Personalised Story: The Shemale Trainer: Part 4 (Patreon)

Over the following weeks Marina wasted no time escalating Matt’s training. On the very first evening she pulled him into her apartment, stripped off his maid uniform, and ordered him onto his knees.

She strapped on a thick black dildo, gripped the back of his blonde wig, and fed the silicone length between his painted lips until his throat fluttered around it. Spit ran down his chin while she rocked her hips and praised how quickly he learned to swallow her cock.

By the end of that same week she bent him over the arm of the leather sofa, worked the pink plug free, and replaced it with the same strap-on. She fucked him in long, steady strokes, one hand fisted in his hair, the other holding the chastity keys that still dangled between her breasts. Matt whimpered and pushed back, the steel cage clicking against the sofa with every thrust.

She began swapping out his wardrobe piece by piece. Hoodies and jeans disappeared; in their place came slim-cut chinos, soft pastel button-downs, and fitted tees that hugged his narrow waist.

Bras and panties replaced his old underwear, and she made him wear them daily under the new clothes. Each morning he texted her a photo of his locked cock and plugged ass before leaving for work.

One Saturday she told him to meet her wearing only male clothing. He arrived in a plain shirt and trousers, but she marched him straight into a transgender salon filled with other clients. In full view of everyone she had the stylists give him a public makeup lesson—foundation, contour, smoky eyes, glossy lips—while he sat blushing in the chair.

Next came the haircut: layers shaped into a soft, feminine bob that framed his face. Finally the aesthetician threaded and arched his brows into delicate, girlish curves. When they finished, Marina paid, clipped a pink collar around his neck, and led him out still in his male clothes but looking unmistakably like a girl.

That night she made him practice walking in heels while she sat on the sofa, idly spinning the chastity keys on their chain and watching his every sway.

Over the next two weeks the steel cage had become a constant, aching reminder of Marina’s ownership. Matt’s cock had long since stopped trying to swell; the flat front of the cage pressed tight against his smooth skin while the pink plug stayed seated deep inside him, shifting with every step he took in his heels.

Each morning he sent the required photo—locked, plugged, dressed in whatever feminine outfit she had chosen—before leaving for work. By evening he was back in her apartment, kneeling in the pink French-maid uniform she kept for him, blonde wig perfectly styled, makeup flawless, stockings clipped to the garter belt that framed his caged cock.

Marina trained him relentlessly. She lounged on the leather sofa in her glossy black latex catsuit, legs spread, and fed him the thick strap-on until his throat opened around it. Spit ran in long strings from his glossy lips while she held his head and pumped her hips, praising how well he took her cock now.

When she grew bored of his mouth she turned, bent slightly, and made him worship the shiny latex stretched over her full ass. He kissed and licked every curve, tongue tracing the seam between her cheeks until she purred with approval. Then she sat back, lifted one heeled boot, and watched him clean the sole with long, obedient strokes of his tongue, the taste of leather and street dirt mixing with his own lipstick.

One evening she had him kneel at her feet after he finished polishing her boots. Still in full sissy-maid attire—blonde wig, heavy makeup, pink dress flaring over his plugged ass—she looked down at him with a satisfied smile.

“Two weeks locked,” she said, spinning the chastity keys on their chain. “You’ve been such a good girl for me, haven’t you?”

“Yes, Mistress,” he whispered, voice soft and eager.

She reached for a small white jar on the side table and held it up so he could see the label. “Estrogen cream. Rubbed on every day it will soften your skin, thin out that little bit of body hair you still have, and start rounding your face and hips. It won’t be instant, but it will help you look more like the pretty thing I want you to become.”

Matt’s painted lips parted. His eyes flicked from the jar to her face, then back again. The idea of his body changing further under her control sent a helpless throb through his trapped cock.

“Please, Mistress,” he breathed. “I want it. I want to be softer for you. I want to look more like a girl… like Maria.”

Marina’s smile widened. She unscrewed the lid, scooped a small amount onto two manicured fingers, and held them out. “Beg properly.”

He leaned forward, still on his knees, and pressed his cheek against her latex-covered thigh. “Please, Mistress, put the cream on me. Make me yours completely. I’ll do anything—anything you want. Just let me use it so I can become the sissy you deserve.”

She smeared the cool cream across his cheeks, down his neck, and over his chest where the fake breasts sat in their bra cups. Then she guided his own trembling hands to rub it in, watching every desperate stroke.

“Good girl,” she murmured, clipping the keys back between her breasts. “From now on this is part of your nightly routine. You’ll thank me every time you apply it.”

Matt nodded quickly, already rubbing more cream into his arms, his voice a breathless whisper. “Thank you, Mistress. Thank you for letting me become Maria for you.”

Marina leaned back, legs crossed, and watched him continue the application with shaking fingers, the keys glinting against her latex as she decided exactly how far she would take his transformation next.

Two weeks of twice-daily estrogen cream had worked faster than Marina expected. Each morning and night Matt rubbed the cool lotion into his face, neck, chest, arms, and thighs exactly as she instructed, and the changes arrived quickly.

