‘sissy’ stories

Active tags
humiliation (397)femdom (381)anal (328)crossdressing (307)cuckold (264)feminization (260)crossdresser (249)panties (236)gay (208)chastity (167)bondage (167)spanking (158)bdsm (151)interracial (144)mistress (142)submission (137)domination (135)blowjob (134)submissive (134)forced (132)oral (128)slave (126)lingerie (113)forced feminization (110)slut (110)cum (102)crossdress (94)fetish (90)incest (89)transvestite (79)strapon (78)bisexual (77)wife (76)bbc (73)orgasm denial (72)sissification (72)transgender (72)tranny (69)first time (67)shemale (67)maid (65)cross dressing (62)punishment (61)stockings (60)blackmail (60)female domination (59)anal sex (53)transsexual (53)forced bi (53)daddy (52)masturbation (51)trans (50)sissy maid (50)transformation (50)whore (49)strap-on (48)high heels (48)blow job (48)master (47)hypnosis (45)whipping (44)dominatrix (44)faggot (44)dominant wife (44)discipline (44)dildo (42)cocksucking (41)lesbian (40)mind control (40)cum eating (39)cock sucking (39)creampie (39)black cock (37)gangbang (37)chastity belt (37)threesome (36)cocksucker (35)pantyhose (35)sissy slut (35)pegging (35)domme (34)transexual (34)non-con (33)pain (33)heels (33)s&m (33)noncon (33)male submissive (32)son (31)submissive male (29)feminisation (29)bitch (29)black (29)husband (27)cfnm (27)strap on (26)big cock (26)hotwife (25)sadism (25)group sex (25)cbt (24)college (23)virgin (23)cross dresser (23)forced fem (22)caught (22)forced gay (22)oral sex (22)mother (22)cumslut (21)feminized (21)reluctance (21)public (21)romance (21)small penis (21)submissive husband (21)sister (20)cuckolding (20)femboy (20)satin (20)gay male (20)dominant male (19)piss (19)bareback (19)ass fucking (18)cross-dressing (18)dominance (17)slavery (17)handjob (17)sph (17)cd (16)trap (16)gang bang (16)twink (16)fantasy (16)makeup (16)toys (16)shopping (16)older man (16)public humiliation (16)denial (15)shame (15)bully (15)gay transvestite (15)teen (15)female dominant (15)butt plug (15)crossdressers (14)exhibitionism (14)dominant female (14)group (14)panty (14)teasing (14)d/s (14)trapped (14)homosexual (14)prison (14)crossdessing (13)nonconsent (13)wimp (13)training (13)thong (13)watersports (13)cuck (13)love (13)sadist (13)bull (13)blowjobs (13)control (12)tease (12)adult arcade (12)cunnilingus (12)cock sucker (12)voyeur (12)sci-fi (12)office (12)cock (12)msub (12)bisexual male (12)slut wife (12)prostitution (12)black man (12)cheating (12)masochism (12)bimbo (12)fingering (11)dad (11)diaper (11)dress (11)femboi (11)family (11)female worship (11)facial (11)bi (11)enema (11)feet (11)rough (11)small penis humiliation (11)milf (11)gloryhole (11)forced feminisation (10)kidnapping (10)reluctant (10)humilation (10)mom (10)cum swallowing (10)finger fucking (10)sucking (10)small cock (10)non-consent (10)cross dress (10)butt plugs (10)bra (10)big black cock (10)degradation (10)panty boy (10)18-year-old (9)taboo (9)rimming (9)mommy (9)fisting (9)huge cock (9)glory hole (9)male chastity (9)gay sex (9)masochist (9)cream pie (9)makeover (9)dominant (9)bottom (9)bukkake (9)romantic (8)straight (8)
sissy 

Uncovering the Sissy Beneath Pt. 05

Tricia's new look, earns her some extra attention.

Transgender & Crossdressers 07/17/2019

Coming Home Again

Every good immigrant father wants to see his family succeed.

Mind Control 07/17/2019

Secret Makes Him a Cuckold Bitch

She finds his secret turns him into a sissy cuckold.

Fetish 07/17/2019

Making of a Sissy Whore

Jeff finds out everyone has to earn their way.

Transgender & Crossdressers 07/16/2019

Sissified by Hypnosis

Guy is turned into a sissy and forced to suck cock.

Fetish 07/14/2019

Payson's Wedding Ch. 02

A gentle sissy and his fiance continue to plan their wedding.

Transgender & Crossdressers 07/13/2019

The Rose Diaries Ch. 21

Blank.

Transgender & Crossdressers 07/13/2019

Summer with Unkie

Feminine boy spends the summer with his Step Uncle.

Transgender & Crossdressers 07/11/2019

A Cell Phone Makes Me Pregnant Ch. 02

A Cell Phone, Mind Control, and a Hot Redhead News Reporter.

Erotic Couplings 07/11/2019

Bambi Takes Over

Bambi Sleep hypnosis has corrupted another listener.

Transgender & Crossdressers 07/11/2019

Transforming Brent Pt. 02

Continuing story of Brents' Wife making him her wife/sissy.

