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 21: Bimbo Milking Ritual

The sharp tang of bleach and Aunt Lydia’s sour musk still clung to the inside of Josh’s nose, warring with the phantom sweetness of his own leaking milk. He stared at the cold kitchen ceiling, the memory of her crushing weight, her demanding hand, the humiliation of his unwanted climax – it all pulsed like a fresh bruise. His chest ached, heavy and alien beneath the ruined t-shirt, damp with sweat and… other things. Mikey. The name flickered, a dying ember in his mind. Football jersey. Tears. Then gone, swallowed by the suffocating silk of Aunt Lydia’s robe. Gone like me?

The overhead light suddenly felt blinding, harsh. He squeezed his eyes shut. When he opened them, the cold linoleum was gone. He was sinking.

Sinking into plush, velvet softness. The air hung thick and syrupy, saturated with an overwhelming perfume – jasmine, vanilla, something cloyingly sweet and artificial. The sharp kitchen smells vanished, replaced by this decadent fog. He blinked, trying to focus. Soft, golden candlelight flickered, reflecting endlessly in countless mirrors lining the walls. He was sprawled on a mountain of pillows, silk and satin whispering against his skin, his swollen breasts resting heavily on the plush surface. Across from him, dominating the low, ornate coffee table, sat a gleaming chrome machine. Tubes coiled like serpents, terminating in wide, pulsating suction cups. A milking machine.

"Joshieeeeee!"

The voice was impossibly high, dripping with saccharine glee. Evelynii. But… more. So much more. She practically bounced into his field of vision, a whirl of pink satin and overwhelming flesh. Her once modest frame was gone, replaced by cartoonish proportions. Her hips flared dramatically beneath a micro-skirt, thighs thick and dimpled, rubbing together with a soft shushing sound. But it was her chest that dominated. Two impossible orbs strained against the flimsy fabric of her baby-doll negligee, each easily the size of her head, round and high and capped by obscenely large, dark nipples pushing visibly against the satin. Her face was almost unrecognizable beneath plumped, bee-stung lips that glistened wetly, perpetually parted in a vacant smile. Her eyes, heavily mascaraed, held a manic sparkle.

"Look at you!" she trilled, clapping her hands together, making her massive tits jiggle violently. "Just look at those beautiful slut-tits you’re growing! Aunt Lydia’s been busy!" She giggled, a high-pitched, airy sound. "But Evie’s gonna make them feel sooo much better!"

Josh tried to push himself up, his movements sluggish, hampered by the unfamiliar weight on his chest and the lingering exhaustion. "Ev… Evelyn? What… what is this? Where…?" His voice felt thick, wrong. The perfume was making him dizzy.

"This is fun, silly!" she chirped, kneeling beside him on the pillows with surprising agility despite her bulk. Her perfume intensified, a physical presence. "This is where we make all the icky tension go poof!" She reached out, her fingers, tipped with long, glittering nails, brushing the damp fabric over his left nipple. The jolt of sensation was immediate, sharp and electric, shooting straight to his groin. He gasped. "Oooh, sensitive!" she cooed. "Just perfect." Her plump, glistening lips curved into a wide, vacant smile. "Auntie Lyds got you all worked up in that nasty kitchen, didn’t she? But Evie’s got the best toy for big-tittied boys like you."

She leaned forward, her immense breasts swinging perilously close to his face. The sheer scale was terrifying. The scent of her skin, warm and musky beneath the perfume, mixed with something vaguely chemical. Before he could react, her hands were on his shoulders, shoving him firmly back down into the pillows. "Stay!"

He struggled weakly. "No, Evie, please… don’t…" His protests were muffled, pathetic. The memory of Aunt Lydia’s crushing weight flashed, merging with Evelynii’s manic energy.

"Shhhh, shhh, big boy," she hushed, patting his cheek with a condescending softness that felt like a threat. Her other hand moved with startling speed, grabbing the front of his pajama pants and yanking them down over his hips, past his knees. Cool air hit his skin. He looked down.

He was wearing panties. Satin, shimmering with purple glitter, straining to contain his soft cock and balls. When had that happened? Panic flared, cold and sharp. "Wh-what? How…?"

"Pretty, right?" Evelynii giggled, tracing the glittery band with a sharp nail. "Suits your new look. Now…" She snatched one of the chrome suction cups from the machine. It pulsed with a low hum. "Time to milk those needy little nips!"

"NO!" Josh tried to buck, to roll away, but Evelynii planted a surprisingly strong forearm across his chest, pinning him. Her massive breast swung down, pressing against the side of his head, soft yet immovable. The scent of her skin, the heat radiating off her, was suffocating. He felt the cold, wet rim of the suction cup press against his left nipple. Then, a sudden, shocking POP-SLURP as the vacuum engaged.

