It started with little comments.
“You’re such a sissy sometimes,” my goth girlfriend would tease, smirking behind her black lipstick. At first, I’d laugh it off or snap back with some gruff retort. But she wouldn’t let it drop.
Even our friends seemed to be in on the joke. They’d say things like, “You’re so pretty, you’d look better in eyeliner than we do” or “You’re practically one of the girls anyway.” I hated it. Or… at least I told myself I did.
Then one night, after an argument about her constantly calling me a sissy, she sighed and locked eyes with me.
“You really don’t see it, do you? You are a sissy. The way you blush when I tease you. How you melt when I take control. You’re not mad—you’re scared because it’s true.”
I denied it, of course. I wasn’t weak. I wasn’t feminine. But she smiled like she already owned the truth.
A week later, she proposed a challenge.
“If you’re so sure you’re not a sissy, prove it. One week. Do everything I say. No arguing. No safe word. At the end, if you still think you’re a man’s man, I’ll drop it forever.”
Cocky, I agreed.
Day one, she took me shopping. Not for clothes for her, as I thought, but for me. Lacy panties, a silk camisole, thigh-high stockings, and a pink chastity cage. I refused at first, but she just leaned in and whispered in my ear.
“A real man wouldn’t be afraid of a little lace, right?”
By the end of the night, I was shaved smooth and locked up. She made me parade for her in my new lingerie while she lounged on the bed in leather and fishnets, sipping wine, laughing every time I tried to cover myself.
The days blurred together after that. She had me practice walking in heels around our apartment. Makeup lessons turned into mandatory daily applications. She taught me how to tuck, how to sit “like a lady,” how to moan like a good little sissy slut.
She would spank me if I forgot to curtsy when I thanked her. I wasn’t allowed to touch myself—not with my hands, not even through my panties. The cage made sure of that.
Our friends noticed the change immediately. “About time,” one of her girlfriends said when I showed up at their hangout in a tight pencil skirt and painted nails. “We’ve all been waiting for her to break you in.”
At first, I wanted to sink into the floor. But then I noticed the way they looked at me—hungry, amused, approving. Something stirred deep in my caged cock… something humiliating and delicious.
By the end of the week, she didn’t even need to order me around. I was begging for her to let me wear my little pink dress. To serve her drinks in my maid outfit. To crawl under her desk and keep my tongue busy while she texted her friends about what a good sissy I’d become.
“You see now?” she said one night, stroking my hair as I knelt at her boots. “You were never meant to be a man. You were made for this.”
She was right.
It didn’t stop there. With her encouragement, I started meeting other dominant women—and even a few men. I became a toy, a doll, a pet. Not one of them treated me like a “real man,” and I didn’t want them to. I loved being their sissy.
Now, there’s no going back. I don’t want to go back.
Part Two: The Sissy Unleashed
By the second week of my “challenge,” there wasn’t much fight left in me. I no longer slept in boxers. Every night it was panties, a silky babydoll, and my cage snugly locked. She’d brush my hair out while I sat cross-legged at her feet, thanking her softly for making me “pretty.”
But the humiliation wasn’t just in private anymore.
It started one Friday when she invited friends over. “Show them what a good girl you’ve become,” she whispered. Before I could argue, she yanked me into the living room.
There I was—pink satin maid dress, thigh-highs, little bell collar jingling—serving drinks while they smirked and whispered.
“Look at you,” one of her friends purred, lifting my skirt just enough to glimpse my caged bulge pressing against lace panties. “Aren’t you adorable?”
My face burned. But my cock strained uselessly in the tiny cage, throbbing at the attention.
Later that night, she had me kneel between her spread legs on the couch while her friends watched.
“Tongue out, sissy.”
I obeyed instantly.
They laughed, took photos, cheered me on as I licked and sucked like the desperate little thing I was becoming.
“See? He was made for this,” my girlfriend said, ruffling my hair like a pet. “Not for fucking—not with that tiny thing. But for serving. For worshipping.”
And they all agreed.
The real breaking point came a few nights later.
She brought home a man. Tall, broad, confident. I froze when she told me to greet him.
“You’re going to be a good girl for him too, aren’t you?” she said sweetly. “We both know real men turn you on now.”
I wanted to protest, to run—but my panties were soaked, and my cage ached.
He took me like it was nothing new. Bent over the bed, face buried in the sheets, her hand on the back of my neck, whispering encouragement.
“Such a perfect little sissy slut. I’m so proud of you.”
And I loved it.
Now, there’s no part of my life untouched by her training.
I only wear women’s clothes—workout leggings, crop tops, lingerie under my skirts. She controls my release schedule (rarely), my wardrobe, even my social media, which is now full of photos of me in heels and garters.
Men and women alike know me as a sissy. They use me, laugh at me, praise me—and I crave it all.
I’m not a man anymore. I never was. She saw it before I did. Now, everyone sees it.