‘crossdresser’ stories

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My First Time Sucking Cock Pt. 02

Teen (18) male with older man.

Transsexuals & Crossdressers 04/15/2017

Ugly Duckling to Sissy Princess Ch. 05

Vicky's very special night.

Transsexuals & Crossdressers 04/14/2017

Sarah's First Time Out Dressed as a Girl

A first time story.

Transsexuals & Crossdressers 04/14/2017

Trash Night

Sweet TV Noreen takes out the trash.

Transsexuals & Crossdressers 04/12/2017

There's Something about Sarah Ch. 05

Sarah discovers Tina is working as a porn star. Sparks fly.

Transsexuals & Crossdressers 04/12/2017

My Introduction to Interracial Sex

Teen (18) male experiences interracial sex with older man.

Interracial Love 04/11/2017

There's Something about Sarah Ch. 04

Sarah meets TV vixen Tina and has her first transbian sex.

Transsexuals & Crossdressers 04/08/2017

Sarah Visits a Sex Club

Sarah in a sex club.

Transsexuals & Crossdressers 04/08/2017

CD Fun at the Truckstop

CD with Truckers.

Transsexuals & Crossdressers 04/07/2017

Fun with the Mechanic

CD caught dressed by mechanic.

Transsexuals & Crossdressers 04/07/2017

Fun at the Hotel

CD with 2 men at hotel.

Transsexuals & Crossdressers 04/05/2017

There's Something about Sarah Ch. 03

Sarah goes to the Prom but Sloane has a vicious surprise.

Transsexuals & Crossdressers 04/03/2017

My Two Lovers Ch. 01

Splitting time between my 'spouse' and my mistress.

Transsexuals & Crossdressers 03/30/2017

There's Something about Sarah Ch. 02

High School TV finds out about sex from her first boyfriend.

Transsexuals & Crossdressers 03/30/2017

House-Sitting Panty Lover Pt. 04

Our house sitting panty thief has an excited car trip.

Transsexuals & Crossdressers 03/29/2017

There's Something about Sarah Ch. 01

Adopted son is transformed into a sissy and lives as a girl.

Transsexuals & Crossdressers 03/25/2017

Sarah Visited an Adult Book Store

Sarah Visited an Adult Book Store and gets to taste cum.

Transsexuals & Crossdressers 03/23/2017

Forcing my Cross-dressing Neighbor

Frustrated man finds a "damsel" in distress on his doorstep.

Transsexuals & Crossdressers 03/17/2017

Kimmy's Discovery Ch. 03

Kimmy submits to her feminine side- engulfed in discovery.

Transsexuals & Crossdressers 03/17/2017

Those Shoes Double Date

A hot double date where the two ladies get to make love.

Transsexuals & Crossdressers 03/16/2017

Sarah has fun at Thanksgiving

Sarah wanted to be naughty dressed as a girl.

Transsexuals & Crossdressers 03/15/2017

Kimmy's Discovery Ch. 02

Young kimmy.

Transsexuals & Crossdressers 03/15/2017

The Coma Girl Brain Transplant

Girlfriend in a coma, oh no, oh no, it's serious...

Humor & Satire 03/15/2017

Girl with Something Extra Ch. 02

Daisy shares her inner feelings and also meets a new man.

Transsexuals & Crossdressers 03/15/2017

Kimmy's Discovery Ch. 01

kimmy the teen journalist loves questions, unexpected answer.

Transsexuals & Crossdressers 03/14/2017

New Mother, New Life Pt. 03

Lottie finds her feet and has an interesting proposition...

Transsexuals & Crossdressers 03/13/2017

My New Family Ch. 03

Problems get solved.

Transsexuals & Crossdressers 03/09/2017

Fancy Dress Party

My first night out dressed as a maid!!

Transsexuals & Crossdressers 03/06/2017

My First Time Dressed for Someone

My first time dressed for someone and eager to please.

Transsexuals & Crossdressers 03/05/2017


Crossdresser struggles with having voice heard.

Transsexuals & Crossdressers 03/04/2017

Wifey's Work Becomes Play Pt. 02

Wifey enjoys a Real Man in front of femme cuck hubby.

Loving Wives 03/03/2017

House-Sitting Panty Lover Pt. 03

The trip to the mall takes an unexpected turn.

Transsexuals & Crossdressers 03/02/2017

Wifey's Work Becomes Play Pt. 01

Wifey gives in to her desires.

