‘sissy’ stories

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sissy

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

Quickie

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

Demographics

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

Gay Male 02/02/2017

Julian to Julia Ch. 01

A panty boy is caught and transformed by sexy cousin.

Incest/Taboo 02/01/2017

A Helping Hand

A sissy gets tied to the bed and left...

Fetish 02/01/2017

Queen for a Night

Anniversary gift turns young hubby into weekend wide.

Transsexuals & Crossdressers 01/28/2017

Sissy Life: Valentine's Day

Wife's lover takes 'ownership' of Sissy.

Transsexuals & Crossdressers 01/28/2017

A Fantasy Night Exposed Ch. 01

Left in a compromising position for my wife's new friend.

Fetish 01/26/2017

Sissy Life: 50 Days in Chastity

A sissy 'celebrates' 50 days.

Transsexuals & Crossdressers 01/25/2017

My Valentine

CD Jessica celebrates Valentine's Day.

Transsexuals & Crossdressers 01/24/2017

The Bus Man Ch. 02

A sissy faggot romance.

Transsexuals & Crossdressers 01/23/2017

To Wear the Horns: A Cuckold Family Pt. 03

Billy's punishment, MotherKnowsBest, and a family friend!

Incest/Taboo 01/22/2017

Sissy Cuckolded by Girlfriend Ch. 01

A sissy slut gets cuckolded by his girlfriend.

Transsexuals & Crossdressers 01/22/2017

The Bus Man Ch. 01

A sissy faggot romance.

Transsexuals & Crossdressers 01/22/2017

Being Good in the Bedroom

Jenny discovers Rod's secret passion for lingerie.

Fetish 01/19/2017

Was I Raped? Ch. 04

A sissy whore continues her training.

Gay Male 01/18/2017

Sissy Life Pt. 04a

A sissy is whipped (a short interlude).

Transsexuals & Crossdressers 01/17/2017

Was I Raped? Ch. 03

My life as a whore starts now.

Gay Male 01/17/2017

No Choice

An explanation from a Domme.

Transsexuals & Crossdressers 01/15/2017

Research

A PHD student looks for answers.

Gay Male 01/15/2017

First Time as Sissy

My story visiting a dominatrix and dressing as a woman.

Transsexuals & Crossdressers 01/14/2017

Simon's Strict Unseen Mistress

A young man becomes a willing slave... but doing what?

BDSM 01/14/2017

From Submissive to Slave Pt. 01

He was already submissive to his wife, but he craved more.

BDSM 01/13/2017

Sissy Instructions

A sissy must prepare humiliatingly for her Mistress.

BDSM 01/13/2017

The Homosexual Sissy Wife

"Fifty Shades of Gay"

Transsexuals & Crossdressers 01/12/2017

What Being a Sissy Wife Means to Me

My conception of being a sissy wife.

Gay Male 01/11/2017

Sissy Life Pt. 04

A sissy prepares to be whipped.

Transsexuals & Crossdressers 01/08/2017

The Gentlemen's Panty Club

A young man joins an exclusive fetish club.

Fetish 01/06/2017

Sissy Initiation

My true journey begins.

Transsexuals & Crossdressers 01/02/2017

Sissy Life Pt. 03

A sissy serves his Mistress - and her lover!

Transsexuals & Crossdressers 01/02/2017

Escape

A sissy makes an escape attempt from 'her' captor.

Transsexuals & Crossdressers 01/01/2017

Blane's Hydraulic Inevitable

Sissy Blane has the obligatory date with Mr. Plumrose.

Transsexuals & Crossdressers 12/31/2016

Two Good Neighbors Ch. 06

The neighbors experience both joy and heartbreak.

Mind Control 12/30/2016

A Tongue Toy

A night pleasuring Mistress as her tongue toy and maid.

Fetish 12/30/2016

Dad My First Lover Pt. 01

Father and his CD daughter with occasional sexual encounters.

Transsexuals & Crossdressers 12/29/2016

Sammy Calls Him Sir

A naughty housesitter gets caught in the rain...

Gay Male 12/29/2016

Sissy Life Pt. 02

A sissy atones for his mistake.

Transsexuals & Crossdressers 12/28/2016

Sissy Life

A pathetic sissy blows the chance to impress his wife.

