‘crossdresser’ stories

Sandy Meets Bob.

My afternoons with my man.

I discover my neighbours are a sexy bi couple.

Mr Wilson wants to know every detail of my date.

Twink boy starts living his truth.

I discover my neighbours are a sexy bi sex couple.

Mr Wilson encourages me to go on a date with Stan.

Alex gets a special Mommy.

I became a monster's mate and I didn't have a choice.

A series short stories about discovery and transition.

Mike's First Time.

A follow up piece to my previous How Jackie gets Blacked.

Sandy spends more time with Kim and meets her friends.

Mr Wilson gives me 'guidance' in new relationships.

Last minute plan change leads to a good sissy fucking!

Man enjoys being a woman wearing his wife's lingerie.

Female transition turns into more.

Mr Wilson introduces me to more pleasure.

Sissy Kristy goes back to Sir's motel room.

Sean (Now named Candy) is blackmailed into modeling!

After a discovery, should he keep their secret or not?

A young CD accompanies his Daddy to a naughty get together.

Dani gets dressed for his date and meets up with Demarcus.

An anonymous hook-up leads to a pleasant surprise for sissy.

Caught in the moment…No mercy!

MArk discovers his true self in college.

A Crossdresser becomes a woman with help from her friends.

My Longtime Enjoyment From Nipple Play.

A locked, plugged, crossdressed sub confronted by cum.

Open wide you, little cock sucker.

A pair of panties changes Sandy's whole life.

My husband had a bit of a turn.

CD gets a fresh start after breakup - 750 Word Challenge

The Queen returns after a victory.

A young man discovers more than they bargained for.

Amy enjoys taking charge of the slave.

Middle-age man hires a babysitter with a surprise...

An indecent business proposal leads to wild sex.

A new start, a new life and a new mom.

Earning that 'A' with my first professor.

A look in a mirror reveals a face Scott's never seen before.

Two sissies get married and explore pleasure together.

A son learns his dad is a cross dresser.

Stepdad suspects stepson wants some cock.

Being a good friend can kinda suck.

Young sissy girl gets more than she bargained for.

Transgender ladyboys and a couple story.

A crossdresser finds his dream girl.

A woman in black drags Scott into self-exploration.

A crossdresser learns of her past, while perched on a rock.

Kristy gets fucked hard by a biker.

How far do I want to go?

Girly clothes doesn't mean I'm a bottom.

A day with the Bakers.

It started with makeup.

Monica turns her husband into a panty wearing sissy slut.

A stranger fucks Kristy's ass on his lunch break.

Opportunity comes knocking at my door thanks to a thief.

Plans continue a pace preparing for the experiment.

The Homosexual Psychology of Femme Sissies.

Alex is conditioned by daddy.

Crossdressing husband Stefany's first porn to camera.

Nika guides her best friend, Billy, down a feminized path.

Two sissies in love work on wedding plans and having fun.

Adele visits Mike.

Straight man meets and falls for crossdresser!

Alex starts his training.

Erica has her first date of the weekend.

I met someone making the same mistakes as me.

Kiera and Valerie transform Eric.

An older sissy replies to an invitation to submit.

My first time dressed playing with another CD.

My going black.

True story of my first hook up while dressed.

Aimee’s first public appearance.

Caught dressed as Adele.

My Stepmother invites an old (famous) friend over.

The beginning of my story discovering my submissive side.

A man meets CD Sasha & partner Charlotte in a bar.

Continuing story of my new Dom and my cuckolding.

Crossdresser gets "caught" in the park during a storm.

James takes further control of Sean!

Was it possible she knew what I did with her panties?

Three friends hope to lose their cherries on prom night.

Black ops operative betrayed, goes deep cover for revenge.

Crossdresser tells mother he wants to be a girl.

Festive Ffion fuels the fun at Christmas.

Two sissies become close friends and encourage each other.

Young Crossdresser fucked by a Mature Stud.

Clean meets someone Special.

Two men try to hire a hooker for a blow job.

The first training session.

Prequel - Alex's virginity is taken by a sexy crossdresser.

A T-Girl gets a surprise from her wife at Christmas.

Adam is taught by Lace how to act like a proper sissy girl!!

Brian gets a taste while Hank finds a way to free himself.

Lace focuses on the little details Adam needs to be a sissy!

An older man takes full ownership of a young crossdressser.

Taking things back to his place.

An intimate dinner party turns erotic.