‘crossdressing’ stories

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crossdressing

Jamie's Descent Pt. 05

Jamie falls further under the control of Fiona.

Transsexuals & Crossdressers 08/21/2016

Mistress Chantel, Tranny Dominatrix Ch. 02

Journey of this Tranny Dominatrix and the men who visit.

Transsexuals & Crossdressers 08/21/2016

Couples Only: Glory Hole Night Ch. 04

How it all began with two male roommates.

Transsexuals & Crossdressers 08/20/2016

Call Me Katie Pt. 02

Kent's transformation begins.

Transsexuals & Crossdressers 08/18/2016

Call Me Katie Pt. 01

Kent is forced to make a difficult decision.

Transsexuals & Crossdressers 08/17/2016

Three Nights in London - Night 03

Cute Dutch Tgirl goes for it!

Transsexuals & Crossdressers 08/16/2016

Finding Gabriel

A little gender play leads to love.

Transsexuals & Crossdressers 08/16/2016

Blackmailed High School Sissy Ch. 02

When two bad girls find out about Max's sissy fetishes.

NonConsent/Reluctance 08/11/2016

Sex, Drugs and My Neighbour Daddy

My hot neighbour blackmails me into being his little sissy.

Gay Male 08/07/2016

Three Nights in London - Night 02

Cute Dutch Tgirl goes out for the first time.

Transsexuals & Crossdressers 08/06/2016

Chronicles of Heather Maureen Ch. 10

The life of one transvestite from start to present.

Transsexuals & Crossdressers 08/06/2016

The Roommate Pt. 10 - Miranda

After church, Merlot.

Transsexuals & Crossdressers 08/04/2016

The Roommate Pt. 09 - Miranda

Heat.

Transsexuals & Crossdressers 08/03/2016

Jamie's Story Ch. 03

Jamie's focus starts to narrow on what he wants.

Fetish 08/01/2016

Strange Love

LGBTQ-training brings a cop together w/ a CD woman.

Transsexuals & Crossdressers 08/01/2016

A Simple Bet

Two friends make a little wager.

Fetish 08/01/2016

The Best of Friends

The nobody of a group of friends finds his place.

Gay Male 07/30/2016

Becoming a Sissy Maid & Slut Vol. 08

More becoming a sissy maid & slut, vol. 8 Chapter 14.

Transsexuals & Crossdressers 07/30/2016

My VideoChat Error Ch 08

Shauna loses her true anal virginity.

NonConsent/Reluctance 07/29/2016

The Roommate Pt. 08 - Miranda

In which Lori comes closer.

Transsexuals & Crossdressers 07/28/2016

My Neighbor's Toys

Male next door neighbors play with adult toys.

Gay Male 07/28/2016

Daddy's Piss Receptacle

A crossdresser is given a dirty challenge by her fuckbuddy.

Fetish 07/27/2016

His First Male Domination

A bi-curious man explores his curiosity in his favourite way.

Erotic Couplings 07/26/2016

Sweet Treat

A secret crossdressing husband comes out.

Transsexuals & Crossdressers 07/26/2016

A Girl And Her Sissy

A girl recounting the feminization of her boyfriend.

Transsexuals & Crossdressers 07/25/2016

Gay Fem Boy Finds His Man

Feminine gay guy and gay masculine man.

Transsexuals & Crossdressers 07/25/2016

Chronicles of Heather Maureen Ch. 09

One transvestite's life from start to present.

Transsexuals & Crossdressers 07/25/2016

Women's Studies Ch. 03

Kennedy finds out Lexi's secret.

Transsexuals & Crossdressers 07/24/2016

The Roommate Pt. 07 - Miranda

Lori's reward.

Transsexuals & Crossdressers 07/23/2016

Blackmailed High School Sissy Ch. 01

When two bad girls find out about Max's sissy fetishes.

NonConsent/Reluctance 07/23/2016

The Roommate Pt. 06 - Miranda

Throwing a curve ball or two.

Transsexuals & Crossdressers 07/23/2016

The Caretaker's Dress

Straight boy gets steamrollered.

Gay Male 07/23/2016

Becoming a Sissy Maid & Slut Vol. 05

Becoming a Sissy Maid & Slut, Vol.5, Chapter 11.

Transsexuals & Crossdressers 07/23/2016

A Different Relationship Ch. 05

The aftermath of a memorable night and meeting some friends.

