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

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
Forced Feminisation on a LiveStream

Forced Feminisation on a LiveStream

Henry wanted to impress the elite club—but stealing his sister’s panties on livestream? That crossed a line. Caught red-handed by Melanie, the tables turned fast. Now he’s Helena, dolled up in pink and heels, with the whole campus watching.

By Tohka Crow07/01/2024
Feminised by Mom’s Friend

Feminised by Mom’s Friend

Noah arrived drenched and uneasy, but one bath, some teasing, silky pajamas, makeup, and a wig later, he left Layla’s house the next morning in pink panties under his jeans—confused, flustered, but carrying a secret thrill he couldn’t quite explain.

By Tohka Crow30/12/2023
Caught Wearing Pantyhose and Thong at Work!

Caught Wearing Pantyhose and Thong at Work!

Arthur wore pantyhose under his slacks for a thrill—then got caught by the director. Offered a promotion if he'd crossdress full-time, he panicked. But after coming clean to his mom and sister, he said yes. Next step: heels, lipstick, and a new life.

By Tohka Crow27/12/2023
First Day At Sissy Academy

First Day At Sissy Academy

Nicholas thought he was signing up for a course. Turns out, it was a one-way trip into pink satin, high heels, and a new name—Nancy. With a smirking Mistress Scarlett calling the shots, Sissy Academy isn't just school... it's total surrender.

By Tohka Crow26/12/2023
Crossdressing Stories - Naughty Reads for Your Girly Side