Loving Wives 07/10/2019

Humiliation Journey The Beginning

How hypnos changed me into a sissy for BBC.

Transgender & Crossdressers 07/10/2019

From Husband to Man's Sissy Wife Ch. 03

Will Chloe find happiness?

Transgender & Crossdressers 07/10/2019

Wife had Bad Day at Golf

She had bad day at the golf course and takes it out on me!

Fetish 07/09/2019

My Medical Vacation

A trip to Poland for dental implants becomes much, much more.

First Time 07/09/2019

Uncovering the Sissy Beneath Pt. 04

Tricia learns more about the daily life of a sissy.

Transgender & Crossdressers 07/09/2019

The Drink

Trans girl encounters a dominant lesbian at a bar.

Transgender & Crossdressers 07/05/2019

Floating My Boat at the Lake Ch. 02

Wicked niece shows me off.

Incest/Taboo 07/05/2019

From Husband to Man's Sissy Wife Ch. 02

More adventures in sissy cuckold submission.

Transgender & Crossdressers 07/05/2019

Anna's Date

Anna attempts a "normal" date with her new pet.

BDSM 07/05/2019

From Husband to Man's Sissy Wife

As my big titted wife takes a lover, I meet a man...

Transgender & Crossdressers 07/04/2019

BBC: Like Son, Like Father

Father catches son sucking BBC & gets very curious.

Gay Male 07/04/2019

Jimmy's Dilemma Ch. 05

The night shift continues...

NonConsent/Reluctance 07/04/2019

A Surprise Blind Date

An Innocent party turns into something more.

BDSM 07/04/2019

Transforming Brent

Wendy and Katherine want Brent as their maid.

Loving Wives 07/03/2019

Family Chastity Story Ch. 02

A nasty mother further experiments on her gimp son.

BDSM 07/02/2019

Cherry

Being neighborly gets me fucked.

NonConsent/Reluctance 07/02/2019

Sissy Gets Punished on His Birthday

Dominant wife punishes sissy husband, ruins orgasm.

Fetish 07/01/2019

Waiting for My Sexy CD Slave

An afternoon with my crossdressing slave.

Transgender & Crossdressers 07/01/2019

The Rose Diaries Ch. 20

Pressure.

Transgender & Crossdressers 06/30/2019

Mommy's Panty Party

She has devious plans for her twin boys.

Incest/Taboo 06/29/2019

Neighbourhood Terror to Sissy Pt. 11

Mark is caught by Lisa yet again.

Transgender & Crossdressers 06/29/2019

Auntie's Revenge

A little tale for aspiring sissy cuckolds.

Incest/Taboo 06/28/2019

Husband's Transformation Ch. 02

Husband's transformation grows with help from wife's friend.

Transgender & Crossdressers 06/26/2019

Aunt Pamela and Leslie Ch. 02

Well-behaved college boy returns to visit mature woman.

Fetish 06/22/2019

Uncovering the Sissy Beneath Pt. 03

My continued journey into becoming a full time sissy.

Transgender & Crossdressers 06/21/2019

Candy's Fashion House Ch. 14

Kelli becomes a woman.

Transgender & Crossdressers 06/21/2019

Cassie's Sissy Bitch Pt. 01

A new sissy gets manipulated by a mysterious woman.

Transgender & Crossdressers 06/20/2019

Wasp and Antman

Three minutes to get to know me.

Transgender & Crossdressers 06/20/2019

Humiliation Journey Never Ends

Small dick white sissy converted to she-male.

Transgender & Crossdressers 06/18/2019

Cuckbitch Pt. 01: Confession

A panty cuckold shares his dark secret with his best friend.

Fetish 06/17/2019

Leftover Lusts

Relationship ends after workplace gangbang.

Transgender & Crossdressers 06/17/2019

The Neighbours Situation Ch. 01

A new neighbour leads to changes in his life.

Transgender & Crossdressers 06/15/2019

A Sissy is Born

A young man has a reason to doubt his sexuality.

Transgender & Crossdressers 06/14/2019

Uncovering the Sissy Beneath Pt. 02

My Journey of being held captive and turned into a sissy.

Transgender & Crossdressers 06/14/2019

My Mother's Boyfriend Shawn

Small boy and his mom's girlfriend develop a special bond.

Transgender & Crossdressers 06/14/2019

The Boifriend Ch. 02

Daughter's boyfriend finds where he belongs- on his knees.

Gay Male 06/11/2019

You Want to Be Feminized and Milked

I feminize you and make you into my milking cow.

Transgender & Crossdressers 06/11/2019

Aficionado Gets in Trouble Ch. 02

Knowing too much about BDSM equipment had him in a fix.

Transgender & Crossdressers 06/10/2019

Sissy/Cock Sucker Dictionary

A list to understand the nature of sissies/cocksuckers.

Reviews & Essays 06/10/2019

No Going Back!

Duvet day desire leads to first time dress-up.

Transgender & Crossdressers 06/08/2019

Finley and his Land-Lady

A gentle boy moves in with an affectionate, mature Land-Lady.

Fetish 06/08/2019

Neighbourhood Terror to Sissy Pt. 10

Lisa grabs her chance at toying with the sissy.

