‘sissy’ stories

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sissy 

Neighbourhood Terror to Sissy Pt. 07

Mark has a surprise humiliating encounter.

Transgender & Crossdressers 04/22/2019

The Rose Diaries Ch. 17

Blackstone 101.

Transgender & Crossdressers 04/21/2019

The Pantysissy Diaries Ch. 03

Jaymie visits Victoria's Secret with her shemale mistresses.

Transgender & Crossdressers 04/21/2019

The Teamviewer Mature Files

Wimp sissified, blackmailed & transformed for black masters.

Transgender & Crossdressers 04/19/2019

No Exit

The time Keith couldn't run away.

Transgender & Crossdressers 04/18/2019

Sissy Meets Master's Male Fiend

Master teaching his sissy to obey his friend.

Transgender & Crossdressers 04/17/2019

Swiping Right on Darla's Sexy Feet

Fresh dick lining up for Wife's sexy blue toe-ringed feet.

Fetish 04/17/2019

House-Sitting Panty Lover Pt. 05

Princess gets picked up by an old acquainted.

Transgender & Crossdressers 04/15/2019

Ella Cucks Her Patient Ch. 03

Ella puts my cock in a cage.

Exhibitionist & Voyeur 04/15/2019

The Long Path to Feminization

Now everything's changed: and you couldn't be happier, sissy.

Mind Control 04/13/2019

Keeping My Sissy Secret

A young sissy fails to keep his secret from an older man.

Transgender & Crossdressers 04/12/2019

Tales of Sub Asian Sissy Ch. 03

Against her will, Jade loses her virginity to Master Dave.

Transgender & Crossdressers 04/11/2019

Gothic Sissy Gets Gangbanged by BBC

Our favorite gothic snowbunny turns fantasy into reality.

Transgender & Crossdressers 04/10/2019

Movie Star Gone Astray Pt. 04

Nate settles into a secret relationship with Dustin.

Transgender & Crossdressers 04/10/2019

Wife Knows My Secret Ch. 01

Wife fulfills her fantasy and mine.

Fetish 04/10/2019

Susan

His wife's affair makes him question everything.

Transgender & Crossdressers 04/10/2019

Sissy Sidney and Sister

He joins a pajama party as an honorary girl.

Transgender & Crossdressers 04/09/2019

Parlor Panties Pt. 02

Massage Parlor controls me.

Transgender & Crossdressers 04/09/2019

The Gentle Master and The New Slave

A sub, new to the scene is gently brought forward.

Gay Male 04/08/2019

On a Scale of 1 to 10

A businessman answers some questions and falls into a trap

Transgender & Crossdressers 04/08/2019

I Used to be Pathetic

Keith's first time scares him a little bit.

Transgender & Crossdressers 04/06/2019

Wife's First Cuckold Date

My idea of a free night for wife went bad for me!

Fetish 04/05/2019

Sissy Maid to Be... Ch. 03

Sissy Jenny discovers Mistress Lizzy's for her.

Transgender & Crossdressers 04/04/2019

Tales of Sub Asian Sissy Ch. 02

Jade's night goes from very bad to even worse...

Transgender & Crossdressers 04/04/2019

And Kerry Makes Three

Mature woman introduces her two young bf's to each other.

Fetish 04/04/2019

Neighbourhood Terror to Sissy Pt. 06

A second visit to CC's brings a whole lot of humiliation.

Transgender & Crossdressers 04/04/2019

Sissy Finds a Friend

Wife submits to work colleague. Sissy finds a friend.

Transgender & Crossdressers 04/03/2019

Sissy, Hypnotized

A night out results in triggers unleashed for this sissy.

Transgender & Crossdressers 04/03/2019

Neighborly Love But Blackmailed! Ch. 02

I better do as I am told or my wife will find out!

Transgender & Crossdressers 04/02/2019

Rosa subrosa

Rosa knows what she wants.

Transgender & Crossdressers 04/02/2019

Modelling

A young man in London finds new opportunities.

Transgender & Crossdressers 03/30/2019

Jimmy's Dilemma Ch. 03

Time to make a choice: girlfriend or cum-dump?

NonConsent/Reluctance 03/30/2019

Sorry Sissy You Lose Pt. 04

Sissy slave buys Mistress sexy things for her hot date.

Fetish 03/30/2019

The Rose Diaries Ch. 16

Second Silence.

Transgender & Crossdressers 03/29/2019

The Sissy Models Ch. 02

A sissy Daddy-son threesome with the manly photographer.

Transgender & Crossdressers 03/28/2019

Miss Guided Pt. 03

Susan tries to occupy her time while Charles is away.

Transgender & Crossdressers 03/28/2019

The Dominatrix Order Pt. 04 Ch. 01 - Med

After Care.

Fetish 03/28/2019

My Sissy Bucket List

A description of some of my sissy goals.

Transgender & Crossdressers 03/27/2019

Tales of Sub Asian Sissy Ch. 01

Jade learns a very difficult and very valuable lesson...

Transgender & Crossdressers 03/27/2019

The Rose Diaries Ch. 15

Glass Houses.

Transgender & Crossdressers 03/26/2019

Neighbourhood Terror to Sissy Pt. 05

Even more changes are made to Mark's life.

Transgender & Crossdressers 03/26/2019

Panty Boy Diaries: Entry 03

Another tryst with my daddy.

Transgender & Crossdressers 03/26/2019

Sam's Cousin Ch. 02

Sam comes over to get used.

Gay Male 03/23/2019

A Tale of Two Sissies Ch. 01

Teen and his best friend are forced to become sissies.

Transgender & Crossdressers 03/23/2019

Stan's Journey into Gentle Femdom

Shae takes Stan to a femdom club.

