‘sissy’ stories

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sissy

A Night at the Club Pt. 02

Even in his bra and panties, Dani must get into the casino.

Transsexuals & Crossdressers 12/29/2017

God's Design Ch. 01

A lustful young cross-dresser is sent to a fantasy world.

Transsexuals & Crossdressers 12/27/2017

Brianna Meets Mommy

Rick introduces Brianna to his wife.

Transsexuals & Crossdressers 12/26/2017

Brianna Spends Time with Daddy

Brianna and Rick spend some quality time together.

Transsexuals & Crossdressers 12/23/2017

My New Life Ch. 02

New life for closet sissy.

Transsexuals & Crossdressers 12/22/2017

Tomorrow was My 25th Birthday Ch. 04

My initiation night as Pricilla.

Incest/Taboo 12/22/2017

Sissy Brainwashing Ch. 02

The next part of my sissy brainwashing.

Mind Control 12/20/2017

Brianna Finds a Father Figure

Brianna is caught crossdressing and finds a new daddy.

Transsexuals & Crossdressers 12/19/2017

Femberly: Worth the Trip

Femberly visits her childhood home and is seduced.

Anal 12/14/2017

Tomorrow was My 25th Birthday Ch. 03

This is the continuing tale of a young sissy boy.

Incest/Taboo 12/13/2017

The New Friend

My new friend shows me more than I realized about myself.

Transsexuals & Crossdressers 12/13/2017

Lexi's Date

Lexi goes out for the night.

Transsexuals & Crossdressers 12/11/2017

Accidental Daddy Pt. 03: Princess

Tory draws Big Daddy further into her lifestyle.

Transsexuals & Crossdressers 12/11/2017

The Task List

A wife leaves her sissy for the weekend.

Transsexuals & Crossdressers 12/10/2017

Help Wanted

Brian finds the job which will change his life forever.

Transsexuals & Crossdressers 12/07/2017

Tomorrow was My 25th Birthday Ch. 02

This is the continuing tale of a young boy and his family.

Incest/Taboo 12/07/2017

Femberly's Special Night

A sissy has a special night out to fulfill her secret desire.

Transsexuals & Crossdressers 12/06/2017

Tomorrow was My 25th Birthday Ch. 01

This story is a tale of a young boy and his development.

Incest/Taboo 12/06/2017

Sammi's Place in College

Sammi lives out her perfect life at college.

Transsexuals & Crossdressers 12/05/2017

The Thrill and The Agony

A white tgirl follows 5 black soldiers after the world ends.

Transsexuals & Crossdressers 12/02/2017

Sammi Goes to College

Sam finally gets to college and his new life.

Transsexuals & Crossdressers 11/30/2017

A Morning's Service Ch. 03

My Dom continues my training and cuckolds me.

Transsexuals & Crossdressers 11/29/2017

A Sissy's Forced Gangbang Pt. 02

The cum humiliation goes on.

Transsexuals & Crossdressers 11/29/2017

Teen Boy Becomes a Girl for his BFF Pt. 03

Ryan takes Kelly on holiday, but there's trouble at security.

Transsexuals & Crossdressers 11/29/2017

The Intruder

An intruder, a wife, and her husband.

NonConsent/Reluctance 11/29/2017

Accidental Daddy Pt. 02: Big Daddy

A new daddy lays down some rules.

Transsexuals & Crossdressers 11/28/2017

Losing Bets

Erick loses a bet to his friend... what could go wrong?

Gay Male 11/27/2017

Adam and Steve

Friends dress up for a party.

Transsexuals & Crossdressers 11/26/2017

Sammi Meets Teddy

Sammi is found out by her uncle Teddy.

Transsexuals & Crossdressers 11/26/2017

Life With Miss Ida Ch. 06

Sissy is in for a BIG surprise tonight!

Transsexuals & Crossdressers 11/26/2017

Life With Miss Ida Ch. 05

Miss Ida introduces Sissy to a vibrator.

Transsexuals & Crossdressers 11/25/2017

Dad Discovers his Trans Daughter Pt. 02

After the first forced fuck Kelly wants more, and has a plan.

Incest/Taboo 11/25/2017

Life With Miss Ida Ch. 04

Miss Ida is aching for hard girliecock!

