Search
Literotica Video
On Demand

Related tags

tagStory Tagscrossdress

Active Tags


Click tags to the right to narrow your search. Unclick tags to remove.

Stories

Jacki's Journey into Sissyhood

 — A crossdresser's journey into be a full-fledged sissy. by jacki697in  Transsexuals & Crossdressers12/17/144.42NEW

Alexander

 — Kyle knows his position in the social hierarchy. by collegecavewriter20in  Fetish11/11/143.71

Losing Sight Of Reality

 — There are many ways to recover from tragedies. by shubhashiniin  Transsexuals & Crossdressers11/03/144.17

La Rose Ch. 02

 — The continued story of Rose and Charles. by Artemis_Danielsin  Fetish11/03/143.40

La Rose

 — A chance meeting with a courtesan changes their worlds. by Artemis_Danielsin  Fetish11/01/143.73

Diary of a Cross-dresser Ch. 01

 — The yearnings of a sissy and his fantasy come true. by Adikon79in  Transsexuals & Crossdressers10/30/144.29

Giving In To Desire Pt. 01

 — 'Straight' guy gets caught in panties and gives in... by jpbiguyin  Transsexuals & Crossdressers10/29/144.58HOT

More Domme Club: The Appointment

 — First exam by Monica's Domme Doctor friend. by NancyPanin  Loving Wives09/16/143.69

Surprise Ch. 05

 — The Castles gear up for their incoming children. by theilluminaughtyin  Transsexuals & Crossdressers09/02/144.00

Becoming A Crossdresser Ch. 02

 — First time dressed and being seen by someone else. by AsianCD1990in  Transsexuals & Crossdressers09/01/144.33

Inaugural Crossdress Sexfight Ch. 02

 — Dani hopes to redeem himself vs a rookie. by danidhotcdin  Transsexuals & Crossdressers09/01/144.32

Anonymous

 — Porn writer becomes the story. by grgy56in  Transsexuals & Crossdressers08/31/144.40

Marriage Plans

 — A wayward mother delights in her son's downfall. by Jamie_in_dressesin  Incest/Taboo08/31/143.00

All the Way Ch. 02

 — Continuing story of George and Clarissa. by NearMissin  Transsexuals & Crossdressers08/30/144.71HOT

Becoming A Crossdresser

 — The beginning. First outfit and toys. by AsianCD1990in  Transsexuals & Crossdressers08/25/144.43

Eventful Birthday

 — Devious wife brings fantasy to life. by itchscratchedin  Transsexuals & Crossdressers08/20/143.98

Not My Fault Ch. 02

 — Paul still has a candle in him, but Brett's his real problem. by Myxyin  Transsexuals & Crossdressers07/17/144.39

Dinner for Two

 — Cross Dressed and forced to fuck Black Dick by Want2BUsedin  NonConsent/Reluctance07/14/144.32

Isabella's Reversion Pt. 02

 — Isabella continues with her journey into ABDL. by silverbackteddyin  BDSM07/01/140.00

My Daughter's Cuckold Ch. 04

 — Forced to service my daughter's friends! by How_Kinkyin  Incest/Taboo06/18/144.11

From Dom To Sub

 — A CD Domme's one night stand gets a bit out of her control. by ScarlettCDin  Transsexuals & Crossdressers06/11/144.28

Behavior Modification Institute Ch. 09

 — Tom's punishment ends and training resumes. by NancyPanin  Fetish06/11/144.28

New Mother, New Life Pt. 02

 — Helen helps Charlie to become Lottie. by Cara_Elainein  Transsexuals & Crossdressers05/13/144.58HOT

Blurred Lines

 — Lines are Blurred- or are they? by PseudonymDePlumein  NonConsent/Reluctance04/29/143.86

New Mother, New Life Pt. 01

 — Crossdresser re-unites with birth mother. by Cara_Elainein  Transsexuals & Crossdressers04/24/144.57HOT

A Story of My Confession

 — A man recounts his life and how he was forced to dress. by Lexavierin  Transsexuals & Crossdressers04/11/144.37

Cara's First Time With A Man

 — Crossdresser Cara discovers herself on an innocent date by Cara_Elainein  Transsexuals & Crossdressers03/31/144.62HOT

The Good Friend Ch. 02

 — The story continues... by Molifyin  Gay Male03/28/144.08

The Seven Dressing Sins: Vanity

 — An unsuspecting sissy porn star? How could that happen? by purekinkin  Transsexuals & Crossdressers03/01/144.45

For The Money Ch. 02

 — He gets an opportunity in a play. by SexyPenelopein  Transsexuals & Crossdressers02/26/144.53HOT

For The Money

 — A young man in need of money takes a job as a model. by SexyPenelopein  Transsexuals & Crossdressers02/26/144.42

Paying Trudi

 — Kinky fun with a street girl. by OpenMouthin  Fetish02/11/143.96

Interrupted

 — Alone time hijinks ended abruptly but well... in the end. by grgy56in  Transsexuals & Crossdressers02/07/144.13

