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Part 1: The Invitation
The car rolled up the winding drive like it was afraid to be too loud.
Simon sat stiffly in the back seat, the leather cool beneath his clammy hands. He could see the house through the tinted windows now--house was a laughable word, really. It was a mansion. Sprawling white stone walls. Tall glass windows like watchful eyes. Balconies wrapped in ivy, fountains in the front like they belonged in some European palace. It was beautiful. Intimidating.
Just like the man who lived inside.
He felt his heart clench.
He hadn't expected Damian's invitation. And he hadn't expected to accept. But here he was, small suitcase in hand, wearing his best button-down (the one that didn't quite fit his bony shoulders), fidgeting with the edge of his sleeves like a boy headed to detention.
The door was opened for him before he even raised a hand.
A woman in a black, form-fitting maid uniform stood in the grand foyer. Her hair was in a severe bun. She looked him up and down, slowly, then stepped aside. "You're expected," she said with a faint smirk.
Simon stepped into the house like it might bite him.
The air smelled expensive. Clean linen, bergamot, and something darker -- like the inside of a humidor. The marble floors echoed under his sneakers.
More women appeared -- all part of the staff, all perfectly dressed, all impossibly graceful -- gliding through the hallways, casting glances his way like he was some kind of... exhibit.
Or prey.
He blushed and kept walking, led by the maid down a wide corridor into a sitting room that looked like it belonged in a Vogue spread.
And then--he was there.
Damian.
He was lounging on a velvet chaise, one leg crossed over the other, a tumbler of something amber and expensive in his hand. He stood as Simon entered, and it was like the room got smaller.
Tall. Broad. Devastating.
His dark complexion was smooth and glowing in the low light. He wore a black button-up shirt, open just enough to reveal the hard plane of his chest, and perfectly tailored slacks. His eyes were sharp and slow. His smirk was subtle but unmistakable.
"Simon," he said, voice smooth as leather. "I'm glad you came."
Simon tried to speak but forgot what to say.
Damian stepped forward, took his hand like they were about to waltz, and kissed the back of it. "You look nervous," he said.
Simon swallowed. "I--I am."
"That's alright," Damian said, gesturing for him to sit. "Nerves mean you're about to grow."
Simon sat on the edge of the plush chair like he was afraid to sink into it.
Damian poured a second drink, handed it to him, then sank back into his own seat with the grace of a predator settling in for the long hunt.
"You read the contract," Damian said.
"I did."
"You understood the terms?"
Simon nodded. "Yes."
Damian smiled wider. "Then let me be clear. If you stay here, Simon, you surrender control to me. I will shape you, not just into the submissive I see beneath your skin, but into something far softer. Far more honest." He leaned forward. "You'll be cared for, trained, molded... corrected."
Simon's breath caught.
"You may leave at any time," Damian said. "But if you stay..." He leaned in until his lips were near Simon's ear. "You become mine."
Simon shivered.
"I'll change everything," Damian whispered. "How you walk. How you dress. What you feel, crave, become. You'll be stripped down and rebuilt. Gently, and sometimes... not so gently."
A pause.
Then Damian pulled back, watching him.
"Well?" he asked.
Simon looked into Damian's eyes. His body was a warzone of panic and desire.
But the word came softly, reverently.
"... Yes."
Damian smiled, victorious and pleased.
"Then let's begin."
Part 2 -- First Obedience
"Strip."
The command cut through the air like a whipcrack.
Simon froze.
He stood in the softly lit dressing room just off the grand foyer -- luxurious but intimate. Velvet curtains, mirrored walls, and a gold-trimmed vanity. He wasn't alone. A few of the female staff remained, tending to quiet tasks: one was refilling Damian's glass at a cart near the chaise, another folded fresh linens, and two more simply stood with arms crossed, watching.
Simon's face flushed as he looked around, voice barely above a whisper. "N-Now? Even with them... here?"
Damian's eyes didn't flicker. "Of course."
He gestured calmly toward the women. "They're used to this. They know exactly what kind of boy you are."
Several of the staff exchanged knowing glances. One of them -- the curvy blonde at the drinks cart -- smirked.
Simon hesitated only a second longer before his trembling fingers began unbuttoning his shirt.