BDSM 03/21/2019

A Rainy Day Ch. 02

The mature woman continues to rescue the timid young man.

Fetish 03/21/2019

Neighbourhood Terror to Sissy Pt. 04

Mark is sent out shopping.

Transgender & Crossdressers 03/20/2019

Let the Games Begin! (JOI Idea)

A new take on a Femdom JOI .

Toys & Masturbation 03/18/2019

Neighborly Love But Blackmailed!

Better remember what your wearing when you leave home.

Transgender & Crossdressers 03/18/2019

Made a Slut

The night I was fucked and used like a slut.

Gay Male 03/16/2019

The Two-Month Break Clause Pt. 02

Natalie and John take a giant leap of trust and humiliation.

Fetish 03/16/2019

My Master

The story of a sissy meeting her real master.

Transgender & Crossdressers 03/15/2019

Becoming a Sissy Cuckold Ch. 02

Neighbor turns me into a sissy cuckold.

Fetish 03/14/2019

Growing Sissy's on Granny's Farm Ch. 02

The teenager's mentor shows Ronald exactly what is expected of him.

Incest/Taboo 03/14/2019

Cream Puff Ch. 05

Getting ass fucked helps with cuckold angst.

Loving Wives 03/14/2019

Mama's Girl

I became a sissy and suck an ebony woman's dick to survive.

Transgender & Crossdressers 03/13/2019

Neighbourhood Terror to Sissy Pt. 03

Mark gets a humiliating surprise at the salon.

Transgender & Crossdressers 03/13/2019

Cream Puff Ch. 04

Sissy can't satisfy his wife.

Loving Wives 03/13/2019

Becoming a Sissy Cuckold Ch. 01

Neighbor turns me into a sissy cuckold.

Fetish 03/12/2019

Smoking Blues

Learning a severe lesson while learning to quit smoking.

BDSM 03/12/2019

Cream Puff Ch. 03

A sissy shouldn't talk back.

BDSM 03/12/2019

Cream Puff Ch. 02

When a straight man wants a cock in every hole.

Gay Male 03/11/2019

A Cell Phone Makes Me Pregnant

A Black New World Begins.

Interracial Love 03/10/2019

Beyond Sissy's Spa Day Ch. 06

Unexpected opportunity overwhelms Sissy.

NonConsent/Reluctance 03/10/2019

Cream Puff Ch. 01

Sissy finds becomes a strong man's bitch.

Transgender & Crossdressers 03/09/2019

The Sissy Models

A Daddy-Son modelling weekend and a couple of studs.

Transgender & Crossdressers 03/09/2019

A Big Change Pt. 04

Continuing Harriet's journey of change.

Transgender & Crossdressers 03/08/2019

A Rainy Day

A mature woman rescues a young man from a very bad day.

Fetish 03/08/2019

Anniversary Treat for Nigella

Nigella is now a bonafide sissy.

Erotic Couplings 03/08/2019

Rescued by a Determined Woman

A woman rescues a man... for a price.

NonConsent/Reluctance 03/04/2019

Thrift Store Encounter

A shy sissy makes a new friend with a Thrift Store owner.

Transgender & Crossdressers 03/03/2019

Jimmy's Dilemma Ch. 02

The nightmare continues for Jimmy.

NonConsent/Reluctance 03/02/2019

A Big Change Pt. 03

The continuing story of an emerging sissy slut.

Transgender & Crossdressers 03/01/2019

Beyond Sissy's Spa Day Ch. 05

Multiple women use, and abuse, Sissy.

NonConsent/Reluctance 03/01/2019

College Boy Cum Eater

I continue to tell of my college thong and sissy experiences.

Transgender & Crossdressers 02/28/2019

Finding a Perfect First Daddy Cock

A young college virgin's first time submitting to a daddy.

Gay Male 02/28/2019

How I Became a Sissy for BBC

The story of how I became a white sissy for BBC.

Transgender & Crossdressers 02/28/2019

I Swallowed an Older Man's Cum

Young bottom serves older man.

Gay Male 02/27/2019

Trained to Love Cock!!

I finally got called to be trained to love cocks mmmm.

Gay Male 02/26/2019

Neighbourhood Terror to Sissy Pt. 02

Johns control tightens.

Transgender & Crossdressers 02/26/2019

Beyond Sissy's Spa Day Ch. 04

Boss lady arranges a 'girls' night'.

NonConsent/Reluctance 02/26/2019

Sissy Walk of Shame

A little sissy exhibition goes wrong.

Transgender & Crossdressers 02/23/2019

Neighbourhood Terror to Sissy Pt. 01

A story about a neighbour who wants some payback.

NonConsent/Reluctance 02/23/2019

The Daddy-Son Dance Pt. 02

Todd wakes up next to his cross-dressing Dad.

Transgender & Crossdressers 02/23/2019

Jimmy's Dilemma

Tough choices for a soon to be cocksucker...

NonConsent/Reluctance 02/21/2019

Femdom with a Touch of Silk

A woman shares her reluctant sissy with a female friend.

NonConsent/Reluctance 02/21/2019

Hubby's Sissy Training Day!!

Told my wife about my fantasy's and I woke up dressed!

Transgender & Crossdressers 02/21/2019

My Sissy Wife Pt. 02

Continuation of our anniversary evening together.

Transgender & Crossdressers 02/19/2019

Sissy Secrets Pt. 02

Sissy's mommy learns how much she wanted a girl.

Transgender & Crossdressers 02/19/2019

Emily's Girlfriend

After I play dress-up with her clothes, Emily plays with me.

Transgender & Crossdressers 02/19/2019

A Sissy's Tale

Honesty is the best policy, especially in matters of love.

Transgender & Crossdressers 02/18/2019

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
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