Headmistress' Regression

by: Airum | Story In Progress | Last updated May 21, 2025


In this CYOA tale, a stern headmistress is slowly turned into a naughty schoolgirl


You stand before the antique mirror in your office, adjusting the lapels of your charcoal suit with practiced precision. The reflection shows exactly what you've cultivated over years in academia: power, control, intellect. Your dark hair is pulled back so tightly it creates a natural facelift, not a single strand daring to escape the severe bun at the nape of your neck.

The morning light filtering through the leaded windows catches on your single concession to femininity—a small silver brooch in the shape of a thorn branch pinned to your lapel. A reminder of your position, of the legacy you're reshaping with uncompromising hands.

"Dr. Blackwood?" A soft knock accompanies the voice of your assistant, Marcus Reed, a young man whose efficiency is matched only by his discretion. "The students are assembled. The faculty are taking their places on the stage."

"Thank you, Marcus. I'll be out momentarily." Your voice is crisp, authoritative.

As you gather your notes, a strange sensation washes over you—a momentary disorientation, like vertigo without the fall. The room seems to expand around you, the furniture suddenly too large, too imposing. For a heartbeat, you feel small, diminished.

You blink, and the sensation vanishes. But as you move toward the door, you catch your reflection again and pause. Something seems... off. Your suit, always impeccably tailored, appears slightly loose around the shoulders. The hemline of your skirt seems to have crept up an imperceptible inch.

Marcus is waiting in the corridor, his expression professionally blank, though you detect something in his eyes—amusement? Curiosity?

"Is everything alright, Dr. Blackwood?" he asks, his tone perfectly calibrated between concern and deference.

"Of course," you reply, though the words feel strange in your mouth, as if your tongue has forgotten the precise shapes of authority. "Why wouldn't it be?"

"No reason," he says, falling into step beside you. "Though Professor Hargrove mentioned he was looking forward to your address. He said something about 'fresh perspectives' being so valuable."

Professor Julian Hargrove—the former interim headmaster who'd expected to be given your position permanently. His resentment has been palpable since your appointment six months ago.

As you approach the auditorium doors, the murmur of eight hundred students awaits. You straighten your spine, lift your chin, and step forward into the harsh fluorescent light of the stage. The faculty row watches your approach—some with respect, others with thinly veiled hostility.

Hargrove, silver-haired and patrician, offers you a smile that doesn't reach his eyes. "Victoria," he says, using your first name deliberately, publicly. "Don't you look... youthful today."

Something in the way he emphasizes the word sends an inexplicable shiver down your spine, a strange heat blooming in your cheeks. For a moment—just a moment—you feel an absurd urge to apologize, to ask permission to speak.

You step to the podium, gripping its edges with white knuckles as you survey the sea of faces before you. The faculty row watches with varying expressions—respect, boredom, and in Hargrove's case, that unsettling smile that seems to know something you don't.

"Students of Blackthorn Academy," you begin, your voice projecting with practiced authority. "Recent events have necessitated a reminder about our standards of excellence and the consequences for failing to meet them."

As you detail the new disciplinary measures—stricter curfews, mandatory study halls for underperforming students, increased faculty oversight—your heart inexplicably accelerates. Each time the word "discipline" passes your lips, a strange flutter disturbs your stomach, like the nervous anticipation of being called to the principal's office.

"Those who cannot adhere to these standards," you continue, fighting against an odd tremor in your voice, "will face immediate consequences."

Professor Hargrove leans toward Dr. Eleanor Winters, the ancient literature professor beside him, whispering something that makes her eyes dart to you with sudden interest.

"Furthermore," you press on, "any faculty member undermining these directives will be subject to review."

You direct this pointedly at Hargrove, but as your eyes meet his, a wave of childish intimidation washes over you. For a horrifying moment, you imagine yourself as a schoolgirl being scolded, not the authority figure doing the scolding.