Transsexuals & Crossdressers 11/24/2017

Cosplay Wife, Cuckold Life

Slur wife and sissy husband discover their new sexuality.

Exhibitionist & Voyeur 11/24/2017

Sammi Gets Adventurous

Sammi takes a trip out.

Transsexuals & Crossdressers 11/24/2017

Life With Miss Ida Ch. 03

Sissy & Miss Ida start to explore more!

Transsexuals & Crossdressers 11/23/2017

Sissy Plays the Game of Thrones Pt. 02

Kelly Waters meets Tyrion, and has a tough decision to make.

Celebrities & Fan Fiction 11/23/2017

Sammi Starts Camming

Sam Meets Sammi for the first time.

Transsexuals & Crossdressers 11/21/2017

A Sissy's Forced Gangbang Pt. 01

A sissy is turned into a gang bang cum slut for the night.

Transsexuals & Crossdressers 11/21/2017

Sissy Plays the Game of Thrones

Kelly Waters begins her journey and training in Westeros.

Celebrities & Fan Fiction 11/20/2017

Nick and Sandi Meet for Lunch

Crossdresser's First Boyfriend.

Transsexuals & Crossdressers 11/19/2017

Becoming Mommy Ch. 03

Sarah pretends to be Jamie's sister and bosses him around.

BDSM 11/18/2017

Counselling Changed Our Marriage

Marriage guidance turns me into a cuckold sissy.

Transsexuals & Crossdressers 11/18/2017

A Sissy's Truth or Dare Pt. 02

The Truth or Dare becomes an orgy.

Transsexuals & Crossdressers 11/18/2017

My Girlfriend's Sissy Roommate Ch. 05

Jessica faces the music.

Group Sex 11/17/2017

Accidental Daddy Pt. 01

A retired vet meets a sexy young woman with a secret.

Transsexuals & Crossdressers 11/17/2017

Sissy Training Vol. 01

Sissy slut craves to wear panties like girls and suck cock.

Fetish 11/16/2017

Becoming Mommy Ch. 02

Sarah bathes, feminizes, diapers and pegs her boyfriend.

BDSM 11/10/2017

The Journey Pt. 05

Josies Journey comes to an end; for now.

Transsexuals & Crossdressers 11/10/2017

Teen Boy Becomes a Girl for his BFF Pt. 02

Part 2 of this story sees Kelly nearly caught by Ryan's mum.

Transsexuals & Crossdressers 11/09/2017

Sissifying Addictions

James meets a special friend that teaches Jamie to exist.

Transsexuals & Crossdressers 11/08/2017

A Sissy's Truth or Dare

Teen sissy plays truth or dare, things get hot fast...

Transsexuals & Crossdressers 11/07/2017

Teen Boy Becomes a Girl for his BFF

Teen sissy reveals her girl self to her best friend.

Transsexuals & Crossdressers 11/06/2017

Neighbors Sissy Son Ch. 03

Mommy meets Daddy Tiffany makes more videos.

Incest/Taboo 11/06/2017

The Becoming of a Sissy Slut

The Becoming of a Sissy Slut.

Transsexuals & Crossdressers 11/06/2017

Maid to Watch

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

Transsexuals & Crossdressers 11/05/2017

Crossdresser's Unexpected First Time

First Time for CD comes randomly.

Gay Male 11/04/2017

Enthralled

Squire Lyr becomes a sissy, thrall of the fae.

Transsexuals & Crossdressers 11/03/2017

My First Crossdresser Pt. 01

The origins to my rise to domination as Princess Rebecca.

Transsexuals & Crossdressers 11/01/2017

A Slut's Triangle Pt. 23

Kryss gets his ass handed to him at the all-girls party.

Transsexuals & Crossdressers 10/31/2017

Full Tank, No Reloads

How Matthew fucked his cousin with a lube loaded watergun.

Gay Male 10/31/2017

A Love Letter to My Fantasy

A night with you, my dream man.

Transsexuals & Crossdressers 10/30/2017

Holly's New Start

Holly's starting to find herself as Jamie's sissy love.

Transsexuals & Crossdressers 10/29/2017

Neighbors Sissy Son Ch. 02

Movers pack mother, son and boxes.