Fetish 07/22/2016

A Night at the Club Pt. 01

Keyshawn and Dani go to a hot interracial club.

Transsexuals & Crossdressers 07/22/2016

The Roommate Pt. 05 - Miranda

Lori signs a contract.

Transsexuals & Crossdressers 07/22/2016

First Time

A crossdresser takes her first venture in a group encounter.

Transsexuals & Crossdressers 07/21/2016

Dani's Night Out

A chastised sissy is sent out to satisfy a huge black man.

Transsexuals & Crossdressers 07/21/2016

Chronicles of Heather Maureen Ch. 08

The life of one transvestite from start to present.

Transsexuals & Crossdressers 07/21/2016

'Jenny' & 'Mike': Date Night

Beginning of a role reversal weekend for a loving couple.

Transsexuals & Crossdressers 07/20/2016

Three Nights in London - Night 01

Cute Tgirl goes out for the first time.

Transsexuals & Crossdressers 07/20/2016

She Wanted Me to Have Fun... Pt. 02

The next day brings more adventures.

Transsexuals & Crossdressers 07/19/2016

Becoming a Sissy Maid & Slut Vol. 04

More on my sissy journey, this is vol. 4 and will be Ch.10.

Transsexuals & Crossdressers 07/18/2016

Chronicles of Heather Maureen Ch. 07

The life of one transvestite from start to present.

Transsexuals & Crossdressers 07/18/2016

Trailhead Ch. 01

Guy out for a hike gets a better workout than planned.

Gay Male 07/17/2016

Jamie's Story Ch. 02

Continuing Jamie’s tale of self-discovery.

Fetish 07/17/2016

High School Sweethearts Pt. 03

The long weekend continues and Jack finally fucks Andi again.

BDSM 07/16/2016

Becoming a Sissy Maid & Slut Vol. 03

To become a sissy maid & slut to a Master Vol. 3, Ch. 7-9.

Transsexuals & Crossdressers 07/16/2016

Mistress Encounter

A deep meaningful relationship between Mistress and Sub.

Fetish 07/15/2016

High School Sweethearts Pt. 01

HighSchool Sweethearts add a D/s dynamic over a long weekend.

BDSM 07/14/2016

Becoming a Sissy Maid & Slut Vol. 02

To become a sissy maid and slut to a Master, Vol. 2 Ch. 4-6.

Transsexuals & Crossdressers 07/14/2016

The Roommate Pt. 04 - Miranda

For you, for me.

Transsexuals & Crossdressers 07/14/2016

Irene's Photoshoot Ch. 01

Cute Tgirl agrees to a photoshoot with consequences.

Transsexuals & Crossdressers 07/14/2016

Becoming a Sissy Maid & Slut Vol. 01

How I became a sissy maid & slut to a Master, vol. 1 Ch. 1-3.

Transsexuals & Crossdressers 07/13/2016

The Roommate Pt. 03 - Miranda

To be or not to be.

Transsexuals & Crossdressers 07/13/2016

My Transformation

A story of one person's feminisation.

Transsexuals & Crossdressers 07/11/2016

Being Watched... Or even more?

Sexy red dress gets me what I craved.

Transsexuals & Crossdressers 07/07/2016

Chronicles of Heather Maureen Ch. 06

One transvestites life from start to present.

Transsexuals & Crossdressers 07/05/2016

My VideoChat Error Ch 07

Denise continues to prepare Shauna.

NonConsent/Reluctance 07/05/2016

Jamie's Story

A boy's journey to his feminine side.

Fetish 07/04/2016

Sara's Amazing Night

Sara fulfills one fantasy and in turn fulfills one of hers.

Transsexuals & Crossdressers 07/03/2016

Jamie's Descent Pt. 04

Jamie discovers what submission is.

Transsexuals & Crossdressers 07/01/2016

My VideoChat Error Ch 06

Denise Prepares Shauna.

NonConsent/Reluctance 06/29/2016

A House to Themselves

A young new couple get a house to their own.

BDSM 06/29/2016

A Girl for a Day

Sam gets found in the girl's locker room. They take it well.

Group Sex 06/25/2016

Jamie's Descent Pt. 03

Jamie continues on his new path.

Transsexuals & Crossdressers 06/24/2016

The Roommate Pt. 02

Miranda lends a hand.

Transsexuals & Crossdressers 06/22/2016

Jamie's Descent Pt. 02

Jamie slips further under Vanessa's control.