"Dr. Blackwood seems quite passionate about punishment today," Hargrove remarks loudly enough for the first few rows to hear. "One might think she's working through some... personal experiences."

A ripple of suppressed laughter moves through the student body. Your cheeks burn with an embarrassment that feels disproportionate, adolescent in its intensity.

"I assure you, Professor Hargrove," you reply, your voice steadier than you feel, "my only experience is watching standards decline under previous leadership."

The assembled students collectively inhale at your direct challenge. Hargrove's smile only widens.

"Of course, Victoria," he says, using your first name again with deliberate familiarity. "Youth often brings such... reformist zeal."

Something about the word "youth" sends another disorienting wave through you. For a split second, you feel your posture changing—shoulders hunching slightly, as if trying to disappear into yourself.

You straighten immediately, concluding your address with a final warning about academic integrity violations. As you step away from the podium, you notice with alarm that your skirt has definitely ridden higher than when you dressed this morning. You tug it down discreetly, but not before catching Marcus's averted gaze and flushed face.

As the assembly disperses, Dr. Winters approaches, her ancient eyes sharp behind wire-rimmed glasses. "Quite the performance, Victoria. Julian mentioned you've been... changing your approach lately. More fire than ice now." She studies you with clinical interest. "Your suit—is it new? The proportions seem... different somehow."

Before you can respond, she pats your arm with her papery hand. "Don't worry, dear. We all go through phases where we're trying to find ourselves again."

The patronizing tone makes you feel inexplicably small, like a child being humored by adults.

You slip away from the dispersing assembly, ignoring the curious glances that follow you down the corridor. The faculty bathroom—a private sanctuary of marble and brass fixtures—feels like the only safe haven in a world suddenly tilting off its axis.

The door locks with a reassuring click. You approach the mirror, hands trembling slightly as you smooth down your skirt that seems determined to ride higher than propriety allows. Your reflection stares back, familiar yet somehow not quite right—like a photograph that's been subtly altered.

"Get a grip, Victoria," you mutter to your reflection. "You're the headmistress of Blackthorn Academy, not some nervous schoolgirl."

The word 'schoolgirl' sends an electric current down your spine, a forbidden thrill that makes you flush with shame. You splash cold water on your face, breathing deeply, trying to recalibrate.

A nagging discomfort at your waistline draws your attention downward. You glance around—still alone—before discreetly lifting your skirt to adjust your undergarments.

What you see stops your breath. Instead of the practical black briefs you distinctly remember putting on this morning, you're wearing pink satin panties with an absurd ruffle of lace around the edges. They sit high on your hips, childishly decorative and utterly inappropriate for a woman of your position.

"This isn't possible," you whisper, fingers brushing against the unfamiliar fabric. "I don't own anything like this. I've never—"

A knock at the door makes you drop your skirt as if burned.

"Dr. Blackwood?" Dr. Winters' voice filters through the door. "Are you quite all right? You left rather abruptly."

"I'm fine," you call back, your voice higher than usual. "Just... freshening up."

"Well, don't dawdle too long. The board members are arriving for your nine o'clock presentation on budget allocations." There's a pause, then she adds with peculiar emphasis, "Though I must say, Julian was right about you looking different today. There's something almost... girlish about you this morning."

The word 'girlish' lands like a slap. You turn back to the mirror, studying your face. Are your cheeks fuller? Your eyes wider? Or is it just your imagination, fueled by Hargrove's insinuations and these impossible panties?

"I don't understand," you whisper to your reflection. "Am I losing my mind?"

Your reflection offers no answers, but as you straighten your jacket, you notice with dawning horror that your conservative silk blouse now has a small but unmistakable Peter Pan collar that wasn't there before. Your fingers trace it with disbelief as a wave of dizziness washes over you, accompanied by a disturbing flutter of excitement low in your belly.

You stride into the boardroom with your shoulders squared, clutching your portfolio like a shield. The twelve board members—old money and older prejudices—regard you with varying degrees of interest as you take your place at the head of the table. Your skirt feels indecently short as you sit, and you tug it down with as much dignity as you can muster.

