‘cross dresser’ stories

My domme ex girlfriend finishes what she started.

Drew thinks he's escaped Mark, Drew is wrong.

A joke costume goes a little too far, or not far enough.

A very dominant man uses his sissy 'wife'.

Mom has to use son as mortgage payment.

College student forced to be their roommate's sissy maid.

I took some time off from college to dress up and get wild!

David is convinced to dress up for Halloween.

Married man role plays at adult rave party; swallows cum.

Girlfriend takes revenge on boyfriend for cheating on her.

A man has anal sex on a train with a stranger.

Married cross-dresser's fantasy is to dress & serve.

A sissy 'girl' gets put on display, for offer to others.

Surprising my straight hubby with a bi guy in drag.

Peter calls Robert for anal sex to finish what he started.

I meet Chad and he begins my journey down the rabbit hole.

A different look at building a successful family.

A visit from the neighbour leads to fun for two brothers,

Wife helps her husband through a sex change.

Sissies submit to their dominant wives.

Rick and I spend the rest of the day on into the night alone.

Divorced male seeks masculine man for marriage.

Rob is forced to become Robin.

Transition: the morning after.

Friend joins couple on a romatic camping getaway.

How one man changed from straight to a cock slut.

Blackmailing my twin sister.

Sex through a glory hole more than I planned!

He finds a beautiful cross-dressing college boy.

Corey's adventures as Cora continue...

Becoming a Wife to a Man.

Peter officially meets Roberta again, the love of his life.

The world is starting to look a little dark.

Love and vintage clothing.

You never really know what to expect from your first BBC.

Quarantine can get a bit lonely.

Sissy maid gives blowjobs and receives new rules to live by.

Michelles training steps into high gear.

Tranny and Boyfriend Tag Team me.

Cross dresser tricked into public scenario.

Jade learns a very difficult and very valuable lesson...

Young Man Debauched; Turns Sex Addict.

A closeted cross dresser is discovered and humiliated.

Young man shares rent and learns to swallow cum.

A new city, a new me, a new friend.

pretty sissy cuckold takes a lover of her own.

A favour for a friend, where could it lead?

Danielle finds she's getting more than she bargained for.

Brandi takes charge.

A man in his thirties realizes the power of his inner woman.

A woman in black drags Scott into self-exploration.

I found a surprise under my neighbor's 'pesky' skirt.

Jennifer enjoys a night out with the girls.

Michelle has an intense training session and date w/ Brenda.

Husband and wife becomes sisters.

Actor gets the role of a lifetime.

Michelle continues with Brenda and spends time in the office.

FANTASY is so much better than REALITY!

A sissy's fantasy becomes a reality.

I return to the bar, and pick up a surprise.

College age Trans girl finds love with Silver Fox.

Dreaming of the first taste of cum.

Nightgown-clad husband spies on unfaithful wife.

Karla tells of her progress to sexual fulfilment.

He had a secret, though he never thought of coming out.

Cross-dressing man gets job as female secretary.

Sam finds a job opening online. Learns a hard lesson.

Husband obeys even more.

Michelle learns a valuable lesson and progresses in her job.

Michelle is falling for Brenda, but Ms. Allison has plans.

Foot fetish holds a Nude Day surprise at the beach.

A weekend with Babette brings a new level of closeness.

College crossdresser finally goes through with it.

Young man recalls his first time as a cum slut.

Gerrig wakes up with his penis on a leash, he's a housewife.

To get dream dyke, he pretends to be a she.

Dress shopping, flirting, party plans & in bed with Babette.

Jerry uses Halloween as his excuse to dress as a woman.

A little experimenting never hurt anyone.

Fraternity pledge coed cross dresser dances sexy for men.

The hot to trot transvestite gets her first real man fuck.

Man on business meets sexy cross dresser.

Lovers and Friends.

Michelle returns to the office after a very busy weekend.

The night of the bachelorette party arrives!

Husband obeys.

Turned into a sissy slut by the older neighbors.

Crossdresser goes out dressed to meet a man.

Mindy starts taking some big steps on her path to ...

A crossdresser gets more than they bargain for in a hotel.

A Transwoman, hunting for a mate, stumbles into an orgy.

Frank/Francine and his wife have launch a new strap-on.

A handyman gets it wrong when things get steamy with Jamie.

Playing a new role at the sauna.

My first Valentine's Day spent "alone" in five years..?

Voyeur; Like mom, like son.

It's thenight of Michelle's graduation party.

A gradual transformation from boy to woman.

Quinn gets a scare before some alone time with Josh.

Embracing the change, going further down the rabbit hole.