He moved slowly. Shame clung to his body heavier than the clothes themselves. Each article he removed made the heat in his cheeks grow, especially under the weight of the women's silent amusement. Their eyes were sharp and curious. Hungry.
By the time Simon stood naked, his shoulders were curled inward, his clitty soft and small, twitching pathetically with humiliation.
Damian stepped forward, slow and calm, his presence consuming the space.
"Fragile," he murmured. "But pretty."
Simon turned away, only to have Damian's hand cup his jaw and force his gaze upward. "Look at me," he said.
Simon obeyed, breath caught.
"You came here for a reason. You want this. All of this. They can see it." He tilted his head toward the staff. "Can't you, girls?"
One of them -- a tall redhead with sharp cheekbones -- snickered. Another giggled behind a manicured hand.
Simon's whole body flinched.
Damian turned to the bed. "Put them on."
Laid out delicately were blush-pink lace panties -- a thong -- and a matching robe so sheer it looked like dew. His hands shook as he pulled them on, the lace cupping his little clitty in a way that made it feel even smaller.
The robe flowed over his pale skin, leaving nothing to the imagination.
Behind him, a quiet ripple of female laughter spread through the room.
"Precious," someone whispered.
Simon's face burned.
Damian circled him once, slow and indulgent. "You'll get used to being seen like this," he said softly. "You'll learn to love it. You already do, don't you?"
Simon's clitty throbbed -- trapped and leaking against lace.
"On your knees."
Simon blinked. "W-What?"
Damian stepped forward, eyes dark. "Get on your knees, place my cock in your mouth, and show me you understand your place."
Simon's breath caught. He hesitated.
He'd never done this before. Not with a man. Not with anyone. And the women were still there, watching -- leaning in now, lips parted, waiting to see if the little sissy would actually obey.
But he was already sinking to his knees.
Damian unfastened his slacks, pulled them open, and freed his cock -- thick, dark, veined, and already hard.
Simon stared, wide-eyed, lips trembling.
Damian wrapped a hand around the base. "Open."
Simon opened.
The first taste was overwhelming -- masculine, musky, dominant. Damian's cock stretched his lips wider than he'd imagined possible, and he gagged as it pushed past his tongue.
"Breathe through your nose," Damian murmured. "Just like a good little sissy."
Simon moaned around him, tears prickling in the corners of his eyes. He didn't know if it was shame or arousal. Probably both.
He could hear the staff behind him whispering, giggling, softly laughing.
"I can't believe he's doing it," one breathed.
"Look how red his ears are," another said.
Simon whimpered and tried to block them out, but Damian's hand gripped the back of his head -- steady, controlling, patient.
"You're doing well," he purred. "Keep sucking."
It went on forever. Simon lost track of everything except the heat in his cheeks, the ache in his jaw, the weight in his mouth...
And then Damian's hand tensed.
The warning came too late -- Damian's cock pulsed, and with a growl, he came, hard and sudden, straight down Simon's throat.
Simon gagged again but didn't pull away. The taste overwhelmed him -- bitter, warm, intimate.
He swallowed automatically.
And to his surprise... it made his clitty throb even harder.
Damian pulled back slowly, wiping Simon's lip with his thumb, smiling down at him. "Good girl."
Simon collapsed back onto his heels, dazed, panting, lips wet.
"I need to--" he gasped, voice hoarse. "Please... please, I need to cum."
Damian's smile sharpened. "Did I give you permission?"
Simon's eyes widened. "No, but--Damian, please..."
The dominant man tsked and sat back on the edge of the chaise, pulling Simon across his lap. The thong offered no protection -- a single tug and it was pulled aside, baring his trembling, pale ass.
Then came the first slap.
Sharp, stinging.
Simon gasped.
Then another.
And another.
Damian's hand was heavy, precise, cruel in its rhythm.
"You think that pathetic little clitty has earned pleasure?" SLAP
"You want to squirt in your sissy panties in front of all these women?" SLAP
"You think you deserve it?"
Simon sobbed. "I-I don't! I'm sorry! I shouldn't--I shouldn't cum!"
Damian leaned down, breath against his ear. "You won't."
Simon's breath hitched.
"You don't get to beg for denial and think that's enough," Damian growled. "If you're going to live under my roof, sissy, your pleasure belongs to me."