Chairman Geoffrey Pembroke, with his silver hair and permanent scowl, taps his Mont Blanc against the polished mahogany. "Dr. Blackwood, we're eager to hear your budget proposals, particularly regarding the... controversial cuts to the legacy admissions office."

You launch into your presentation with practiced precision, fighting against the strange sensation of your clothes. The Peter Pan collar of your blouse feels childishly prominent against your neck, but you power through, detailing efficiency measures with ruthless logic.

Twenty minutes in, an uncomfortable pressure builds in your lower abdomen. You shift your weight, continuing without pause, but the sensation intensifies with alarming speed. It's as if your bladder has suddenly shrunk, the need to urinate becoming urgent in a way that feels foreign to your adult body.

"Furthermore," you say, your voice tightening as you cross your legs beneath the table, "the reallocation of funds from the rowing team to the science facilities will position Blackthorn more competitively for—"

"Dr. Blackwood," interrupts Pembroke, "you seem... distracted. Is there a problem?"

"Not at all," you manage, though sweat beads at your hairline. "As I was saying—"

The pressure becomes unbearable. Your thighs press together with desperate force as you rush through your final points, abandoning your carefully prepared notes.

"I believe that concludes the essential matters," you announce, gathering your papers with trembling hands. "The full report is in your folders. If you'll excuse me, I have an urgent matter to attend to."

You don't wait for a response, fleeing the room with as much dignity as you can salvage. Behind you, whispers flutter like autumn leaves: "Most peculiar behavior..." "Not what I expected from Blackwood..." "Julian mentioned she's been acting strangely..."

The bathroom door barely closes behind you before you're yanking down your skirt, those absurd pink panties, and dropping onto the toilet seat. Relief floods through you as your bladder releases, but horror follows immediately—a damp patch stains the front of the pink satin, evidence of your failure to maintain even this basic bodily function.

"What's happening to me?" you whisper, voice cracking with something between fear and humiliation. The sound that escapes your throat is higher, softer than your normal tone.

As you clean yourself as best you can, you notice with dawning terror that the pink panties now have a small cartoon unicorn embroidered on the front—a detail definitely not present earlier. Worse, they seem to have thickened slightly, the material more substantial between your legs.

"This isn't real," you tell yourself, but the evidence is undeniable beneath your fingertips. "This can't be happening."

You make your way to the infirmary, composing a story about headaches and dizziness—symptoms that aren't entirely fabricated given the morning's disorienting events. The sterile white room smells of antiseptic and institutional cleanliness, a stark contrast to the mahogany warmth of your usual domain.

Nurse Olivia Chen looks up from her desk, surprise registering on her youthful face. At perhaps twenty-six, she's one of the newest staff members, hired during your tenure despite Hargrove's objections about her 'limited experience.'

"Dr. Blackwood," she says, rising quickly. "This is unexpected. Are you unwell?"

"I've been experiencing some... unusual symptoms," you explain, trying to maintain your authoritative tone despite the dampness between your legs and the ridiculous unicorn panties hidden beneath your skirt. "Dizziness, disorientation. Perhaps low blood pressure?"

Nurse Chen gestures to the examination table. "Please, sit down. When did these symptoms begin?"

"This morning," you say, perching on the edge of the table, acutely aware of how your feet now barely touch the floor—had this table always been so high? "During the assembly."

She takes your wrist, checking your pulse. Her touch feels strangely maternal, triggering an inappropriate urge to lean into her care. "Your heart rate is elevated," she notes, frowning. "Have you been under unusual stress?"

"No more than running an academy full of entitled adolescents and resentful faculty," you attempt to joke, but your voice comes out higher, almost whining.

Nurse Chen's eyebrows lift slightly. She reaches for the blood pressure cuff. "Let's check your vitals. Could you remove your jacket, please?"

