paved highway linking Baltimare and Canterlot, leading to the boom in glass exports across the Celestial Sea, was completed in 493. Nod if true."

Luna squeezed her eyes closed, blocking out the sight of the other mare's exposed body so she could try to think. Cheerilee had said something about the glass exports, and the highway being under construction, but- oh, that wasn't fair! The mare on her lap had begun grinding against her, soft breasts pushing against her chest, her single remaining stocking sliding against Luna's thigh. It felt so good, and the vibrations within her were driving her crazy and if she gave the wrong answer, or didn't answer, it would all stop! If she had to go and sit on the train in public for hours without a chance to cum, she'd just snap!

Memory clicked into place. It had been due to be completed that year, but landslides had delayed construction. She shook her head, eyes still closed.

"Very good," cooed Cheerilee into her ear, her breath hot on Luna's skin. "Next question. During the 4th century, Star Chaser built the second national Equestrian observatory at the lip of the Galloping Gorge. True or false?"

Luna squirmed beneath Cheerilee, drawing on every shred of self-discipline she possessed to ignore the thrumming of the enchanted dildo buried within her, the way that the chains so deliciously held her prisoner, unable to escape no matter how hard she tried, brought low and humiliated in her depraved mockery of a school filly outfit. She had to think! Was it really Star Chaser? Was it the second observatory of the era, or the third? Galloping Gorge, or Ghastly Gorge? There were ruins at both, so-

Warm hands slid over her straining blouse, cupping her breasts. Agile fingers found the shape of her nipples beneath the cloth, squeezing and pinching.

"Nnnnh!" groaned the Princess of the Night into the panties that filled her mouth. Stars above, she was so close, and it wasn't fair, and she wanted this so badly she could scream! It was the second, wasn't it? Wasn't the south observatory the third? She had to risk it! Shuddering in her chains, she nodded abruptly.

"That's two. Two more bonus questions, and you will get your extra credit," Cheerilee said brightly, then leant closer, nibbling at Luna's ear as she ground back and forth in her lap. "In the summer of 461, Silent Charm became the first mute mayor of Fillydelphia. True, or false?"

This time, Cheerilee didn't even give her the precious few seconds to think unmolested. As she finished the question, she yanked at Luna's blouse; the surviving buttons pinged off, and before the captive mare had time to even gasp, Cheerilee's warm mouth was on her breasts, sucking and flicking her nipples. One hand slid down between them, nails scratching lightly along Luna's inner thighs. It was torment, sweet and inescapable, and the chair rocked and bounced as she struggled against her bonds.

Biting down against the fabric filling her mouth, Luna tensed her body into a rigid statue, trying desperately to deny the sensations that were shattering her mind from the inside out. Each delicate caress of Cheerilee's nails drew closer to her dripping pussy, and a shiver of almost dread came over her as she realised that she had only seconds to answer before the other mare caressed her tender sex where the thrumming shaft entered her. Think!Think!

It had to be a trick. Didn't it? Wasn't it? Luna moaned helplessly as Cheerilee lightly bit her nipple, head tilting back. It sounded right, but - but Silent Charm had won around Hearth's Warming, hadn't she? Or - no! There was a problem with the paperwork, and they realised she had been improperly sworn in and it needed to be done again the following summer!

Cheerilee's nails slid between the curved base of the dildo and her heated body, and strummed Luna's clit.

An agonized, muffled howl escaped Luna's lips, tears seeping from beneath her tightly closed eyelids as she forced herself not to cum. Fighting her own locked muscles, she managed a jerky nod. Through the pounding in her ears, she heard Cheerilee praise her, "Good girl, Luna! Just one question left. The individual known as Arimaspi was the first to successfully steal the Idol of Boreas. True... or false? Ten seconds."

