‘sissy’ stories

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A Sissy's Story

What happened to Gabrielle before and after she met him?

Transsexuals & Crossdressers 05/11/2017

Cucky Trained by CD DOM Pt. 01

Wife arranges for cuck to spend a weekend being trained.

Transsexuals & Crossdressers 05/10/2017

Along Came the Mistress

The mistress makes her move, will Gabrielle be jealous?

Transsexuals & Crossdressers 05/09/2017

Mrs C

A lonely cougar enjoys some summer romance.

Mature 05/08/2017

Sissy Slut

A sissy BDSM story.

BDSM 05/08/2017

Little Larry Ch. 01

Little Larry is used for practice.

Transsexuals & Crossdressers 05/07/2017

Nephew's Readjustment Pt. 17

Nicholas becomes accustomed to his new gay life.

Gay Male 05/07/2017

Sissy Fantasy to Nightmare

Blackmailed into living out his fantasy on a stag gone wrong.

Transsexuals & Crossdressers 05/07/2017

Girlfriends (Chandra and Nikki)

Nikki and Chandra make a pact to share their men.

Transsexuals & Crossdressers 05/07/2017

Dressing But Not Passing

Sissy in public.

Transsexuals & Crossdressers 05/06/2017

Two Good Neighbors Ch. 07

Kyle and Mark Roberts discuss their feelings and find a way.

Mind Control 05/06/2017

Nephew's Readjustment Pt. 16

Nicholas gets a new wardrobe and gets used to his new life.

Gay Male 05/06/2017

My Sister's Boyfriend

A drunken misconception leads to a life changing experience.

Transsexuals & Crossdressers 05/05/2017

Filipina Cuckolds Her Sissy Husband

A married couple have sex with black men.

Transsexuals & Crossdressers 05/04/2017

First Time Together

Gabrielle is more than she appears.

Transsexuals & Crossdressers 05/03/2017

Rear Naked Choke

A crossdressing sissy boi gets a rough fucking in a booth.

Transsexuals & Crossdressers 05/03/2017

Beyond the Valley of Jerkboy

Husband 'meats' his wife's work friend.

Exhibitionist & Voyeur 05/02/2017

From Homeless to Sexy Sissy Slut

Continued from homeless to sexy sissy.

Transsexuals & Crossdressers 05/02/2017

Cuckolded on the High Seas Ch. 02

Cuck's proposal.

Loving Wives 05/02/2017

New BBC Whores Abby & Lillie Pt. 01

The story of Lyle (Lillie) And Abby becoming whore for BBC.

Interracial Love 04/30/2017

A Damsel in Distress Ch. 02

A fair maiden emerges from the knight.

Transsexuals & Crossdressers 04/29/2017

X-Change: The Frat House Blues

Matt allows his roommate Rick to watch him transform.

Sci-Fi & Fantasy 04/29/2017

A Damsel in Distress Ch. 01

A knight will do anything to get his sword back. . . anything.

Transsexuals & Crossdressers 04/28/2017

A Slut's Triangle Pt. 19

Ashleigh ventures into Brenda's all-girls party.

Transsexuals & Crossdressers 04/27/2017

A Husband Named Cathy Ch. 02

Cathy begins to think about her recent shameless behavior.

Transsexuals & Crossdressers 04/26/2017

For Their Pleasure Pt. 03

Alexis awakens and meets her first new man, Mr. Nail.

Transsexuals & Crossdressers 04/25/2017

Lattés and Logic Pt. 03

Dick me Daddy.

Transsexuals & Crossdressers 04/25/2017

Don't Fuck with Hiroyuki Ch. 01

A gender-bending nano attack rocks the Hiroyuki crime family.

Sci-Fi & Fantasy 04/21/2017

Ryan's Blackmail Ch. 01

A college student gets in over his head with online blackmail.

Transsexuals & Crossdressers 04/20/2017

Lattés and Logic Pt. 02

Bruce cums around.

Transsexuals & Crossdressers 04/19/2017

Alex's Sissy Time Goes Wrong Ch. 02

Alex thinks he's in the clear, he is in for a shock.

Transsexuals & Crossdressers 04/19/2017

Introspection Ch. 02

Maddy confesses and pushes Jackie much further.

