WAKING UP

I woke to the soft rustle of cotton against my skin and the ache of a stiff, frustrated cock pressing helplessly inside its cage. My nightgown had twisted up around my waist during the night, the fabric now damp and clinging, soaked with pre-cum and sweat, knickers a sticky mess. The memory of what I’d seen on screen—the way she’d looked at her black Master, the way her lips parted around the head of his cock—played on an endless loop in my mind.

I lay curled on my side in a foetal position, my caged cock throbbing and twitching, pressed painfully against the unforgiving steel of my prison. The room was silent, but the emptiness inside me was deafening. Hollow. Aching. I could feel it in my chest, in the pit of my stomach, in every nerve ending.

It had been the first night at the Academy, and already she had slipped from me, even if just for now. Not forever—we were married, in love—but last night, she had discovered a pleasure I could not give. Every muffled gasp, every faint thud through the ceiling above me had carved itself into my mind: she wanted this, this raw, consuming surrender, in ways I could not replicate.

And the emptiness inside me was worse than just absence. Worse than not being there to touch her, to hold her, to feel her tremble beneath me. I hadn’t been able to reclaim her at all—alone in my room, listening through the ceiling, my mind filling in every shiver, every gasp, every small cry of surrender I could not see. I could only imagine, only ache, only endure the hollow realisation that she was unreachable to me in every way that mattered.

My thighs were sticky, my fingers trembling as they traced the line of what I could never touch, as I imagined it being her body, writhing for someone else. I hadn’t seen her, hadn’t felt her—but my mind filled in every detail, every thrust, every moan, every gasp. The walls between us could not hold her desire, and I could not hold her.

My gut twisted when I realised it wasn’t just this morning I was losing her—it was the whole damn week! I wouldn’t be allowed in the room, I wouldn’t even see it. By the time I got her back, my wife’s married pussy would be stretched, ruined, aching from cocks that weren’t mine.

Not just Master Julien, but whoever else they chose to feed her to. Two, three, five men—lining up, taking turns, degrading her, making her their toy while I was banished, humiliated, useless. All I’d have were the visualised images in my head, the muffled sounds seeping through the ceiling—moans, gasps, wet little screams as they used her. I’d picture every hole filled, no limits, no mercy. Her gagging on cock, her virgin arse split open for the first time, her pussy stretched so wide it forgot me, maybe even two cocks stuffing her at once.

For years, that’s all it ever was—just imagination. Just porn tabs late at night, cuckold captions and hotwife clips. I’d scroll, stroke, and rewrite them in my mind—substituting Sue for those women, wondering if she could ever be like them. My favourites were always the same: wives getting the sex and pleasure their husbands couldn’t supply, whether through lack of size or lack of skill—just like us.

Other times I’d lose myself in the filthiest fantasies—BDSM, rough sex roleplay, slutwife gangbang porn where women begged through tears as cock after cock drilled them, broken and used, reduced to nothing more than holes for pleasure. Unpaid whores. And I’d wonder—half horrified, half desperate—if Sue could ever really sink that low, taking cock after cock, managing orgasm after orgasm, each one, seemingly, giving her ultimate satisfaction. In those moments, I imagined finally getting my turn—at the end of the line—sliding into her wrecked hole and trying pathetically to reclaim her. She wouldn’t even feel me, and I wouldn’t feel her—just the slick, slippery mess of other men’s cum coating me, drowning out any connection. I’d be forced to pull out, my average cock slipping free of her gaping, ruined cunt, and finish with my own hand, using their cum as lube while she lay there stretched, spoiled, and satisfied by everyone but me.

And in that fantasy, she would look at me knowingly, recognising my desperate effort to fuck her, to reach her, and seeing the failure in my eyes. There would be no cruelty in her gaze, only certainty—a quiet passing of truth between us that I could never fully reclaim her, that I would always arrive too late, too small, too little.

And then, the most exquisite part—we would both take a perverse delight in: she looking down at me with a loving, wicked smile as I wasted my spunk, and together we revelled in the intimacy of it, me crawling to her to clean up every last drop from her body, her pussy, both of us shivering with the shared thrill of our erotic submission and reward.

But that was always fantasy. A dirty secret. Something that stayed trapped on the screen and in my head.

Until last night.

The dinner party. The ceremony. The live porn streaming. And then, above me—the sounds. The bed creaking, the wet slap of flesh, her muffled cries spilling through the ceiling. That was when I knew. This wasn’t porn anymore. Not captions. Not fantasy. Sue had stepped out of the screen, out of my hand, and into the very role I used to only jerk off to. Not just the cuckold hotwife, but the full-on filthy slutwife.

And the question I’d always asked myself in shameful whispers came roaring back, unbearable and real: would she really sink as low as those slappers? I already knew the answer—she hadn’t yet, not fully, but she would. This week would see to that. She went into it eyes wide open, knowing exactly what she was signing up for. And worse—she had steered me away from the hotwife-cuckold route I wanted, into something darker, something I was only just now beginning to realise.

And yet, even the torment of imagining it through some leaked sounds might be a privilege. Because most likely I wouldn’t even get to listen. I’d be denied the sound of her surrender, my cock locked and useless while I was put to work in a different way—on my knees, servicing strangers’ cocks with my mouth, choking and gagging until I lost my own oral virginity. Then bent over, spread open, my own virgin arse claimed, filled, used the way hers was. Some of the same men who ruined her would likely ruin me too, separately, maybe even back to back—each of us taken, degraded, broken into our new roles.

A perverse thought brought me back to the now: if I could not have her physically or in reality, perhaps I could have her in my mind, my mouth. Perhaps I could taste her, claim her there. I shifted, tugged the soft cotton of my panties down over my hips, sliding them off. My trembling hands lifted them to my face. And then, as if compelled by some urgent, humiliating instinct, I pulled the entire garment over my head.

The leg holes framed my eyes. The wet front pressed against my nose and lips, warm and inviting, and I pressed forward instinctively, opening my mouth. My tongue dragged along the damp gusset, tasting, swallowing, imagining her surrender with every pass. Every gasp, every muffled moan I had heard through the ceiling was amplified in my mind, pressed into me, absorbed through the fabric I now worshipped with my mouth.