She'd heard that name! The one-eyed goat who had-

The crack of skin on skin echoed around the room. Luna's eyes snapped open, the chair rocking as her whole body jerked with a burst of nigh-unbearable sensation. Cheerilee met her shocked gaze with a smile, and said, "Nine seconds." Her hand moved again, and another stinging crack lit up Luna's body as Cheerilee back-handed her other breast. "Eight seconds." A third smack landed directly on one of Luna's tender nipples, shooting a bolt of pleasure-pain straight up her spine. "Seven."

It was too much! She couldn't think, couldn't even brace herself for the cruel impacts of her teacher's hand across her breasts, not while she was so desperately trying to stop herself from cumming! Arimaspi had definitely stolen the idol, but was he the first? Was that the trick? Shocks of white light burst behind her eyes with every stinging blow, and all she could do was whimper helplessly. He'd taken it, and the griffons had blocked his escape, and he'd fallen into the abyss, wasn't that it?

"One."

"Nnrrh!" Luna shook her head violently, her school-filly pigtails sweeping back and forth over her shoulders.

Cheerilee's hand withdrew from Luna's pussy, and the schoolteacher sat back, raising an eyebrow. "I'm sorry, Luna, is that your answer? False?"

She nodded, quick and spasmodic. Had she got it right? Had she seen the trap?

"Are you saying Arimaspi wasn't the first to steal the idol?"

Luna shook her head again, groaning into her gag in frustration. Her body was shuddering with arousal, the unceasing torment of the vibrating shaft that she couldn't escape holding her on the edge.

"He was the first, but your answer is still false? Very good, Luna, that was a tough one. He might have taken the idol, but dying in the escape doesn't really make it a successful theft, does it? You've really earned that special credit today."

The thrumming of the shaft within her stopped. Luna sagged in her bonds, sucking in air through her nose, trying and failing to lick her lips around the mass of fabric in her mouth. Her thin blouse was stuck to her skin with perspiration, her thighs were slick with her own juices and her pussy ached with unsatisfied need, but just for a moment, she could relax her self-control without immediately breaking the rules by orgasming without permission.

Sliding off her lap, Cheerilee stood up. Her face was flushed with arousal, her nipples jutting, her skirt falling back to momentarily hide her dripping sex before she unfastened the garment and let it drop to the floor. Her mane was ruffled askew, her makeup subtly smudged, and the hungry light of arousal glittered in her eyes. To Luna, she looked unspeakably enticing.

Disappearing behind her pupil, Cheerilee bent to work. A moment later, the web of ropes and chains binding Luna to the chair slackened, though the Princess's hands remained bound firmly behind her, her wing bands locked up tight. Speaking directly into her ear, Cheerilee commanded, "Get up."

"Yfff," Luna managed through the gag, trying to persuade her legs to carry her. Slowly, awkwardly, she pushed herself up from the seat, whimpering as the thick shaft slid out of her, inch by inch. It felt like it might never end! Then, all of a sudden, she was free, barely able to even stand. Forcing herself to stay upright, she couldn't help but shudder as Cheerilee reached out and lifted her tiny, humiliatingly exposing skirt. Her panties were already askew to bare her pussy; the other mare hooked her fingers into the waistband, and tugged the little scrap of sodden cloth down her long legs. Cool air touched her sex, tingling over her over-sensitised skin.

"You won't need those for the remainder of today's class, Luna. It's time for you to come to the front, please."

Leaving her cute little panties abandoned on the floor as she had been commanded, Luna sucked in a breath through her nose and began moving forward, taking step after wobbly step over to Cheerilee's desk. Chains and ropes trailed after her from her wrists, thighs and ankles, like ragged pennants.

"That's very good," Cheerilee praised from beside her. Gesturing beside her chair, the school mare added, "You can kneel now. That is where you seem to be happiest."

Gratefully slumping to the ground, Luna sucked in a breath, then straightened into a proper kneeling pose, her thighs spread wide and back straight. Her thin, tight blouse hung open, framing her firm, dark tits, her moon-marked tie dangling down her impressive cleavage. Her tiny skirt couldn't hope to give any modesty, rucked up around her waist by her pose to expose her ass and tender pussy. Her cute white knee socks were rumpled, unevenly tugged down her long legs. Whorish, inexpert makeup and her twin pigtails completed the depraved vision.