Fetish 04/19/2017

Sissy Pool Wager Pt. 01

Young sissy gets more than he bargained for in bet.

Transsexuals & Crossdressers 04/16/2017

A Slut's Triangle Pt. 18

Kimberly tells Ashleigh that she’s pregnant.

Transsexuals & Crossdressers 04/15/2017

A Sissy Cuckold to another Sissy

Unable to satisfy his wife, he is cuckolded and sissified.

Fetish 04/15/2017

Ugly Duckling to Sissy Princess Ch. 05

Vicky's very special night.

Transsexuals & Crossdressers 04/14/2017

The Sexy Cuckold Couple Pt. 17

Cuckold Story about an Owned Couple.

Fetish 04/14/2017

Lattés and Logic Pt. 01

Lattés, logic, tattoos and a sissy girl.

Transsexuals & Crossdressers 04/14/2017

My Ardent Desire

My dinner date with a man. Romantic. No harsh words.

Transsexuals & Crossdressers 04/12/2017

Slave History

A sissy slave describes her past.

BDSM 04/11/2017

A Friend Catches Me Ch. 02

This is the second part to my story, enjoy!

Transsexuals & Crossdressers 04/10/2017

Wife's Subservient Husband

Wife cements her dominance over husband in dramatic fashion.

Loving Wives 04/08/2017

Soames's Seminar

Master Soames has a "how to" seminar for his followers!

BDSM 04/08/2017

Soames's Store

Soames is meeting new masters and slaves at the Gift Shop!

BDSM 04/07/2017

You're My Bitch Now Ch. 03

Rick has an encounter with his boss at work.

Transsexuals & Crossdressers 04/06/2017

Nephew's Readjustment Pt. 14

Nicholas has a varied, gay, week.

Gay Male 04/05/2017

Nephew's Readjustment Pt. 15

Nicholas has a rather extreme sissy faggot experience.

Gay Male 04/05/2017

You're My Bitch Now Ch. 02

Rick gets much closer to Chris.

Transsexuals & Crossdressers 04/05/2017

A Slut's Triangle Pt. 17

Ashleigh dodges Kryss and Kimberly has a surprise.

Transsexuals & Crossdressers 04/04/2017

You're My Bitch Now Ch. 01

Rick from the IT Helpdesk discovers a life-changing secret.

Transsexuals & Crossdressers 03/31/2017

Nephew's Readjustment Pt. 13

Nicholas learns some new things about his life.

Gay Male 03/30/2017

House-Sitting Panty Lover Pt. 04

Our house sitting panty thief has an excited car trip.

Transsexuals & Crossdressers 03/29/2017

The Bus Man Ch. 04

Sissy Faggot Romance.

Gay Male 03/29/2017

Sissy's Lazy Sunday

A sissy awaits a lazy Sunday, but her Master has other plans.

Transsexuals & Crossdressers 03/28/2017

Soames's submissives: Trevor

Lunch between a Master and his pitiful mid-life slaveboy.

BDSM 03/28/2017

A Wife's Lover, His Boss Ch. 02

the reality of cuckold slave status hits home, literally.

Fetish 03/28/2017

The Bus Man Ch. 03

Sissy Faggot Romance.

Gay Male 03/28/2017

Humiliated Sissy Husband Ch. 03

Sadistic wife Tanya puts Max through Sissy Hell.

Transsexuals & Crossdressers 03/28/2017

The Sissy and The Gardener

The Gardener surprises The Sissy.

Transsexuals & Crossdressers 03/28/2017

Master Soames's submissives: Calvin

Cal needs Soames to continue the disciplinary work of Mom.

BDSM 03/27/2017

The Contest

How far can you push these chaste males?

BDSM 03/27/2017

The Surprise Party

Submissive comes home to humiliation...and angry women!

BDSM 03/27/2017

The Black Doctor & My Wife

This is the story of how my wife became a black cock slut.

Interracial Love 03/27/2017

I Asked for Humiliation

A story of feminization, strap on, humiliation and more.

Transsexuals & Crossdressers 03/25/2017

Slut for All Pt. 06

Taken by a big black cock.

BDSM 03/25/2017

Research Pt. 02

Working towards my PhD.