You comply, revealing the full extent of your blouse's transformation—the Peter Pan collar now complemented by subtle puffed sleeves that definitely weren't part of your wardrobe this morning.

"That's a... different look for you," Nurse Chen comments, wrapping the cuff around your arm. She pumps it tight, watching the gauge. "Your blood pressure is actually quite normal." She releases the valve, studying you with increasing curiosity. "Dr. Blackwood, forgive me for asking, but have you changed your skincare routine recently? Your complexion looks... different."

"Different how?" you ask, a tremor in your voice.

"Fresher. Younger." She leans closer, professional but invasive. "The fine lines around your eyes are less pronounced."

A wave of dizziness crashes over you. "I need to use your restroom," you manage, sliding off the table.

"Of course. Through that door." Her eyes follow you with clinical interest. "Dr. Blackwood? Are you sure there isn't something else you want to tell me? Something about... changes you've been experiencing?"

The knowing tone in her voice freezes you mid-step. You turn back, searching her face. "What do you mean?"

"Professor Hargrove mentioned you might come see me," she says, her voice dropping to a confidential murmur. "He said you might be... regressing in certain ways. That I should document any changes I observe."

Your blood runs cold. "Hargrove sent you instructions about me?"

Nurse Chen's expression shifts to something unreadable. "Not instructions, exactly. Just... observations he thought might be relevant to your care."

You force a smile, deciding to play along to extract information. "I'm surprised Professor Hargrove has taken such an... interest in my health," you say, perching back on the examination table. "What exactly did he tell you to look for?"

Nurse Chen retrieves a clipboard, flipping through pages with clinical efficiency. "He mentioned potential cognitive fluctuations, possible physical changes, and—" she hesitates, "—behavioral regressions. He described it as an unusual stress response in high-achieving individuals."

"Did he now?" You keep your voice light despite the rage building beneath your breastbone. "And when did he first approach you about this... condition?"

"Last Thursday," she answers, uncapping a pen. "He seemed quite concerned about you."

Thursday—the day after your heated budget meeting where you'd slashed funding to his pet research project. The timing can't be coincidental.

"Has he asked anyone else to observe me?" you press, watching her face carefully.

Chen's eyes flick away momentarily. "He mentioned consulting with Dr. Winters about historical cases. And I believe Marcus has been asked to note any... unusual behaviors."

The pieces begin falling into place—Hargrove, Winters, perhaps others, all watching you, waiting for something. But what exactly are they doing to you?

"I'd like to check your temperature," Chen says, approaching with a thermometer. "Open wide, please."

The infantilizing request sends a jolt through you, but you comply, allowing her to slip the thermometer under your tongue like a child. Her hand brushes your forehead in a maternal gesture that makes something inside you squirm with confused pleasure.

"You do feel a bit warm," she murmurs, studying you with increasing curiosity. "Your complexion is quite flushed. And your eyes—they seem different somehow. Wider, perhaps?"

She leans in closer, her clinical gaze traveling down to your blouse. "That collar—it's not your usual style, is it?"

You try to respond around the thermometer, but she shushes you with surprising authority. "Don't speak yet. Thirty seconds more."

The command silences you instantly, your protest dying unvoiced. This compliance feels wrong, yet somehow natural, as if your body is responding to a deeper programming than your conscious mind recognizes.

Suddenly, a familiar pressure builds in your lower abdomen—urgent, demanding, impossible to ignore. Your thighs clench involuntarily as heat floods your face.

"Dr. Blackwood?" Chen notices your distress. "Are you—"

You snatch the thermometer from your mouth. "Bathroom," you manage, sliding off the table and rushing toward the small adjoining restroom.

Behind you, Chen's gasp tells you what you already know—a small dark spot marks the white paper covering the examination table where you sat. The evidence of your humiliation displayed for her professional assessment.

You barely make it to the toilet, yanking down those ridiculous unicorn panties that now feel thicker, more substantial between your fingers. Sitting with your knees pressed together, you realize with dawning horror that the childish underwear has absorbed most of the leakage—exactly as it was designed to do.

