Becoming Her: A Dream of boobies

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Josh starts to have strange huge breast focused dreams about growing up and over time they start to slowly change is memories about growing up. Slowly the dreams start to shift to him becoming obsessed with having his own sissy boobies. Slowly the dreams start effecting his reality and feminizing him and making him wanting breast to wanting bigger and bigger breast. The dreams start start getting more sexual slowly turning Josh into a busty chubby cock-craving sissy boy.

Chapter 23: The First Dose

The glitter sparkled mockingly on his damp skin. Each tiny fleck caught the candlelight like captured stars against the sweat-slicked canvas of his transformed body – a body that felt less like his own with every shuddering breath. The hollowness in his chest echoed the emptiness where Mikey’s face used to be, replaced only by the lingering phantom suck of the machine and the raw sting of Evelynii’s greedy mouth. He stared at the mirrored ceiling, his reflection a grotesque parody: swollen breasts leaking thin trails onto his ribs, glitter-streaked thighs framing a limp, sticky cock, the purple satin panties a torn banner of surrender around his knees.

Evelynii’s tuneless humming stopped abruptly. "Oopsie!" Her voice, sharp as shattered glass, cut through the perfumed haze. She bounced off the edge of the four-poster, her massive tits swaying like overfilled water balloons. "Forgot the main event! Auntie Lyds'll have Evie’s ass if you ain't properly prepped!" Her glitter-coated fingers dug into the meat of his inner thigh, nails scraping skin already hypersensitive. "Gotta stretch that cute boy-pussy for Daddy."

Panic, cold and sharp, sliced through Josh’s exhaustion. "No... Evie, please. Not again. I can't... it hurts." His voice cracked, weak as the protest itself. Memories – vague impressions of tearing pressure, of being split open – surfaced only to dissolve like sugar in acid. Who was he begging? The friend who braided his hair at seven? This vacant, inflated thing pinching his ass cheek?

"Shut your tit-sucking mouth," Evelynii hissed, her bimbo facade cracking to reveal something colder underneath. She snatched a fat bottle of iridescent lube from a nearby shelf, popping the cap with her teeth. Thick, cold gel splattered directly onto his exposed hole, making him yelp. Her middle finger, slick and relentless, didn’t tease – it pressed hard, knuckle-deep in one brutal shove. "Ungrateful cunt. Shoulda left you leaking in that kitchen like the little bitch you are." She twisted her wrist, the friction burning despite the lube, her nail scraping inside him.

Josh arched, a raw gasp tearing from his throat. The intrusion was violent, a violation that ignited white-hot sparks behind his eyes. His cock, traitorous despite the recent draining, gave a feeble twitch against his belly. "Fuck! Stop! It’s too much!" He tried to buck, but her other hand slammed down on the small of his back, pinning him to the sweat-damp pillows. Her strength was terrifying, inhuman.

"Too much?" Evelynii cackled, adding a second finger alongside the first, stretching him obscenely wide. The burn intensified, a deep, internal ripping sensation. "This is just warm-up, tit-boy. Auntie’s special surprise needs room." Her fingers scissored ruthlessly inside him, the wet, squelching sounds loud in the opulent room. "Bet your asshole’s tighter than your sister’s was." She leaned down, her hot breath ghosting over his ear, her inflated lips brushing his skin. "Remember Sarah? Screamed real pretty when they strapped her down."

Sarah. The name hit like a physical blow. A flash: freckles, a gap-toothed smile, shared ice cream. Then gone. Vanished into the same void as Mikey. Replaced only by the image of Evelynii’s glistening lips and the brutal stretch of her fingers pistoning inside him. A sob choked him. "No… Sarah… who…?" The words dissolved into a guttural moan as she crooked her fingers, rubbing hard over a spot that sent an unwanted jolt of electric pleasure straight to his abused cock. His hips jerked involuntarily.

"See?" Evelynii purred, withdrawing her fingers with a slick pop. "Toldja you’d like it, you little anal slut." She stood, wiping her hand on the bedspread, and grabbed something from the shadow beside the milking machine. It gleamed in the candlelight – thick, veined silicone, unnervingly lifelike, glistening with more iridescent lube. "Daddy’s impatient." She hefted the strap-on harness buckled around her thick waist, the monstrous dildo bobbing obscenely. Its bulbous head looked impossibly wide.