Transsexuals & Crossdressers 03/02/2017

Pretty in Pink Ch. 04

Crossdressing husband and wife continue to evolve.

Fetish 02/23/2017

Against the Wind

Healing, sailing and loving on Lake Champlain.

Transsexuals & Crossdressers 02/21/2017

A Long Ride Home

Public Femdom in a car on the way home.

BDSM 02/20/2017

House-sitting Panty Lover Pt. 02

The trip to the mall. A build up to next part.

Transsexuals & Crossdressers 02/14/2017

Raymond My First Man Pt. 01

First time with a friend discovering being a woman!

Transsexuals & Crossdressers 02/13/2017

Aphora's Mission Ch. 12

We plant a garden.

Transsexuals & Crossdressers 02/13/2017

Toni in the Park... Again

Sexy Cd likes it rough with two strangers.

Anal 02/13/2017

Toni Gets Two Guys in the Park

Slutty CD wants it rough in public.

Transsexuals & Crossdressers 02/13/2017

Becoming Jessica Pt. 05

Jessica has an erotic evening after shopping.

Transsexuals & Crossdressers 02/12/2017

House-Sitting Panty Lover Pt. 01

Sissydream come true housesitting for his two neighbours.

Transsexuals & Crossdressers 02/07/2017

Virgin Sissy Sex Drive

Sissy virgin's on-the-road, romantic defloration.

Transsexuals & Crossdressers 02/07/2017

Becoming Jessica Pt. 04

Jessica goes shopping at the mall.

Transsexuals & Crossdressers 02/07/2017

Girl with Something Extra

Transsexual woman plays with married couple.

Transsexuals & Crossdressers 02/07/2017

A Friend Catches Me

Caught by a friend dressed in lingerie.

Transsexuals & Crossdressers 02/05/2017

Aphora's Mission Ch. 11

The all-American girl and bunna.

Transsexuals & Crossdressers 02/05/2017

Aphora's Mission Ch. 10

Melting in, in a mushroom forest.

Transsexuals & Crossdressers 01/29/2017

Twin Hearts

Managing a "girl" band of boys is a new experience.

Transsexuals & Crossdressers 01/26/2017

Pleasure Giver: The Substitute Wife

In which PG fills in and makes a disturbing discovery.

Transsexuals & Crossdressers 01/24/2017

Ugly Duckling to Sissy Princess Ch. 02

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

Transsexuals & Crossdressers 01/24/2017

My Valentine

CD Jessica celebrates Valentine's Day.

Transsexuals & Crossdressers 01/24/2017

Sissy Cuckolded by Girlfriend Ch. 01

A sissy slut gets cuckolded by his girlfriend.

Transsexuals & Crossdressers 01/22/2017

Love Letter to a Former Boyfriend

Crossdresser gets married.

Transsexuals & Crossdressers 01/20/2017

Aphora's Mission Ch. 09

Miss U.S.A. in the Sky with Jewels.

Transsexuals & Crossdressers 01/20/2017

The Consequences of a Winter Storm

A college aged babysitter is caught dressed as the wife.

Transsexuals & Crossdressers 01/20/2017

Becoming Jessica Pt. 03

Before shopping, Jessica goes to the gym with Emma.

Transsexuals & Crossdressers 01/18/2017

Aphora's Mission Ch. 08

Double your pleasure, double your trouble.

Transsexuals & Crossdressers 01/16/2017

No Choice

An explanation from a Domme.

Transsexuals & Crossdressers 01/15/2017

First Time as Sissy

My story visiting a dominatrix and dressing as a woman.

Transsexuals & Crossdressers 01/14/2017

Dress like Mia when She's Gone Pt. 05

How I gave my first Blowjob and got my first man crush.

Transsexuals & Crossdressers 01/10/2017

Becoming Jessica

A wife helps her husband transform into a beautiful woman.

Transsexuals & Crossdressers 01/09/2017

Those Shoes Threeway

A couple finds a new friend to share the evening with.

Transsexuals & Crossdressers 01/03/2017

Dad My First Lover Pt. 02

New Year's Eve with Dad.

Transsexuals & Crossdressers 01/01/2017

Blane's Hydraulic Inevitable

Sissy Blane has the obligatory date with Mr. Plumrose.

Transsexuals & Crossdressers 12/31/2016

Dad My First Lover Pt. 01

Father and his CD daughter with occasional sexual encounters.