Transsexuals & Crossdressers 06/20/2016

Sarah Was Caught Masturbating

She sets herself to be caught in her roomie's panties.

Transsexuals & Crossdressers 06/20/2016

Sarah Meets a Friend

Sarah finds a cum buddy online.

Transsexuals & Crossdressers 06/19/2016

My Life in High Heels Ch. 09

A good weekend.

Transsexuals & Crossdressers 06/19/2016

Jamie's Descent Pt. 01

James is an intern and takes an online quiz - bad move!

Transsexuals & Crossdressers 06/18/2016

The Roommate

Becoming roommates offers more than sharing the rent.

Transsexuals & Crossdressers 06/16/2016

Chronicles of Heather Maureen Ch. 04

The life of one transvestite from start to present.

Transsexuals & Crossdressers 06/16/2016

Chronicles of Heather Maureen Ch. 05

One transvestite's life from start to present.

Transsexuals & Crossdressers 06/15/2016

The Sweet Taste of Honey Pt. 02

A young man's ongoing transformation.

Transsexuals & Crossdressers 06/13/2016

Cockatoo Pt. 29

James stays as Scarlett with Shane and Alex on the boat.

Transsexuals & Crossdressers 06/13/2016

High Fashion Queen Redux

The evening is retold from Jesse's perspective.

Transsexuals & Crossdressers 06/13/2016

To Bind a Witch Ch. 01

The prince mistakes him for a girl, and he wakes in a dress.

Sci-Fi & Fantasy 06/13/2016

Chronicles of Heather Maureen Ch. 03

One transvestite's life from start to present.

Transsexuals & Crossdressers 06/12/2016

Living Next Door to a Closet Sissy

Peeping Tom turns into a sexy girl for his lesbian neighbor.

Text With Audio 06/09/2016

I Visited My Sister In-Law

I visited my sister in-law and got a naughty surprise.

Transsexuals & Crossdressers 06/09/2016

Becoming My Neighbor's GF Ch. 01

Kyle's neighbor is interested in his new crossdressing habit.

Transsexuals & Crossdressers 06/08/2016

Crossdressing Cum Sluts Pt. 02

His wife surprises him with a night from his fantasies.

Transsexuals & Crossdressers 06/07/2016

Rm 209: First Sex as a Crossdresser

My first sex as a crossdresser.

Transsexuals & Crossdressers 06/03/2016

Chronicles of Heather Maureen Ch. 02

The life and times of a transvestite from start to present.

Transsexuals & Crossdressers 06/03/2016

Cockatoo Pt. 28

Jamie meets Shane again and becomes Scarlett.

Transsexuals & Crossdressers 06/03/2016

Chronicles of Heather Maureen Ch. 01

The life and times of one transvestite.

Transsexuals & Crossdressers 06/02/2016

Unicorn Hunts the Hunters

Unicorn Hunters find their Unicorn in an unlikely place...

Erotic Couplings 06/02/2016

Director's Choice

Hired to Play Romeo to cross-dressed Juliet.

Transsexuals & Crossdressers 05/31/2016

Women's Studies Ch. 01

A young man's odyssey trying to attend an all girl college.

Incest/Taboo 05/29/2016

Dating Diana

A genderfluid person has a Wonder-ful date.

Celebrities & Fan Fiction 05/27/2016

How I Became a Crossdresser

Straight married man turned into cock loving slut.

Transsexuals & Crossdressers 05/19/2016

Powerless

A sissy cuckold story.

Transsexuals & Crossdressers 05/19/2016

We Dot Our I's With Hearts Pt. 01

Fall semester is starting. Sami meets her roommate Brandi.

Transsexuals & Crossdressers 05/18/2016

Story of Sissy Blackmail Ch. 01

Actual Story of how I was first discovered and used...

Transsexuals & Crossdressers 05/15/2016

Helen, my Wife and Cuckoldress

Wife goes Black and feminizes her pathetic hubby.

Fetish 05/12/2016

First Time Sissy at the Gloryhole

I wanted to be seen in my frilly things, but I got more.

Transsexuals & Crossdressers 05/11/2016

The Sweet Taste of Honey

A young man's fantasies transform into reality.

Transsexuals & Crossdressers 05/09/2016

Traveling Has Its Rewards

Nick finds that a baggage mistake changes his life.

Transsexuals & Crossdressers 05/04/2016
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