You emerge from the bathroom with your dignity in tatters but your resolve hardened. Nurse Chen stands by her desk, reviewing notes with a furrowed brow that deepens when she sees you.

"I know what's happening," you declare, your voice wavering between authoritative and childishly high. "Hargrove is behind this. Whatever he's told you about my 'condition' is a lie. He's doing something to me—changing me somehow."

Chen's expression shifts from professional concern to something more complicated—pity mixed with skepticism. "Dr. Blackwood, please sit down. You're clearly distressed."

"I don't need to sit down," you snap, though your body betrays you as you perch on the edge of the examination table. "I need answers. What exactly did Hargrove tell you to look for? What 'historical cases' is Winters consulting?"

Chen sighs, pulling on latex gloves with a snap that makes you flinch. "Professor Hargrove mentioned potential psychosomatic regression triggered by extreme stress. It's rare but documented." She moves closer, her clinical gaze traveling down to your skirt. "May I check something?"

Before you can answer, her gloved fingers slip beneath your skirt hem, touching the waistband of your ridiculous underwear. "These are... interesting. Did you choose these yourself this morning?"

"No!" The word bursts from you. "I wore black cotton briefs. These appeared—they changed somehow."

"Changed," she repeats, her tone gentle but patronizing. "Like your blouse changed? And your voice?"

"Yes! Exactly!" You grasp at this validation. "So you've noticed it too?"

Chen's fingers continue their examination, pulling the waistband slightly to check the absorbency layer. The intimate inspection makes you squirm, heat flooding your cheeks.

"The mind-body connection is fascinating," she says, ignoring your question. "When we experience psychological regression, physical manifestations often follow. Your bladder control issues, for instance—"

"This isn't psychological," you interrupt. "It's Hargrove. He's doing something to me. Some kind of... I don't know. Drugging me, maybe."

Chen releases your waistband with a soft snap. "Tell me more about these conspiracy theories," she encourages, her tone identical to one you've heard teachers use with imaginative children. "What would Professor Hargrove gain from such elaborate machinations?"

"My position," you say immediately. "My authority. My dignity."

"I see." She makes a note on her clipboard. "And these changes to your clothing—how do you think he's accomplishing that? Magic?"

The word 'magic' sends an electric current down your spine. Something about it resonates, clicks into place like a key in a lock.

"Not magic," you say slowly, though the denial feels hollow. "Something else. Something... older."

Chen smiles indulgently. "Well, whatever it is, I think we should focus on managing your symptoms for now. These training pants seem to be helping with your accidents. Would you like me to provide more for you to use throughout the day?"

The infantilizing offer strikes like a slap. "They're not training pants," you protest, though even as the words leave your mouth, you know they're a lie. The thickness between your legs, the absorbent padding—they're exactly that.

"Of course," Chen soothes, patting your knee. "Now, would you like a lollipop before you go back to class?"

The question hangs in the air between you, horrifying in its casual diminishment of everything you are.

You open your mouth to protest, but Nurse Chen seizes the opportunity, slipping a cherry-red lollipop between your parted lips with practiced efficiency. The sweet burst of artificial cherry floods your mouth, triggering an involuntary response—your lips close around the candy, tongue working against the smooth surface before you can stop yourself.

"There we go," Chen says with a satisfied nod. "Sugar can help with shock symptoms."

You should spit it out. You should demand respect. You should remind her exactly who runs this institution. Instead, you find yourself sucking on the candy, the childish comfort of it sending a confusing wave of pleasure through your body. Your free hand rises to remove it, then falters, dropping back to your lap.

"Now," Chen continues, turning to a cabinet behind her desk, "let's get you properly supplied for the day." She retrieves a small pink package, tearing it open to reveal three more pairs of training pants identical to the ones you're wearing—pastel pink with cartoon unicorns prancing across the front panel.