Transgender & Crossdressers 06/05/2019

Cum at the Mall

Sissy eats cum in the parking lot.

Transgender & Crossdressers 06/05/2019

Yesterday Afternoon

A Compromising Situation.

Transgender & Crossdressers 06/04/2019

Swipe Right Ch. 05

Justine adapts to Samantha's home life.

Transgender & Crossdressers 06/04/2019

Zenit

Russian mob forces punk to crossdress & seduce soccer star.

Transgender & Crossdressers 06/02/2019

How I Got My Sissy Name

A Gift begins a new chapter.

Transgender & Crossdressers 06/02/2019

Beyond Sissy's Spa Day Ch. 07

Sissy faces decision of a lifetime.

NonConsent/Reluctance 06/01/2019

Jimmy's Dilemma Ch. 04 - A New Toy

Jimmy's new job comes with free food.

NonConsent/Reluctance 06/01/2019

Project Alice

Boy trained into a girl to reduce crime.

Transgender & Crossdressers 05/31/2019

A Weekend Visit to the Office

I usually work from home as I have a very private place with.

Transgender & Crossdressers 05/30/2019

Swipe Right Ch. 04

Samantha's sister Justine shakes things up.

Transgender & Crossdressers 05/29/2019

The Dominatrix Order Pt. 05 Ch. 04

Conclusion Book 5

Fetish 05/29/2019

The Rose Diaries Ch. 19

The Price of Joy.

Transgender & Crossdressers 05/29/2019

The Talent Scout

First he took me then he took my wife.

Gay Male 05/29/2019

Blackmailed Pt. 07

Bambi makes a big decision and goes shopping.

Transgender & Crossdressers 05/28/2019

Sissy's First Boyfriend

Sometimes you find a winner at the club.

Transgender & Crossdressers 05/27/2019

When Cultures Collide

A man convinces coworker to have sex with his wife and him.

Fetish 05/26/2019

A Starlet is Born

An elven bar owner makes her new slaves into dancers.

Sci-Fi & Fantasy 05/25/2019

Payson's Wedding

A gentle young man and his fiance make wedding plans.

Transgender & Crossdressers 05/25/2019

Transformations - Rose Ch. 10

Sugar Tits vs. The Mob. Lisa perverts. A revelation.

Mind Control 05/25/2019

The Neighbor Daddy Next Door

Daniel falls further into one older man's feminization trap.

Transgender & Crossdressers 05/24/2019

A Disturbing Desire

A fantasy of mine.

Transgender & Crossdressers 05/22/2019

Neighbourhood Terror to Sissy Pt. 09

Things take a surprising turn.

Transgender & Crossdressers 05/22/2019

A Very Public Sissy Adventure

A BDSM story.

BDSM 05/22/2019

The Seductive Seed of a Tranny MILF

One sip and you just might find yourself hooked like he did.

Transgender & Crossdressers 05/22/2019

The Dominatrix Order Pt. 05 Ch. 03

Sissy foot worship.

Lesbian Sex 05/18/2019

Choices Ch. 01

Got caught.

BDSM 05/17/2019

Double Jeopardy

Man becomes sissy sex slave for wife and in laws.

Transgender & Crossdressers 05/17/2019

Transformations - Rose Ch. 09

Lisa and Mary pervert. Jason hunts. Stan wakes up.

Mind Control 05/16/2019

A Taste of Step-Cock

A young gurl meets her new step-father.

Transgender & Crossdressers 05/16/2019

Trucker Turned Me Out Pt. 01

Young man meets a trucker online.

Gay Male 05/15/2019

Susan Ch. 02

I make a promise I can't keep.

Transgender & Crossdressers 05/15/2019

Neighbourhood Terror to Sissy Pt. 08

Things go horribly wrong for Mark.

Transgender & Crossdressers 05/14/2019

House Boy - Casey's Wild Ride

Casey wants more and Daddy's gives it to him.

Gay Male 05/14/2019

His "Special" Secretary Pt. 05

Second day of the evaluation week, big change for Dani!

NonConsent/Reluctance 05/11/2019

Slave Gets Punished and Redeemed

An ERP me and a friend made together.

Transgender & Crossdressers 05/11/2019

The Dominatrix Order Pt. 05 Ch. 02

Free Domme-Lesbian fisting squirting.

Lesbian Sex 05/10/2019

Chrysalis of Kirsten Ch. 03

Kirsten's first time in Greg's world.

Transgender & Crossdressers 05/01/2019

Nurse Jenny Lends a Hand

ER visit leads to him learning to be a small cocked sissy.

Fetish 05/01/2019

House Boy Likes Being Watched

Casey let's Michael watch him play.

Gay Male 05/01/2019

The Rose Diaries Ch. 18

Frilly Ferocity.

Transgender & Crossdressers 04/28/2019

House Boy

Casey gets the perfect summer job.

Gay Male 04/27/2019

Finally a Real Sissy

Treated like the sissy I want to be.

Transgender & Crossdressers 04/25/2019

Tales of Sub Asian Sissy Ch. 04

Jade's errands for Master result in brutal anal abuse.

Transgender & Crossdressers 04/24/2019

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