Cover of The Sissy's Secret Obsession

The Sissy's Secret Obsession

Read the story

16 chapters · 32575 words · Read 0 times

Josh accidentally hears Hypnosis written to put big tits on sissy boys. It starts with a obsession with huge breast through watching porn. Slowly that will shift to a need to grow your own breast.. the file will finish with you doing what the file says to grow larger breast.

Chapter 13: More bustier memories

The fluorescent bulb in the bathroom hummed like a trapped insect. Josh stared into the mirror, steam from the shower fogging the edges of the glass but leaving the center horrifyingly clear. Water dripped from his messy brown hair onto his shoulders, tracing paths down his chest. His reflection showed a landscape irrevocably altered. The lean, unremarkable torso was gone. In its place, mounds swelled beneath his damp skin, full and heavy, the pale flesh marbled with faint blue veins. The nipples, darker and larger than he remembered, stood taut and hypersensitive. They ached with a deep, persistent throb that echoed the low hum in his bones since he’d woken tangled in the emerald satin.

He touched one tentatively. A jolt of sensation, sharp and electric, shot straight to his groin, followed by the familiar, grinding ache deep in the tissue. It felt… right. Horrifying, alien, but undeniably part of him. The memory of the night before – the satin, the kneading, the crushing release – flooded back, hot and shameful. The notification on his phone. DDD Cup.

A sharp knock at the apartment door startled him. He flinched, his new weight shifting uncomfortably. Hastily wrapping a towel around his waist, feeling the absurdity of needing to cover his chest, he padded to the door. A bored delivery driver thrust a small, discreet package into his hands. The return address: Silky Embrace.

His fingers trembled as he tore open the cardboard. Emerald satin spilled out, impossibly soft, impossibly small. The bra cups looked cavernous, yet he knew they would fit. He felt they would fit. The command echoed in his skull: Your bra must be tighter. Hold them close. Lift them higher. He dropped the towel. The cool air made his nipples pucker painfully. With clumsy, reluctant fingers, he fumbled with the clasp behind his back. It clicked shut on the loosest hook. He looked down. The satin encased him, the underwire a rigid frame beneath the heavy swell. It lifted, separated, presented. He instinctively reached for the clasp again, hooking it tighter. Tighter. The pressure increased, the ache intensified, a grim counterpoint to the strange sense of containment, of rightness. He pulled on the matching panties, the silk a whisper against his skin, a constant, undeniable declaration he couldn't escape.

He pulled on a loose, worn-out band t-shirt, his usual armor. It strained across his chest, the fabric taut. His old hoodie swallowed him, but the bulge beneath was unmistakable. He felt monstrous.

The file had dug deeper than his waking hours. It was rewriting the bedrock.

He was sixteen, standing awkwardly in Jenny Miller’s dimly lit basement rec room. The air smelled of stale popcorn and cheap perfume. They’d been awkwardly making out on the lumpy sofa, fumbling hands, nervous laughter. His hands, clumsy and eager, had slid under her shirt. Her bra felt flimsy. Then, his own chest… it felt… warm. Full. Jenny’s hand, tentative, brushed against it through his thin t-shirt. Not recoiling in surprise, but lingering, curious. “Wow,” she’d breathed, her voice husky. “You’re… bigger than I thought.” Her fingers brushed his nipple through the fabric. That same sharp jolt, the electric spark that had made him gasp then, just as it did now. He remembered the flush of heat, the confusing mix of embarrassment and a strange, burgeoning pride. He remembered the weight shifting as he moved, the slight bounce he’d tried to hide. Had Jenny really said that? Had he always felt that… fullness? The memory felt vivid, tangible, layered over the reality he knew was false. He could smell the popcorn, feel the scratchy fabric of the sofa.

Josh stumbled back against the bathroom door, gripping the edge of the sink. The cool porcelain grounded him for a second. No. No, that didn’t happen. But the feeling lingered – the phantom weight of sixteen-year-old breasts under Jenny’s curious touch.

He needed air. Or caffeine. Or to not be in his apartment. He grabbed his backpack, the strap digging uncomfortably between his shoulder blades and pressing the underwire painfully against his ribs. He headed for the campus library, a place that used to be a sanctuary of logic and code.

