Crossdressing Stories

crossdressing stories

Ready to slip into her shoes? Our crossdressing stories are packed with juicy twists, secret desires, and unapologetically femme fun. Whether you're a curious first-timer or a seasoned sissy, these tales are here to turn you on and pull you deeper into the world of silky lingerie, soft moans, and total surrender.

From slow-burn feminisation to cheeky roleplay, each story explores the thrill of transformation—mental, emotional, and oh yes… physical. Some are sweet, some are filthy, all of them written to get under your skin in the best way. You’ll find dommes who take control, sissies learning their place, and fantasies that might just hit a little too close to home.

So go ahead, darling. Pour a drink, lock the door, and let your girly side out to play. These stories aren’t just fiction—they’re invitations.

Posts in Crossdressing Stories

Caught Crossdressing When Babysitting

Caught Crossdressing When Babysitting

Bryan took the babysitting gig. One black dress, a little curiosity, and a surprise walk-in later… he’s standing in heels, makeup, and lace—caught by John. But instead of fury? Just a smirk. “Beth, huh? Cute.” And just like that… the game changed.

By Tohka Crow02/03/2024
Secret Femboy Valentine

Secret Femboy Valentine

Pizza, beer, and games turned into makeup, lingerie, and one bold question: “Wanna make me your secret femboy Valentine?” Chris stood in red lace, heart racing, lips painted—and Ben? Oh, he wasn’t ready… but he didn’t say no.

By Tohka Crow13/02/2024
My Boyfriend Becomes a Sissy Star!

My Boyfriend Becomes a Sissy Star!

Tim lost his job. Kate had a plan. One comment, one bath, one silky step at a time—and suddenly “Tiffany” was born. Bills need paying, and shame? That’s just part of the show. She’s the star now, dolled up, camera-ready, and oh-so-filthy-fabulous.

By Tohka Crow10/02/2024
Student Boy To Gamer Girl

Student Boy To Gamer Girl

Daniel was just a shy gamer, hiding secrets behind his screen. But one click, one wig, one soft swipe of lipstick—and Yukari was born. From awkward silence to sweet stardom, she found herself, her voice… and a whole community that loved her for it.

By Tohka Crow01/02/2024
Wife Turned Me Into BARBIE!

Wife Turned Me Into BARBIE!

Matt just wanted to feel the fabric. One slip into Alice’s dress turned into lashes, heels, and a pink wig... then a full-blown Barbie line for men. Caught in satin and love, he became her muse, her model, and her masterpiece.

By Tohka Crow24/01/2024