The bag of chains clinked as Cheerilee reached into it, removing a strap-on that was a near-twin of the toy fixed to Luna's chair. Wrapping the long straps around her waist, she buckled them, the shaft bobbing obscenely before her as she settled into her teaching chair with the same ceremony as a monarch taking their throne. Spreading her thighs, exposing the shaft and her flushed pussy beneath, she said, "You've done excellent work today. I'm afraid I'm out of gold stars, so we'll have to make do with something else."

Luna's pupils widened as she gazed at the strap-on, leaning forward, unthinkingly drawn towards it. She was exhausted from trying to think, her self-control battered and broken, and after so long being filled by Cheerilee's thick toy, she felt empty without it. All that mattered to her now was being used by the other mare, to have every last trace of her thoughts fucked away. Whimpers and grunts filtered through the panties wedged between her lips as she incoherently begged into her gag.

"It does make me happy when my students are eager," remarked Cheerilee. Her slim fingers tugged at Luna's impromptu gag, undoing the knotted stocking, then gently withdrew the sodden mass of her panties from the enslaved pony's mouth. "There... better?"

Gulping down air, Luna licked her lips, though she truly didn't know whether to nod or shake her head. Voice hoarse, she managed, "Yes, Miss Cheerilee."

"Good girl! Now open wide..." the schoolteacher purred. Taking firm hold of Luna's star-laden pigtails, she pulled the kneeling alicorn's head forward, shoving her thick shaft between the dazed demigoddess's lips.

There had been a time when Luna would have, could have, fought back against the casual way she was being abused. A time when it truly was beneath her dignity to be treated like this. But now... now her eyes closed, her tongue curled around the shaft obediently, and she swallowed the tip of the toy, drooling as Cheerilee rammed it down her throat. Rule twelve. Luna is an obedient cocksucking bitch.

"Oh, Luna," sighed Cheerilee, forcing the divine mare's head up and down by her grip on her mane, working deeper into Luna's mouth each time until her deep blue lips brushed the base of the strap-on and then holding her there, "you're the kind of student teachers shouldn't dream of." She giggled, then added, "Though you'd know. Mmmh. I just love the way you look with my cock down your throat. I could fuck your face all afternoon."

Whimpering with each yank of her pigtails, Luna barely heard the words. The thick toy filled her throat, filled her mind, and the fluttering thread of her thoughts was a distant, far-off thing. Time had disappeared; she was a puppet, an object to be used however her Owner wished. Her chains rattled as her arms jerked against their restraints; wetness trickled down her inner thighs. Patterned indentations left by the ropes striped her cutie marks. Her body's instinctual struggle to breathe couldn't reach her, didn't matter.

And then the shaft pulled back; not just enough for her to take another breath, but all the way out. She coughed, shaking her head dazedly, gaze slowly focusing on the mare above her. Cheerilee had shed her waistcoat and blouse, and as she watched, the schoolteacher shook her pink mane loose, letting it tumble down her back. The saliva-slick toy jutted from her hips, glistening wetly.

"Up on my lap, Luna," coaxed Cheerilee. "That's enough preparation. It's time you were rewarded for your hard work."

It was as though puppet strings were attached to her limbs; Luna rose without her conscious intervention, her body obeying the command that she had yet to fully process. Cheerilee's hands curled around her to grasp handfuls of her firm ass, drawing her forward to straddle the schoolteacher. The tip of the shaft grazed her pussy as she settled into the other mare's lap.

"You've already passed your test for today, Luna, but I do hope you'll get these questions right," teased Cheerilee, her cheeks flushed, eyes glittering feverishly with her desire. Rocking her hips slowly back and forth to stroke the strap-on up and down against Luna's cunt, she asked, "Are you my slut?"

"Yes! Your slut, thy debased chattel! Please take me!"

