‘sissy’ stories

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sissy 

The Massage Away Ch. 07 Pt. 13-14

My Queen's pleasures continue, as do mine and the gents'!

Fetish 02/17/2019

Sissy Arlene's Soul Mate

A continuation of Sissy Wants Her Wife's Boyfriend series.

Transgender & Crossdressers 02/17/2019

The Daddy-Son Dance

A son is surprised by how beautiful his dressed up Dad is.

Transgender & Crossdressers 02/14/2019

Sissy Secrets

Sissy learning what a sissy is.

Transgender & Crossdressers 02/14/2019

Flowers in Her Hair Ch. 15-16

Chap. 15 Alpha Male and Chap. 16 - Questioning Authority.

Fetish 02/14/2019

Her Property Ch. 01

Tony's new life is honey on a razorblade...

Transgender & Crossdressers 02/13/2019

My New Neighbours Ch. 03

Katie starts to explore her dominant side.

Transgender & Crossdressers 02/13/2019

The Rose Diaries Ch. 14

Introductions for a Nightmare.

Transgender & Crossdressers 02/12/2019

A Sissy's New Daddy Ch. 09

The final chapter in Billies story.

Transgender & Crossdressers 02/09/2019

The Dominatrix Order Pt. 02 Ch. 04

The conclusion of book 2 "Bound By Laws".

Transgender & Crossdressers 02/08/2019

Alex, The Closet Sissy

A short sissy story.

Transgender & Crossdressers 02/08/2019

A New Friend

A new city, a new me, a new friend.

Transgender & Crossdressers 02/07/2019

After Church Ch. 05

More fun with a crossdressing teenager and an old couple.

Transgender & Crossdressers 02/07/2019

Family Chastity Story Ch. 01

A mother keeps her son in chastity with monthly milkings.

Incest/Taboo 02/07/2019

Snap! to it Divina

A story of my latest session experience.

BDSM 02/06/2019

After Church Ch. 04

'Stacey' is pimped out to an old couple after a hard morning.

Transgender & Crossdressers 02/06/2019

After Church Ch. 03

Two guys and an 18 year old crossdresser.

Transgender & Crossdressers 02/05/2019

How I Became a BBC Sissy Slut

A reluctant sissy finds herself addicted to BBC.

Transgender & Crossdressers 02/04/2019

The Massage Away Ch. 06 Pt. 11-12

The pleasure of my Queen continues with her suitors.

Fetish 02/03/2019

College Boy in Thong

College boy experience in girl's thongs.

Exhibitionist & Voyeur 02/03/2019

Sissy's Spa Day

Younger woman seizes control.

NonConsent/Reluctance 02/03/2019

Ultimate Sissy Fail

A closet cross-dressers first attempt to become a sissy.

Transgender & Crossdressers 02/02/2019

Sissy Idea Backfires

Lingerie fetish gets the best of me.

Fetish 02/02/2019

The Dominatrix Order Pt. 02 Ch. 03 - Romance

Forbidden Romance in Femininus and ruined orgasm.

Transgender & Crossdressers 02/01/2019

Sorry Sissy You Lose Pt. 03

Mistress continues to tease sissy slave by sucking cock.

Fetish 01/30/2019

Neighborly Relations Pt. 03

I give Mike my ass and become completely his.

Fetish 01/27/2019

Flowers in Her Hair Ch. 14

Victor suffers corporal punishment for lying to his wife.

Fetish 01/27/2019

My Wife Caught Me Cross Dressing Pt. 03

How being caught crossdressing changed.

Transgender & Crossdressers 01/26/2019

Growing Sissy's on Granny's Farm

A self-sucking teen, his horny granny and becoming a girl.

Incest/Taboo 01/26/2019

Retired to a Whole New Life Ch. 02

Retired guy finds kinky love with an old friend.

BDSM 01/26/2019

Sissy for Mommy's Nipple Cream Ch. 04

Jaime learns what BBC really is, but is too addicted to stop.

Transgender & Crossdressers 01/26/2019

Happy Together

A man, a woman, and their bitch.

Transgender & Crossdressers 01/26/2019

Just Going to the Car Wash

Being surrounded by my thoughts. And so much more.

