“Am I a Sissy?” — A Fetish Journey of Awakening
It started as a whisper. A late-night thought in front of his laptop, legs crossed, fingertips trailing down lace panties he wasn’t supposed to wear.
“Am I a sissy?”
Ethan had always felt something stir when he saw men locked in chastity, kneeling in maid outfits, or blushing as dominant women made them pose like pretty dolls. He didn’t just get turned on—he ached. But it was always at arm’s length—Reddit forums, Tumblr blogs, and private browser tabs filled with keywords like forced feminization, femme boys, sissy humiliation. He’d scroll for hours, but still he wondered:
Was this just a kink? Or was this who he was?
One night, heart racing, he posted anonymously on a fetish board:
“How do I know if I’m a real sissy and not just turned on by the fantasy?”
A woman replied. Mistress Ivy. Her message was short:
“Try it. Fully. Come to the other side. Then ask yourself again.”
He couldn’t resist. She sent him a list:
- Pink lacy panties
- Matching bra (with inserts)
- Thigh-high stockings
- Lip gloss
- A chastity cage
- A webcam
And one final instruction: “You’ll report to me Saturday night. As my sissy. If you feel nothing, you’re not one. But if you beg to come back—well… you already know the answer.”
Ethan was trembling as he ordered everything. He told himself it was “just a dare.” Just curiosity. But when Saturday came, and he stood in front of the mirror—nipped waist in a frilly French maid corset, lips shimmering, legs smooth and clad in sheer white hose—his cock twitched in its brand-new steel cage.
He looked helpless. Gorgeous. Owned.
The webcam flickered on.
Mistress Ivy was even more powerful than he imagined. Dark hair, crimson lips, and a commanding gaze that sliced right through his shame.
“Well, well,” she said with a smirk. “My little wannabe sissy is already dripping. Maybe you’re not wondering anymore.”
She had him twirl. Bend. Moan with his hands behind his back. The humiliation of saying “I’m a sissy, Mistress” while locked and needy only made his arousal deeper—more helpless. She knew just how far to take him. That night, Ethan was ordered to edge 10 times with his hands tied. He couldn’t touch his cock—but he didn’t need to.
Just being seen, degraded, adored as a sissy filled him with a pleasure he never knew existed.
Over the next few weeks, Ethan’s world transformed. Mistress Ivy renamed him Lacey. She made him get a real sissy maid outfit, tighter lingerie, a collar with a lock, and soon enough—he was doing chores in heels while calling her during lunch breaks. She sent him videos of other sissies. Had him rate their outfits. Told him to try new ones and walk around the block as punishment when he didn’t edge right.
But it wasn’t just online. Lacey wanted more.
She went to a private BDSM club dressed in a pastel pink sissy dress and matching panties with a cock cage so small it was invisible. The moment she walked in, eyes devoured her. A domme in leather smirked. A gay couple whispered and pointed. One of them came over, handed her a leash, and said, “Our puppy didn’t show. Want to play instead, little sissy?”
She didn’t even answer—she dropped to her knees.
Hours later, lipstick smeared and cheeks sore from smiling, Lacey was used, spanked, praised, and filled in more ways than she imagined. Her mouth tasted of men, her thighs were wet, her ego destroyed—and all she could do was beg Mistress Ivy for more.
That night, with mascara-stained cheeks and her cage still locked tight, Lacey whispered aloud:
“I don’t need to wonder anymore. I am a sissy.”
“Lacey’s Sissy Training Week”
Mistress Ivy didn’t ask—she commanded.
“You’re going to spend an entire week living as who you truly are. Not Ethan. Not in hiding. As Lacey. Completely. I’ve arranged everything.”
Lacey gasped.
Mistress had sent an address, a private estate in the hills—far from prying eyes, but fully outfitted for one thing only: sissy immersion.
When Lacey arrived, dressed in a hoodie and jeans over her lingerie, she was met by a stunning blonde woman in black latex and towering heels. She didn’t smile—just looked her up and down.
“Strip. Sissies don’t wear boy clothes.”
Lacey obeyed immediately. Standing outside, trembling in the breeze, her sheer pink panties and cage visible beneath her garter belt, she whimpered as a second woman arrived. A busty redhead in leather gloves, holding a collar and leash.
“Mistress Ivy sent us your file. You’re ready to break.”
They brought her inside, and the transformation began. Lacey was locked into her training uniform: a soft pink babydoll dress with puffed sleeves, see-through enough to show her chastity cage and nipples, plus frilly sissy bloomers with “Owned” printed across the back. They tied bells to her collar, heels to her feet, and replaced her thoughts with commands.
And she wasn’t alone.
There were four other sissies already there. All in different stages of training. One was dressed like a cheerleader, complete with a vibrating plug for “motivation.” Another wore a skin-tight latex maid outfit and was constantly bent over, offering herself. A third—blonde, demure, in a full bridal gown—was preparing to be “married off” to a mystery man at the end of the week.
Lacey would be trained, tested, and used—every single day.
Day One: Obedience.
She was taught to curtsy, to say “Yes, Mistress” and “Please punish me” with genuine enthusiasm. When she slipped or hesitated, her bloomers were yanked down and her caged clit spanked with a paddle that said “SLUT” in mirror letters.
Day Two: Pleasure Denial.
Her cage was teased—ice, feathers, plugs, even light edging through a vibrating wand—but never release. By the end of the night, Lacey was grinding helplessly into the pillow while another sissy licked her thighs under Mistress’s orders.
Day Three: Public Shame Night.
They took a limo into the city and brought the girls to a private VIP lounge. Lacey was made to dance on a pole while men and women watched, clapping and laughing. Tips were tucked into her garter. She wasn’t just a sissy—she was entertainment.
Day Four: Role Reversal.
Lacey was ordered to serve the other sissies. She massaged their feet, painted their nails, even kissed their cages in a line while the Mistresses watched. One of them climaxed from a plug while Lacey was licking her boots. She felt humiliated—and incredibly aroused.
Day Five: Use Night.
The sissies were auctioned to “guests.” Lacey ended up kneeling between two tall, muscular men who whispered filthy praise into her ears. She was passed between laps, bent over leather chairs, and made to serve—her mouth, her thighs, her entire purpose given. One whispered in her ear as she gagged on him:
“You were made for this, weren’t you, sissy?”
And she nodded. Willingly. Gratefully.
Day Six: Reflection.
The Mistresses had her journal every humiliating act. Every compliment. Every orgasm denied. Lacey wrote until her hands shook—realizing it wasn’t just lust. This was her truth.
Day Seven: Graduation.
Mistress Ivy arrived in person. She pulled Lacey aside, alone.
“So tell me, slut. What’s your name?”
Lacey dropped to her knees, eyes wide, tears mixing with mascara.
“Lacey, Mistress. Your obedient, broken sissy. Forever.”
Mistress smiled. She unlocked the cage—not to let her cum, but to slip in a prettier one: gold, heart-shaped, engraved with the word “MINE.”