“Becoming Her: A Sissy’s Awakening”
Jason had always carried this quiet question deep in his chest, the kind that hummed in the back of his mind when no one was looking. Was he a sissy? Or was it just a fantasy—something he scrolled through online late at night but never dared let out into the world?
He didn’t even know how to find out. Until, one Friday night, he found himself staring at the homepage of a site called Mistress Evelyn’s Sissy Academy.
“Find your truth. Embrace your sissy self. Or walk away knowing for sure.”
The bold tagline made his stomach flutter. Was this what he needed? A chance to know, once and for all? He poured a glass of wine, hesitated only a moment, then clicked “Apply.”
A week later, Jason found himself in a small but elegant loft in the city. The air smelled faintly of perfume and leather. Mistress Evelyn—tall, poised, and exuding the sort of dominance that made his knees weak—smiled knowingly as he stepped inside.
“So,” she purred, circling him like a predator, “you want to know if you’re really a sissy. You want to know if this is you or just a dirty little fantasy you can hide from in the light of day.”
Jason nodded. His throat was dry.
“Then we’ll find out together. But you don’t get to just watch from the sidelines.” She snapped her fingers, and a door opened to reveal rows of delicate lingerie, tiny spandex panties, ultra-micro thongs, stockings, heels… and even MTF-style feminizing bodysuits hanging neatly on mannequins.
Jason’s breath caught.
“You’ll try it all. Every level. I’ll push you further each time. And at the end, you’ll either leave here ready to live as my perfect little sissy—or you’ll leave knowing it’s not for you. No shame either way.”
The first day was simple: silk panties under his jeans. The second day? A full matching bra and panty set with sheer stockings under his office clothes. He’d felt his heart pound all day at work, terrified someone would notice, but equally thrilled at the forbidden softness clinging to his skin.
By the end of the week, Mistress Evelyn had him fully shaved, slipping into a skin-tight, feminizing spandex bodysuit with a perfectly molded camel toe front. “There,” she whispered, adjusting his garters. “You already look like a perfect little slut. Let’s see if you feel like one.”
That night, she led him into a private club. Other sissies were there—beautiful, confident, teasing each other in the tiniest latex skirts and micro-thongs. Some wore cages under their panties; others strutted with a natural feminine sway that made Jason’s heart ache with longing.
“You see them?” Mistress Evelyn whispered in his ear. “They didn’t know either. But now they do. Do you want to join them? Or do you want to run back to your boxer briefs and boring vanilla life?”
Jason felt his breath hitch. He looked down at his painted nails, the tiny thong barely covering him, his new feminine curves in the mirror.
Was this who he was?
“Becoming Her: A Sissy’s Awakening – Part 2”
Jason hadn’t expected the second part of his journey to feel like falling in love—not with a person, but with a version of himself he didn’t know he craved.
The night at Mistress Evelyn’s private club hadn’t just opened a door; it had ripped it off its hinges.
The First Test
“Tonight is your real sissy test, darling,” Mistress Evelyn purred, her nails dragging lightly down Jason’s newly smooth thigh.
He sat perched on a velvet stool in her dressing room, staring at his reflection. The feminizing bodysuit clung like a second skin, transforming his frame into an hourglass fantasy. His cock—what little bulge was left after days of tight tucking—was locked away in a tiny pink chastity cage that peeked out from under the lace trim of his micro-thong. His lips were painted a sinful cherry red.
“You’ll serve cocktails. You’ll let them look. Let them touch.” Evelyn’s hand cupped his chin. “No flinching, no hiding. Be my perfect sissy slut, or admit right now this isn’t you.”
Jason’s cheeks burned. His heart raced. But his cock twitched uselessly in its prison, a pathetic throb against the cage’s unforgiving metal.
“Yes, Mistress,” he whispered.
“Good girl.”
The Club
The club floor pulsed with deep bass, neon lights flickering over bodies—men, women, and sissies like Jason—grinding and laughing and exploring every fantasy imaginable.
Jason teetered out in his six-inch heels, holding a tray of drinks as instructed. Heads turned. Hands reached.
“Cute little slut,” a woman in latex whispered as she ran her fingers up Jason’s stockinged thigh.
“Such a pretty sissy,” a man cooed, tugging lightly on his garter strap.
Every touch sent shivers through Jason’s trembling frame. He was humiliated… but his body sang with heat. He felt wanted. Desired in a way Jason—the boring, nervous man—never had been.
“Say thank you, sissy,” Mistress Evelyn reminded from the shadows, her voice sharp.
“T-thank you,” Jason whispered, his voice cracking, soft and feminine from the vocal training Evelyn had started making him practice.
The Initiation
Near midnight, Evelyn beckoned Jason to the VIP lounge. Waiting for him were three of her other sissies—taller, curvier, fully in their element, wearing glittering micro-G-strings and tiny spandex bras.
“This is your final test,” Evelyn purred. “They’ll play with you. Tease you. If you can handle it—if you crave it—you’re one of us.”
Jason’s knees almost buckled. But as the sissies pulled him down onto the chaise, their painted nails teasing at his thong, he felt his last thread of resistance snap.
“Ohhh, she’s shaking,” one giggled, sliding a hand over his caged bulge. “Poor thing. So desperate already.”
“Let’s see how deep her sissy side goes,” another whispered, pushing Jason onto his back.
They kissed him—sweet and wicked—while their hands explored every curve of his feminized body. One sissy straddled his chest, grinding against his painted lips, while another teased the edge of his thong, whispering filthy encouragement into his ear.
“Beg, slut. Beg to be used. Beg to be our little sissy toy.”
Jason gasped, eyes fluttering as his cage throbbed painfully. “P-please… I… I’m your sissy. Use me.”
The Morning After
When Jason woke up tangled in soft sheets and lace lingerie, Mistress Evelyn was sitting in a chair by the window, sipping coffee.
“You passed,” she said simply. “You’re not just a man with a kink. You’re mine now. My sissy. You’ll stay here for full training—makeup, posture, walking, serving, pleasing. You’ll live it.”
Jason felt his heart swell. Fear mingled with excitement. He could still walk away. But he didn’t want to.
“Yes, Mistress.”
“Good girl.”