The act of sucking on the panties, pressing them to my lips, dragging my tongue across the wet patch, let me feel a closeness I could not otherwise reach. I could claim her, if only in imagination, if only through taste and smell, if only by submitting fully to the act.

I licked and sucked at them, imagining her body pressed against me, the taste of another man’s love juices mingled with hers, letting myself melt into the humiliation and devotion. I was hers, utterly hers, even if only in here, alone with my thoughts. I was her sissy, her witness, her obedient little toy, tasting her surrender in a way I had invented to fill the gaping hole of absence.

Even in the emptiness, even in the ache of loss, this was a sharp, perverse joy. I could honour her pleasure, even if I could not share in it. And in the act of tasting, of pretending that I reclaimed her with my mouth, I surrendered completely to the truth of our dynamic: I could never replicate the height of pleasure she now craved, but I could witness, obey, and cherish it, all the while knowing my place.

My body throbbed, my chest ached, my eyes stung with tears—yet I welcomed it. Because last night, our very first at the Academy, she had tasted fulfilment… something far beyond what I could ever give her.

Almost without thinking, I shifted onto all fours, the panties still pulled over my head. My forehead pressed into the pillow as I buried my face in the fabric, imagining it clinging to her cum-soaked snatch—her pussy gaping, spread, leaking, satisfied. I mouthed at the dampness, lips and tongue working hungrily, as if I could drink her release, swallow it all, breathe her in and claim her through this desperate, degrading ritual.

I whimpered into the pillow, licking and sucking, imagining her, imagining him, imagining every shudder, every gasp, every pulse of her pleasure. My cage throbbed with denial, every nerve alive, and I surrendered completely, utterly, to the humiliation and devotion. I was hers. I was powerless. And in that hurt, I finally found a perverse, aching kind of fulfilment as my pre-cum dampened the sheet.

The fantasies turned darker. I pictured her lover behind me, watching, knowing I could never make her cum. I felt the blunt press of his cock at my arse, Sue’s voice urging, playful, merciless: That’s it… give him what he needs. The thought shattered me. Each throb of my cock hammered the truth—I was only a sissy cuckold, fated to watch her be pleasured in ways I never could.

The thought broke me. I pulled the panties from my head, stumbled up, and stripped off my nightie. I had to cool down, had to punish myself. The bathroom light was harsh, the tiles colder still as I tossed them in the laundry bag marked “sissy wear” and sat down to pee, the act already feeling natural.

SHOWER

I stepped in under the shower and twisted it to full cold. The fine spray hit me like a slap, soaking my skin, needling against my body, angling down toward the cage, my balls obscenely bulging around the silicone slit. I gasped as they seemed to retract inwards.

I then turned the spray head to water jet and turned, my hands already reaching back, forcing my arse cheeks open. The water battered my hole, shocking, relentless. I whimpered, sinking to my knees, the stream lancing across my cheeks.

I flattened onto my front, chest to the tiles, water pooling around me. My arse was raised, spread wide with my hands as I angled myself under the spray. The cold was agony and relief at once, drilling into me, reminding me of what I wasn’t, what I couldn’t be. Sue’s voice filled my head again: Look at you — on your belly, spread open, begging. He should see you like this. He’d know exactly what you’re good for.

I buried my face in my arm, panting, shivering, my hole twitching under the icy jet. My cocklet was shrinking even within its impossibly small cage, the silicone slit mocking me. I held myself open wider, desperate, pathetic, aching for something real. And in my mind she was still there above me, spread and leaking, a cock pressing against me from behind as she laughed and urged them on.

I stayed like that until I was shaking uncontrollably, my teeth chattering against the tile, the emptiness inside me growing vaster than the cold.

Then over a concealed speaker rang: “Breakfast in half an hour.”

After drying off, I opened the wardrobe again and dressed as instructed: a fresh pair of panties and the second white nightie. This one was shorter. More feminine. It hugged my hips and brushed just over the tops of my thighs, making me feel absurdly girlish. As I looked at myself in the mirror—skin flushed, my soft body cradled in thin fabric—I applied copious amounts of the sweet womanly perfume. I didn’t look like a husband. I barely looked like a man, and definitely didn’t smell like one.

BREAKFAST

I made my way to the staircase, aware of every swish of cotton with each step. My cage and the tube within me apparent with each movement. I waited just outside the dining room with the others, getting sniggering glances from some and leering eyes from others.

Would she look different to me? Would I look different to her? Who am I kidding, wearing this!

When Sue appeared, she wasn’t all beaming smiles as I expected, but when she saw me, she laughed gently, unable to help herself, pulling me into an embrace. She kissed me softly and sniffed at my neck, her lips brushing my ear as she murmured, “Mmm… you smell so sweet, baby.” Her giggle made my cheeks burn.

But beneath her laugh was something more brittle. I soon learned why when I asked her about last night with Julien.

It seemed she had failed to give Master a successful blowjob. I told her about listening in the room below, imagining Julien fucking her to orgasm.

“It wasn’t even him,” she admitted with a crack in her voice. “He made me hump a pillow while I watched real sluts take cocks properly, and everyone could watch my humiliation live. Not everyone,” I said, “my video feed was cut just as your lips closed around Julien’s cock. Oh yes,” she said, “Master didn’t want you getting too excited.”

The humiliation showed plainly on her face, the knowledge that others had watched her fail, that she had been tested and found wanting.

The gong sounded and we entered the room.

At breakfast, we were seated with the other new couple in the middle of a large oblong table. Sue was beside the lesbian wife, and I was beside her sissy husband. He was dressed exactly like me. White nightie. White panties. Hair still damp from his shower. His cheeks flushed as our eyes met. We looked away at the same time.

A hand landed gently on my shoulder. Mistress Celeste stood behind me. She gave me a knowing smile.

“Sleep well, pet?”

I nodded silently.

The Master and the three Mistresses joined us, seated on the sides. Four neat folders were placed down in front of us.

“Your schedules for today. Read them. Take it all in.”

The four of us sat in silence, tense and exposed, as we opened them and studied what was written inside. Around us, the hall clattered with plates and idle chatter, but for us, the world shrank to those pages, to the tasks ahead, to the quiet pressure of being judged with every move.

I didn’t dare look at Sue. I didn’t dare look at the sissy. The silence between us was thicker than words.