First Time 01/25/2019

Unintentional Homewrecker

Feminine boy falls for his boss's husband.

Gay Male 01/25/2019

HR Gets Fucked Up Pt. 01

A white boy in Africa goes through more changes than wanted.

Gay Male 01/23/2019

Corey or Cora Pt. 02

Corey's adventures as Cora continue...

Transgender & Crossdressers 01/23/2019

Reminiscing about Her Deliciousness

A time of discovery. Not knowing where it leads.

First Time 01/19/2019

Another Weird but Satisfying Dream

Another weird but satisfying dream.

BDSM 01/19/2019

Marabogo: Cuckold Island Ch. 03

Joshua's mind fills with thoughts of Megan and Obali in bed.

Interracial Love 01/18/2019

How I Became a Sissy Pt. 03 - Final

Sammy is a whore after all.

Gay Male 01/18/2019

MILF Mom & The Bullied "Housefag"

Frat boys and college jock bully move in with mom & I.

Mature 01/18/2019

The Dominatrix Order Pt. 02 Ch. 01 - Sissies

Sissification and budding romance in Femininus.

Transgender & Crossdressers 01/18/2019

Sorry Sissy You Lose Pt. 02

Mistress is picked up for her date while her slave suffers.

Fetish 01/17/2019

College Boy Buys a Thong

This is my first time of buying thongs.

Transgender & Crossdressers 01/16/2019

Retired to a Whole New Life

Retired guy finds kinky love with an old friend.

BDSM 01/15/2019

Owned

He gives himself away for a night, but she has more planned.

BDSM 01/15/2019

First Cum, First Serve Pt. 02

A boy and a girl try to scam a free meal. Big mistake!

Sci-Fi & Fantasy 01/14/2019

How I Became a Sissy Pt. 02

Sam's about to go full change.

Gay Male 01/13/2019

Candi is a Sissy Cam Girl Ch. 01

Candi's put to work earning money on cam.

Transgender & Crossdressers 01/12/2019

Sorry Sissy You Lose Pt. 01

Mistress teases sissy slave while choosing hung Gentleman.

Fetish 01/11/2019

Halloween Rabbit Holes

I go out for Halloween to the gay bar as Jessica Rabbit.

Gay Male 01/11/2019

Broken In by BBC

Discovering his feminine side, and love for BBC at a party.

Transgender & Crossdressers 01/10/2019

Corey or Cora

Corey dresses as a girl for a friend, but ends up liking it.

Transgender & Crossdressers 01/09/2019

The Deal Ch. 03

Keith starts to accept his true desire.

Transgender & Crossdressers 01/09/2019

After Church

Crossdressing teen and the dirty old man.

Transgender & Crossdressers 01/08/2019

Daddy Takes Jenna's Virginity

Jenna dives deeper in her place as Daddy's girl.

Transgender & Crossdressers 01/08/2019

Jean Pierre Ch. 04

Jean Pierre is sold to a retired naval captain.

NonConsent/Reluctance 01/08/2019

Best Friends Forever Pt. 09

The monster in the closet.

Transgender & Crossdressers 01/08/2019

This is Me!

A sissy boy reflects while looking into the mirror.

Transgender & Crossdressers 01/06/2019

The Rose Diaries Ch. 13.5

The Problem Child Pt. 2.

Transgender & Crossdressers 01/06/2019

Sissy Sperm Bank

The CUMplete story: One sissy. So many men.

Transgender & Crossdressers 01/05/2019

Flowers in Her Hair Ch. 12

Chapter 12 - The Morning After.

Fetish 01/05/2019

Sissy Cristal Used by Mistress

Mistress dressed her sissy up as a whore and used her.

Transgender & Crossdressers 01/04/2019

Neighborly Relations Pt. 02

I am prepared and complete part #1 of my commitment process.

Fetish 01/04/2019

Hero Losing Himself

A hero finds himself beaten and sees his feminine side.

BDSM 01/04/2019

The Deal Ch. 02

Keith doesn't know what to do.

Transgender & Crossdressers 01/03/2019

Flowers in Her Hair Ch. 10

Chapter 10 Maid.

