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 By Sales Assistants!

Caught Crossdressing By Sales Assistants!

Robert was all business by day—but one dress, three giggling shopgirls, and a makeover later, Roberta was born. A party, a kiss, and a spark with Alex? What started as a secret fitting turned into heels, heat, and a whole new self. Ready for more?

By Tohka Crow20/01/2024
Business Negotiations in Heels!

Business Negotiations in Heels!

Ryan agreed to wear a dress to save his job. One makeover, one business dinner, and a dangerously close kiss later—Vivienne closed the deal. But when the wig came off, something felt missing. Maybe Vivienne wasn’t just an act… maybe she was real.

By Tohka Crow17/01/2024
Femboy’s First Time As A Girl

Femboy’s First Time As A Girl

Luke’s got a girlfriend back home… but tonight? It’s all heels, lipstick, and a hot invite from Greg. One bath, one makeover, one little skirt—and boom, the femboy inside steps out to play. He’s not just dressing up… he’s becoming.

By Tohka Crow15/01/2024
Mom Turned Me Into a Maid!

Mom Turned Me Into a Maid!

Hungover, humiliated, and out of options, Alexander agrees to work as the family maid—only to find the uniform is frilly, the heels sky-high, and the lessons deeply humbling. But somewhere between lipstick and tea service, he starts to like it.

By Tohka Crow12/01/2024
Businessman Regressed To a Daugther (ABDL Diaper Sissy Boy Story)

Businessman Regressed To a Daugther (ABDL Diaper Sissy Boy Story)

Chris was drowning in debt, desperate, and nearly broken—until a rich, mysterious woman offered him salvation... for a price. Her condition? Give up his name, his life, and become her baby girl, Daisy. One signature, and everything changed.

By Tohka Crow09/01/2024