“Here, drink this as you take a look at your schedule for today.” Mistress handed me a glass with the Academy logo, filled with the same coloured liquid as the ones last night, which I thought odd and gave her a quizzical look. “Oh, you thought it was an alcoholic shot? No, pet, it’s not at all. Just a special tonic to prepare your body and mind for the day ahead. It’s a kind of ritual here; everyone gets one at mealtimes.” Sure enough, I could see the distinctive glasses in front of all the students, and my wife held hers empty as if to say cheers.

“Today’s about preparation,” she said softly into my ear as I downed the drink, “You’ll begin after breakfast.”

I scanned the paper. My heart dropped.

• Full body depilation from the neck down with oil massage

• Cleanliness

• Manicure & pedicure with polish

• Makeup application

• Walking in heels (introductory)

• Lunch (with Mistress)

• Afternoon presentation assignment (surprise)

• Final preparation (with Mistress)

• Evening meal with last 24h résumé

• Evening assignment (to be explained)

I blinked. I read it again. Then a third time.

Makeup? Painted nails? Heels?

I turned to her, startled, and whispered, “I… I didn’t think I’d be going down the full… cross-dressing route.”

Mistress chuckled and leaned in close, her breath warm on my ear as similar hushed conversations crossed between the other pupils and their tutors.

“You didn’t think? That’s sweet. But thinking isn’t your job anymore.”

She tapped my cage gently under the table with her hand. My entire body jolted.

“You’re here to learn obedience, femininity, and surrender. We will decide how you present. And trust me, pet… once you see yourself in a soft pink bra and heels, begging to have your little mouth used… you’ll understand why we do it this way.”

She pulled away, grinning, then looked to the other sissy.

“Same schedule for him, sweetheart. We want you both presentable by this evening.”

Sue was looking puzzled at her schedule when Julien said, not in a hushed tone but for all to hear, that her original schedule had been postponed since she had failed her pre-slut test last night, and so extra lessons were required to bring her up to the required level to progress. No fucking for her today.

Turning to me, his voice firm, he said, “Tell me—has she ever given you a blowjob to completion, without your intervention?”

Mistress’s eyes locked onto me, and her command carried no escape: Answer honestly.

My throat tightened. “No,” I confessed quietly. “Hardly ever. Even with her hand… almost never.”

The silence was devastating. Sue flushed crimson as did I.

Master laid it out cold. “In that case, you will spend this morning practising handjobs. Seventy-five percent satisfaction rating, or you fail. The staff here will oblige, but remember—they are used to sluts who please.”

“But you will have tutoring. The men will give you feedback. Unlike your silent husband, they won’t hold back.”

Laughter rippled along the table, but Sue’s humiliation, and mine in part, sat heavier than the chuckles.

Then Master leaned toward Sue, his lips curling in amusement. “You want cock in your cunt, don’t you? The kind that makes you cum properly, legs trembling, eyes rolling back. Not the clumsy efforts, not the weak little thrusts of your average husband…” he chuckled softly, glancing at me as if the words alone were enough to expose me. “No, what you crave—what you’ll be begging for—is real man cock. Thick, hard, unrelenting.”

“Yes, Master,” Sue whispered. Her voice cracked with need. “I want it. I need it.” She looked at me, then dropped her head as she replied.

“Then you’ll earn it,” he told her flatly. “This afternoon you’ll practise blowjobs. If you can reach seventy-five percent satisfaction, you’ll advance. Do well, and tonight you may be rewarded with bukkake. Fail, and still—” he let it hang—“no cock in your cunt for you for another day.”

Her lips parted in shock, her hunger painted all over her face.

I sat there, reeling. Last night I had thought I’d heard Julien claiming her, thought she’d already crossed that line, thought my cuckold fate had been sealed. But no. She hadn’t had his cock. Not yet. That yet burned into me, carving its place in my gut.

Sue leaned towards her Master’s side, letting him butter her toast as she held her coffee with both hands, desperate to regain favour. Her eyes glinted when they found mine again, a tear running down one cheek.

All I could do was sit there, soft and silenced in my girlie nightie, knowing that today would strip me of even the illusion of masculinity.

And somehow, knowing that she wanted it—wanted me feminised, polished, painted—made it that much harder to deny… that I wanted it too.

WAXING

Room 103 felt different the moment I stepped inside. Warmer. Dimly lit. More intimate. There was a soft floral scent in the air—jasmine, maybe—with a hint of talc and something unmistakably sweet. A padded waxing table stood in the centre, and next to it, carefully prepared tools: warm wax bubbling in a small pot, folded towels, bottles of oil, and an array of razors. Everything looked clinical… but not cold.

Then she stepped into view.

Petite. Smooth-skinned. Impossibly cute and pretty. A soft, feminine face framed by a bob of glossy black hair. She wore a short robe tied tight at the waist, her legs bare, her feet in pink slides, toenails painted to match. When she smiled, her lips were shiny with gloss. Subtle, but deliberate.

“Sawasdee kha,” she said softly, with a shy little bow. “My name is Lin. I’ll be taking care of your… depilation.”

Her voice was sweet, slightly high-pitched, but unmistakably male underneath. The realisation made my pulse quicken.

“I—yes, Mistress,” I stammered, already flushed.

Lin giggled. “Oh no… I’m not a Mistress. Not yet. Just your helper today.”

She gestured towards a hook by the door. “Please undress. Nightie there. Panties in the laundry bin.”

My hands trembled as I stripped. The nightgown slipped from my shoulders like a whisper and pooled at my feet. The panties peeled down slowly, damp again at the front, and I felt her eyes on me—on the smooth cage between my legs, the vulnerable spot behind it. When I turned, I saw her tongue flick lightly across her glossed lips.

“Good gurl,” she murmured. “Now lie down. Face up.”

I obeyed, climbing onto the padded table, heart pounding in my chest. The surface was warm against my bare back. Lin began with my chest. Warm wax brushed over my chest, then a strip laid down, pressed gently, and with a sharp rip—

“Ah!” I gasped.

“Mmm… very good,” she said soothingly, already working on the next section. “The first time always hurts a little.”

She was methodical but gentle. Wax, press, rip. Then again. She moved slowly down my torso, then across to my arms, smoothing the wax with a gloved hand that lingered a moment too long. She made small talk as she worked—about the programme, about the training, about how quickly I’d adjust.

