‘cross dressing’ stories

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cross dressing

Unexpected Encounter Pt. 01

Cd has an ex re-emerge in his life unexpectedly.

Fetish 02/23/2018

Chris' Adventures Ch. 02

Chris is caught in his wife's lingerie by the neighbor.

Fetish 02/22/2018

Riding the Boss Another Day

Conflicted for our third time together.

Transsexuals & Crossdressers 02/14/2018

Perfect Little Slut

CD's fantasy comes true with the help of a trusted friend.

Transsexuals & Crossdressers 01/27/2018

Chris' Adventures Ch. 01

Chris slips into his wife's lingerie and plays online.

Fetish 01/25/2018

Oh, Mr King! Pt. 03

Mr King begins Julian's transformation.

Transsexuals & Crossdressers 01/21/2018

I Feel Like a Woman Ch. 02

What the woman needs.

Transsexuals & Crossdressers 01/19/2018

Chat Room Hookup

A gay chat room encounter becomes reality.

Gay Male 01/12/2018

I Feel Like a Woman Ch. 01

What the woman wants.

Transsexuals & Crossdressers 01/12/2018

Confronting the Maid

A mistress talks to her slave, supervising his preparations.

BDSM 01/11/2018

The Office Ch. 04

Tom's transformation is almost complete.

Transsexuals & Crossdressers 01/10/2018

My VideoChat Error Ch 18

Party pt II Shaun(a) is forced to service more men and Emma.

NonConsent/Reluctance 01/09/2018

The Live-in Maid Ch. 01

Married man loses everything due to crossdressing.

Transsexuals & Crossdressers 01/07/2018

Sweet MILF Shannon Ch. 02

Twas the week before Christmas and the week after...

Incest/Taboo 12/21/2017

A Merry Christmas Lock In

A close knit group of friends get trapped in Mall...

Transsexuals & Crossdressers 12/19/2017

Counselling Changed Our Marriage Ch. 03

Locals see me dressed & my training continues.

Transsexuals & Crossdressers 12/15/2017

All I Want for Christmas, Is You! Ch. 01

A beautiful gift from GF.

Transsexuals & Crossdressers 12/09/2017

Unlocked Secrets Ch. 01

Bad habits sometimes are good.

Transsexuals & Crossdressers 12/01/2017

My VideoChat Error Ch 17

The Party Pt I. Shaun(a) is forced to service Real Men.

NonConsent/Reluctance 11/28/2017

Cosplay Wife, Cuckold Life

Slur wife and sissy husband discover their new sexuality.

Exhibitionist & Voyeur 11/24/2017

Life on the Gay Side Ch. 02

Dressing up like a school girl & woman, then a dinner date.

Gay Male 11/24/2017

Trophy - The Preys Story

There are two sides to every story.

Transsexuals & Crossdressers 11/13/2017

Riding the Boss Again

The second time I met the boss dressed as Brianne.

Transsexuals & Crossdressers 11/12/2017

My Life as a Secretary

Ger goes to the office.

Transsexuals & Crossdressers 11/11/2017

The Journey Pt. 05

Josies Journey comes to an end; for now.

Transsexuals & Crossdressers 11/10/2017

Maid to Watch

A maid with a secret watches as her mistress gets some.

Transsexuals & Crossdressers 11/05/2017

Judy's Turn

She picks this week's game.

BDSM 10/31/2017

Riding the Boss

I find my boss at the C & C Adult Bookstore.

Transsexuals & Crossdressers 10/21/2017

The Pocahontas Game

Dressing up games end up in fantasy fuck.

Gay Male 10/05/2017

L/J's (A One Week Chronicles Story)

A night of celebration at L/J's.

Transsexuals & Crossdressers 10/05/2017

Cockatoo Pt. 38

Jamie finds trouble looking for whoever trashed the room.

Transsexuals & Crossdressers 10/04/2017

TGIF in Lexington

Special servicing Realtor in Virginia horse country.

Gay Male 10/04/2017

Kidnapped (A One Week Chronicles)

Crystal may just have gone too far this time...

Transsexuals & Crossdressers 09/26/2017

The Office Ch. 03

Tom begins to adapt to his changes.

