Becoming Hers: A Sissy’s Awakening
Caleb had always known he wasn’t like the other boys. While they chased sports and flexed their muscles for girls, Caleb found himself mesmerized by lipstick shades, sheer fabrics, and the way heels clicked against hardwood floors. He tried to hide it, dressing quietly in stolen panties at night, exploring the softest sides of himself when no one was watching. But the truth—the deep, burning truth—was that he didn’t just want to feel pretty.
He wanted to be owned. To surrender. To be made into what he truly was: a perfect, submissive sissy.
That revelation didn’t fully bloom until he met her—Mistress Dahlia.
She was older, elegant, commanding. A friend of a friend from an underground club Caleb had visited once on a dare, where men wore latex and women wore leashes. Dahlia saw through him instantly. “You’re not a man,” she whispered the first time they spoke, brushing her nails down his bare forearm. “You’re aching to be trained, aren’t you?”
His mouth went dry. She smiled.
The Training Began
Dahlia didn’t rush. No, she was a connoisseur of obedience, of refinement. She started by having Caleb wear panties every day—lace, mesh, satin, nothing dull. His boxers were confiscated. He was made to take selfies in the bathroom at work, lifting his slacks just enough to show the frilly waistband peeking out.
Then came the cosmetics. “Every sissy has a look,” she told him, applying blush to his cheeks while he knelt naked between her legs. “You’ll learn to paint yourself until you’re beautiful. Until no one doubts what you are.”
Makeup tutorials, slutty poses, voice training. She made him practice moaning. “Sissies don’t grunt, they whimper, they whine, they beg,” she cooed.
Punishment and Pleasure
Of course, he slipped up. Missed a training session. Let his polish chip. Each failure earned him punishment—light spankings at first, then plug training, then humiliating trips out in public in subtly femme outfits. “Confidence,” she said, “comes from owning your sissiness.”
His first public outing in thigh-high stockings and a miniskirt had his heart thundering. But the way Dahlia held his leash made him feel safe. Proud. Owned.
The sex became more intense too. She never let him top. He was made to wear chastity, then later an ultra-short cage she padlocked with a pink heart-shaped lock. His pleasure came only from serving her or being taken—by her toys, by her guests, and eventually by other dominant men she invited into his training.
“You’re not a boy,” one of them growled as Caleb sucked him obediently in front of Dahlia, mascara streaking down his face. “You’re her perfect little cumslut.”
Dahlia clapped, pleased.
Fully Owned
Months passed. Caleb’s name became “Chloe.” He had sissy ID cards, a collar with “Dahlia’s Girl” engraved in gold, and an Instagram account full of pouty lingerie selfies. Mistress posted him there often, reminding him how proud she was of her good girl. Chloe lived in a chastity cage full time now, her penis tucked and hidden beneath soft panties or gaffed away into nothing.
She moaned when she was spanked, cried when she was edged, and begged for approval like a proper sissy should.
Her transformation was complete the day Dahlia made her walk into the sissy club wearing nothing but clear heels, a sheer dress, and a pink FuFu Clip between her legs, making her bulge vanish into a delicious, feminine cleft. Heads turned. Hands explored. Mistress Dahlia watched it all, sipping champagne.
And Chloe? She didn’t want to run or hide anymore.
She wanted to serve.
Because the truth had always been there—deep, secret, and undeniable.
She was never a man.
She was a sissy.
And now she was finally free.
Title: Becoming Hers: A Sissy’s Awakening — Part 2: The Sissy Showcase
Mistress Dahlia didn’t waste time once Chloe was fully trained. She had molded her sissy into perfection—soft, obedient, feminine in every move, voice, and reaction. But Chloe’s final test was yet to come.
A full weekend. Live-in service. And most importantly: The Sissy Showcase—a private party for dominant women and their sissies to flaunt, share, and celebrate their creations.
Friday Night: Arrival and Obedience
The moment Chloe arrived at Mistress Dahlia’s estate, her male clothes were taken and locked away. Dahlia had chosen her outfit—a white lace corset, a peach silk thong, pink nipple clamps under a sheer cropped blouse, and ballet heels that made walking a trembling challenge. Her hair was in pigtails. Her lips glossy and parted in nervous arousal.
Dahlia handed her a list. Tasks. Cleaning, edging, dressing, presenting.
“Tonight you serve me. Tomorrow… you serve them all.”
Chloe’s heart skipped, her caged clitty already straining and pulsing under the pressure. Her weekend had just begun.
Saturday Afternoon: The Gag and the Plug
After serving breakfast to Mistress on her knees—spilling a bit of tea on her trembling fingers and earning a sharp swat—Chloe was prepared.
Mistress inserted a vibrating jeweled plug deep into Chloe’s tight hole, the remote resting in her palm as she worked makeup into Chloe’s flawless sissy face. She gagged her with a pink ball gag labeled “USE ME.” A sign was clipped to her collar: Free to Touch. Ask Mistress to Use.
Chloe moaned behind the gag, helpless and dizzy with submission.
“You’re not a man. You’re a sissy display doll. And tonight, my doll gets shown off.”
Saturday Night: The Party
Mistress’s estate shimmered with soft music, low lighting, and the sound of heels and laughter. Dozens of dominants in corsets and latex wandered through, leading their boys—some on leashes, some in cages, some on display stands like lingerie mannequins.
But none drew eyes like Chloe.
Mistress Dahlia made her kneel on a mirrored pedestal, leash clipped to a silver pole. Her plug buzzed on low. Her outfit was barely legal: a sheer heart-shaped cutout bodysuit, crotchless, with garters holding lace-top stockings. Her FuFu Clip smoothed her front, making her look like a pretty girl in heat.
Guests surrounded her.
“Is she tucked?”
“No, that’s the Koalaswim design. Clever little slut.”
Hands touched her thighs, tugged her nipple clamps. One domme slipped a finger past the plug’s base. “So tight,” she purred. “She hasn’t had cock yet, has she?”
Mistress smirked. “Not real cock. But tonight’s her debut.”
Later: First Use
Chloe was made to crawl to the center of the room, in front of everyone. Dahlia removed her gag. “Beg for cock like a good sissy.”
Chloe’s mascara was already ruined from hours of teasing and edging. Her lips trembled. “Please… please use me… I want to be filled… I need it, Mistress…”
A masked man was brought forward—big, dominant, invited for this very moment. Dahlia had chosen well.
Chloe was laid over a leather bench, legs spread, plug removed slowly with a slick pop. Her slick hole glistened.
The man pressed inside slowly, and Chloe let out a cry—a mix of pain, bliss, and perfect surrender. Cheers and moans surrounded her. Mistress whispered in her ear, “You’re mine. But tonight, they all get to see what being mine means.”
He began to thrust. Hard. Deep. Chloe sobbed into the cushion, her little caged clitty dripping helplessly.
She was being used, taken, shown off.
Loved—for exactly what she was.
By Sunday night, Chloe could barely walk. Her throat was sore from sucking, her body ached in that deep, used way sissies dream about. But her soul?
Her soul sang.
Because she wasn’t pretending anymore. She was Dahlia’s sissy. Her pet. Her trophy. Her girl.
And she would never go back.