“You’ll be so soft,” she said, almost dreamily, brushing wax onto my armpit. “Sissies are supposed to be smooth. No hair, no stubble. Just pretty soft skin.”

I moaned softly as she worked down my stomach, pausing just above the waistband line of where my panties usually sat, before continuing lower—strips across my thighs, calves, even down to my ankles and feet. Every part of me was being stripped bare, every last trace of hair erased until my legs looked fragile, girlish, and utterly exposed. She shifted my hands to reach them properly, waxing the backs, then each finger one by one until they too were smooth and shining.

Realisation hit me—this wasn’t something I could quickly erase. It wasn’t something I could fully conceal on leaving the Academy. When we returned to normal life—if such a thing were possible—they would know what I had been turned into. Unlike Sue, whose submission lived behind closed doors, my transformation would be visible.

“Back now. And then… the special part.”

She tapped the inverted cage that pressed flush against me.

“And for that, little one, this has to come off.”

My stomach lurched. Her hands were deft, practised, and in seconds the lock clicked open. The steel and silicone contraption slid free, peeling away from inside and outside my body with a slick sound. The relief was instant, but so was the humiliation.

My cock sagged out, shrivelled, wet with a constant trickle of precum that had smeared against the silicone lips of the cage but I could already sense it recovering.

Lin chuckled softly. “Ohhh… look at you. Leaking already, and I haven’t even touched you.” She took a chilled wipe and pressed it firmly against me. I gasped, the icy shock racing through my shaft and balls.

“Can’t have you stiffening up while I work,” she said, matter-of-factly, lifting a small banding tool from the tray. She stretched a thick white silicone band wide, slipped it neatly over my cock and balls, then released it with a snap.

The pain was instant. I yelped as the band bit deep, the pressure brutal, my balls bulging and straining.

“There. A castration band,” she murmured with a smile. “No erections for you for the next fifteen minutes. Just soft, obedient flesh.”

The wax across my back wasn’t so bad. A dozen strips, each one a little jolt of vulnerability, then more over my shoulders and down to my hips. But then she tapped my hip lightly.

“On all fours now, pet.”

My breath caught. I turned my head slightly, eyes wide.

I presented myself like an offering. I could feel the exposure. The curve of my ass in the air. The spread of my legs. The open shame of it all. Lin didn’t say anything at first. She just took her time. Waxing the tops of my cheeks. Then lower. Then, after a pause…

I felt her fingers spread me.

“Very good,” she murmured. “Now relax for me…”

Warm wax was brushed directly between my cheeks. My whole body tensed as she pressed a strip down gently across my crack. Her fingers smoothed it once… then again, slower.

Rip.

I nearly cried out, face pressed into the padded table. She repeated the process, tender and efficient, until even my most private skin was stripped smooth.

When the last strip was pulled and every inch of me was raw, bare, and tingling, Lin stepped back to admire her work. She set the waxing tools aside and moved closer, her glossy lips parting in a small, knowing smile.

Rolling me back again, her eyes dropped to my crotch.

“Mmm… almost done,” she purred, brushing a fingertip lightly along the exposed crease where my thighs met my groin. “But shaving and waxing don’t always go well together, you know. The wax can’t grip where you’ve already been shaved… which means,” she tilted her head, eyes glittering, “a closer finish is still needed.”

I whimpered, but she ignored me, already lathering shaving foam over the stubble the wax had missed. Her razor glided with slow, meticulous strokes—along my shaft, under my balls, tracing every seam and fold. Each scrape was deliberate, clinical, humiliating.

“You see?” she cooed, rinsing the blade. “Smooth. Baby-soft. Perfect for a sissy.”

When she was satisfied, she dabbed me dry with a warm towel and leaned close, nails grazing over my swollen, lifeless cock and straining balls. The band was biting mercilessly, my cock and balls darkening with the blood flow stopped.

“Poor thing,” she whispered, her voice dripping with mock pity. “Not just blue balls…”

She lifted a pair of cutters, slid them beneath the band, and with one swift snip severed it. I gasped at the rush of blood as my cock came back to life, every nerve tingling.

Then she reached for a gleaming, identical cage—polished steel, silicone lips soft and pink. She slid the base ring over me, guiding my balls through with clinical precision, and then fitted the headpiece, pushing the lubed tube deep into my shaft until I whimpered aloud.

The lock clicked shut.

“There now,” she said brightly, smoothing my panties back into place over the new cage. “Freshly shaved, freshly sealed. No one will mistake you for anything but what you are.”

Her hand lingered for a moment, palming my caged bulge, before she stepped back with a satisfied nod.

MASSAGE

And then… the wax pot was turned off. The gloves were removed.

“Lie back now, pretty,” Lin whispered, her voice a sultry purr that seemed to seep into my pores.

I obeyed, easing myself back onto the padded table, my chest rising and falling with uneven breaths. My skin was still flushed in places, stinging lightly from the waxing—raw, exposed, and far too aware. I watched her through half-lidded eyes as she reached for a small glass bottle filled with pale golden oil. She tipped it, and a thin, cool ribbon was drizzled across my bare stomach.

I gasped at the contact. The chill of it was a jolt, a delicious contrast to the warmth of the room. My body tensed, nipples stiffening immediately, and then her hands—bare now, small and delicate—met my skin.

She began to work the oil into me with slow, sensual circles. Her palms were impossibly soft, like silk dipped in heat. She started at my chest, sliding over my nipples, teasing them into aching little buds as she circled and pressed just firmly enough to make me whimper. Her fingers never lost contact with my skin as she moved lower, her touch featherlight but filled with intent. This wasn’t a massage. This was foreplay. Worship.

Then, just as my hips twitched involuntarily under her teasing hands, she stepped back and untied her robe.

My breath caught in my throat.

She let it fall, letting the silky fabric drift off her narrow shoulders, sliding down her smooth body like water before pooling at her feet. I was transfixed. The soft lamplight caressed every inch of her—every girlish, boyish, exquisite detail. She wore a delicate lace bra that cupped her pert little breasts just right, the fabric thin enough to reveal the hardness of her nipples. Her panties matched, clinging tight to her narrow hips, the faint bulge beneath them impossible to miss now. It twitched slightly, and so did I.