"These should get you through until this evening," she explains, folding them into a discrete paper bag. "They're our premium brand—extra absorbent with leak guards. Much better than regular underwear for your... current situation."

The lollipop prevents your verbal protest, reducing you to an indignant mumble around the candy. Chen smiles at the sound, her expression softening further.

"It's nothing to be embarrassed about, Victoria," she says, using your first name with casual familiarity that would have earned any other staff member a formal reprimand. "Many high-functioning adults experience temporary regression under extreme stress. The important thing is managing the symptoms while we work through the underlying causes."

She presses the paper bag into your hands, her fingers lingering on yours in a maternal gesture. "I've made a note in your file. We'll schedule regular check-ins to monitor your progress."

The word 'file' sends a jolt of alarm through you. Written documentation of your humiliation, available to anyone with access to the medical records. To Hargrove.

You finally manage to remove the lollipop, though your mouth chases it for a fraction of a second before you catch yourself.

"There will be no file," you say, your voice emerging higher and less authoritative than intended. "And I don't need these." You try to return the bag, but Chen gently pushes it back toward you.

"I think we both know that's not true," she says softly, glancing meaningfully at the damp spot on the examination table. "Better safe than sorry, don't you think?"

The reasonable tone, the gentle insistence—it's the voice of an adult speaking to a child who doesn't know what's best for themselves. And the worst part is, some treacherous part of you responds to it, wants to nod and comply and be told what to do next.


You sit on the examination table, the lollipop bobbing between your lips as you glower at Nurse Chen. The childish posture—shoulders hunched, brow furrowed—feels both foreign and unnervingly natural to your body. The sweet cherry flavor dissolves on your tongue, each suck sending a wave of soothing calm through you that battles against your rising indignation.

Nurse Chen observes your sullen silence with the practiced patience of someone accustomed to difficult patients. She sighs, setting her clipboard down and leaning against her desk.

"Victoria," she says, her voice softening to a tone that makes something inside you squirm with discomfort. "I understand this is difficult. But fighting against medical reality won't help your condition."

She picks up the paper bag containing the training pants and places it deliberately on your lap. The weight of it feels like an anchor, tethering you to this new, diminished reality.

"Now, Vikki," she continues, the diminutive version of your name slipping out so naturally you almost don't register it, "be a good girl for Nurse Chen and take your training panties. Do you want me to help you change into a fresh pair?"

The question hangs in the air between you, breathtakingly intimate and infantilizing. Your mouth works around the lollipop, struggling to form words of refusal, but something in Chen's expectant gaze makes your protest wither. The regression is working its insidious magic—not just on your body, but on how others perceive you, how they speak to you.

"I can manage myself," you finally mutter, removing the lollipop with a wet pop that sounds obscenely loud in the quiet room. "And my name is Dr. Blackwood, not Vikki."

Chen's smile doesn't falter. "Of course, Dr. Blackwood. My apologies." But there's something in her tone—not mockery, exactly, but the indulgent accommodation one shows a child playing dress-up in adult clothes. "Just remember what we discussed about managing your symptoms. If you need assistance, don't hesitate to return."

You slide off the examination table, clutching the paper bag with its humiliating contents. The training pants you're already wearing rustle softly beneath your skirt as you move, the sound audible only to you but deafening in its implications.

"I have a school to run," you say, trying to reclaim some authority. "This... situation... won't interfere with my duties."

"Of course not," Chen agrees, but her eyes flick meaningfully to the lollipop still clutched in your hand. "Though perhaps you might want to finish that in private?"

Heat floods your cheeks as you realize you're still holding the candy like a child's security blanket. Worse, part of you doesn't want to throw it away.

Nurse Chen's eyes narrow with clinical interest as she notices your hesitation about discarding the lollipop. She reaches into her desk drawer, extracting another cherry-red candy with a deliberate slowness that feels like a test.

"Unless you want another?" she suggests, her tone dripping with condescension. "That way you can keep sucking allll day..." She twirls the wrapped candy between her fingers. "Does that sound good, Vikki?"