Walking was different. A subtle, unavoidable sway had entered his hips. His center of gravity felt off. His chest pulled forward with each step, demanding balance. The tightness of the bra, the constant pressure, was a drumbeat under his thoughts. He passed a group of students. A guy glanced, his eyes lingering just a fraction too long on Josh’s chest before snapping away. Josh hunched his shoulders, trying to disappear into the hoodie, the flush on his cheeks burning.

In the library stacks, surrounded by the smell of dust and paper, another shard of false memory stabbed into him.

College, sophomore year. The third floor, quiet study carrels. He was cramming for a midterm, stressed and exhausted. Sarah Chen, from his algorithms class, had slid into the carrel beside him. “Hey, brainiac. Stuck?” Her perfume was subtle, clean. She leaned close to look at his screen, her arm brushing his. Her gaze, though, dipped. Not to his screen, but to his chest, clearly outlined beneath a thin cotton henley. He remembered the flush creeping up his neck. He remembered the fabric tightening as he took a breath, the swell undeniable. Sarah didn’t look away. Her hand rested lightly on his thigh, warm through his jeans. “You look tense,” she murmured, her voice low. Her thumb traced a small circle. Her other hand drifted upwards, not to his shoulder, but resting high on his chest, her palm cupping the side of one breast near his armpit. The pressure was light, possessive. “So soft,” she whispered, leaning closer. He remembered the shock of it, the forbidden thrill in the quiet corner of the library, the way her touch ignited that deep, familiar ache and made his nipple tighten instantly against the fabric. He remembered nodding, mute, letting her hand stay, a secret shared in the silence. Had they…? Had he just let her…? The memory felt scorchingly real, the phantom weight of her hand, the heat blooming under his skin.

Josh slammed a book shut on the carrel desk, the sound echoing sharply in the quiet. He pressed his palms flat on the cool wood, trying to steady his breathing. His heart hammered against the constriction of the bra. Goosebumps rose on his arms. Beneath the satin, his breasts felt impossibly heavy, warm, the nipples hard points of sensation. He could almost smell Sarah’s perfume. It didn’t happen. It couldn’t have. Yet the feeling, the visceral memory of her touch, the secret thrill… it resonated with the desperate, compelled need the hypnosis cultivated. It felt like a truth his body had always known, now dragged into the light of his conscious mind.

He needed to focus. He opened his laptop, the screen glowing in the library dimness. Algorithms. Code. Logic. Safe, predictable patterns. He tried to dive in, forcing his attention onto the lines of Python. But the ache in his chest was a constant, low thrum. The tight satin bra was a cage and a caress. His mind kept drifting back to Jenny’s basement, to Sarah’s hand in the library… memories that felt more substantial than the equations on the screen.

He clicked open a browser tab. Almost without conscious thought, his fingers typed: Breast sensitivity relief. Then deleted it. Typed again: Satin bra care. Then: DDD cup sports bra. The searches felt illicit, shameful, yet driven by a need he couldn't deny. His thumb brushed against his nipple through the hoodie and t-shirt and satin. The jolt made him gasp softly. His hand lingered, pressing slightly, massaging the ache deep within the dense tissue. Oh god. He was doing it again. In public. Compelled. Obsessed.

The library air grew thicker, harder to breathe. The weight on his chest felt crushing. He needed… something. Release? Comfort? More? The conflicting impulses warred – horror at the transformation, the false memories, the public display, warring against the insistent, hypnotically implanted need that made the pressure, the ache, the sensitivity feel like the only real things in the world.

He stared blankly at the code on his screen. The characters blurred. Behind the algorithms, beneath the logical structure, a deeper program was running. Rewriting his past. Reshaping his present. Commanding his future. The hum began again, not from the laptop speakers, but resonating deep within the twisted pathways of his own mind, a silent echo of the file’s relentless pulse: Bigger. Fuller. Softer. Needing. Always needing more. His fingers, hovering over the keyboard, trembled. The next command was already coiling in the silence, waiting to root itself deeper.

The hum inside Josh’s skull intensified, a low-frequency thrum resonating in his teeth. He stared blankly at the Python code, the logic structures dissolving into meaningless symbols. Algorithms felt abstract, distant, irrelevant against the visceral reality pressing against his ribs. His fingers twitched on the keyboard. DDD cup sports bra. The search bar mocked him.