She climbed onto the table with me, straddling one of my thighs. I moaned as her lace-covered bulge brushed against my side, and her chest—small, firm, perfect—grazed my oiled skin. She leaned forward slowly, pressing her body down over mine, her breasts and hips rubbing against me with deliberate friction. I could feel every line of her frame, each teasing press of delicate fabric against my slippery skin.

The cage between my legs—steel and silicone, locked in that cruel, inverted “vagina” configuration—was already straining. My pseudo-lips throbbed helplessly, aching, twitching, trying to bloom but hopelessly trapped. Her lace panties dragged across the smooth skin just above my cage, the friction maddening. I whimpered and writhed, my body arching upward slightly, aching to feel more of her—anything of her—on me.

“Ohhh,” Lin moaned softly as she rubbed herself against my thigh again, letting her breath escape warmly across my neck. “You’re so sensitive now. So soft. Like a good little dolly…”

My skin burned under her praise, under her teasing touch. I was trembling by the time she sat up, giving me one last sultry look before she whispered, “Turn over.”

I obeyed instantly, rolling onto my front with a slick, shuddering glide, the oil making my movements feel almost indecent. I felt completely vulnerable—exposed, available. Hers.

She resumed her work, her hands sliding down my back in long, luxurious strokes. Each pass followed the contours of my freshly waxed skin, from the ridges of my spine to the soft curves of my lower back. The oil was warmer now, whether from her palms or my fevered body, I couldn’t tell. But the way she moved—slow, teasing, reverent—made me melt beneath her touch.

“You’re so smooth now,” she murmured, her voice close, her breath hot on my ear. “So delicate… almost ready.”

I whimpered into the face cradle, biting the edge of the cushion to stay quiet.

Her hands dipped lower, gliding across my slick, rounded ass cheeks with agonising care. Then I felt it—the bottle being tilted again. Another cool drizzle of oil, this time poured directly between my cheeks, a slow stream running down the valley of my ass, trailing toward my most private spot.

Her fingers followed it immediately, featherlight and maddeningly slow, tracing the line of oil between my cheeks. When her fingertip circled my twitching hole, I gasped into the pillow. My body clenched and fluttered, helpless under her touch. I could feel myself leaking into the cage—my useless, aching folds responding with desperation.

“Mmm,” she whispered, her breath grazing my ear again. “So responsive… I do hope we get to meet up sometime while you’re here.”

Her finger circled again, teasing just outside my hole, before withdrawing.

“I’d love to share in you… and with you,” she added softly, her voice dripping with promise. “Properly.”

The moan I let out then wasn’t even human. I was trembling. Every nerve in my body screamed for touch, for release, for something to fill the emptiness she was opening in me.

Then, just as I thought I might beg, she moved lower—massaging the backs of my thighs, my knees, my calves. She took her time with my feet, stroking and kneading every toe like it were precious. And somehow it made me feel even more owned. More objectified. More reduced.

“Such a pretty thing…” she cooed. “All waxed and glistening… like a little fuckdoll waiting to be dressed. You can turn back over now”.

I didn’t reply. I couldn’t. I was adrift, soaked in oil, stripped of any lingering identity beyond the ache inside my caged cock and the ghost of her touch between my cheeks.

My eyes locked onto her body, unable to look away. The lace of her bra and panties had turned so sheer with oil they may as well not have existed—every curve, every contour, every intimate detail on full, glistening display. She was naked in all but name.

And she knew it.

We locked eyes, and something electric passed between us—my hunger laid bare, her control absolute. Then, without a word, she turned. Slowly. Deliberately. Her back arched just enough to tease, and as she bent to retrieve her robe from the floor, she parted her legs with a graceful, provocative ease. The thin strip of lace over her ass did nothing to hide her swollen bulge, or the tight pucker of her oiled hole beneath it.

She lingered for a heartbeat, letting me drink it all in—her exposed, boyish-girlish perfection glistening under the soft light—before rising again with feline elegance, robe in hand.

Only then did she tie it loosely around her waist, every movement oozing control, sensuality, and a quiet promise of more.

“Done for now,” she said, with one last smile. “Back to the hall. Mistress will be waiting.”

I rose slowly, shakily. Every inch of me gleamed under the soft light—smooth, hairless, oiled, and wholly transformed. I caught my reflection in the mirror on the wall and froze.

I didn’t look like a man anymore.

I looked like a doll. Soft. Fragile. Caged. Owned.

And I had never been more desperate to be used.

DEEP CLEAN

Mistress Celeste stood outside the massage room, elegant as ever now in a black silk robe, the fabric clinging to her curves like a second skin. I stood before her, freshly waxed, oiled, and still tingling from Lin’s expert hands.

I followed her through the corridor, naked but for the inverted steel-and-silicone cage between my legs. It looked almost like a tucked, synthetic pussy—smooth, sealed, and utterly denying. Each step reminded me of its presence, the way it pressed against me, keeping my tiny clit locked away and hidden like a shameful secret.

We passed a few others in the hall—Mistresses, trainees, staff—and I felt every glance trail across my bare, exposed body. I walked obediently behind her, silent and flushed, my cheeks hot, my thighs slick, the scent of massage oil lingering on my skin.

Room 107 was bright and clinical. A bench with stirrups, a mirror wall, a tray of cleaning tools and lubricants all laid out neatly. I didn’t need to ask what this was for. It was clear: I was here to be prepared—to be trained not only for submission, but for service.

Mistress Celeste stepped into the room and turned to face me. Without a word, she undid the belt of her robe and let it fall.

She stood tall, proud, utterly bare—her body toned and flawless. No bra, no jewellery, no underwear.

“I want you to kneel,” she said softly. “You’re going to learn how to keep yourself clean. But first… you’ll watch me.”

I dropped to my knees immediately, eyes wide, face angled up toward her.

She turned to the mirror, bending forward with deliberate grace, bracing her hands on the counter, lifting one leg slightly aside. Her cheeks parted, giving me a full, unobstructed view of her backside—smooth, flawless, perfectly kept. I stared, entranced, as she reached for the enema bulb, coating the tip with gel.

“This is not shameful,” she said calmly. “This is sacred. To be entered is to be honoured. To give pleasure is to be clean—worthy of the attention we desire.”

