‘crossdresser’ stories

How might my first blowjob go?

Crossdressing boss forces Sam to take a ride on his lap.

Beta male learns to become a perfect submissive sissy boi.

Tiny and undesirable boy discovers a new life as a sissy.

The next day.

Chloe shops for shoes and gets more than she expected.

A young man's transformation into a sissy whore.

Young, Sissy CD's First Time with her Daddy.

Young closet crossdresser smokes with his friends as a girl.

I may have over committed to my girlfriend’s costume idea…

Young man applies to work in lingerie dept.

Closet CD discovered by flatmate who has fun with him.

Loving femdom: the rode dress traveled.

Crossdresser receives her first taste and loves it.

She sees what he looks like when not in drag.

He wears the dress to marry his Tomboy dream girl.

My domme ex girlfriend finishes what she started.

My step sister has me do things that were nasty.

Jan becomes a sister to his wife and her lover. (novella)

Learning to make love as a girl.

A recount of my first slut adventure alone.

Male nurse is forced to become a tranny nurse & fuck the Doc.

Jamie meets his dream girl, only to find out it was him.

CD Jessica's neighbor becomes her FWB.

Jenna dives deeper in her place as Daddy's girl.

Husband enjoys first time as crossdresser after losing wager.

Hot night at a bi/tg swingers party.

A sissy gets a visit and his wishes come true.

A babysitter gains the upper hand on the drive home.

The next day in Nikki's little world.

A boy and a girl have sex at a party. Or wait, is it a girl?

A transvestite gets dominated by a stud.

David goes further than he thought he could.

My step-sister takes me out for the day.

First Time for CD comes randomly.

She's not the kind of girl he was expecting.

Steve gets his first taste of cream Part 2.

Transvestite blackmailed by Uncle & forced to submit.

Daddy's 3rd divorce hits him hard. What can I do?

Still blackmailed, but enjoying it.

Caught crossdressing and blackmailed into submission.

Brian dives deeper into sissification and anal sex.

CD gets Valentine's Day surprise from neighbor,

Actor gets the role of a lifetime.

He finds a gift sent by his ex-girlfriend's father.

Jasmine meets a new friend.

Closet crossdresser gets to play when roommate's away.

A submissive white TV meets a black gangsta online.

First time dressed as Rebecca in front of him.

White CD's date with married Black man.

Crossdressing male nurse becomes grieving man's wife.

A feminine guy willingly seduces and submits to his boss.

She calls and he gets ready.

Shemale lover.

Mandy in the city.

Nick's femdom journey begins gently, but that won't last.

A white sissy boi ends up in the wrong part of town.

Crossdresser meets first time man in hotel.

Hooking up with my ex-girlfriends cousin.

Sissy learning what a sissy is.

Guy gets into an adventure while wearing his friend's panties.

Young man starts a job he isn't quite ready for.

All dressed up and finally must choose between 2 suitors

A smoking sissy is on the hunt for black cock.

submissive cd slut meet with two bisexual guys.

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

A guy finds love only to be his boyfriends girl.

A shy sissy makes a new friend with a Thrift Store owner.

Halloween!

A transvestite's date turns rough.

Riding the cock of passed out cousin.

A 30 year old loses his virginity to three men.

Freshman learns how to sneak into Frat House party as a girl.

Marilyn works to take care of her daughter.

Tom must be Tamsyn once more to cross the border.

Crossdresser Enjoys Intercourse As A Girl.

Crossdresser caught in the act by police.

College stud is put in his place by his roommate.

Male comes to terms with his feminine side.

Crossdresser re-unites with birth mother.

Amy's first day as a tease.

Mistress makes her sissy slave pay the rent - the hard way!

Dressed pretty for Mistress Viv.

Nw experience for the horny young woman from Alabama.

Joe discovers that his best friend Brian is a crossdresser.

Wife's cross-dressing game with husband opens new frontiers.

Susan continues John's transformation.

Allie loses her virginity.

One of the hottest graduation parties changes one boy's life.

Grad student transforms with help from three new room mates.

Me and my best friend sitting round one night.

A closet crossdresser treated rough.

Daughter accidentally discovers her father's kinky secret.

A married couple have sex with black men.

A young sissy fails to keep his secret from an older man.

The consummation period of Martin's marriage is now over.

Sissy goes shopping.

Girlfriend takes revenge on boyfriend for cheating on her.

Airport custodian bangs faggot asses.

My story visiting a dominatrix and dressing as a woman.