Transsexuals & Crossdressers 09/25/2017

Daddy the Cocksman

Daddy fucking women after wife dies.

Incest/Taboo 09/22/2017

A Highland Holiday Pt. 04

Highland Games.

Transsexuals & Crossdressers 09/22/2017

Quarter on the Pinball Machine

A Loving Wives tale way beyond sissy.

Loving Wives 09/20/2017

Jewel Pt. 02

Older woman and younger man.

Fetish 09/19/2017

The Journey Pt. 04

Josie becomes a woman.

Transsexuals & Crossdressers 09/16/2017

Dressed up for Halloween

A costume decision ends up with sex.

Transsexuals & Crossdressers 09/07/2017

A Highland Holiday Pt. 03

Josie plans to take things to the next level.

Transsexuals & Crossdressers 08/28/2017

Dottie and Me Pt. 04

Dottie decides I should cross dress and service her friends.

NonConsent/Reluctance 08/16/2017

Nephrite (The One Week Chronicles)

A One Week Chronicles Story.

Transsexuals & Crossdressers 08/16/2017

Aunt Em's Legacy

Twins spank each other and masturbate.

Incest/Taboo 08/07/2017

Prom? Ch. 05

The fallout from prom, and an encounter with a stranger.

Transsexuals & Crossdressers 08/05/2017

The Journey Pt. 03

Josie gets deeper in to sissyhood.

Transsexuals & Crossdressers 08/04/2017

Murphy Ch. 04

Mary asks Josie to dress as a guy.

Transsexuals & Crossdressers 08/02/2017

My First Time as a Sissy Ch. 03

Tara has her first date and gets her anal cherry taken.

Transsexuals & Crossdressers 08/02/2017

My Life as a Maid Pt. 01

Down on his luck Gerry is rescued by an old school friend.

Transsexuals & Crossdressers 08/01/2017

A Highland Holiday Pt. 02

Fiona and Josie discover more of the highlands & themselves.

Transsexuals & Crossdressers 07/29/2017

The Journey Pt. 02

Our heroine's journey of discovery continues.

Transsexuals & Crossdressers 07/28/2017

Not So - New Experiences

Can't call it a new experience if you do it twice!

Gay Male 07/27/2017

Chase N' Justice

A Low Country love story...

Gay Male 07/27/2017

Sam's Panties Ch. 02

Sam suggests a way for Jean to cuckold her sissy more often.

Transsexuals & Crossdressers 07/25/2017

Murphy Ch. 03

Josie is attracted to her delivery driver.

Transsexuals & Crossdressers 07/22/2017

Strange Feelings

Recent sissy discovers new cravings she can't ignore...

Transsexuals & Crossdressers 07/15/2017

The Interview; Number 02

The second interview.

Transsexuals & Crossdressers 07/13/2017

The Interview; Number 01

The first interview.

Transsexuals & Crossdressers 07/12/2017

The Maid

A bad servant gets humiliated.

BDSM 07/12/2017

Living Doll Ch. 01

Andrew’s desperate times equals taking desperate measures.

Transsexuals & Crossdressers 07/10/2017

Murphy Ch. 02

Murphy and Josie role play again.

Transsexuals & Crossdressers 07/08/2017

How Aliens Learned To Fear Earth

Probing little gray men mistakenly abduct a working Mistress.

Humor & Satire 07/06/2017

My Master Pt. 01

Local regular hookup makes me his own.

Transsexuals & Crossdressers 07/06/2017

The Journey Pt. 01

Leaving the old life behind.

Transsexuals & Crossdressers 07/04/2017

A Highland Holiday Pt. 01

A invite to the highlands takes an unexpected turn.

Transsexuals & Crossdressers 07/04/2017

Could I Spank Another Guy?

Ad says guy wants a spanking. Was it gay to want do it?

Gay Male 07/01/2017

Chaste (A One Week Chronicles Story)

The story of Emma and how she got so twisted.

Transsexuals & Crossdressers 07/01/2017

Prom? Ch. 03

Anna, Natalie and Mike go to a bar. The tension rises.

