‘crossdressing’ stories

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crossdressing

The Work Shower

How far will a chastised sissy go for an orgasm?

Transsexuals & Crossdressers 04/24/2018

Crossing on Route 66

Two guys cross-dress on Route 66.

Transsexuals & Crossdressers 04/24/2018

Diary of a Panty Lover's Wife Ch. 03

Fun on an airplane.

Fetish 04/24/2018

My name is Lulu

How i came to dress up

Transsexuals & Crossdressers 04/24/2018

Caught Wearing Girlfriend's Panties

Friend catches him wearing his girlfriend's lingerie bottoms.

Gay Male 04/23/2018

Kayla Caught Me Ch. 01

Got caught xdressing.

Transsexuals & Crossdressers 04/23/2018

The Trap... Trap...

Lost my virginity. Not getting it back. Traps involved.

First Time 04/23/2018

Wannabe Cuckold Pt. 03

Wannabe cuckold is pushed further by his unknown tormentor.

Transsexuals & Crossdressers 04/21/2018

A Stripper Comes To Stay

Forces wife to become lesbian & husband to become her maid.

Lesbian Sex 04/21/2018

Guys Trip, Lace Causes a Stir Ch. 04

A friendly wager brings thrilling consequences.

Transsexuals & Crossdressers 04/20/2018

I Love Men to wear my Satin Panties Pt. 01

What do you do when your kinky dreams come true?

Transsexuals & Crossdressers 04/20/2018

Tables Turned at the Mall

A sissy gets more than she reckoned with at the mall.

BDSM 04/20/2018

Morning Glory

Caleb has an unexpected reunion at the local gloryhole.

Transsexuals & Crossdressers 04/19/2018

Orphans (The Raccoon)

A pregnant wife, her lover, husband, daughter discuss things.

Erotic Couplings 04/19/2018

Diary of a Panty Lover's Wife Ch. 02

The complicated art of seducing a panty-lover.

Fetish 04/18/2018

Afro Stress Relief Ch. 03

White Boy continues with social experiment.

Transsexuals & Crossdressers 04/18/2018

Chris' Adventures Ch. 04

Chris' wife takes him out for a day of shopping and fun.

Fetish 04/13/2018

Wannabe Cuckold Pt. 02

Wannabe cuckold finds himself in a sticky situation.

Exhibitionist & Voyeur 04/12/2018

My Boyfriend is a Better Sister

Girl catches boyfriend crossdressing, makes him weekend slut.

Transsexuals & Crossdressers 04/11/2018

In from the Rain

The cute girl on Mike's doorstep has a secret...

Transsexuals & Crossdressers 04/11/2018

Le Sexe Superieur Ch. 08

Gasping for Luis.

Transsexuals & Crossdressers 04/10/2018

Afro Stress Relief Ch. 02

White Boy continues social experiment at Afro club.

Transsexuals & Crossdressers 04/10/2018

The Gods Must Be Horny

Primitive warrior finds an unusual "conquest" in the jungle.

Transsexuals & Crossdressers 04/09/2018

Hung like a Grape Ch. 03

Sherry entertains some new friends at Lisa's party!

Transsexuals & Crossdressers 04/07/2018

Entertaining is Hard Work!

Dani has to entertain three black men at a private party.

Transsexuals & Crossdressers 04/06/2018

Afro Stress Relief Ch. 01

White Boy coerced into social experiment at Afro club.

Transsexuals & Crossdressers 04/06/2018

Hung like a Grape Ch. 02

Lisa continues to strengthen her hold over Sherry!

Transsexuals & Crossdressers 04/05/2018

My Second Me

Have U ever accepted a dare then wondered what U got into?

Transsexuals & Crossdressers 04/04/2018

Le Sexe Superieur Ch. 07

A long-buried memory.

Transsexuals & Crossdressers 04/03/2018

The Clothes Shop... Pt. 01

Temptation can be a killer...Being caught is even worse...

Transsexuals & Crossdressers 04/03/2018

Ellie's Weekend

Crossdresser meets transgender.

Transsexuals & Crossdressers 04/03/2018

Hung like a Grape

A small dicked Sissy is outed and humiliated.

Transsexuals & Crossdressers 04/01/2018

The Landlady Pt. 01

We all need a room where we can dress in secret, but...