"Very good girl, Luna! Manners are very important in the classroom, even for desperate, cock-hungry bitches. Deep breath, now."

Cheerilee's hands took hold of Luna's hips, and pulled her down hard. The slick shaft slid into her effortlessly, transmuting her in one instant of glorious fulfilment into a different pony entirely; one that knew nothing of honour, nor dignity, nor responsibility. She knew only the ever-lasting now, the feeling of her Owner's breasts stroking against her own, the firmness of the other mare's assertive hands, and above all, the sensation of that cock thrusting into the centre of her body and soul.

"Oh, oh my teacher..." Luna groaned, the words escaping her with a heated sigh. "I want this, I always want this... you drive me to delirium..." Her thighs tensed, lifting her, then with a heavy moan she slammed herself down against the other mare's shaft. The chair creaked loudly, and it was Cheerilee's turn to gasp as the base of the sex toy ground against her tender sex.

"Nnhh! I want to hear what you want, Luna!" groaned Cheerilee, seizing the Princess's dark breasts and squeezing them together obscenely.

"Punishment! I crave punishment!" The words leapt from her lips as she forcefully rode Cheerilee's cock, throwing back her head as she felt the other mare's nimble fingers pinch and twist her throbbing nipples. Her wings jerked and shifted beneath their bonds, the leather bands straining to contain them. Every violent thrust sent a shockwave through her whole body, her tail twitching higher in mindless invitation.

Clinging to Luna's writhing body, Cheerilee roughly lapped and bit at her student's tender breasts, all pretence of professional detachment long abandoned. "What have I taught you?" she demanded, her mane in disarray, face flushed, nude but for her garter belt and a single rumpled stocking.

"You have taught me to obey! That you can break me at your whim! That all my pretence of decorum and dignity is a lie to shield my eager sex and tender breasts! I am destroyed in your presence, remade as your sexual plaything!" Luna bit her lip hard enough to leave stinging tooth marks, driven halfway out of her mind by the feeling of the other mare's mouth on her tits, the way the huge strap-on split her open and filled her beyond escape. Her hips slammed down again, the chair scraping across the floor with the force of her bucking. "I love every instant of this! I cannot exist without it!"

Cheerilee lifted her head, expression overtaken by a violent, near-predatory lust. Slamming her hands down on the arms of the chair, she forced herself upwards beneath Luna, shoving the alicorn backwards onto her desk. Papers fluttered everywhere, the long ruler clattering loudly to the floor, and the inkpot sprayed a stain of blue across the floorboards as it struck them. "I want this!" she gasped. "I want you so badly!"

"More! Please, more!" Luna begged, her bound arms and wings trapped beneath her and forcing her back to arch. Her own breasts obscured her sight of the school mare's strap-on as it pistoned into her, every thrust jerking her back and forth against the smooth wood and sending seismic ripples through her bouncing tits. Her senses were alight with the vividness that only battle had once brought, scenting the mixture of their musks overlaid with a sharper note of chalk dust, noticing for the first time the initials playfully carved by some mischievous student into a ceiling beam directly above her. The other mare's breathy moans were as unique as a fingerprint, as a kiss. Overwhelming adoration that she'd never dared voice hammered through her to the rhythm of her pulse.

"Are you - ready for - permission?" Cheerilee forced out, fighting every syllable through the delicious tension wracking her body. Sweat slicked her maroon skin, strands of her mane stuck to her forehead, nipples reddened as she roughly tweaked and twisted them with one hand while the other clung to Luna's thigh, fingers indenting her divine cutie mark.

"Yes!" near-sobbed Luna, nodding with such force that her head swam. It had been easier to subdue Tartarus than withhold her own orgasm for so long! "I beg of you, grant me this release! I - I have obeyed the rules, I swear it!"

"You have done - very well, Luna," Cheerilee managed, her hips slamming back and forth in brutal punctuation of her every word, "so please cum for the class!"

