‘sissy’ stories

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sissy

Claire's New Start

Claire's short ordeal before maybe finding a way to live.

Transsexuals & Crossdressers 03/17/2018

My Husband a Pornstar Ch. 04

End of the Story.

Transsexuals & Crossdressers 03/16/2018

Amazon Sissy Jock

Chris becomes Chrissy as his BF's girl turns him out.

Transsexuals & Crossdressers 03/16/2018

A Handy Surprise Ch. 02

An unexpected person complicated things further.

Transsexuals & Crossdressers 03/15/2018

Snowed In

Becca allows Heather to seduce Matt.

Transsexuals & Crossdressers 03/15/2018

The Long Trip Pt. 02

Now in Japan Dave finds himself becoming a sissy.

Gay Male 03/14/2018

The Babysitter Takes Over Ch. 03

Our sissy gets in deeper by the babysitter and others!

BDSM 03/14/2018

My Husband a Pornstar Ch. 03

Fairy husband tells the story of how his training went on.

Transsexuals & Crossdressers 03/13/2018

The Babysitter Takes Over Ch. 02

Teri the babysitter ups the ante with her sissy.

BDSM 03/13/2018

A Handy Surprise Ch. 01

A gurl has the house all to herself, or does she?

Transsexuals & Crossdressers 03/10/2018

Sissy Whore Ch. 04

Sissy's taken for a drive.

Transsexuals & Crossdressers 03/09/2018

Dominatrix Makes Him a Slut Ch. 05

Second session: more humiliation.

BDSM 03/09/2018

Mistress Kate Pt. 03

Leslie becomes the house whore.

Transsexuals & Crossdressers 03/09/2018

Re-tooled

Mark finds the solution to his being a neckbearded incel.

Transsexuals & Crossdressers 03/09/2018

Primrose Ch. 00

Bret is prepared for the Headmistress of Primrose University.

Transsexuals & Crossdressers 03/07/2018

Sissy Whore Ch. 03

Sissy meets her new Pimp and the Journey begins.

Transsexuals & Crossdressers 03/07/2018

Jackie Becomes a Wife

A second take on Jackie learning to be a wife.

Transsexuals & Crossdressers 03/07/2018

Dominatrix Makes Him a Slut Ch. 04

His first session: the aftermath. Laying ground for more.

BDSM 03/06/2018

The Molly Virus Ch. 05

Jackie and Jeri turn Billie and take her to Cherry.

Transsexuals & Crossdressers 03/05/2018

The Babysitter Takes Over

A closet Sissy is discovered by a teen babysitter.

BDSM 03/05/2018

Proud Beta

The story of a beta learning the real truth.

Transsexuals & Crossdressers 03/04/2018

How I went from Domme to Slut Ch. 03

Ms. Linda summons amber and I to clean her condo as peers.

BDSM 03/03/2018

Sissy Whore Ch. 02

A young sissy indulges in his own fantasy.

Transsexuals & Crossdressers 03/03/2018

Best Friends Forever Pt. 02

Little things with Brian and I start adding up.

Transsexuals & Crossdressers 03/03/2018

Dominatrix Makes Him a Slut Ch. 03

His first session with a dominatrix ends in a naughty way.

BDSM 03/03/2018

Hank's Hell Ch. 03

Hanks transforms into Heather on the journey home.

Transsexuals & Crossdressers 03/01/2018

Sissy Whore Ch. 01

An online fantasy chat leads to a career change.

Transsexuals & Crossdressers 02/28/2018

Movie Star Gone Astray Pt. 01

Teen learns a lot about himself while filming amateur movies.

Transsexuals & Crossdressers 02/28/2018

Dominatrix Makes Him a Slut Ch. 02

First session with a dominatrix continues.

BDSM 02/28/2018

Jackie Meets Her Sister

Jackie's sister comes home and offers Jackie a new life.

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

The Intern Ch. 04

Mengxia's boss transgresses and is punished.

BDSM 02/22/2018

Humiliating Hook-Up

An undercover sissy gets humiliatingly sharked in the park.

NonConsent/Reluctance 02/21/2018

Alex

A boy named Alex is taken advantage of by an older man.

NonConsent/Reluctance 02/20/2018

Blackmail by Choice

Chris decides it's time to start living out his fantasy.

Transsexuals & Crossdressers 02/19/2018

The House Sitter

House sitting just took an interesting turn for Francis.

Transsexuals & Crossdressers 02/18/2018

Best Friends Forever Pt. 01

In the shadows of my mind.