Transsexuals & Crossdressers 03/28/2018

My Girlfriend's Mum Pt. 01

I can't believe she would do this to me...

Transsexuals & Crossdressers 03/27/2018

Work Day, Fun Day

The wife finally gets to see her panty husband.

Transsexuals & Crossdressers 03/23/2018

Now Put Your Nurses Uniform On...

How a young man's life changes following a devastating event.

Transsexuals & Crossdressers 03/23/2018

The Artist's Model Pt. 04

Harry starts to embrace being Olivia.

Fetish 03/23/2018

My Secret Revealed Ch. 03

Wife takes control after she discovers husband loves panties.

Transsexuals & Crossdressers 03/22/2018

Reversals Ch. 15

A successful woman embarks on a FLM and role reversal.

Fetish 03/22/2018

Cum and Dress for Me... Pt. 01

Have U ever been tempted 2 ring a No & complete yr fantasy?

Transsexuals & Crossdressers 03/21/2018

Rachel's Crossdressing Daddy

Daughter accidentally discovers her father's kinky secret.

Transsexuals & Crossdressers 03/20/2018

Starlit Petal Ch. 01

Petal goes after another girly boy.

Transsexuals & Crossdressers 03/17/2018

My Job as a Tester Ch. 05

Mac learns about himself and the ladies he works with.

Fetish 03/16/2018

Being a Wife to My Wife

Living as a girl an being a wife to my female wife.

Transsexuals & Crossdressers 03/14/2018

The Streamer

What happens behind the camera of your favorte streamer?

Transsexuals & Crossdressers 03/12/2018

The Book Club

A sequel to Expectations.

Transsexuals & Crossdressers 03/11/2018

Sanctuary Pt. 01: Aubrey Ch. 01

Aubrey finds an escape.

BDSM 03/11/2018

My Secret Revealed Ch. 02

Panty wearer becomes submissive.

Transsexuals & Crossdressers 03/10/2018

Mistress Kate Pt. 03

Leslie becomes the house whore.

Transsexuals & Crossdressers 03/09/2018

For Andrea

Therapist helps a woman with an unusual request from husband.

Transsexuals & Crossdressers 03/09/2018

Reversals Ch. 14

A successful woman embarks on a FLM and role reversal.

Fetish 03/06/2018

The Babysitter Takes Over

A closet Sissy is discovered by a teen babysitter.

BDSM 03/05/2018

Finding Our Real Selves

Sammie and Britt's senior year (transmale x transfemale)

Transsexuals & Crossdressers 03/05/2018

Goddess' Good Girl for the Night

Goddess Nida turns me into a filthy slut.

Fetish 03/03/2018

I'm Now Called Dee Ch. 07

Spermbank and hormones.

Transsexuals & Crossdressers 03/02/2018

My Secret Revealed

Wife accidentally finds out about my panty fetish.

Transsexuals & Crossdressers 03/01/2018

Caught

Caught and forced to give a blowjob.

Transsexuals & Crossdressers 02/28/2018

Serving the Dark Lady Ch. 06

Karee struggles with his new accessory.

Sci-Fi & Fantasy 02/28/2018

I'm Now Called Dee Ch. 06

Reflections, revelations, as Dee tries to decide her future.

Transsexuals & Crossdressers 02/28/2018

Letter from Lythgoe Heights

Shoeblossom hears from a gender-fluid tranny...

Transsexuals & Crossdressers 02/27/2018

Dominatrix Makes Him a Slut Ch. 01

First time for a young guy with a dominatrix.

BDSM 02/27/2018

The Adventures of Sissy Madison Ch. 02

Kent (Madison) gets a snack in the car going to the mall.

Transsexuals & Crossdressers 02/27/2018

The Adventures of Sissy Madison Ch. 01

Kent wakes up and transforms into Madison and gets exposed.

Transsexuals & Crossdressers 02/26/2018

I'm Now Called Dee Ch. 05

Visit a gay club, intending to hook up.

Transsexuals & Crossdressers 02/23/2018

Babysitting

Dressing up after the kids are asleep.

Transsexuals & Crossdressers 02/23/2018

Mistress Kate Pt. 02

Jordan becomes Leslie as debt payments begin.