Transsexuals & Crossdressers 07/01/2017

Inheritance (One Week Chronicles)

Gary is forever changed as Louise and Jade enter his life.

Transsexuals & Crossdressers 06/23/2017

One Week Ch. 06

The misadventures of Louise continues.

Transsexuals & Crossdressers 06/17/2017

You're My Bitch Now Ch. 08

Rick has a crisis and Chris takes him to a gay pub.

Transsexuals & Crossdressers 05/25/2017

My First Time as a Sissy

Young closeted cross dresser sucks cock for first time.

Transsexuals & Crossdressers 05/18/2017

Suzy and 'Mistress' Danielle

Suzy is spanked and filled by a cross dressing mistress.

Transsexuals & Crossdressers 05/11/2017


Josie needs Money fast, Murphy is the last resort.

Transsexuals & Crossdressers 05/09/2017

Grandma & Me Again

Too much alcohol.

Incest/Taboo 05/08/2017

Cuckolded on the High Seas Ch. 02

Cuck's proposal.

Loving Wives 05/02/2017

X-Change: The Frat House Blues

Matt allows his roommate Rick to watch him transform.

Sci-Fi & Fantasy 04/29/2017

You're My Bitch Now Ch. 06

Rick is busted by his boss and tries to tell Chris it's over.

Transsexuals & Crossdressers 04/23/2017

You're My Bitch Now Ch. 05

Rikkie gets to be in the show.

Transsexuals & Crossdressers 04/19/2017

For Her Pleasure

Two pantyboys put on a show.

Transsexuals & Crossdressers 04/12/2017

Stepmom and Me Ch. 07

Playing with Stepmom.

Incest/Taboo 04/08/2017

Finding Her Secret Emails Ch. 02

Hubby gets spanked & reads more emails.

Transsexuals & Crossdressers 04/03/2017

You're My Bitch Now Ch. 01

Rick from the IT Helpdesk discovers a life-changing secret.

Transsexuals & Crossdressers 03/31/2017

Alternate Reality Ch. 02

Krystal remains stuck in SIM: Slut City.

Transsexuals & Crossdressers 02/16/2017

The Lesbian Nights Pt. 03

The Third Lesbian Night. Things get kinky.

Lesbian Sex 02/09/2017

Promiscuous Parents and Sons Ch. 05

Brad and Sandy last days together as lovers.

Gay Male 02/07/2017

Promiscuous Parents and Sons Ch. 04

Brad and sandy go public with Sandy dressed as a young woman.

Gay Male 01/31/2017

Being Good in the Bedroom

Jenny discovers Rod's secret passion for lingerie.

Fetish 01/19/2017

Chubby Tales Pt. 01

A chubby guy gets a workout by muscle jock.

Gay Male 01/13/2017

Horny on Halloween Pt. 03

Ryan's final hours in the dress.

Gay Male 01/12/2017

Horny on Halloween Pt. 02

Chase & Travis can't help but see Ryan in a new light.

Gay Male 01/10/2017

The Office Party and a Dare

F/M / Bondage / Forced orgasm / Cross dressing.

Erotic Couplings 11/23/2016

A Favor for My Best Friend Ch. 06

After bringing Stephen home to his parents, Franky's father.

Incest/Taboo 11/22/2016

Crossdresser's First Anal Orgasm

A cross dresser has their first sissygasm.

Anal 11/13/2016

Wanda Wants to Play

3 CD Bi guys a sunday school teach with her panty boi and Me.

Fetish 11/07/2016

Learning to Crossdress Pt. 03

Seduced by a Beautiful Older Lady.

Transsexuals & Crossdressers 11/02/2016

Amanda Adams becomes My Queen Ch. 16

Amanda probes the depths of Buttercup's psyche.

BDSM 10/30/2016

Saturday the 14th (Effy)

Rubber clad slave assists Mistress punishing another slave.

BDSM 09/28/2016

To Serve Her Pt. 03

She is everything to him.

BDSM 09/22/2016

The Sins of the Fathers Ch. 15

'Nick' gets caught in MacKenzie's bedroom by her father!

Incest/Taboo 09/16/2016
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