Anna from Amsterdam

 — A story from my recent visit. by OpenMouthin  Erotic Couplings01/14/142.83

Chrissy Gets Caught

 — Husband is caught en femme by wife by femininechrissyin  Transsexuals & Crossdressers12/24/134.40

The Life and Times of Lady Vargos Ch. 06

 — Martin begins his duties as lady of the house. by rik581in  Transsexuals & Crossdressers12/06/134.20

The Life and Times of Lady Vargos Ch. 05

 — An experimental piece about Martin's trip to the spa. by rik581in  Transsexuals & Crossdressers11/29/134.40

Abducted and Turned Out Ch. 07

 — The continuing progression of a tg whore. by dawnib66in  Transsexuals & Crossdressers10/19/134.64HOT

Dirty Dream

 — Bi curious guy calls his dream guy. by Jamie_in_dressesin  Gay Male10/05/134.05

Remember / Forget

 — You wake up from a hypnotic trance bound & blindfolded. by Alicetv_in  Transsexuals & Crossdressers09/27/133.80

The Life and Times of Lady Vargos Ch. 04

 — Martin begins his week at the spa. by rik581in  Transsexuals & Crossdressers09/14/134.17

Pantsed Again

 — I'm found out at the office by my manager. by grgy56in  Transsexuals & Crossdressers09/05/134.28

Abducted and Turned Out Ch. 06

 — The latest chapter in the life of a sissy whore. by dawnib66in  Transsexuals & Crossdressers08/24/134.57HOT

Arabian Nights Ch. 01

 — Discovered dressed in a Dubai hotel. by kayla_femboiin  Transsexuals & Crossdressers08/07/134.26

Birthday Wishes Ch. 03

 — She finds out what one feels like inside of her. by b_wishingin  Transsexuals & Crossdressers07/08/134.32

Future Mother-in-Law is My Mistress Ch. 02

 — Mother in law advances the relationship. by gregorymike40in  Transsexuals & Crossdressers07/05/134.40

Sissy Downfall

 — My journey from sissy to transformed slut slave. by davinein  Transsexuals & Crossdressers07/04/134.39

Future Mother-in-Law is My Mistress

 — Mother in law catches me with panties and takes control. by gregorymike40in  Transsexuals & Crossdressers05/22/134.25

Some English

 — A guy and his kinky teacher have some fun with feet. by Theladder45in  Fetish05/13/133.95

The Life and Times of Lady Vargos Ch. 02b

 — The continuation of Family Portrait. by rik581in  Transsexuals & Crossdressers05/13/134.31

Housemate Deception

 — Who has the bigger secret? by EnojadoConsadoin  Transsexuals & Crossdressers05/11/134.71HOT

One Fine Day

 — "Do you wear girl's underwear?" by TomCarterin  Transsexuals & Crossdressers05/10/134.07

Caught Ch. 01

 — It was a sunny day and I didn't have anything planned... by jadecummingscd1in  Transsexuals & Crossdressers04/13/134.17

Aaron to Ashley Ch. 02

 — Ashley finds a way to make up with Ryan. by abc100in  Transsexuals & Crossdressers04/06/134.52HOT

Abducted and Turned Out Ch. 04

 — Another chapter in the continuing saga of a t-gurl whore. by dawnib66in  Transsexuals & Crossdressers04/05/134.51HOT

Mr. Wallace and Me Pt. 01-05

 — My fat, ugly boss makes me dress like a girl. by oberon_52in  Transsexuals & Crossdressers04/05/134.69HOT

Moment of Truth

 — A closet crossdresser is caught by his wife. by sharkinlacein  Transsexuals & Crossdressers03/02/134.56HOT

Valuation

 — Unexpected visitor gives a cd her first time with a man. by Jamie_in_dressesin  Transsexuals & Crossdressers02/07/134.66HOT

Rich Bitch

 — She catches him dressed and claims him. by Jamie_in_dressesin  Transsexuals & Crossdressers02/07/134.38

Identity Crisis 02

 — The next day... by BabyDreamerin  Transsexuals & Crossdressers01/31/134.61HOT

Mom Teaches Son to be a Slut

 — Mom and son fuck go on an adventure, fucking guys by aitbin  Incest/Taboo01/29/133.95

Identity Crisis 01

 — Posted to a school with wrong name, wrong gender! by BabyDreamerin  Transsexuals & Crossdressers01/26/134.37

Boi Toy

 — Teen is awakened by a caress by Jamie_in_dressesin  Transsexuals & Crossdressers01/22/134.13

Girl for Charlie Ch. 02

 — He takes her viginity in the bedroom. by Jamie_in_dressesin  Transsexuals & Crossdressers01/20/134.58HOT

Tranny at the Truck Stop

 — Tranny is trapped in truckstop restroom and fucked by bikers. by MicheleNylonsin  Transsexuals & Crossdressers12/28/124.50HOT