He reached beside the chaise and pulled out a polished, stainless steel chastity cage. Sleek. Small. Final.
"This is your future."
Simon moaned as Damian knelt and slipped the cage around his leaking clitty -- it barely filled the narrow shaft before Damian clicked the ring into place and locked it with a delicate, golden key.
The pressure was immediate -- gentle but unforgiving. There was no room for swelling. No hope of escape.
"You are now locked," Damian said calmly. "And you'll stay that way until I decide otherwise."
Simon's whole body trembled.
"Thank me."
"Th-thank you, Sir," Simon whispered. "Thank you for owning my... my clitty."
Damian stood, zipping his pants, towering over Simon with dark, slow satisfaction.
One of the maids clapped politely.
"Miss Simone will need her own room," Damian said smoothly, glancing toward the staff. "And a full wardrobe fitting."
"Of course, sir," one woman replied with a smirk.
Simon didn't even protest the name.
He simply stood on shaky legs, panties back in place, the cage snug and wet with humiliation.
And as he was led away -- hips sore, mouth used, caged and pink and trembling -- he knew one thing with absolute certainty:
He was theirs now.
Part 3 -- Training & Transformation
Simone had started taking the hormones three days ago.
She hadn't wanted to, not at first. Damian had offered them the night of the cage -- two little pink pills in the palm of his hand, cradled like candy. He'd explained their effects in soft, measured tones: breast growth, softer skin, emotional openness, sensitivity, mental rebalancing. A chemical shift toward the woman he saw inside her.
She had stared at them with wide, uncertain eyes.
"I don't think I'm ready," she'd whispered.
"You're not supposed to be," he'd replied gently. "You will be."
And then, slowly, trembling, she had opened her mouth and let him place the pill on her tongue.
She had swallowed.
And Damian had kissed her forehead and said, "Good girl."
The sun rose soft and golden through the gauzy curtains of Simone's room.
Not Simon's. That name had already begun to fade from use, replaced in hushed giggles and pointed smirks by "Miss Simone." Damian hadn't called her Simon in days. The staff hadn't since the morning after the cage clicked closed.
She hadn't dared to correct them.
Her room -- her room -- was a vision in cream and blush. A vanity lined with powders and perfume, a closet full of silk and lace. A soft chaise in the corner for kneeling, stretching, presenting.
It had been three days since the cage. Three days since the thong. Since the swallow. Since the spanking.
And every day had followed the same ritual.
Damian entered the room just after sunrise.
He never knocked. He never needed to. She was always already awake -- her body trained by arousal, tension, and the painful ache of her denied release.
She kneeled by the chaise in nothing but her pink robe, the cage snug and glinting beneath.
"Good morning, Simone."
Her clitty twitched uselessly at the sound of his voice.
"Good morning, Sir," she whispered.
He approached her with slow, measured steps. His presence always made her feel like the air had thickened. He smelled like cedarwood and leather and authority.
"On the bed."
She obeyed instantly.
Damian always began with an inspection. He slid the robe off her shoulders, letting it fall in a whisper of fabric to the floor. Her skin was pale, smooth, hairless -- exactly as he preferred it. Her nipples were slightly swollen, more sensitive than before.
Damian smiled as he brushed a thumb across one. "The hormones are starting to do their work."
Simone blushed. "Yes, Sir."
He traced his fingers down her stomach, pausing at the delicate cage nestled between her thighs. It was wet again.
"You're dripping."
She whimpered, embarrassed. "I'm sorry..."
"You'll learn not to apologize for your nature. You're meant to ache. Meant to need."
He unlocked the cage with a flick of the key. Her clitty twitched, already helpless.
Damian shook his head fondly. "Still so soft. Still so pretty." He leaned in close, whispering, "Still so useless."
Her breath hitched.
"On your stomach."
She flipped over, burying her flushed face into the silk pillows as Damian retrieved the plug for the day.
Each morning brought a new size. She had started with something modest, and now... the stretch was beginning to feel real.
Today's plug was thick and obsidian, perfectly smooth and ominous in its girth.
"You'll take this one without protest."
"Yes, Sir."