Transsexuals & Crossdressers 12/26/2016

His Fantasy Brought To Life

Stefan's femdom dreams came to fruition.

Anal 12/26/2016

Are You a Sissy?

Exposed at work and entrapped by a co-worker.

Transsexuals & Crossdressers 12/22/2016

Caught In Lingerie

Young man gets caught by neighbor and leads to sex!

Transsexuals & Crossdressers 12/20/2016

Was I Raped? Ch. 02

I confront the man who took my ass.

Gay Male 12/19/2016

Humiliated Sissy Husband Ch. 02

Max suffers more humiliation at the hands of his wife Tanja.

Transsexuals & Crossdressers 12/19/2016

The Interview

Josh does what he has to do to get hired.

NonConsent/Reluctance 12/19/2016

The Prostate Exam Pt. 05

Married Sissy is sent by Mistress to serve Master.

Transsexuals & Crossdressers 12/16/2016

Sissy Chantel, New Reality Ch. 11

Sunday Afternoon Fun.

Transsexuals & Crossdressers 12/14/2016

Humiliated Sissy Husband

A wimp of a husband is forced to be a sissy by his wife.

Transsexuals & Crossdressers 12/14/2016

Truth or Dare Sissy

A high school party game of 'truth or dare' goes wrong.

Transsexuals & Crossdressers 12/13/2016

Arthur's Hypnotic Transition

Arthur's college roommates ensure college life is exciting.

Mind Control 12/10/2016

Sissy Veronica

My First Blowbang.

Gay Male 12/08/2016

The Sexy Cuckold Couple Pt. 15

Cuckold Couple Becomes an Owned Couple.

Fetish 12/08/2016

The Prostate Exam Pt. 04

A married man succumbs to Sissy transformation for his Doc.

Transsexuals & Crossdressers 12/08/2016

Hotel Club Ch. 03

Cindy invites Roger back into the Club.

Transsexuals & Crossdressers 12/07/2016

Panties Pulled Down by My First Man

Trans woman has first time sex with a man after strapon.

Transsexuals & Crossdressers 12/06/2016

Sissy Chantel, New Reality Ch. 10

My First Saturday and Sunday at 'The Agency.'

Transsexuals & Crossdressers 12/06/2016

Nephew's Readjustment Pt. 10

Nicholas' gets something he wasn't expecting.

Gay Male 12/01/2016

Kneeling for Daddy

Caught crossdressing and Daddy takes advantage and control.

Incest/Taboo 12/01/2016

Sissy Chantel, New Reality Ch. 09

A full shift to pull today and tonight.

Transsexuals & Crossdressers 12/01/2016

Tales of Seth and Travis Pt. 01

The shopping trip exposes the sissies...

Transsexuals & Crossdressers 12/01/2016

Sissy Slave Toy

How I became a cock slave.

Gay Male 12/01/2016

To Wear the Horns: A Cuckold Family Pt. 02

Monthly orgasm time for the boys! But can Billy last?

Incest/Taboo 11/26/2016

Ugly Duckling to Sissy Princess

Tiny and undesirable boy discovers a new life as a sissy.

Transsexuals & Crossdressers 11/26/2016

The Snow Sissy Ch. 01

An icy sissy fairy tale.

Transsexuals & Crossdressers 11/26/2016

To Wear the Horns: A Cuckold Family Pt. 01

Three fat women, three incestuous cuckolds.

Incest/Taboo 11/22/2016

Mistress Monique Pt. 02

Monique discovers the joys of dominance.

Fetish 11/22/2016

Letter from Walsingham Pt. 01

Tulke escapes one bitch just to end up with another!

BDSM 11/22/2016

Sissy Chantel, New Reality Ch. 07

My New Start To My Sissy Life.

Transsexuals & Crossdressers 11/22/2016

Balls on Your Chin

A boy finally gets put in his place by his bully.

Transsexuals & Crossdressers 11/22/2016

A Deal Offered

Rob is caught and offered a deal.

Fetish 11/21/2016

The Sexy Cuckold Couple Pt. 14

Cuckold Couple Becomes an Owned Couple.

Fetish 11/18/2016

The Sexy Cuckold Couple Pt. 13

Cuckold Couple Becomes an Owned Couple.

Fetish 11/17/2016
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