“Josh? Hey, earth to Josh?” Liam’s voice, sharp with its usual sarcastic edge, cut through the internal haze. Liam leaned against the carrel, peering at the screen. Josh slammed the laptop lid shut, too fast. “Whoa, easy, man. Whatcha hiding? Porn or finals panic?” Liam chuckled, his gaze drifting downward, lingering just a beat too long on the straining fabric of Josh’s hoodie.

Josh hunched further, heat flooding his face and neck. The underwire dug deeper, a constant, punishing reminder. “N-nothing. Just… stuck on this loop.” His voice sounded thin, higher than usual to his own ears.

“Right,” Liam drawled, unconvinced. He tapped the closed laptop. “Looked like bra shopping to me. Got a secret admirer buying you frillies?” His laugh was loud in the quiet stacks. Josh flinched. He could smell Liam’s cheap energy drink, see the faint smirk playing on his lips. The memory of Jenny Miller’s hand, phantom and insistent, brushed against the swell beneath his hoodie. ‘Bigger than I thought.’ Liam’s gaze felt like a physical echo, amplifying the ache. “Whatever, freak.” Liam pushed off the carrel, shaking his head. “Later.”

Josh waited until Liam’s footsteps faded. He reopened the laptop with trembling hands. The Amazon page loaded, displaying the emerald satin set he’d worn last night. ‘Recently Purchased’. Below it, algorithmically suggested: Silky Embrace Maximum Support Underwire - F Cup. His breath hitched. His fingers hovered. The deep ache in his chest pulsed, a dull, demanding pressure. Bigger. Fuller. Necessary. The command wasn’t a whisper now; it was a vibration in his bones. He clicked ‘Add to Cart’. Confirm Purchase? His thumb hovered over the fingerprint sensor.

He couldn’t. Could he? The image of the F-cup bra, its cups impossibly cavernous yet terrifyingly plausible, filled his vision. The memory of Sarah Chen’s hand possessively cupping his chest in the library carrel surged, hot and vivid. The phantom touch merged with the real, deep throb beneath his sweatshirt. He pressed his thumb down. The screen flashed: Order Confirmed. Expected Delivery: Tomorrow.

A wave of nausea warred with a dizzying rush of compelled relief. He needed air. Now. Gathering his things felt clumsy; his backpack strap dug into the fleshy curve where his shoulder met the unnatural swell, pulling the bra strap tighter. The movement made his breasts shift heavily within their satin prison. He hurried towards the library exit, the sway in his hips more pronounced, less controllable, each step jostling the tender weight. He felt eyes. Everywhere.

Outside, the late afternoon sun felt harsh. He pulled his hood lower, shielding his face. Crossing the quad, the slight incline made his calves burn; his center of gravity was undeniably altered, pulling him forward. He passed a group of sorority girls. One glanced, then nudged her friend. He saw the flicker of confusion, then amusement, on their faces. Heard a stifled giggle. Freak. Liam’s word echoed. His cheeks burned.

He ducked into the small campus coffee shop, ‘The Grind’, craving the anonymity of noise. The rich aroma of espresso usually soothed him. Today it felt cloying. He ordered a large black coffee, keeping his head down, voice barely above a murmur. The barista, a girl with pink streaks in her hair, smiled brightly. “Heavy studying?”

Josh nodded mutely, fumbling for his wallet. As he reached across the counter, his hoodie gaped slightly. Her gaze flickered down, then snapped back to his face, her smile faltering for a microsecond before returning, overly bright. “Long day, huh?” she chirped, handing him the cup. Her eyes held a question she wouldn’t ask. He practically snatched the coffee, spilling some scalding liquid on his hand. He didn’t feel it. The tight satin bra felt like a brand against his skin.

He slumped into the deepest corner booth, shrouded in shadow. The hot ceramic burned his palms, a counterpoint to the deep, internal heat radiating from his chest. He cupped the mug, trying to absorb its solidity. He needed to think. To fight. The F-cup confirmation was a physical blow. How could this be happening? The hypnosis wasn’t just planting bizarre memories about Jenny and Sarah; it was actively reshaping his body, hijacking his will, forcing him to participate in his own transformation. He sipped the bitter coffee, its taste ashen.