His skin lost its roughness and took on a silky, almost glossy feel that caught the light when he moved. The sparse hair on his legs and chest thinned until it was nearly invisible; only a faint shadow remained around his groin, easily hidden by the smooth pink panties she now made him wear beneath everything.

Most striking were the small, tender swells that pushed against the cups of his bra—barely an A-cup, but unmistakably breasts, the nipples darker and more sensitive than before. Every time the lace brushed them he felt a helpless throb inside the steel cage.

Marina watched the progress with quiet satisfaction. She had him strip to his lingerie every evening so she could inspect the results. Tonight he stood in the center of her living room wearing only the pink satin bra, matching thong, garter belt, and sheer stockings.

The blonde wig framed his made-up face, and the pink heels forced his posture into a feminine arch. The flat front of the chastity cage pressed tight against the thong, a constant reminder that his cock had no say in any of this.

She circled him slowly, running one manicured finger along the new curve of his chest. “Look at these little tits already forming. So sensitive too.” She pinched one nipple through the satin and watched him gasp, knees trembling. “Still desperate in that cage, aren’t you?”

“Yes, Mistress,” he whispered, voice soft and breathy.

“Show me.”

He dropped to his knees without hesitation, crawling the short distance to her chair. Marina lounged in her black latex catsuit, legs spread just enough for him to see the thick strap-on already strapped in place.

He took the realistic silicone cock between his glossy lips and slid down until his nose pressed against the latex at her crotch. Spit coated the shaft as he worked it deeper, throat relaxing around the girth the way she had trained him. Each bob of his head made the small breasts jiggle inside the bra.

When she grew tired of his mouth she turned, presenting the shiny latex stretched over her ass. He pressed his face between her cheeks and licked long, worshipful strokes across the glossy material, tongue tracing every curve until she hummed with approval. Then she lifted one booted foot and he immediately lowered himself to clean the sole, the taste of leather and street grit mixing with his lipstick.

After he finished, Marina had him sit back on his heels. She reached for the jar of estrogen cream and scooped a generous amount onto her fingers. “Twice a day from now on, and you’ll thank me every time.”

She smeared it across his new breasts first, rubbing slow circles until the cream disappeared into the soft skin. Then she guided his own hands lower, making him massage it into his thighs and the smooth skin around the cage. The cool lotion contrasted with the constant heat trapped inside the steel.

He kept rubbing even after the cream was absorbed, desperate to please. “Thank you, Mistress. Thank you for making me softer… for giving me these little tits.”

Marina clipped the chastity keys back between her breasts and leaned forward, cupping his chin. “Good girl. Maria is coming along nicely. Soon those breasts will need real bras, and we’ll decide what else needs to change.” She gave his cage a light flick with one finger, watching him flinch and moan. “But for now, keep that tongue ready. I’m not finished using my pretty sissy tonight.”

That same evening Marina reclined on the leather sofa, legs spread wide in the glossy black latex catsuit. The thick strap-on jutted upward, glistening with spit. Matt—no, Maria—knelt between her boots, the pink satin bra stretched over his budding chest, the flat steel cage trapped inside the matching thong.

The pink plug remained seated deep inside him, stretching his hole even while he worked the silicone cock down his throat.

He had improved fast. Each time Marina pushed his head lower he relaxed, letting the head slide past his tongue and into his throat until his nose pressed flat against the latex at her crotch. Saliva ran down the shaft in thick strings. He held there, swallowing around the girth, eyes watering but obedient.

"Good girl," Marina murmured, stroking his blonde wig. "Take it all."

When she finally pulled him off, thick strands of spit connected his glossy lips to the tip. She stood, turned him around, and bent him over the arm of the sofa. The plug came out with a wet pop.

She replaced it immediately with the strap-on, pressing the head against his loosened ring and sliding in with one steady thrust. Maria moaned, high and needy, as the full length sank into him. His caged cock throbbed uselessly against the steel, leaking a steady drip that soaked the front of the thong.

Marina set a firm rhythm, hips slapping against his ass with every stroke. Each time she bottomed out he gasped, the new sensitivity in his chest making his nipples ache inside the bra cups. She reached around, pinching one tender bud through the satin.

"Look at you, taking every inch like a proper slut," she said, voice calm while she fucked him harder. "Now answer me while I’m inside you."

She slowed just enough for him to speak between thrusts.

"Do you want real tits, Maria? Big, heavy ones that bounce when I fuck you?"

"Yes, Mistress," he panted, voice cracking. "Please give me real tits."

"And a fat, juicy ass? Something wide and round that jiggles when you walk in heels?"

"Yes, Mistress—please, a big fat ass for you."

Marina drove in deeper, grinding against his prostate until his knees shook.

"A soft, feminine voice? A pretty face with plump lips and high cheekbones?"

"Yes, Mistress—yes, yes, turn me into your perfect bimbo slut. I want it all. I’ll do anything."

She smiled, satisfied, and picked up the pace again, pounding him until the only sounds were the wet slap of latex on skin and his broken moans. When she finally pulled out she left him bent over, hole twitching and empty, still begging in a breathless whisper.

"I’ll book the surgeries," she said, clipping the chastity keys back between her breasts. "Soon you’ll have everything you just begged for. And you’ll thank me every single day for making you exactly what you were meant to be."