Damian lubed the toy generously, pressed it to her entrance, and began to push. Simone whimpered, legs trembling, hands gripping the sheets.
"Relax."
She tried. The head popped in. Then more. More.
By the time it was seated fully inside, Simone was shaking and leaking, the pressure deep and intense.
Damian slid her panties up over the base. "Keep it in all day."
"Yes, Sir..."
He tapped the tip of the plug through the lace with a satisfied hum. "You'll be surprised how easy you get stretched when you know it's the only way you'll ever cum again."
Simone moaned at the reminder.
Damian refastened the cage -- the familiar click locking her back into aching denial.
"Time for your pill."
She knelt at his feet, and he handed her a delicate pink capsule and a glass of cucumber water.
She took it, swallowing quickly.
Damian stroked her cheek. "Good girl."
Downstairs, the staff greeted her with smirks and snide little glances.
"Morning, Miss Simone," one chirped. "Love the lace -- is that the new cage I see peeking through?"
"Didn't she get plugged today?" another whispered. "That's why she's walking like she's full of secrets."
Simone said nothing. She simply nodded, face flushed, and clutched her morning tea like it could protect her from their eyes.
But part of her liked it.
Part of her loved it.
Later, in the private studio Damian had arranged for her "training," Simone found herself kneeling before the mirror, holding the massive dildo he had given her two days prior.
It was molded from Damian's own cock -- thick, long, curved just enough to hit the exact spot that made her moan without meaning to.
At first, she could barely fit the head. It was too much. Her body rebelled. But she had kept trying, as ordered.
Now, she could get halfway. Sometimes more.
Damian entered the room just as she was lubing up.
He watched from the doorway, arms crossed, amused.
"Well? Go on, then. Let me see how far you've come."
She positioned it, the plug already removed for this session, and pressed the dildo against her tight, needy hole.
The stretch was painful. Beautiful. Shameful. She moaned as she took the head, then an inch, then two.
Her thighs quivered.
"Deeper," Damian ordered.
She whimpered but obeyed.
It wasn't easy. But she wanted -- needed -- to show him.
By the time she had almost five inches inside, her voice broke into a sob. Not from pain.
From pride.
Damian walked over and caressed her cheek. "You're blooming, Simone. You're finally learning what your body was made for."
Her clitty pulsed inside its cage, useless and soaked.
"You'll train every day," he whispered. "And when you can take all of it..." He traced the edge of the dildo. "That's when you'll be ready."
"Ready for what?" she asked, breathless.
He smiled. "Me."
That night, as she lay in bed, plug tucked inside her, her cage weeping, and the hormone pill still warm in her belly, Simone touched her own chest gently.
Were her nipples... more sensitive?
Were her hips... rounder?
It didn't matter.
Damian saw her.
And that meant she was real.
Part 4 -- Breaking Point
Simone woke up soaked.
Her cage was dripping, her thighs slick, the plug still snug inside her, and her entire body hummed with shameful, pent-up need. It had been two weeks of training. Of swallowing hormone pills, daily inspections, progressive plug sizes, and practicing with his cock -- the dark, heavy dildo molded from Damian himself.
She could barely remember what it felt like to wake up without that ache. Without that pressure. Without that humiliating emptiness inside her that begged to be filled.
And today, something felt... different.
"Good morning, Miss Simone," the nurse said sweetly, pulling on her gloves with a snap.
She was tall and blonde, with icy blue eyes and the poise of a queen. Simone lay naked in a gynocological chair, legs up in stirrups, arms trembling as her clitty lay exposed -- tiny, pink, caged, and helpless.
The humiliation was crushing.
Her face was red, heart pounding. The stirrups forced her wide open, made her feel completely defenseless -- like a doll laid out for inspection.
Damian sat nearby, watching silently. As always.
"Skin: smooth, soft, no signs of irritation," the nurse noted aloud. "Nipples: enlarged, sensitive. Small tissue growth forming -- quite promising."
Simone whimpered softly.
"She's been emotional," Damian added coolly. "More reactive. Weepy after orgasm denial."
"Excellent," the nurse murmured. "Mood changes align with proper dosage levels."
She moved her gloved fingers lower, inspecting Simone's little caged clitty. It twitched pathetically. It was, as usual, dripping.