Gay Male 03/23/2017

Rite of Passage Ch. 03

Jamie's corruption furthers with help from his crush, Kelly.

Transsexuals & Crossdressers 03/22/2017

Slut for All Pt. 05

Night out to find me a cock.

BDSM 03/22/2017

A Slut's Triangle Pt. 16

Ashleigh and Kimberly’s relationship begins.

Transsexuals & Crossdressers 03/21/2017

Hook Pt. 01

Find out what happens when ditching school turns into sex.

First Time 03/19/2017

Nephew's Readjustment Pt. 12

Nicholas first month as a sissy faggot.

Gay Male 03/13/2017

Dena Goes for the Stars Ch. 02

Dena's slow rise into Stardom.

Transsexuals & Crossdressers 03/10/2017

Down Under Dee

A mix of story and homage to Dee, one of Lit's delights.

Loving Wives 03/09/2017

A Husband Named Cathy

A husband's dream comes true. He becomes Cathy.

Transsexuals & Crossdressers 03/06/2017

Operation Pucks and Panties Pt. 01

A pantyboy heads to Victoria's Secret for the first time.

Fetish 03/05/2017

House-Sitting Panty Lover Pt. 03

The trip to the mall takes an unexpected turn.

Transsexuals & Crossdressers 03/02/2017

A Slut's Triangle Pt. 15

Kryss hurts Ashleigh, Brenda and Kimberly come to the rescue.

Transsexuals & Crossdressers 03/02/2017

Another Tasty Creampie

Chloe shows her Daddy the thick creampie he gave her.

Transsexuals & Crossdressers 02/24/2017

Sweet Awakening

Unknowing sub wakes to an orgy.

Transsexuals & Crossdressers 02/21/2017

Julian to Julia Ch. 03

A sissy is fucked by sexy cousin.

Incest/Taboo 02/20/2017

Caught in Her Panties Ch. 03

Dressed up and taking the town by storm.

Transsexuals & Crossdressers 02/18/2017

BBC Worship Guide

Teaching whitebois how BBC should be handled.

Transsexuals & Crossdressers 02/16/2017

Making a Sissy

Disabled man's love-hate relationship with me and panties.

Fetish 02/16/2017

A Slut's Triangle Pt. 14

Kimberly catches Kryss cheating on her with Ashleigh.

Transsexuals & Crossdressers 02/15/2017

Escapism: Nightingale

A reflection of a sissy's journey to womanhood.

Transsexuals & Crossdressers 02/14/2017

House-sitting Panty Lover Pt. 02

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

Transsexuals & Crossdressers 02/14/2017


After girlfriends pass out, two guys have crossdressing fun.

Transsexuals & Crossdressers 02/13/2017

Daddy Discovers I'm a Sissy Ch. 01

My sissy secret isn't a secret anymore, and that's okay.

Incest/Taboo 02/13/2017

When Chastity Goes "Wrong"

Getting over masturbation addiction can get really kinky.

Gay Male 02/13/2017

Adventures with Dave and Chloe

Seven Interactions between Daddy Dave and baby girl Chloe

BDSM 02/12/2017

John and Erin Ch. 02

The continuing adventures of John and Erin.

BDSM 02/11/2017

Julian to Julia Ch. 02

A sissy's coming out party.

Incest/Taboo 02/09/2017

HypnoSissy: Cum Cravings

Videos entrench his hunger for cock and cum.

Fetish 02/09/2017

Weekend of Love Pt. 06

Getting to know our hosts.

Transsexuals & Crossdressers 02/08/2017

House-Sitting Panty Lover Pt. 01

Sissydream come true housesitting for his two neighbours.

Transsexuals & Crossdressers 02/07/2017

Escapism: The Modern Man

Escapism can be a wonderful thing.

Transsexuals & Crossdressers 02/07/2017

Virgin Sissy Sex Drive

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

Transsexuals & Crossdressers 02/07/2017

Few of My Ultra-Perverted Fantasies

Some of the juiciest stories you will ever encounter.

Transsexuals & Crossdressers 02/07/2017

Liz and John Solve Their Problem

John can't impregnate Liz. Another man has a go.

Fetish 02/07/2017


A strong Arab man fucks a married French couple every day.

Gay Male 02/02/2017
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