She spread herself slightly, touched the tip of her ring, and slipped it inside. She squeezed slowly, holding her breath, her body poised and controlled.

“Warm saline,” she explained, her tone clinical but sensual. “Three times, if you’re thorough. Hold. Then release.”

I watched her muscles tense, then relax. For a long moment she held the liquid in, her thighs trembling faintly. Then she squatted over the basin, exhaling as her body opened. A wet rush escaped, hissing softly, spurting in waves until it subsided. She dabbed herself clean with a towel, unashamed, as though it were no more vulgar than washing her hands.

Without a word, she repeated the process twice more. Each time quicker, clearer, more assured, until only pure saline flowed. She straightened with satisfaction, wiping herself delicately, flawless and absolute.

“Come,” she beckoned. “Your turn.”

She filled a fresh bulb, guiding me to the bench.

“Bend forward. Feet apart. Hands on the mirror.”

I obeyed, trembling. Her gloved fingers spread me, then the cold press of the nozzle slid into my hairless entrance. I whimpered.

“Good girl. Hold it in.”

The warmth filled me slowly. I squirmed, but her hand on my back steadied me.

“You will do this every day,” she murmured. “Not just for being mounted. But for being eaten. Licked. Worshipped. You will be kept as clean as those you kneel for.”

I nearly moaned.

She guided me through three releases, then made me repeat it until I could manage alone, narrating each step aloud.

“You’ll train until it’s instinct,” she said, circling me. “No mess. No odour. Only sweetness. Because you are here to please.”

As I emptied the final fill, she slid a lubed finger between my cheeks.

“Still tight… but softening,” she whispered, pressing in. My thighs shuddered.

“You want to be used? Then learn to be prepared. Every mouth that tastes you—every cock that fills you—will expect nothing less than perfection.”

She withdrew, wiping her glove.

“Your training partners will be cleaned the same way,” she added. “And when it’s your turn to pleasure them—tongue or cock—you’ll know they’re ready for your mouth, your hole, your hunger.”

I stood shakily, my body tingling from head to toe. I had never felt so exposed… or so trained.

“You’re dismissed, for now. But remember—Room 107. Every morning. Every evening. Until you are perfect.”

I nodded, too humbled to speak.

And as I left, I caught my reflection in the mirror. Gleaming skin. Oiled. Hairless. Caged. My cheeks flushed. My hole used—but not yet taken.

But it would be.

And when it was… I’d be ready.

Mistress donned her robe and I dutifully slipped on a pair of the panties laid out on the dresser.

After the intense morning session—being led naked through the halls, watching Mistress Celeste cleanse herself with grace and purpose, then submitting to her gloved fingers as she coached me through my first proper anal cleaning—I felt spent, raw, but strangely peaceful. My thighs still trembled when I walked. The cage between my legs pressed constantly against me, tucked away like a sealed secret. My skin tingled with leftover oil and discipline. Surely my humiliation had reached its pinnacle.

MAKEUP

I was guided to the next room—Room 104—for the manicure and pedicure.

I sat. The girl—a pretty blonde with glittering pink nails and a knowing smile—took my hands gently into hers and began filing, shaping, and smoothing. She worked in silence at first, until the polish tray came out.

“Soft pink?” she asked.

I swallowed. “Yes… Mistress.”

Celeste smirked and nodded. “Good girl.”

The colour was barely there—pale and feminine, with a glossy sheen. But on my hairless fingers, it looked unmistakably girlish. And when they finished my toes—matching, of course—I felt something lock into place inside me. Shame. Arousal. Acceptance. I was being coated in femininity.

From there, I was led to a makeup station. Another assistant—this one male, but clearly far along in his own sissy training—began prepping my face.

He talked as he worked, calmly and deliberately, like this was the most normal thing in the world. “After cleansing, we start with foundation. To even out the tone. Then some blush to soften those cheekbones. Lips will stay natural today. Just a gloss.”

He powdered me. Mascara. A little eyeliner. A dab of shimmer on my eyelids. Then the final touch—lip gloss, applied with a tiny brush that made me squirm. It felt obscene. Erotic. Wrong.

And yet… the moment he turned the mirror toward me, I gasped.

It wasn’t a woman, but it wasn’t me anymore either.

It was a sissy. Painted. Pretty. Soft. Shamefully aroused.

Then, all was wiped away and I was given the task of applying it myself… several times over until I had a reasonable grasp of the task.

Once all were happy with my progress, I was presented with my own makeup case with everything I had been using and a few other colours for me to take back with me.

HEELS

Heels were next.

The assistant handed me a pair of simple white pumps—just two inches, nothing extreme—but they felt like stilts when I stood. My legs trembled immediately. My balance was off. I gripped the side of the vanity, panting slightly.

Celeste laughed softly. “You’ll learn. You’ll walk for us tonight. Until then… practice.”

I was instructed to walk the length of the hallway and back. Every step felt exaggerated, my hips forced to sway, my thighs brushing lightly together. The tube inside me shifted with each step, dragging against the tender inner walls of my cock, a raw burn that pulsed deep within me.

By the end of my second lap, I was flushed and sweating, my calves aching, my cock on fire, and my pride in tatters. Celeste looked pleased.

“You’re not a man in heels,” she said. “You’re a sissy learning how to carry herself. A big difference.”

I nodded.

And then she smiled kindly, brushed my smooth chest lightly, and said, “Lunch in your room. Shower first, then panties and your nightgown again. We’ll dress you properly for this evening.”

As I left the room—heels clicking, makeup still fresh, and polish gleaming—I passed by a mirror in the hall and stopped.

I looked utterly… owned.

And the most terrifying part was that I didn’t feel humiliated anymore.

I felt chosen.

LUNCH

I floated down the hallway like I was walking through a dream—click, click, click—my dainty white pumps tapping out a rhythm of submission with every unsteady step. The mirrors on the wall caught my reflection again and again, and each time, I lingered. The slim, painted boy in the reflection wasn’t me, not really. He was a fantasy version of myself—flushed, fragile, aching to be seen… and used.

By the time I reached my room, my cock was straining pathetically in the cage, a drooling, twitching mess beneath my panties. I closed the door behind me and leaned against it, chest rising and falling, the smell of powder and perfume clinging to me now like a second skin.