The diminutive version of your name should ignite fury—this woman works for you, after all—but instead, a different heat blooms between your legs. Your breath catches as a pulse of inappropriate arousal mingles with the humiliation. The conflicting sensations leave you momentarily paralyzed, unable to formulate the cutting reprimand that would normally flow so easily from your lips.

"I..." Your voice emerges small and uncertain. The childish want for the sweet and the adult desire sparked by Chen's patronizing tone create a dissonance that makes your head swim.

Chen misinterprets your hesitation as simple embarrassment. "It's perfectly normal to find comfort in oral fixations during periods of regression," she explains, unwrapping the candy. "The sucking motion activates parasympathetic responses that can be quite soothing."

She holds the fresh lollipop out to you, and to your mortification, your hand reaches for it automatically. Your fingers brush against hers as you take it, and the contact sends another inappropriate jolt of pleasure through you.

"Thank you," you murmur, the words emerging in that same high, girlish voice that keeps ambushing you.

"You're very welcome," Chen responds, her professional demeanor softening into something maternal. "Now, I've noted in your file that you're experiencing some emotional instability along with the physical symptoms. Mood swings, inappropriate emotional responses—all consistent with the regression pattern."

She scribbles something else on her clipboard while you stand frozen, the new lollipop clutched in one hand, the paper bag of training pants in the other, caught between contradictory impulses—to flee this humiliation or to sink deeper into it.

"I should also mention," Chen adds, not looking up from her notes, "that sexual arousal can sometimes accompany these episodes. The brain's regulatory systems become confused, crossing wires between different types of stimulus. Nothing to be ashamed of, but something to be aware of."

Your cheeks burn hotter. How could she possibly know? Is it that obvious? Or is this part of Hargrove's plan—to make you doubt not just your body but your most private thoughts?

"I need to get back to work," you manage to say, backing toward the door, the rustling of your training pants suddenly deafening in your ears.

"Of course, Dr. Blackwood," Chen replies, though her emphasis on your title carries a hint of indulgence rather than respect. "Remember, I'm here if you need me. For anything at all."

You march down the hallway toward the English Department, the paper bag of training pants clutched tightly in your hand, the lollipop still between your lips. With each step, the fabric of your clothing shifts subtly—your pencil skirt shortening, your blouse thinning to near transparency. Your severe bun loosens, hair tumbling down before twisting itself into childish pigtails tied with pink ribbons.

You feel the changes happening but can't quite process them, your mind sliding away from the evidence like oil on water. The cognitive dissonance leaves you dizzy, unable to reconcile what you know (you're dressed professionally) with what's actually happening (you're transforming into a parody of a schoolgirl).

When you reach Professor Winters' office, you knock with more force than necessary, the sound echoing down the empty corridor. The door swings open to reveal Eleanor Winters, her silver hair gleaming in the morning light that streams through her window. Her office smells of old books and Earl Grey tea, academic gravitas incarnate.

"Dr. Blackwood," she begins, then stops, her eyes widening as she takes in your appearance. "My goodness, don't you look like an adorable little girl today."

You open your mouth to deliver your prepared accusation, but the words die in your throat as you catch a glimpse of yourself in the small mirror hanging on Winters' wall. The reflection shows a woman-child hybrid—your adult face framed by girlish pigtails, your body squeezed into a mockery of professional attire that now resembles a naughty schoolgirl costume.

"I—" you stammer, the lollipop clicking against your teeth. "This isn't—I didn't—"

"Come in, dear," Winters says, her voice honeyed with false concern. "You seem distressed."

She guides you to a leather armchair, her hand on your lower back. The touch feels proprietary, knowing. You sink into the chair, your shortened skirt riding up dangerously high, exposing the edge of your training pants.

"I know what you're doing," you finally manage, pulling the lollipop from your mouth with a wet pop. "You and Hargrove. This... transformation. It's not psychological. It's something else."