The nurse arched a brow and looked up at Damian with a smirk. "Still leaking, I see."
Simone's whole body flushed. She could feel the heat crawl all the way to her toes.
"Every day," Damian confirmed. "Can't keep her dry for more than an hour."
The nurse gently pinched the cage between two fingers and hummed thoughtfully. "It's even smaller than last week. At this rate, she might not need the cage at all. There'll be nothing left to contain."
Damian chuckled. "Don't tell her that. She still likes pretending it matters."
Simone's breath caught. Her eyes watered.
"Still soft?" the nurse asked.
"Always," Damian said.
They didn't even wait for a response.
"She's responding beautifully," the nurse concluded, pulling her gloves off and tossing them into the bin. "Continue as you have. She's right on track."
Damian stood as the nurse left and stepped over to Simone, still trapped in the stirrups, legs open, soaked and silent with shame.
He brushed her damp hair off her forehead and leaned down, whispering, "Did that embarrass you?"
She nodded, trembling. "Yes, Sir..."
"Good," he purred. "It means you're still growing."
He kissed her temple.
That night, Simone knelt before the mirror.
The dildo gleamed with lube in the lamplight. Her cage had been removed. Damian stood behind her, arms crossed, watching. Silent.
She looked down at the thing she'd been practicing with for weeks. The first time she'd seen it, she couldn't even fit the tip. Now...
She pressed it to her hole and began to sink down.
The stretch hurt. But she was ready.
Inch by inch, she lowered herself, moaning softly, eyes watering, breath catching. She could hear her heartbeat in her ears. Hear the soft sound of Damian exhaling as he watched.
Three inches. Then five. Then seven.
She paused, body trembling.
"Keep going."
She whimpered. "I--Sir, I--"
"You will."
She nodded, tears slipping down her cheeks.
Then, with a choked moan and one last push, she took all of it -- the full nine inches buried inside her.
Her body screamed and melted and fluttered, all at once. She sat there, fully impaled, gasping and shaking -- every nerve on fire.
Damian approached her slowly, kneeling behind her.
His hands slid over her waist.
"You did it," he whispered. "You're ready now."
Simone sobbed. Not from pain. From everything.
He kissed her bare shoulder, slow and reverent.
"Take it out and present for me."
She obeyed with trembling hands, carefully pulling the toy free, her hole gaping and leaking in the aftermath.
Damian pointed to the bed. "There. Now. On your back."
Simone crawled onto the bed, her chest heaving, heart pounding.
Damian climbed on top of her, spreading her legs wide, positioning himself between her thighs.
Her legs wrapped instinctively around his hips.
She gasped when his cock -- hard and hot -- pressed against her entrance.
He reached down and gently cupped her soft, leaking clitty.
"You'll never cum through this again."
Simone moaned.
"You'll only cum... when I'm inside you." His voice was low. Commanding. Absolute.
"Is that what you want, Simone?"
"Yes, Sir," she sobbed. "Please. Please make me yours."
Damian lined himself up.
And pressed in.
The first inch made her gasp. The second made her whine.
By the third, she was a mess of broken cries and raw need.
He didn't go slow. He didn't rush. He claimed her -- deliberately, deeply -- face-to-face, his hips cradled between her thighs, cock filling her perfectly stretched body until she felt nothing but him.
"Say it."
"I'm yours," she gasped. "I'm your girl. I was made for this."
He fucked her slow. Hard. Deep.
Simone's body sang.
Her clitty didn't even try to stiffen -- it just leaked, forgotten and soft, while Damian's cock hit her in the only place that mattered.
When she came, it was from her prostate alone -- a sobbing, trembling, soul-shattering orgasm that left her dizzy and wet and weak in his arms.
Damian grunted low against her neck and spilled himself deep inside her, thick and hot, filling her with everything she'd earned.
Damian stayed inside her as she came down, stroking her hair.
"You're perfect," he whispered. "Perfect and mine."
Then, as gently as ever, he reached between them and clicked her cage back into place.
He slid off the bed and picked up the plug from where she had left it. Still warm, still glistening. Without a word, he lubed it lightly and pressed it back into her hole -- slow, steady, inevitable -- sealing his cum deep inside her.
Simone whimpered as it slid home, her body clenching instinctively.