Following Mistress Celeste’s instructions, I showered and then slipped into one of the shorter white nightgowns—clinging, absurdly feminine—and the plain girlie panties that had become my uniform. The polish gleamed on my fingers and toes. My lip gloss still shimmered faintly. I looked like a toy waiting to be played with.

Lunch had been placed on the table—a small tray with cucumber sandwiches, fruit slices, and a protein shake, the same colour as the shots and the morning juice. There was a note beside it in Celeste’s careful handwriting:

“Pretty girls eat light. Stay soft for us.”

I obeyed, cheeks flushed. I sipped the shake slowly, crossing my legs like I’d been shown, my calves still aching from my practice walk. Every movement made the cage shift inside my panties. I didn’t know how I was going to survive the evening if I was already this wet, did I even have any real cum left inside me?

After lunch, I tried to rest, curling up on the bed like a co-ed waiting for a late-night visit. The scent of my body, my arousal, and my makeup—it was dizzying. My thighs pressed together and I whimpered softly, barely able to lie still, yet it was only the afternoon.

The knock came just as the sun dipped lower.

Three firm raps.

I stood, heart hammering, and opened the door.

Two women waited there.

The first was Mistress Celeste, now dressed in sleek black—a long-sleeved bodysuit with a plunging neckline and tall boots that clicked even louder than mine. Her eyes raked over me, from my flushed cheeks to my bare toes peeking from beneath the hem of the nightgown. Her smile was lazy, hungry.

The second woman was older—taller, too—with striking silver-blonde hair and sharp cheekbones. She wore a blood-red pencil dress that hugged her body like a secret. She didn’t speak. Just looked at me like she was measuring a piece of meat.

“This,” Celeste said coolly, “is Headmistress Lorraine.”

I swallowed.

She stepped forward, fingers under my chin, tilting my head side to side, examining me.

“She’s coming along,” Lorraine said finally. “Still a little stiff in the hips. But that’ll change. Pain or humiliation is a wonderful teacher. We will have to see what she needs.”

Celeste chuckled. “She’s eager to please.”

I didn’t even hesitate. “Yes, Mistress. I am.”

That earned me a small nod of approval.

“Very well,” Lorraine said. “Let’s dress her. I want to see her presented to check that she is ready for tonight, or if she needs some persuasion.”

The word sent a jolt of heat straight through me.

Celeste led me to the wardrobe. It was already laid out: a sheer pink babydoll dress with delicate white bows, white panties with lace trim, and a satin ribbon choker with a tiny golden heart at the centre. No bra. No stockings. Just softness and exposure.

They dressed me like I was their doll. Hands moving over my body, smoothing fabric, adjusting straps, tugging here, fluffing there. These panties were even snugger—delicate and it was impossible to ignore how my small cage pressed against me, forcing my balls to bulge lewdly on either side to form an exaggerated cameltoe in the fabric that intensified my humiliation. The babydoll floated over my hips, but left nothing hidden.

They made me look in the mirror again.

I didn’t gasp this time.

I moaned.

“You’ll feel their eyes on you. Maybe even their hands. Do you understand?”

My whole body trembled. My throat was tight.

“Yes, Headmistress.”

Celeste kissed my cheek. “Good girl.”

And then they led me out—heels clicking, night air brushing my thighs, my heart pounding like a drum.

I was to be presented, my coming-out parade.

And I’d never felt more utterly… surrendered.

PRESENTATION

They led me down a long hallway, lit only by soft sconces and flickering candles. My heels clicked with every step, echoing off the polished stone floor. I felt exposed—shimmering with lip gloss, nipples stiff beneath the sheer pink babydoll, the cage outlined clearly beneath the gossamer panties. The satin choker clung to my throat like a collar, and every breath reminded me I was owned.

At the end of the corridor, a heavy double door stood ajar.

Soft music wafted out—slow, sensual, jazzy. Laughter, clinking glasses, the low hum of arousal thick in the air.

And then I saw him—her… gurl was the word that fit now, the only one that made sense, stripping away thoughts of man or woman. The idea of calling him a man made my stomach twist with shame, yet the thought of what we might do together—exploring each other in ways that went far beyond words—sent a thrill through me.

The other sissy.

She stood just beyond the doorway, hands folded primly in front of her, head bowed slightly. Her outfit was nearly identical to mine—lavender instead of pink, her baby-blue choker glinting in the candlelight. She had soft features, big eyes, and lips painted glossy like mine. Her heels were higher, though—three inches, at least—and she swayed a little from the effort of keeping her posture so perfectly submissive.

When she looked up and saw me, her eyes widened slightly. Not with fear. With recognition.

Sisterhood.

We’d both been chosen.

“Go,” Mistress Celeste whispered, giving me a gentle push.

I stepped forward and crossed the threshold.

The air in the presentation room was cooler than I expected, but my skin was already flushed, tingling with exposure and anticipation. The soft carpet beneath my bare knees felt like luxury—deliberate, sensual luxury meant to contrast with the humiliation of being displayed.

I was guided into the centre of the white rug, spotlighted from above like a stage. The second sissy—my counterpart—was brought beside me, and we knelt together, side by side, the hem of our babydolls fluttering just above our trembling thighs. We were matched and coordinated like a performance duo at a decadent pageant, even down to the white panties, the significance of which didn’t go unnoticed by either of us, or any of the onlookers. They were remote—virtual voyeurs, their faces displayed on large monitors lining the walls. Dozens of screens surrounded us, a gallery of elegantly dressed women and stern-eyed men sipping wine, lounging in dimly lit parlours or gleaming offices. Some leaned forward, their gazes fixed hungrily on the sight of us—two soft, shivering sissies offered up like prizes, and the word “virgins” could be picked out most.

A camera hovered above us, red light blinking. We were being streamed. Every glance, every tremble, every shift of our hips was being captured.

Headmistress Lorraine’s voice cut through the hush. “Welcome, honoured guests. This is Day One for these new students. Both gurls began their training just this morning. The course is a week long. By the end, they should be fully fledged sissies. But today… we let them be touched—for the first time. By each other.”

The guests didn’t cheer. That wasn’t their style. But the monitors lit up with smirks, knowing nods, glasses raised in toasts.