Terror seized Josh. "Please, Evie! I can’t take that! It’ll tear me apart!" He scrambled back on the pillows, his swollen breasts aching with the movement, glitter raining onto the silk. His father’s face surfaced briefly – stern, disapproving, holding a baseball glove. Be a man, Josh. The memory flickered, warped. The glove melted into the shape of the dildo. The stern face softened, lips curling into Aunt Lydia’s hungry smile.

"Hold still, fuckpig," Evelynii commanded, climbing onto the bed, her knees bracketing his hips. The dildo pressed against his stretched, throbbing entrance, cold and massive. She didn’t ease it in. She leaned her full weight forward, using the leverage of her thick thighs, and shoved.

Agony. White, blinding. Josh screamed, a raw, animal sound as the thick silicone head breached him, stretching tissue already raw from her fingers. It felt like being impaled, ripped in two. He clawed at the pillows, back arching violently. "GOD! NO! IT HURTS! STOP!" Tears streamed down his face, mixing with the sweat and glitter.

"Takes it like a champ!" Evelynii grunted, rutting forward another inch, the dildo’s thick ridge catching brutally on his inner muscles. The burn was excruciating, a deep, tearing fire. Yet, beneath the agony, a sickening pulse of sensation sparked where the silicone rubbed over that unbearably sensitive spot inside. His body betrayed him. His cock, trapped beneath his belly, began to thicken again, a painful, shameful erection. "Yeah... feel that, whore?" Evelynii panted, driving deeper with short, brutal thrusts. "Bet your slutty prostate’s singing." She grabbed his hips, nails digging in, and slammed home, sheathing the entire monstrous length inside him in one gut-wrenching push.

Josh convulsed, gagging on his own scream. The fullness was unbearable, a violation that scraped his insides. The dildo pulsed against that hidden bundle of nerves with every tiny movement, sending jolts of unwanted pleasure radiating outwards, tangling with the pain. His cock leaked helplessly onto his stomach. Evelynii began to fuck him in earnest – no rhythm, just relentless, piston-like drives, the wet slap of silicone against flesh echoing off the mirrored walls. Schluck. Schluck. Schluck.

"Look at those titties bounce!" she crowed, each thrust jiggling his swollen breasts painfully. "Fuckin’ perfect milf-feeders! Gonna be bigger than mine soon!" She leaned down, her massive tits smothering the back of his head as she fucked him harder, faster. The dildo hammered into him, its rigid length scraping, stretching, relentlessly massaging that spot. The pain and pleasure blurred into a terrifying crescendo. He felt his balls tighten, the orgasm building not from desire, but from sheer brutal overstimulation. "Gonna milk that prostate, bitch! Squirt it all out like the little cocksleeve you are!"

Her filthy words, the obscene squelching, the brutal fullness, the overwhelming scent of sex and lube and her cloying perfume – it shattered him. With a final agonized cry, his body seized. Thick ropes of cum spurted uselessly onto the silk beneath him, untouched by any hand but his own tortured nerves. It was a dry, convulsive release, wrenched from him by the relentless assault on his ass. He went limp, utterly spent, the dildo still buried deep inside him, a grotesque plug.

Evelynii gave a final, grinding thrust and pulled out with a wet, sucking noise. Josh whimpered at the sudden emptiness, the raw ache. She unbuckled the harness, letting the slick dildo thud onto the bed beside him. "Auntie’s gonna love that stretched-out hole," she giggled, patting his ass cheek hard. "Perfect for her cock." She flopped down beside him, one heavy arm thrown possessively over his trembling body, her fingers idly tracing the glitter on his heaving flank. "My pretty, broken girl." Her voice softened, a grotesque parody of affection. "Just like Sarah."

Josh stared blankly at the ceiling, tears drying on his cheeks. Sarah. Mikey. Dad. Names without faces. Without meaning. Only the deep, throbbing ache in his ass remained, the constant weight on his chest, the glitter embedded in his skin. The mirrored walls reflected a stranger – hollow-eyed, swollen, streaked with fluids and shame. Evelynii’s breathing deepened into sleep beside him. The candlelight flickered. He closed his eyes, waiting for the door to open. Waiting for Aunt Lydia. Waiting for the next piece of himself to be ripped away. The ache pulsed, a relentless rhythm where his memories used to be.

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