‘crossdressing’ stories

What happens in the pool stays in the pool.

Our CD finally loses her virginity and does some catching up.

Prom night! Blackmail, blowjobs, and more for Anna!

The guys get to their destination, the hotel fun unforgotten.

The Best Friend has been convinced to extend his trip.

Lexi comes out to her family, goes out and meets a war vet.

I’m Lewis’s Slut Now.

First time experience for a feminine boy at an Onsen

Jack uses Kieran's sissy side to act out his fantasies.

Embracing the change, going further down the rabbit hole.

Sissy Riley serves her Mistress and friends.

Chris's neighbours help him become who he wants to be.

A death leads to a new life.

Jaina's desires begin to conflict with Aaron's.

Hiding my secret until I found those who were accepting.

A release for Rory, with her favourite friend!

Rory meets a new, bossy friend.

Steve lets his "Sarah" side date a TV/CD admirer.

Dressed like a woman, fucked like a woman.

Gina gives Joey a makeover, turning him into Julia.

Dressed up, he finds adventure in the city.

Howard reflects on how it all began, and joins the party.

Sissy tries the real thing.

Crossdresser doesn't know why everyone thinks she's a woman.

Meaghan's practice pays off, but only creates more problems.

Formerly Daniel, Diana accepts the path to femininity.

Pao had just been stabbed at Cockatoo. Its pandemonium.

You were a cheerleader?

James meets Areeya's father. Something new happens with Alex.

Sharing is caring.

Laurie goes out in public as a woman, twice.

Chris takes two cocks in his ass at once

Jaina has her first encounter with another crossdresser.

The need to be Rory grows stronger and stronger...

The transition continues.

Straight guy comes to a new realization from watching porn.

Continuation of the series, John becomes Joanie.

Trans woman helps others to be themsleves.

Xmas brings costumes, elves - and a big present from Daddy.

The makeup arrives and our narrator goes all the way.

Nikki joins her friends by the pool in Scottsdale.

Sarah experiences more life as a woman.

The Adventures of Jim and Erica Continue.

Hailey surprises me with an adventure (bi).

Two more travellers find solace and more within my refuge.

A holiday meeting brings about tremendous changes.

Camila convinces me to go to a Halloween party dressed up.

Dani and Kevin finish the trip with more plans in store.

Jacob has an offer for Kylie.

Percy becomes Priscilla; laundry duty beckons.

A guy discovers how wearing lingerie can change his life.

International manhunt for man disguised as a woman heats up.

A college aged babysitter is caught dressed as the wife.

Rick confesses about his boss and goes shopping.

Jay advances his position with the newly enabled twins.

Rene comes to stay the weekend.

A pair of panties gives him a start.

Ra'Chelle goes off on her own and finds more friends.

A confession, an offer and action!

Tai continues his voyage of self discovery.

Mac' fun continues at the Medical Supply Store.

Trip Pt I Shauna is forced to have anal orgasm.

Loving Femdom: the rode dress traveled.

Loving Femdom: the rode dress traveled.

He's caught by his stepdaughter wearing her panties.

Becoming Joscelyn, with bondage and heartache in the mix.

A drinking game with new friends changes everything.

Guy changes school and sex to fit in.

Nicole sinks deeper into submission.

How far would you go to save your best friend marriage?

Day 2 of the friends' adventure in the country.

Jerry Goes for a Run With Teen Stud RyanH.

New clothes and a night alone for Gen and Jamie.

A man embraces his feminine side when encouraged by his wife.

Halloween surprise.

Liam finds a surprise and gets finger fucked.

A Sissy Son gets a Gift.

Day 2 of cd and her online bf in NYC.

Rita acquires a sister and they submit together.

Tim wants to re-live his crossdressing/cocksucking surprise.

James explores his feminine side with his crush's roommate.

Rita continues her training, now with her Granny and Mommy!

Jemima learns that it's best not to mess with an ex...

Mike would do anything for his crush Tiffany. Anything.

Dustin Struggles to come to terms with being Desiree.

A spell misfires and turns a nerd into a hot babe.

Former Girlfriend Joins Jamie's Coming Out Celebration.

First unsteady steps on heels almost fall flat.

The second day in a row of fun for an eager sissy.

Continuing where we left off with the street walker.

Jamie is traveling on business. She is caught enfemme.

A sissy loses the key to their cage and soon loses control.

Kelli the awakening.

Jamie meets Shane again and becomes Scarlett.

CD builds bondage bench for mistress and her sissy husband.

Andrew becomes Andrea and falls in love with his sister.

Grandma, Grandson, and Aunt live together.

Every relationship has problems. But can they be fixed?

Dakota, despite her shame, explores kinky side with Desiree.

Becky finds out about Chrissy's other life.