Fetish 01/03/2019

The Deal Ch. 01

Shy crossdresser has a laundry room adventure.

Transgender & Crossdressers 12/30/2018

Jean Pierre Ch. 03

Jean Pierre is removed from the pony herd and feminized.

NonConsent/Reluctance 12/30/2018

Clitty Transformation - One Month In

The transformation of a mislabeled "cock" into a clitty.

BDSM 12/29/2018

Deal with a Demon

Femboy makes a deal with a Demon.

Gay Male 12/29/2018

My Boyfriend's Father

Getting to know his boyfriend's father.

Gay Male 12/27/2018

You're My Bitch Now Ch. 10

Rick and Rhoda visit a sex club.

Transgender & Crossdressers 12/27/2018

The Rose Diaries Ch. 13

The Problem Child Pt. 1.

Transgender & Crossdressers 12/26/2018

Twenty-One More Questions

Jasmine answers more questions from readers.

Reviews & Essays 12/26/2018

The Rubber Duck Wedding

Sequel to "Welcome to the Rubber Duck Club".

NonConsent/Reluctance 12/24/2018

"Sissified": 12 Days of Sissy-mas

Straight man is turned into a submissive sissy by...

Transgender & Crossdressers 12/22/2018

Cuckold Hypno Assignment

A truestory of my decent into sissification and cuckolding.

BDSM 12/22/2018

My Estranged Sister Eve

Merry Xmas/Incest - Wincest sissy w/ his transgender sister.

Incest/Taboo 12/21/2018

Slip into Ownership

Story of how my life slipped into submission and ownership.

BDSM 12/21/2018

The Sissy in the Loft

James finally gets to try out the life of his dreams.

Transgender & Crossdressers 12/21/2018

The Story of Keith

Keith's last day as a temp is spent at a Halloween party.

Transgender & Crossdressers 12/20/2018

Accidental Daddy: A TS/CD Novella

A retired vet meets a pretty young co-ed with a secret.

Transgender & Crossdressers 12/20/2018

Discovering Amber Ch. 05

A day of teasing turns into a very wild outing.

Transgender & Crossdressers 12/19/2018

Katelyn's New Sissy Pt. 01

Learning to be a sissy and liking it.

Transgender & Crossdressers 12/19/2018

My Metaphor

A digital affair between a sissy and her mistress.

Fetish 12/18/2018

Sissy Hotel Play

When I'm alone I try sissy things.

Fetish 12/17/2018

My Therapist's Chinese Doll

Asian man is reborn after divorce.

Transgender & Crossdressers 12/14/2018

First Time for Daddy's Girl

Young, Sissy CD's First Time with her Daddy.

Transgender & Crossdressers 12/13/2018

My Neighbor's Submissive Ch. 05

Our relationship becomes more formal.

Transgender & Crossdressers 12/11/2018

Falling into Being a Sissy

Sonny meets Josh at a reunion very quickly becomes Sunshine.

Transgender & Crossdressers 12/08/2018

House Calls Ch. 01

Reminiscing about an older sissy...

Transgender & Crossdressers 12/05/2018

Alice has a Playmate

Mistress finds a live in playmate for them.

Transgender & Crossdressers 12/05/2018

My Neighbor's Submissive Ch. 04

My service expands and my servitude deepens.

Transgender & Crossdressers 12/04/2018

My Father, The Maid Ch. 03

Oliver's father has some fun before work.

Transgender & Crossdressers 12/02/2018

My Neighbor's Submissive Ch. 03

Things start to get real.

Transgender & Crossdressers 11/30/2018

I Adore Crossdressers Pt. 04

A sissy gets displayed in public and loves it.

Transgender & Crossdressers 11/29/2018

Sissy Crossdresser Needs to Please

A sissy crossdresser wants to give her man pleasure.

Transgender & Crossdressers 11/28/2018

Dinner Date with Mommy Pt. 04

Daddy's gives it, Sophie takes it, and Mommy joins the fun.

Transgender & Crossdressers 11/28/2018

Candi Gets an Upgrade

A high tech suite of sissy training tools gets delivered.

Transgender & Crossdressers 11/28/2018
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