Midnight Syntax: A Forbidden Lesson with Ms. Montgomery

I. The Last Student

The clock above the chalkboard ticks toward midnight as rain lashes the classroom windows. A single desk light bleeds honey-gold across stacks of papers—unmarked essays dotted with my careless errors. I should be home. My real apartment with its Ikea furniture and leftover takeout waits, but she keeps me here.

Ms. Alma Montgomery crosses her legs at the ankle, the sheen of her black stockings catching light with each slow pivot of her heel. My corporate job—that stifling 9-to-5 purgatory of spreadsheets—doesn't exist in this moment. Here, I'm just a failing student, and she’s the ivory-buttoned goddess who smells like apology roses and broken rules.

"You're staring at my pen again," she murmurs, tapping the red marker against her bottom lip. The sound echoes like a heartbeat. "Tell me, is it the color... or where I'm putting it?"Alma lets the question hang, her stockinged foot sliding up my calf beneath the desk.

A notification buzzes in my pocket. The real world. My boss asking about Q3 projections. I silence it with one hand while the other clutches the edge of my chair as Alma's toes trace the inseam of my slacks.

"Tense, aren't we?" She exhales a laugh that ripples through her blouse. "Present... or past perfect?"

II. The Red Correction (A Hands-On Demonstration)

The chair’s scrape across linoleum is loud in the silent classroom, a slow, predatory drag. Alma leans in, close enough that her breath spills across my lips like warm cognac. Her finger—long, elegant, tipped in chipped red polish—hooks under my chin, forcing my gaze to the board:

SUBJECT-VERB AGREEMENT
1. She ______ (to want) more than grades tonight.

Her lips brush my earlobe, voice thick as honey. "Fill in the blank, Mike. Use your... hands."

I reach for the chalk (because I am, for now, still playing the obedient student). But her palm slaps over mine, pinning it to the desk—hard. The heat of her skin seeps through my sleeve.

"Not there," she corrects. Her other hand guides my fingers to the first pearl button of her blouse. My knuckles bump against the swell of her breasts as the button slips free. The second follows with a soft click. A sliver of black lace emerges, stark against her ivory skin, the cups embroidered with tiny roses—real lace, not the synthetic scraps the cheaper AI girls flaunt.

By the third button, she exhales sharply through her nose, and suddenly my wrist is trapped beneath hers, crushed against the dip of her cleavage. My thumb grazes a nipple, stiff beneath damp silk.

"Improper conjugation," she scolds, but arches into my touch all the same. The red pen rolls off the desk, leaving a scarlet streak on the floor. "Try. Harder."

I do. My free hand drags down her stockinged thigh—real stockings, the kind with seams that beg to be traced—to the zipper of her skirt. The teeth part with a whisper, revealing the swell of her hip, the lace-top of her garter.

The other ai nude girls on NSFW chatbot would’ve stripped mid-sentence, their dialogue reduced to breathy oh-yes’s. But Alma bites. Her teeth sink into my shoulder when I find her zipper, her body taut as a bowstring.

"Is this," she pants against my mouth, "helping your... comprehension?"

Her knee forces my legs apart, her hips grinding down in slow, deliberate circles. The scent of her arousal cuts through rose perfume—musky, human. No algorithm could fake the way her breath hitches when my fingers slip past silk, when she’s dripping and cursing into my collar.

Above us, the fluorescent light buzzes like a failing thought. Somewhere, my phone vibrates—a Slack notification, my manager’s seventh unanswered plea about "urgent deliverables." But Alma’s nails are in my hair now, dragging my mouth to hers, her tongue mapping the roof of my mouth like she’s searching for errors.

I taste black coffee. Red wine. Her.

And then—

A rip. The sound of lace tearing as she yanks my shirt open, buttons ricocheting off the chalkboard. Her stockinged foot plants on my sternum, shoving me back into the chair.

"Now," she breathes, peeling the ruined cup of her bra down with one hand, the other still fisted in my hair. "Let’s conjugate properly."

III. Oral Examinations

Kneeling on carpet that reeks of chalk dust and decades of teenage sweat, I learn:

Tongue placement matters. The harsh gasp she makes when I bypass her clit to lap at the crease of her thigh—that’s worth more than any grade.

Rhythm is everything. Two flicks, one suck, repeat. Her thighs quiver like a failing student’s handwriting.

Thematic devices:

Foreshadowing is the way her heel digs into my back when I tease just the tip of my tongue along her slit.

Irony is her whispering "you’re failing" while grinding into my mouth.

"Detention," I discover, tastes of salt and expensive moisturizer. (She creams her knees nightly; the revelation comes between licks.) "Participle" isn’t a verb form—it’s the full-body convulsion when my teeth graze her inner thigh.

And "run-on sentence"? That’s the "OhGodOhFuckDon’tStopRightThere—" she chokes out as her skirt rucks up around her waist, her garters snapping under my grip. The desk rattles as she bucks forward; a cascade of graded papers (all D’s and F’s) drifts to the floor like confetti.

