‘crossdresser’ stories

Tom finally has the courage to get fucked by another man.

Sissy finally taking it to the next step with Opa.

Evening in the school common room. Will punishment follow?

A trip to my local bookstore video arcade.

My first sex with a man while dressed as a woman.

Janice and Dennis try anal sex for the first time.

Jim gets a home and a few surprises.

Student has no time to clean, offers roommate a hand job.

The journey continues as Opa and C got closer.

Basil learns the true purpose of being a fairy boy.

The seduction trip.

The story of a young curious teen's transforming adventure.

An older gent sees a boy dressed up as a girl for Halloween.

Jim discovers more about his parents and angels.

Crossdressers seeks "help" from a black shemale.

Rose plots to corrupt Angelina, Domi plots to seduce Dolly.

Boyfriend dresses up in women's underwear as a surprise.

A crossdresser meets a man at a snowy hotel.

Eric tried an escape with his new friend.

Classes begin for our girl in disguise. Trouble lies ahead.

Elizabeth turns Dan into Dani while at a music festival.

My first time at Linda's was just to learn the rules.

The journey to fulfilment reaches the end.

A journey to fulfilment continues.

A crossdresser's journey to fulfilment.

Trish gets me ready.

This is a diary of my sexual encounters.

A service to help sissies live a new life gets a new client.

Leah has decided to fight back... will it work?

Paula loves cocks.

The Uber Driver gets a nice fare!

Paula becomes a woman.

Mykal's been gone on business, and is returning home late.

Aspen gives his Alpha a little surprise.

Meeting my long time friends for the first time. As Georgia.

Gabriel takes Rolo home and gives her a bath.

Ellie promised punishment if Leah ever broke the rule...

Submissive returns to her master to please him again.

A tour around the school goes badly wrong...

Allyssa and Nikki meet guys for the first time.

The sensual process of turning into Jessica.

A night walk with Robert ends in an erotic adventure.

Femboy becomes his best friend's girl for a day...

Fully dressed as a women on a stroll and the car won't open.

The weekend continues.

Mark let's me blow him as Seth loosens me up.

Leah's roommate knows her secret...does she enjoy that?

Alex makes bet with Jamison and Amy isn’t to pleased about it.

Doug learns more about Marsha.

K wakes up tied to Rose's bed, about to be punished...

Another adventure for the Three Cocks Service.

I become a maid for a sadistic couple.

The descent into becoming sissies continues for Mitch and Paul.

Mistress puts Chrissy in bondage then whores her out.

Bridget rebels.

Alessia plays with her tennis coach!

Suzanne wants to celebrate with her boyfriend's alter ego.

Mark finally gets what he wants.

The things Lisa makes me do.

A friendly meet-up turns into a date.

The morning after Mitch and Paul get caught in lingerie.

Crossdresser drives for a ride share company.

Liam finds himself in the wrong school with a big secret.

Mike's crossdressing gets him much closer to his stepdad.

A story about forced feminization.

An intense short story of Cuckoldry.

Romance and railways.

Crossdresser lets herself be pulled.

From trying on lingerie to pleasing a real man.

Spanking? Sure. Panties? Okay... Strapon? Wait no!

It wasn't my idea to put on a dress - but I'm glad I did.

From trying on lingerie to becoming a desired woman.

Chrissy buttfucks Mistress.

My very first time as woman in public.

Female classmate discovers my fetish. And hers...

Carla takes another step towards my slow feminization.

Short story of my journey being pimped out by my mistress.

Being transformed into a woman by my girlfriend's mom.

Carla starts to take me down the rabbit hole, slowly.

Maid serves three masters and is assigned new tasks.

Two women's needs.

Nikki finds out more about the hotel staff.

From admiring a woman in lingerie to trying it on myself.

A robbery gone wrong forcing Jeff to disguise as a woman.

Femboy executive assistant learns on his first day.

A young couple tries to spice things up with role play games.

College crossdresser finally goes through with it.

The aftermath…

Submissive faggot becomes a man’s cumdump!

Joe tells his story from “Tina’s Play Thing”. The BJ.

Life changes dramatically and Michelle returns.

A crossdresser becomes his wife's personal french maid.

Lisa's story takes a twist. Things are not what they seamed.

Brandi punishes her stepson for stealing her sex toy.

Prince must take the place of his sister to save his people.

Amy decided I needed new undergarments so we went shopping.

Crossdressing suprise for a bi couple during mmf fun.

Amy confesses she been giving me hormones.

Wife gets excited learning her husbands part of the rainbow.

A cross-dressing author has a wild night with a fan.