Damian kissed her cheek. "Keep me in you until I say otherwise."
"Yes, Sir," she whispered, voice shaking.
Part 5 -- The Claiming
The morning light spilled across Simone's satin sheets.
She was lying on her side, eyes still closed, her thighs pressed together, the soft hum of soreness between them like a private echo of the night before.
She could still feel him -- the weight of Damian's body on hers, the stretch of him inside her, the sound of his voice claiming her. Her clitty was caged once more, as always, but she didn't even try to fight the ache. It was part of her now. Like her softening chest, her moody cravings, the way her hips seemed to sway without her noticing.
Simone smiled sleepily.
She was his.
And she loved it.
Her morning ritual was already familiar -- comforting, even.
She stood at the vanity in her robe, chest bare, the air cool against her large, sensitive breasts. Her areolas were wide, her nipples prominent, almost constantly erect and tender. She couldn't wear anything tight anymore without feeling flushed and needy. And she didn't want to.
She took her pink hormone pill with water infused with cucumber and mint, like a spa treatment.
The little gold key that locked her clitty away dangled on a thin chain Damian had hung around her neck. She never took it off.
The plug -- today's size -- was waiting on a polished silver tray, gleaming like a mirror beside her hairbrush. Lubed, clean, black, wide.
She inserted it slowly, like a prayer, and sighed as her body stretched to welcome it.
She could take so much now.
She hoped Damian noticed.
Downstairs, the staff were already busy.
"Morning, Miss Simone," a maid called with a teasing smile.
Another added, "Looking flushed. Did Sir keep you up again?"
Simone said nothing. She simply smoothed her robe and walked past, head high, cage tight, plug deep.
She didn't need their approval anymore.
She had his.
Damian was waiting for her in the study, seated in his leather armchair, dark suit crisp, legs crossed, coffee steaming.
"Good morning, my girl," he said without looking up.
Simone blushed and walked to him, kneeling beside the chair, placing her hands on his knee.
"Good morning, Sir."
He finally looked down, those sharp eyes softening. He touched her chin and tilted her face up.
"You're glowing."
Simone beamed. "I feel... different."
"You are different." He traced her cheek. "You're exactly what I wanted."
He reached into the side drawer and pulled out a small envelope, embossed with gold trim.
"Your appointment is confirmed," he said, handing it to her.
Simone opened it slowly, heart pounding.
"Facial feminization consultation," she read aloud. "Private suite. Dr. Mathers..."
"You'll go next week," Damian said. "She already has your file. And your pictures. I sent her everything."
Simone's throat closed.
"You... did all that for me?"
Damian smiled. "For us, pet. I've invested too much in you to stop now."
Tears welled up in her eyes, but she didn't sob. She just nodded.
"Thank you, Sir."
He leaned down and kissed her lips softly -- not possessively, not aggressively.
Just his.
"You'll rest today. No training. No guests. Just my girl in her softest robe and nothing else."
"Yes, Sir."
"You'll stay plugged. No release."
"Yes, Sir."
"You'll wear that cage for me, and tomorrow..." He smirked. "We'll talk about piercings."
Simone's clitty pulsed helplessly in its cage, dripping once again.
She was melting.
"May I sit on your lap?" she whispered.
"You may."
She climbed up into his lap, curling against his chest, warm and light, caged and plugged and adored.
And for the first time in her life -- not just her training, not just her transformation -- she felt complete.
That night, as the mansion fell quiet, Simone stood before the mirror again.
She wore only a sheer lace nightgown, her chest clearly visible beneath the soft fabric -- busty now, with large areolas and nipples that remained almost constantly erect, firm and sensitive from her hormones.
Her skin glowed. Her collarbones were more pronounced. Her lips fuller, her waist narrower.
She turned slightly and ran her hands over her hips, down to the plug nestled between her cheeks, locked in place beneath her cage.
Her reflection looked back at her, uncertain and radiant and real.
Simone.
Not Simon.
Never again Simon.
Behind her, Damian's reflection appeared -- tall, dark, undeniable.
He wrapped his arms around her waist, pulled her against his chest.
"You're mine," he said.
"I'm yours," she echoed.
He kissed her shoulder.
"Good girl."
The end?
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