"Oh! Fuck!" Josh arched off the pillows, a cry torn from his throat. It wasn't just suction; it was a deep, rhythmic pull, a relentless mechanical demand deep inside his swollen breast tissue. The sensation was excruciating and bizarrely arousing at the same time. His nipple was pulled taut into the cup, the sensitive flesh stretched. Milky white fluid, thicker than before, began immediately flowing through the transparent tube attached to the cup.

"See?" Evelynii squealed with delight, watching the stream. "Told you they were full! Look at all that yummy cream!" She quickly attached the second suction cup to his right nipple with another POP-SLURP. Twin streams of milk pulsed rhythmically through the clear tubes into a collection reservoir on the machine. Josh writhed, whimpering, the combined sensation of deep internal pulling, hypersensitivity, and shame overwhelming him. His cock, trapped in the ridiculous glitter panties, twitched and began to firm up against his will, arousal coiling tight in his gut despite the violation.

"Oooh, look who likes it!" Evelynii purred, her gaze dropping to the tent forming in the purple satin. Her bee-stung lips curved into a hungry smile, a thin strand of drool escaping the corner of her mouth and landing with a warm splat on Josh’s forehead. "Getting hard in your pretty panties while your titties get pumped? You dirty, dirty boy!" She giggled, the sound like shattering glass.

Still pinning him with her forearm, her massive breast still smothering the side of his face, she ducked her head. Her plump, wet lips, impossibly large and soft, glistening with saliva, descended. They engulfed the head of his cock through the thin satin. The heat, the wetness, the sheer pressure of those inflated lips pressed against his trapped erection was maddening. He could feel the fabric stretch, dampen. She moaned, a low, vibrating hum that traveled straight to his balls, her lips working, sucking hard, creating a wet, obscene slurping noise against the glittery satin.

The machine continued its relentless thrum-thrum-PULL on his nipples, drawing out thick streams of milk. Evelynii sucked harder, her head bobbing slightly, her lips smearing wetness over his confined cock. The conflicting sensations were unbearable: the deep, rhythmic milking agony-pleasure in his chest, the wet, muffled suction on his cock, the suffocating heat and scent of her breast against his face, the glitter panties a constant, humiliating reminder. His body betrayed him utterly. Pleasure, sharp and unwanted, spiked higher, fueled by the sheer overload and the mechanical stimulation. Aunt Lydia’s face swam in his mind – Good boys cum for Auntie’s tits – merging with Evelynii’s relentless sucking and the machine’s rhythmic demand. Who was Mikey? Had he screamed like this? Had he felt this terrifying weight, this relentless suction, this dissolving self?

"Oh god… oh fuck… no…" Josh’s moans were ragged, lost against the soft prison of Evelynii’s tit. He was losing the fight. His hips bucked involuntarily against her face. The pressure built, a terrifying wave cresting beneath the combined assault. The milking machine throbbed. Evelynii sucked harder, humming filthily. The glitter panties felt like they were melting onto his skin. He was going to… he couldn't stop…

With a guttural cry drowned by flesh, Josh’s body convulsed. Thick, hot cum pulsed violently into the confining satin of the panties, soaking through instantly, the wet warmth spreading against his skin. At the same moment, the milking machine seemed to pulse harder, pulling twin gushes of creamy milk through the tubes. The orgasm was brutal, a tidal wave of shame and involuntary release that left him trembling violently, gasping for air against Evelynii’s suffocating breast.

She pulled her wet, glistening lips away from the soaked satin with a final, loud pop. She sat back, breathing heavily, a strand of saliva mixed with his seeped cum stretching between her lower lip and the damp purple fabric. Her eyes were wide, manic with satisfaction. "Mmm, messy boy!" she giggled, wiping her chin with the back of her hand. She gazed down at his heaving chest, the cups still rhythmically pulling the last drops of milk, his cock a wet bulge in the ruined glitter panties. "Look at you. So pretty. So used." She patted his cheek again. "Auntie Lyds is gonna be so proud of my work. Just like…" Her voice trailed off, a vacant look flickering across her overly plumped features. She tilted her head. "…like who? Hmm."

The relentless thrum of the milking machine filled the opulent silence. Josh lay there, pinned, drained, the scent of sex and expensive perfume and his own milk thick in his throat. His chest felt strangely hollow, yet heavier than ever. Mikey. Who was Mikey? Was he just… gone? Swallowed up by soft, suffocating flesh and the rhythmic thrum-thrum-PULL of the machine? The glitter on his panties sparkled mockingly in the candlelight. He closed his eyes, the question echoing in the hollow space where his memories used to be: Did Mikey disappear into Aunt Lydia’s robe too? The suction cups pulsed, demanding more. He had nothing left but the ache and the terrible, growing emptiness.

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