Transsexuals & Crossdressers 10/28/2017

The Photographers Assistant Pt. 01

Force fem a young man into a swishy little panty sissy.

Transsexuals & Crossdressers 10/28/2017

Finding Claire

Hayden goes deeper into becoming the sissy Claire.

Transsexuals & Crossdressers 10/28/2017

Opening Up: Going Deeper

Things get interesting.

Fetish 10/26/2017

Being a Sissy for Viv Ch. 06

Serving Mistress Viv.

Transsexuals & Crossdressers 10/26/2017

Lou Ciphers Tale

A Halloween tale.

Fetish 10/24/2017

Yet Another Story

The narrator goes off script and finds more trouble...

Transsexuals & Crossdressers 10/20/2017

My Sissy Life

This sissy's life. Non-fiction.

Transsexuals & Crossdressers 10/20/2017

Big Bobby and Sweet Sally Ch. 02

The road calls and Sweet Sally follows.

Transsexuals & Crossdressers 10/18/2017

Daddies Slut

Skylar entertains his lover...

Group Sex 10/13/2017

Emotional Blackmail Pt. 02

You escape her dress but fresh humiliation awaits.

Fetish 10/13/2017

A Conversation with a Lady

A short sissy fantasy inspired by Gemsissy's shopping trips.

Transsexuals & Crossdressers 10/12/2017

My Day

CD Jessica has an afternoon with her lover.

Transsexuals & Crossdressers 10/08/2017

What Did You Expect?

As a sub-par beta male, I really should've seen this coming.

Fetish 10/07/2017

The Secret of the Island Pt. 03

The long awaited part 3.

Transsexuals & Crossdressers 10/04/2017

Mistress Emma's Revenge

Mistress's newest slave going to regret his mistake.

Fetish 10/03/2017

My Husband a Pornstar Ch. 02

Wife watches the first film with husband's master.

Transsexuals & Crossdressers 10/01/2017

One of the Girls

Mike would do anything for his crush Tiffany. Anything.

Transsexuals & Crossdressers 09/30/2017

Just Another Story

It's impossible to describe this...

Transsexuals & Crossdressers 09/29/2017

Straight Guy Gets Some "Strange"

An unhappily married man finds the "woman" of his dreams.

Interracial Love 09/28/2017

Coffee with Danielle

I meet a new friend and we bond over coffee.

Transsexuals & Crossdressers 09/28/2017

Jailhouse Faggot

Life is Hell for a weak young Caucasian behind bars!

Anal 09/27/2017

My Husband a Pornstar

A loving and caring husband is made to explore his sexuality.

Transsexuals & Crossdressers 09/27/2017

Tim's Transforming Weekend

A pantie wearing boy is discovered by his family...

Incest/Taboo 09/27/2017

A Sissy is Forged

A crossdresser meets a fork in the road. Fun lies ahead.

Transsexuals & Crossdressers 09/26/2017

The Vixen

A young man is seduced and feminized by a red headed beauty.

Transsexuals & Crossdressers 09/26/2017

Filipina & White Husband Go Black!

A married queer and his Filipina wife cheat on each other.

Erotic Couplings 09/26/2017

Adult Bookstore Whoring

A crossdressing whore has a hot night out!

Transsexuals & Crossdressers 09/26/2017

The Office Ch. 03

Tom begins to adapt to his changes.

Transsexuals & Crossdressers 09/25/2017

Sweet Treat Ch. 03

The crossdressing husband heads to the photography studio.

Transsexuals & Crossdressers 09/25/2017

How Did I Get Here

Emasculation is the start of his journey.

Gay Male 09/25/2017

It

A sissy fuckdoll used as a toy in a public sex festival.

Transsexuals & Crossdressers 09/23/2017

A Straight Man's Perspective

A married man finds relief in adult arcade video booth.

Erotic Couplings 09/23/2017

Transition from Man to Lady

A married man becomes the sissy he always knew he was.

Erotic Couplings 09/22/2017

Tara has a Threesome

Tara has her first gangbang.

Transsexuals & Crossdressers 09/20/2017

My Black Son

White guy turns sissy slut for his adopted black son.

Incest/Taboo 09/20/2017

Quarter on the Pinball Machine

A Loving Wives tale way beyond sissy.

Loving Wives 09/20/2017
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