Transsexuals & Crossdressers 02/22/2018

I'm Now Called Dee Ch. 04

Secret discovered.

Transsexuals & Crossdressers 02/20/2018

beta Alpha

A sissy gets found out by her childhood bully.

Transsexuals & Crossdressers 02/18/2018

Casey's Submissive Journey Pt. 08

Mistress Betty - Part 2.

Transsexuals & Crossdressers 02/16/2018

Two Free Tickets Pt. 02

Sexy memories slip through the amnesia.

Mind Control 02/15/2018

Casey's Submissive Journey Pt. 07

Mistress Betty - Part 1.

Transsexuals & Crossdressers 02/14/2018

Caught In Lingerie Ch. 02

Sissy boy used again...and loves it!

Transsexuals & Crossdressers 02/14/2018

Serving the Dark Lady Ch. 05

Karee's mom tracks him down.

Sci-Fi & Fantasy 02/14/2018

My VideoChat Error Ch 19

Shaun(a) gets put in chastity.

NonConsent/Reluctance 02/14/2018

Last Friday: First Sissy Experience

A couple has a night with sissy chastity and a black cock.

Transsexuals & Crossdressers 02/13/2018

Serving the Dark Lady Ch. 04

Karee learns what a safeword is.

Sci-Fi & Fantasy 02/13/2018

Serving the Dark Lady Ch. 03

Karee has a chat with the high priestess.

Sci-Fi & Fantasy 02/12/2018

I'm Now Called Dee Ch. 02

Learning how to project as a woman

Transsexuals & Crossdressers 02/11/2018

I'm Now Called Dee Ch. 03

First time going out presenting as my new persona.

Transsexuals & Crossdressers 02/11/2018

Serving the Dark Lady Ch. 02

Karee's initiation.

Sci-Fi & Fantasy 02/11/2018

The Fantasy

A birthday fantasy turns into something kinkier.

Lesbian Sex 02/10/2018

Serving the Dark Lady Ch. 01

Femboy joins a new religion... and gets fucked a lot.

Sci-Fi & Fantasy 02/10/2018

Sissy Prince: Origin Ch. 03

The Prince's misadventures as he travels home.

Fetish 02/07/2018

Marriage Transformation Ch. 10

Couple take mini-vacation and take sex to a new level.

Fetish 02/07/2018

Le Sexe Superieur Ch. 03

Seafood footsie.

Transsexuals & Crossdressers 02/05/2018

I'm Now Called Dee Ch. 01

Male admits to wife he fantasizes about being lesbian.

Transsexuals & Crossdressers 02/05/2018

Two Free Tickets

Two guys win front-row seats at a hypnotist's show.

Mind Control 02/02/2018

Le Sexe Superieur Ch. 02

Peyton flies.

Transsexuals & Crossdressers 02/02/2018

Trusty

A young man auditions as an older man's "Wife".

Gay Male 02/01/2018

Lisa at Last

Fran's amputee son lives as a woman. What could be better?

Transsexuals & Crossdressers 02/01/2018

Happy Birthday to Me!

Sam buys his first panties and the shop owner surprises him.

Transsexuals & Crossdressers 02/01/2018

Accepted Ch. 03

Sasha checks-in for Orientation and has a wild first night.

Transsexuals & Crossdressers 01/31/2018

Marriage Transformation Ch. 09

Couple continue new adventures.

Fetish 01/31/2018

Sissy Prince: Origin Ch. 01

A young prince submits to his sissy side, as a slave.

Fetish 01/31/2018

Accepted Ch. 02

Sarah helps Sasha get ready for college.

Transsexuals & Crossdressers 01/30/2018

My Wife Hands Me Over to My Dom Ch. 01

A wife brings her cheating husband to his gay Dom.

Gay Male 01/30/2018

Accepted Ch. 01

A scholarship winner finds out an error in his application.

Transsexuals & Crossdressers 01/29/2018

A Sissy Surprise "The House Warming"

First sissy story ever and is a deep confession of desire.

Transsexuals & Crossdressers 01/28/2018

Coworker Found Me Out

A man gets busted posting a CL ad by a coworker.

Gay Male 01/26/2018

Expectations? Ch. 03

"Fortunes rise and fall with fate."

Transsexuals & Crossdressers 01/26/2018
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