Transsexuals & Crossdressers 02/18/2018

beta Alpha

A sissy gets found out by her childhood bully.

Transsexuals & Crossdressers 02/18/2018

Girls Club Ch. 01

Crossdressing escort juggles double life.

Transsexuals & Crossdressers 02/15/2018

Caught In Lingerie Ch. 02

Sissy boy used again...and loves it!

Transsexuals & Crossdressers 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

Sissy for Mommy's Nipple Cream Ch. 03

Julia further feminizes sissy daughter Jaime with BBC Cream.

Transsexuals & Crossdressers 02/11/2018

The Sissymaiden's Tale Ch. 01

Cataclysmic disease creates a revolutionary new world order.

Transsexuals & Crossdressers 02/10/2018

My New Daddy Ch. 02

My new Daddy's partner helps to train me.

Gay Male 02/08/2018

Sissy Training

A casual sissy finally takes it to the next level.

Fetish 02/08/2018

Sissy Prince: Origin Ch. 03

The Prince's misadventures as he travels home.

Fetish 02/07/2018

My New Daddy Ch. 01

A young man discovers joy in the arms of an older dom.

Gay Male 02/05/2018

Big Black Cock: A Sissy Surprise

A wife joins her husband as a slut for a teen BBC.

Illustrated 02/05/2018

Jackie Begins her Transition

Jackie begins her transition to womanhood.

Transsexuals & Crossdressers 02/03/2018

Sissy Prince: Origin Ch. 02

The Prince's life as a sissy slave. And a little adventure.

Fetish 02/02/2018

Winning Big in Las Vegas

Winning more than $ in Vegas.

Transsexuals & Crossdressers 01/31/2018

Sissy Prince: Origin Ch. 01

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

Fetish 01/31/2018

A Slut's Triangle Pt. 24

Ashleigh has sex with Rick.

Transsexuals & Crossdressers 01/31/2018

A Sissy Surprise "The House Warming"

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

Transsexuals & Crossdressers 01/28/2018

Perfect Little Slut

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

Transsexuals & Crossdressers 01/27/2018

Sissy for Mommy's Nipple Cream Ch. 02

Jim's mother continues to addict him to her BBC cream.

Transsexuals & Crossdressers 01/27/2018

Anna's Little Girl

Anna discovers her son is a crossdresser and has some fun.

Incest/Taboo 01/25/2018

Being My Roommate's Sissy Pt. 03

Carly wakes to the sight of Kara and Tanner the night after.

Transsexuals & Crossdressers 01/25/2018

Sissy for Mommy's Nipple Cream Ch. 01

Mom uses breastfeeding to turn her son into a sissy cumslut.

Transsexuals & Crossdressers 01/25/2018

Birthday Camping Trip

Camping trip accident gone sexual.

Gay Male 01/25/2018

Taking Donna's Dick

A sissy taken by his female lodger.

Transsexuals & Crossdressers 01/20/2018

God's Design Ch. 03

Our hero gets to grips with his new dick.

Transsexuals & Crossdressers 01/20/2018

Daddy's Sweet Sissy Pt. 01

A young man is forced into a new relationship with his daddy.

NonConsent/Reluctance 01/20/2018

Taking Mom's Place

Jack returns home to his sad house to find himself.

Transsexuals & Crossdressers 01/17/2018

Big Bobby and Sweet Sally Ch. 03

Big Bobby teaches Sweet Sally not to talk to strangers.

Transsexuals & Crossdressers 01/10/2018

You're Like a Little Boy at Times Ch. 06

James is set up to cheat with Rachel.

Fetish 01/10/2018

The Office Ch. 04

Tom's transformation is almost complete.

Transsexuals & Crossdressers 01/10/2018

Pimped Out Sissy Bitch

Powerful executive exploring his femme sissy desires is used.

Fetish 01/05/2018

A Sissy's Forced Gangbang Pt. 03

A sissy's cum filled finale.

Transsexuals & Crossdressers 01/04/2018

Brianna Goes to the Mall

Diane takes Brianna to the mall, and things fall into place.

Transsexuals & Crossdressers 01/03/2018

Brianna's First Day as a Daughter

Brianna experiences her first day as Diane and Rick's daughter.

Transsexuals & Crossdressers 12/30/2017

God's Design Ch. 02

Rose admires her body and meets her first locals.

Transsexuals & Crossdressers 12/30/2017

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

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

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
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