‘sissy’ stories

Active tags
humiliation (361)femdom (347)anal (326)crossdressing (293)cuckold (246)feminization (240)crossdresser (239)panties (214)gay (190)bondage (158)chastity (151)spanking (147)bdsm (142)interracial (135)mistress (133)blowjob (129)submissive (127)forced (125)submission (124)domination (123)slave (121)oral (117)slut (105)lingerie (103)cum (102)forced feminization (100)crossdress (87)transvestite (77)bisexual (74)incest (74)fetish (73)strapon (73)orgasm denial (71)bbc (70)wife (65)tranny (63)first time (62)maid (62)transgender (62)shemale (61)punishment (59)cross dressing (59)sissification (58)stockings (57)female domination (55)blackmail (54)anal sex (51)daddy (49)transformation (49)sissy maid (48)whore (48)masturbation (47)high heels (47)strap-on (46)trans (45)master (45)dominatrix (44)blow job (44)dominant wife (44)discipline (44)whipping (43)forced bi (43)faggot (43)transsexual (42)cocksucking (40)dildo (40)gangbang (39)black cock (38)cock sucking (38)creampie (38)chastity belt (37)hypnosis (37)cocksucker (35)pantyhose (34)sissy slut (34)lesbian (33)threesome (33)s&m (33)mind control (33)pain (32)transexual (32)pegging (32)male submissive (31)heels (30)cum eating (30)domme (29)bitch (29)black (28)big cock (28)submissive male (27)sadism (26)son (26)strap on (25)hotwife (24)caught (23)college (23)cbt (21)cfnm (21)forced gay (20)feminized (20)feminisation (20)reluctance (20)public (20)virgin (20)mother (20)cross dresser (20)submissive husband (20)sister (19)cuckolding (19)cumslut (19)dominant male (19)piss (19)group sex (19)non-con (18)oral sex (18)husband (18)romance (18)ass fucking (18)small penis (18)bareback (18)forced fem (17)gay male (17)dominance (17)makeup (17)satin (16)fantasy (16)shopping (16)cross-dressing (16)sph (16)shame (15)gay transvestite (15)femboy (15)crossdressers (15)cd (15)gang bang (15)female dominant (15)handjob (15)noncon (15)butt plug (15)bully (14)teen (14)panty (14)d/s (14)public humiliation (14)trapped (14)homosexual (14)prison (14)crossdessing (13)wimp (13)training (13)trap (13)sadist (13)older man (13)bull (13)blowjobs (13)denial (12)adult arcade (12)watersports (12)facial (12)slavery (12)cock (12)love (12)group (12)msub (12)bisexual male (12)black man (12)cheating (12)masochism (12)bimbo (12)bukkake (12)control (11)diaper (11)tease (11)femboi (11)cock sucker (11)nonconsent (11)thong (11)twink (11)sci-fi (11)office (11)toys (11)rough (11)small penis humiliation (11)teasing (11)big black cock (11)slut wife (11)prostitution (11)dress (10)cunnilingus (10)family (10)humilation (10)voyeur (10)mom (10)dominant female (10)finger fucking (10)sucking (10)cross dress (10)butt plugs (10)bra (10)degradation (10)panty boy (10)18-year-old (9)dad (9)reluctant (9)exhibitionism (9)glory hole (9)bi (9)non-consent (9)masochist (9)feet (9)milf (9)cream pie (9)makeover (9)gloryhole (9)paddling (8)gender conversion (8)trannsexual (8)white (8)black leather skirt (8)cum swallowing (8)boss (8)knickers (8)huge cock (8)gay sex (8)corporal punishment (8)father (8)gay anal (8)daughter (8)dom/sub (8)dominant (8)hot wife (8)bottom (8)cum slut (8)

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


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
Active tags
Separate tags with commas. More info in the FAQ
Related Tags