‘crossdressing’ stories

An anthro experiments with his sister's toys and clothes...

Stumbling upon a young man with limitless potential...

Trans girl semi-accidentally hypnotizes a cute male friend.

The Prince goes shopping.

Bi-curious Mom divorces. Tessy and Diana take her to bed.

David explores his sexuality with Justin.

Devil Redd had a busy weekend.

Costumed monster sluts drive Tess and Diana together.

Alex is made to give an intimate apology to Stuart.

Continuation of Krissy's dental chair experience.

A magical first time experience, while dolled up.

Diana’s fantasy: men in nylons. She turns Ted into Tessy.

My pantyhose fetish continues to expand.

Carla finds love.

A mishap in the washroom leads to an unexpected yoga outfit.

Chloe and Sarah take humiliating and messy revenge on Ethan.

Diana blackmails her brother Ted for "loving" her nylons.

The Prince meets the mans friends.

Carter decides what the rest of his life will look like.

A new job filled with heels, tights, and unique challenges.

Dyri is forced into his female role.

Old Army buddies reunite with some surprises.

Sim sissy visits her mistress.

Getting back into crossdressing after missing a few years.

Heather is officially born.

Caught in panties.

George is a young lad subsidising his income by gardening.

Sim Sissy is returning home after meeting her new Mistress.

Carter gets his sentence reduced, but at what cost?

A couple teaches a young guy about the joys of crossdressing.

Desperate to keep his job, Alex agrees to bizarre conditions.

You catch me exploring a taboo kink... and encourage it.

A Sissy gets the oppurtunity to dress up on Halloween.

Alex becomes more adventurous.

A sissy crossdresser's unfinished feminine journey.

Dominant religious parents insist their son joins the church.

Sim Sissy will finally meet her BlackMailer.

Mom forces her son to dress up as a girl.

My hot bodyguard and I are alone...

A very short story about preparing a bull for my wife.

After his Prom, our hero is equipped for her new life.

More femboy fun. A sequel to Saturday at the Cafe.

I'm manipulated into becoming Stroud's beknighted slavegirl.

His boundaries are pushed to servicing three men at once.

Mother turns son into sissy maid.

After my first meet more fun follows.

An office meeting with Simon my online admirer.

Roommate helps his friend some more.

Ryan's frat journey begins!

The Prince gets desperate home alone.

Jex attends the local community college.

Sophi catches Will with a littler more than his pants down.

Art can take many forms.

Azure preps for a resort weekend.

Some jobs just require a sissy...

A tale of a first time hotel meet as a crossdresser.

The Prince and Vesper reach the safehouse.

The turning point, the birth of Heather.

Becoming Chloe.

Whiteboy's AMIRAP journey delayed.

SimSissy visits Paul and is going to fix his computer.

Kelly's night of firsts continues.

I'm seduced by a perv stalker and blackmailed by gangsters.

Roommate needs help to get off. What will I do?

Ash and I have a naughty evening.

A story from the collected works of TVWintergreen.

Simon has to dress as a woman at the club and meets a guy.

Sim Sissy is forced to go to a public park.

Sam trip continues differently than he had planned.

Joe and his friends have a cross dressing weekend. Oh my!

Middle aged man humiliated by younger lady.

Using lottery money to go MTF, Ron fears the future.

Hank is Maid to clean up at the gloryhole.

I'm stalked after an emasculating news story is published.

Sim Sissy is forced to perform tasks.

After some tipsy dress up, Stuart makes an entrance.

A story from the collected works of TVWintergreen.

Fourth part of SimSissy, still getting blackmailed.

A ridiculous story of forced fem, trans top, milking, etc.

A cute feminine boy fools around with his friend.

Third part of SimSissy, who suddenly gets blackmailed.

This is a story of an imagined first meet.

Sissy maid is put in chastity by her three masters.

Shae teases Alex and has some fun while out shopping.

Working from home has its perks.

I spend a weekend with Sue and her Room mates.

Alex visits Coach's office as he ponders their relationship.

A story from the collected works of TVWintergreen.

Jesse has a realization and futures are settled.

“Troubled” youth lands in a prison for repressed men.

One small step for man... One giant leap into depravity.

A story about forced feminization.

Prepped for the party.

A Geek's Prom becomes a journey of self discovery.

Britney ups the ante ahead of the big day.

19-year-old boy fantasizes about being with dominant men.

Following a tip, Jennifer finds a hidden "Back Room"

Will the threesome become a throuple?

A young man can't resist the temptation of the hole...

Do it Yourself.