Winters settles behind her massive oak desk, fingers steepled beneath her chin. "Transformation? I'm not sure what you mean, Vikki. May I call you Vikki? It seems more... appropriate, somehow."

"No, you may not," you snap, but your voice emerges in that same childish pitch that's been plaguing you all morning. "It's Dr. Blackwood. And I want answers about the ancient texts you've been consulting for Hargrove."

A flicker of something—surprise? respect?—crosses Winters' face before her patronizing smile returns. "My, what an active imagination you have. Perhaps you've been working too hard? The pressure of your position..."

"Stop it," you hiss, leaning forward. "I know you're gaslighting me. Making me think I'm crazy while you... while you do this to me." You gesture at your transformed appearance, fighting back tears of frustration.

Winters sighs, reaching into her desk drawer. "I think what you need is a little something to calm those nerves." She extracts a pink pacifier, the sight of which sends a jolt of both revulsion and longing through your body. "Open wide, sweetheart."

You recoil, pressing yourself back into the chair. "Keep that thing away from me."

"Now, now," Winters chides, rising from her desk. "Let's not be difficult."

As she approaches, pacifier extended like an offering, you feel your resolve weakening, your lips parting involuntarily.

You swallow hard, your eyes fixed on the pacifier. The rational part of your mind screams to flee, but another part—growing stronger by the minute—yearns for the comfort it promises. A compromise forms in your mind.

"Fine," you say, your voice wavering between defiance and surrender. "I'll suck that... thing, if you tell me what you're doing with Hargrove."

Winters' eyes gleam with triumph. She moves closer, the pacifier hovering inches from your lips. "A bargain, is it? How delightfully childish to think you're in a position to negotiate."

Despite her mockery, she nods. "Very well. Open wide, little one."

You part your lips reluctantly, and she slides the pacifier in with deliberate slowness. The rubber nipple feels alien against your tongue, yet somehow familiar. Your cheeks burn with humiliation as you begin to suck, the rhythmic motion sending waves of inappropriate calm through your body.

"Beautiful," Winters murmurs, stroking your pigtail with maternal affection that makes your skin crawl even as you lean into it. "Now, as promised—my role in all this."

She returns to her desk, settling into her chair with regal composure. "I am the mother figure, Victoria. The nurturing hand guiding you into your new place here."

"New place?" you try to ask, but the pacifier transforms your words into infantile mumbles.

"Don't speak with your paci in, darling. It's unbecoming." Winters smiles, enjoying your frustration. "Julian approached me with ancient texts—pre-medieval manuscripts describing rituals of transformation. Not just physical, but psychological. Identity itself made malleable."

You reach to remove the pacifier, but your hand stops halfway, caught between conflicting impulses.

"The modern mind dismisses such things as superstition," Winters continues, "but the ancients understood that perception shapes reality. What we're doing isn't magic in the childish sense—it's deeper. Fundamental."

She leans forward, her academic detachment slipping to reveal genuine fascination. "You're experiencing a rewriting of self, Victoria. Your essence reconfigured to a more... appropriate state. The headstrong girl who needs guidance rather than the stern woman who presumes to lead."

Your sucking intensifies involuntarily as anger rises. You manage to pull the pacifier out with a wet pop. "You can't just... remake someone against their will!"

"Can't we?" Winters raises an eyebrow. "Look at yourself, dear. Feel the changes. Part of you welcomes them, doesn't it? The relief of surrendering control?"

You want to deny it, but the words stick in your throat because she's right—beneath the outrage lurks a treacherous relief, a dark pleasure in relinquishing the burden of authority.

"That's what makes the process so beautiful," Winters says softly. "It works with desires already present, just... buried. We're simply bringing them to the surface."

She extends her hand. "Now, shall we continue our discussion? Or would you prefer your paci back?"


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End Chapter 1

Headmistress' Regression

by: Airum | Story In Progress | Last updated May 21, 2025

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