For an instant, Luna didn't even know how to relax the part of herself that was hanging on desperately to prevent her orgasm striking. Then, all at once, a full-body convulsion slammed through her, forcing a howl of agonised release from her lips. Crackling sparks of grounded magic flared around her horn ring, her pussy tightening around the huge toy buried in her as if to hold it there forever, and her chest locked in place, unable to breathe. It was utterly overwhelming. It dismantled her mind, scattering the pieces beyond reach.

It was everything her life as a Princess could not offer her.

Her body twisted and writhed as aftershocks raced through her, echoes overlapping with Cheerilee's own hissed gasps of pleasure - the schoolteacher always orgasmed quietly, as though she might be overheard. Exhausted, feeling as though she were mere detritus left stranded by a retreating tidal wave, Luna sank back against the desk, never looking away from the mussed, panting figure of the other mare. So, so beautiful... The words whispered at the back of her mind, and it took a moment for her to realise they had escaped her lips.

Cheerilee pushed a handful of her mane out of her eyes, her cheeks burning a deeper red. Breathlessly, she murmured, "It's no wonder you're my favourite."

Luna lay, stretched out full-length, on an old blanket spread out across the floor. It was a tatty, worn thing, something Cheerliee had used to use for picnics, the interlocking pattern faded by the sun. It was also, as far as Luna was concerned, the safest place in the whole wide world. Her head was propped up, resting in the school mare's soft lap. She could have stayed there forever.

Cheerilee's brush stroked softly through Luna's flowing, star-littered mane, smoothing out the tangles. "I should have gotten my chair magically reinforced as well. Once we were on it together, I wasn't sure it'd survive us."

A little smile quirked Luna's lips. "Clearly I will have to try harder, next time."

Giggling, Cheerilee bopped Luna on the nose with the tip of the brush. "I'm not sure I'd survive that. I'm not complaining, though."

"Did I score well for this class?" Her tone mock-innocent, Luna fluttered her eyelashes winsomely at the mare above her. "I do hope so. If I haven't, I would have to make up for it in other ways."

"Very, very well. You earned your reward, you really did. Levitate the left drawer from my desk over to me, please." Cheerilee sat up a little straighter as Luna obediently did what she was told, reaching into the hovering drawer and withdrawing a little sheet of stickers. With ceremony, she peeled off a big gold star, and stuck it to the end of Luna's half-undone tie where it rested between her bare breasts. "There. A gold star for you."

Luna blushed, feeling oddly delighted by the gesture. "I thought you had said you had none of those left."

"I did say that. Very good! I will be setting you homework to make sure you remember all the other things I taught you today as well; I don't want to have fucked all of that precious knowledge out of your head. Take the dildo from your chair; I want it inside you while you work. Highest setting."

Sticking her tongue out, Luna groaned in playful protest. "Is it not enough that I must travel all the way back to Canterlot in these ruined clothes, scarcely covered by my cloak?"

"I'm afraid not. That is my reward, you see." Cheerilee smiled down at her fondly, then hesitated. Luna's brow had just enough time to furrow in puzzlement before the schoolteacher's lips descended to meet hers, in a warm, gentle kiss.

Luna melted into the kiss, tears welling in her eyes as she tasted the warm sweetness of the other mare's mouth and felt the softness of her lips against hers. It was the first time Cheerilee had kissed her that way, outside of their dominance games. It felt like a step towards a future that even Luna couldn't see yet. "Thank you," she whispered. She could have said more; words of deeper adoration that waited upon the tip of her tongue, unspoken, and yet didn't. But she came closer to voicing them than she had the last time, and still closer than the time before that.

She'd get there.

Cheerilee kissed the very tip of Luna's horn, beginning to brush her mane once more. "Anything for my favourite student."

Author's Note

Time and again as I wrote this, one persistent thought kept coming back to me: this is the kind of smutty story that Twilight would write.

Commissioned by DbzOrDie
Suggestions and proofing by: Equimorto, DbzOrDie, Fylifa, Implausible Deniability and Djmill.