Transsexuals & Crossdressers 12/29/2016

Surrendering Virginity

First step into a new life as a cock slut.

Transsexuals & Crossdressers 12/28/2016

Dress like Mia when She's Gone Pt. 03

How a stranded CD gets rescued by a man.

Transsexuals & Crossdressers 12/20/2016

Caught In Lingerie

Young man gets caught by neighbor and leads to sex!

Transsexuals & Crossdressers 12/20/2016

Queen of Paradise

Couple checks in seashore resort and get lots of surprises.

Transsexuals & Crossdressers 12/19/2016

Dress like Mia when She's Gone Pt. 02

My first time crossdressing in public and I'm stranded.

Transsexuals & Crossdressers 12/16/2016

Dress like Mia when She's Gone Pt. 01

I coped with my wife's 7 month deployment by becoming her.

Transsexuals & Crossdressers 12/15/2016

Panties Pulled Down by My First Man

Trans woman has first time sex with a man after strapon.

Transsexuals & Crossdressers 12/06/2016

Barrack Room Betty Ch. 16

Final chapter-Michele goes full time trans and moves on.

Transsexuals & Crossdressers 12/03/2016

Kneeling for Daddy

Caught crossdressing and Daddy takes advantage and control.

Incest/Taboo 12/01/2016

Aphora's Mission Ch. 01

From regular Joe to irregular captive.

Transsexuals & Crossdressers 11/29/2016

Sarah Visits at a Nudist Beach

Sarah has fun at a nudist beach.

Transsexuals & Crossdressers 11/28/2016

A Valentine Present

A crossdresser gets his wish.

Transsexuals & Crossdressers 11/26/2016

Barrack Room Betty Ch. 15

Trannies down under have a great time fucking Aussie men.

Transsexuals & Crossdressers 11/20/2016

Home Alone Pt. 01

At least for a little while.

Transsexuals & Crossdressers 11/17/2016

Sneaking into a Frat House Party

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

Transsexuals & Crossdressers 11/16/2016

Sissy Chantel, New Reality Ch. 06

On My Way To 'The Agency'.

Transsexuals & Crossdressers 11/16/2016

Barrack Room Betty Ch. 14

Michele falls in love with a lovely Ladyboy in Thailand.

Transsexuals & Crossdressers 11/15/2016

A Weekend in Jail

A weekend in jail with a crossdresser, leads to great sex.

Transsexuals & Crossdressers 11/14/2016

Barrack Room Betty Ch. 13

Tranny Wrens take shore leave in Naples and get very naughty.

Transsexuals & Crossdressers 11/09/2016

Sissy Chantel, New Reality Ch. 05

Oh, Oh, My Surprize.

Transsexuals & Crossdressers 11/08/2016

Women's Studies Ch. 04

Innocence lost, secrets shared, and laws broken.

Transsexuals & Crossdressers 11/07/2016

Barrack Room Betty Ch. 12

Michele renews her sexual relationship with LEUT Winters.

Transsexuals & Crossdressers 11/05/2016

Mistress Chantel, Tranny Dominatrix Ch. 17

T-Girls on a Honeymoon and more.

Transsexuals & Crossdressers 11/04/2016

First Time

Very close to the truth about first trans experience.

Transsexuals & Crossdressers 11/02/2016

The Therapist

Beta male learns to become a perfect submissive sissy boi.

BDSM 11/02/2016

Sissy Chantel, New Reality Ch. 04

Another Hookup with Master, Chantel's life begins to change.

Transsexuals & Crossdressers 11/01/2016

Barrack Room Betty Ch. 11

Michele and her TV whores run a brothel aboard a navy ship.

Transsexuals & Crossdressers 10/31/2016

Alex's Sissy Time Goes Wrong

Alex's sissy masturbation goes horribly wrong.

Transsexuals & Crossdressers 10/30/2016

The Roommate Pt. 16 - Miranda

Lori plays with the other side.

Transsexuals & Crossdressers 10/27/2016

Halloween Party

A Halloween to remember.

Transsexuals & Crossdressers 10/24/2016

My Fantasy Journey Pt. 03

The final chapter in my journey from CD to slut.

Transsexuals & Crossdressers 10/22/2016

My Fantasy Journey Pt. 02

The journey to cum addiction continues.

Transsexuals & Crossdressers 10/21/2016

Sissy Chantel, New Reality Ch. 02

Sissy Chantel serves and services two Dominant men.

Transsexuals & Crossdressers 10/21/2016
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