INITIAL ASSESSMENT

Celeste stepped forward and crouched between us. She brushed my cheek with the back of her hand, then turned to the other sissy and did the same. “No kissing yet,” she murmured. “You haven’t earned that. But touching? Stroking? Exploring what the other hides beneath her lace? That… yes.” My face flushed. Kissing was the last thing I ever wanted to do with another man, even a sissy; my gut twisted at the thought. But touching, yes, that would be good, to touch a man sexually for the very first time.

She stood, eyes flashing. “Begin. Slowly.”

Our eyes met—uncertain, hungry—and then our hands moved, hesitant at first, drawn by gravity and desire. Fingers brushed thighs, trembling and smooth. We reached beneath the sheer fabric, past the bows and frills, to touch the secrets we both hid… trembling flesh, confined and slick, the aching proof of who we were becoming. My breath hitched. My body betrayed me.

It was my first time touching another man like this and I suspected also his—and it felt filthy, tender, erotic beyond reason.

On the walls, the guests leaned forward. Eyes full of hunger. Some grinning. Some biting lips. One woman on the top-right monitor adjusted her position and murmured, “Yes… let them taste.”

Celeste moved between us again, calm, composed, utterly in control. “You’ve touched,” she said softly. “You’ve explored. But now you’ll worship. Not cock—those are locked. But what’s been given in place of it. The scent, the shame, the wetness. Taste each other, through the fabric. Learn what it means to devour another sissy’s frustration.”

She stepped back.

“Side by side. Sixty-nine. Gently. Show them how desperate gurls behave.”

I turned as the other sissy did, mirroring each other with shy glances and flushed cheeks. We eased down slowly onto the carpet, heads meeting in opposite directions, bodies curved into one another like matched parentheses. Her panty-clad ass was just inches from my face, trembling. My own panties were pulled tight against the wet curve of my cage and the obscene swell of my silicone slit.

We both hesitated—just for a second.

Then leaned in.

The scent hit me first. Sweet. Tangy. Humiliating. Her panties were soaked with caged need, the damp cotton clinging to the contours of her steel prison. I could see her balls just below the ring of the cage, straining outwards, tender and swollen, clearly aching. Her cock twitched uselessly behind the bars.

I pressed my face in.

And she did the same.

Our mouths found each other’s panty crotch, lips parting, tongues seeking the moisture. I moaned into her lace as she nuzzled into mine, her breath hot against the soft, dripping lips of my silicone slit. Her tongue flattened and dragged upward across the slick fabric, and my hips jolted.

I squirmed.

I couldn’t help it.

I buried my face deeper into her panties, inhaling her arousal, sucking the wet cotton between my lips, teasing the base of her cage with the tip of my tongue. My hands found her thighs—so smooth, freshly waxed, trembling under my touch. I slid my palms slowly up, fingertips dancing higher until I cupped her panty-clad balls, so swollen and tight. She gasped around my slit.

Her hands mirrored mine. Exploring. Mapping. Worshipping.

Fingers traced along my thighs, my hips, the sharp curve of my waist. Then down—underneath me—slipping between my legs and cupping my balls, the pair pushed low beneath the tight cage and frame, bulging so obscenely against the soft fabric. She massaged them gently through the cotton, and I moaned again, hips rocking faintly, face grinding against her dripping cage.

The monitors flickered with motion. I caught glimpses between the legs pressing against my cheeks—guests touching themselves, stroking, licking lips, fascinated by our pathetic, eager ritual.

And then—her fingers went further.

Still above the panties. Still technically chaste.

But they found the cleft of my ass, the narrow seam pressed tight by the fabric. They pressed there—firm, searching—until they found the shape of my hole, still virginal, untouched, but now maddeningly sensitive.

I gasped into her cage, my body jolting like I’d been shocked.

I did the same.

My hand curved over her rear, my fingertips running along the soft swell of her panties until I, too, found the centre. I pressed just lightly—barely any pressure—but she whined into my slit, her breath stuttering, her body shivering beneath my hand.

We were panting now. Squirming.

Not humping.

Grinding.

Rolling our hips just slightly as our faces worked against each other’s soaked crotches, tongues teasing lace, lips sucking the fabric inward, our fingers kneading swollen balls, ghosting over tender virgin holes that pulsed against our touch like tiny, begging mouths.

The heat was unbearable. My panties were soaked through. My cock drooled steadily through the urethral tube, slicking the slit of my cage until I could feel it dripping against her chin.

The guests were losing composure now. One screen showed a couple—both fingering themselves, panting in unison. Another guest had their camera angled low, stroking slowly, deliberately, at the sight of our glistening panty worship.

But we couldn’t see them for long.

Because we were locked in each other.

Face to crotch.

Hand to heat.

Tongue to soaked cotton.

Two soft, hairless, helpless sissy trainees, trembling on Day One.

But we could hear their comments, their lewd, perverse suggestions of what they wanted us to do, not just with each other but to have done to us by others. Much of which I suspected would likely be realised by the end of the week, though my mind was more concentrated on today.

The taste of her shame was salty and sweet. The feel of her fingers ghosting over my hole made my legs shake. Every nerve ending in my body screamed for permission—for something deeper, harder, realer.

But we weren’t ready for that.

Not yet.

We kept tasting. Kept touching. Kept moaning into each other’s panties as the monitors around us glowed brighter, the air thick with heat and tension. The afternoon swelled with the unbearable promise of what was waiting for us that evening.

Deep down, I knew I would have to face the truth of my growing sissy self—learning to kneel, submit, and fully pleasure real men, to revel in their dominance, and to own the shame that came with what I was becoming—even as I played with my fellow sissy, knowing that, for now, our only relief would come from each other.

Eventually, we were told to stop—we were clearly becoming too aroused. But neither of us moved at first, caught in the dizzying fog of scent and sensation. It wasn’t until our mistresses intervened and gently pulled us apart that we finally broke contact, still panting, our bodies twitching with unsatisfied need, our caged cocks aching behind damp cotton.

PASSED

On the way back, Mistress was clearly pleased. She told me that she and the Headmistress were impressed with both of us. No corrective therapy had been needed. No coaxing. Our responses had been natural, uninhibited. We had passed the first test. And now, she said, we were ready for what came next.