Another memory fragment pierced the panic. High school locker room, post-gym. He’d been changing, back turned. A loud, familiar voice boomed – Mark Henderson, football captain. “Damn, Anderson! When’d you get the tit upgrade? Stealing your sister’s push-ups?” Raucous laughter echoed off the tiles. Josh remembered whirling around, clutching his gym shirt to his chest, face crimson. He remembered the awful feeling of exposure, the heavy warmth trapped against his ribs under the thin cotton. He remembered the nickname sticking: “Double D.” He’d hated it then. But now, the memory carried a strange, twisted undercurrent: a perverse validation of the weight he now carried. The humiliation felt real. The sensation of having that weight, even then, felt horrifyingly real.

He squeezed the mug so hard his knuckles turned white. It wasn’t real. It couldn’t be. But the ache was. The F-cup bra arriving tomorrow was. The way people stared was. The constant hum, the invading thoughts, the compulsion to touch, to feel, to need the pressure… it was all devastatingly real. Logic was crumbling. His own history was being rewritten, brick by brick, replaced with a narrative where breasts were always part of him, always growing, always demanding attention. The coffee tasted like defeat.

He set the mug down with a thud. His free hand, seemingly of its own accord, moved under the table. It slipped beneath the hem of his hoodie, finding the curve of his satin-covered breast through the t-shirt. He pressed his palm flat against the firm swell. The ache flared, a deep, resonant throb that seemed to vibrate through his entire torso. His thumb found the stiff peak of his nipple through the layers. Rubbed. The sharp, electric jolt made him gasp, his hips shifting involuntarily against the vinyl seat. He couldn’t stop. The pressure felt necessary, grounding, the only response to the impossible conflict tearing him apart. A low whimper escaped his lips. His eyes scanned the near-empty cafe, terrified someone would see his hidden struggle, see the flush on his neck, the slight, rhythmic movement under his hoodie.

The pink-haired barista glanced over, a slight frown creasing her brow. Josh froze, hand still trapped beneath his clothes. Her gaze met his for a split second – seeing his panic, his shame. He yanked his hand out, knocking over the coffee mug. Dark liquid gushed across the table, splashing onto his jeans. He scrambled up, muttering apologies, grabbing napkins to mop the mess, his movements clumsy and frantic. The wet denim clung coldly to his thigh. The barista hurried over with a towel. “It’s okay, accidents happen!”

Her kindness felt worse than mockery. He avoided her eyes, mopping furiously, the awkward bulk on his chest hindering his movements. He needed to escape. Now. He threw the sodden napkins down. “Thanks,” he mumbled, shoving past her towards the door. The bell jingled harshly as he burst out into the cooling evening air.

He didn’t head back to his apartment. He walked, fast, without direction, the damp patch on his leg chilling him. The campus lights flickered on. His chest felt like lead weights strapped to him, each step sending a fresh wave of discomfort radiating from the tight band of the bra. The F-cup order confirmation burned in his mind. Bigger. The command pulsed with every heartbeat. He found himself walking towards the older part of campus, towards the deserted science annex, a place usually silent after hours. A place to hide. To think. To maybe scream.

He rounded the corner of the brick building. A small delivery van was parked haphazardly near a service entrance. The logo: Silky Embrace. A man in uniform was just closing the back doors. Josh stopped dead. His apartment was across campus. Why was the van here? The driver turned, spotted him, checked a handheld device. “Josh Anderson?” he called out, his voice echoing slightly in the quiet.

Josh’s blood ran cold. The F-cup bra wasn’t coming tomorrow. It was here. Now. The driver reached back into the van, pulling out a small, unmistakable package – the same discreet cardboard as before. He held it out. “Sign here.” Josh stared, paralyzed. The hum in his skull crescendoed, drowning out thought. Necessary. Support. Bigger. Feel the embrace. His hand moved. He took the stylus, scrawled something illegible on the screen. The driver thrust the package into his hands. It felt heavier than last time. Fuller. “Have a good night,” the driver said, already turning away.

Josh clutched the package, its smooth surface cool against his palms. He stood alone in the deepening twilight behind the science building, the weight of the box mirroring the unbearable weight on his chest. The tight satin bra felt suddenly like a precursor, a child’s garment. This package held the next stage. The inevitable progression. The hum settled into a deep, satisfied purr within him. Resistance felt futile, a distant memory. He traced the outline of the bra inside the cardboard, feeling its structure, its promised capacity. His fingers trembled. He needed to put it on. Now. The command wasn’t a whisper or a vibration anymore. It was the only thought left, echoing in a suddenly silent, surrendered mind. He looked around furtively, towards the dark service entrance. A deeper shadow. A place to hide. To obey.

Read on DreamPress