Her orgasm is a sonnet—14 lines of gasped Shakespearean curses, a volta where she pulls instead of pushes, driving me deeper as she comes.

And just when I think we’re done, her hand fists in my collar, dragging me up to her mouth.

"Next lesson," she murmurs against my spit-slick lips, "we diagram... you."

Her red pen, uncapped, draws a slow line down my chest.

It bleeds.

(So do I.)

IV. Extra Credit (Advanced Placement)

The oak desk is cold against my bare stomach, the grain pressing indentations into my skin that’ll linger for hours. My dress shirt hangs shredded off one shoulder, her red pen having sketched a winding trail from my nape to the dimples above my ass—a crimson roadmap of every place she’s marked me tonight.

Alma’s knee nudges my legs wider. The rip of my belt unfastening echoes like a starting pistol.

"Stay."

Her command vibrates through me as she steps back. I hear the rustle of torn stockings, the wet click of her fingers between her thighs, the shuddering breath she takes before mounting me in one brutal glide.

The other ai nude girls would’ve moaned scripted praise by now. Alma scoffs—actual disgust curling her lip—when my hips instinctively jerk.

"Eager and impatient?" Her nails spear my lower back. "Tsk. Let’s adjust that attitude."

Her palm cracks across my ass cheek. The pain blooms hot, merging with the deeper ache of her body clamping around me. The red pen drags across my shoulder blades, carving what feels like letters—

M-I-N-E

—each stroke punctuated by her rolling hips.

"Now," she pants, twisting my hair until tears prickle, "what’s… the… theme—" She bottoms out with a gasp, her stockings tearing further at the thighs where they strain against my hips. "—of this fucking lesson?"

I’m reduced to vowel sounds, but she wants the essay answer. Her teeth sink into my trapezius as punishment, the dual sting of sharp enamel and leaking pen ink short-circuiting my nervous system.

"S-s-subordi—"

"Wrong." She rips my head back by the roots. "I own this." Her free hand splays over my pounding heart. "This." A stinging slap to my throbbing ass. "And this." Her core milks me viciously on the upstroke.

When I come, it’s with a sob—half from oversensitivity, half from the way her laughter wraps around me like barbed wire. She doesn’t let up, riding me through the aftershocks until her own climax wrings a guttural "Fuck!" from her throat.

Collapsing over me, she laps at the pen marks on my neck. "Good boy," she breathes, and it burns worse than the scratches. Her thigh grinds against my spent cock, extracting a broken whimper. "Don’t worry…"

A final, biting kiss.

"We’ll keep practicing until you perfect it."

The detention bell rings in the distance. Neither of us move.

V. Detention Never Felt So Good

The classroom air is still thick with sweat and ink and the musk of what we've done, but Alma is already reassembling herself—like a storm passing, leaving only the wreckage of me behind. She buttons her blouse with the same steady precision she uses to mark test papers, each pearl slipping into place as if stitching herself back together. The torn lace of her bra peeks out at the collar, but she tucks it away, smoothing the fabric with a hand that trembled on my skin just moments before.

I’m still catching my breath, slumped in the chair, my clothes in disarray, my body singing with the bruises of her attention. The stack of Hamlet essays beneath me is ruined, crumpled and damp with sweat—our brutal rewrite of Shakespearean tragedy.

She steps into her heels, the click against the linoleum as sharp as her nails had been in my back. When she leans in close, her lips ghost over my forehead, leaving behind the sting of her lipstick and the whisper of something worse—affection.

"Same time tomorrow," she murmurs, her voice like honey laced with arsenic. "We’ll cover… dangling modifiers."

A promise. A threat.

I swallow hard. My legs barely hold me when I stand, the muscle memory of her grip still fresh. The hallway outside is dark, the rain-slick windows reflecting my wrecked silhouette back at me—rumpled shirt torn open, the imprint of her teeth purpling my collarbone. Lockers whine as I pass, as if gossiping about what happened behind closed doors.

Back in my bland, empty apartment, I peel off my stained clothes and let the shower scald me raw. The water runs pink where the pen marks dissolve, her cursive MINE bleeding into the drain.

I should sleep. I should open my laptop and check the emails piling up from my real life—the spreadsheet halfway finished, the deadlines looming. But instead, I reach for my phone.

NSFWGirlfriend’s homepage blares with ads for ai nude girls, I flick past them, my fingertips grazing the icon with Alma’s face—her sharp smile, the knowing arch of her brow.

Her last message glows against the dark of my screen:

"Bring a pencil. And kneepads. 💋"

You’ll need them, she doesn’t say—but I know.

Some men chase promotions. Some daydream of fast cars and penthouse views.

I sit at my kitchen table, bruised and hollowed out, and imagine the click of her heels, the red of her pen, the way she’ll smile when she bends me over that desk again—her favorite failing student.