Study Abroad Bisexual Threesome Ch. 02

 — Jessica asks Nick to wear some sexy lingerie. by faneuilwritesin  Fetish12/28/124.52HOT

A New Spin on Role Playing Games

 — CD plays damsel for a live RPG and becomes a sissy slut. by shawnavinyltvin  Transsexuals & Crossdressers12/11/124.70HOT

Abducted and Turned Out Ch. 03

 — A T-Girl becomes a working whore. by dawnib66in  Transsexuals & Crossdressers11/26/124.64HOT

While You Were Away Ch. 01

 — Our protagonist gets caught playing in his sister's wardrobe. by SweetsFWin  Transsexuals & Crossdressers11/25/124.09

Feminine Enough Ch. 01

 — Chris dresses to please a roommate. by oneironatorin  Transsexuals & Crossdressers11/15/124.29

Maid up for Halloween

 — An agreement leads to more than Noah bargained for. by amberbmaidin  BDSM11/11/124.41

My Roommate, Brian

 — He gets feminized and loves it. by OptimusCrimein  Transsexuals & Crossdressers11/05/124.31

Laying Down Some Tracks

 — A guitarist didn't know what he was getting himself into. by nolfon1in  Transsexuals & Crossdressers09/26/124.56HOT

Trained to Have Transvestic Fetish

 — Husband trained to have a severe fetish. by Everyday2in  Fetish09/14/124.42

Virgin Ch. 03

 — Twenty one year old virgin moves into new house. by SissyKirstyin  Transsexuals & Crossdressers09/01/124.37

Virgin Ch. 02

 — Twenty one year old virgin moves into new house. by SissyKirstyin  Transsexuals & Crossdressers08/27/124.56HOT

Charlie

 — Warning - Never fall in love with your best friend. by Dennis_St_Johnin  Gay Male08/12/124.27

Lockerroom Run-In

 — I catch John, but he ends up getting me! by Hidden2320in  Transsexuals & Crossdressers08/07/124.29

The Awakening Ch. 03

 — Michele succumbs to blackmail and is forced to fuck. by MicheleNylonsin  Transsexuals & Crossdressers06/19/124.34

The Cottage Ch. 03

 — Transvestite trapped in snowbound cottage fucks her uncle. by MicheleNylonsin  Transsexuals & Crossdressers04/30/124.58HOT

Shattered

 — A terrifying, hot based-on-a-true-story of how I was outed. by kayla_femboiin  Transsexuals & Crossdressers04/24/124.23

Working with Trista Ch. 05

 — The final days of my trip withTrista. by amberbmaidin  BDSM03/25/124.55HOT

The Cottage Ch. 01

 — Teen TV hides in closet and watches mom with uncle. by MicheleNylonsin  Transsexuals & Crossdressers03/15/124.46

Second Chance

 — After he breaks up, she'll only take him back as a girl. by Tomspartyin  Transsexuals & Crossdressers02/27/124.35

I Lucked Out with a Lover in Reno

 — The man I met knew just what I needed. by Clintdearin  Gay Male02/18/124.27

Marion Turns Me On Ch. 03

 — Loving Femdom: training. by jomarin  Transsexuals & Crossdressers02/17/124.73HOT

Marion Turns Me On Ch. 02

 — Loving Femdom: shaping. by jomarin  Transsexuals & Crossdressers02/10/124.67HOT

Marion Turns Me On Ch. 01

 — Loving Femdom: beginnings. by jomarin  Transsexuals & Crossdressers02/03/124.57HOT

Caught in High Heels

 — He gets caught dressing up then something surprising happens. by BigAndy922in  Transsexuals & Crossdressers01/26/124.44

My Life in High Heels Ch. 05

 — Lisa's life continues. by cdandiein  Transsexuals & Crossdressers01/25/124.51HOT

A New Me...

 — College boy caught by sister; has his life changed. by teencdgirly22in  Transsexuals & Crossdressers01/21/124.49

She Dad Ch. 02

 — Darla entertains the pastor father of his son's girlfriend. by FirstTimer69in  Transsexuals & Crossdressers01/15/124.51HOT

Blame it on the Wedding Dress

 — A crossdresser is caught the day before his sister's wedding. by Pitterchenin  Transsexuals & Crossdressers01/03/123.53

Maid to Order

 — A chance to shine... by fantasywriterin  Transsexuals & Crossdressers12/21/114.20

The Point Of No Return

 — Another finally takes control. by fantasywriterin  Transsexuals & Crossdressers12/07/114.18

Working with Trista Ch. 03

 — Day 4 of working with Trista, another day of agony. by amberbmaidin  BDSM12/06/114.54HOT

Magic Panties Ch. 06

 — The end of the saga, Rachel completes her transformation. by nolfon1in  Transsexuals & Crossdressers11/28/114.60HOT

What Price Desire

 — A door awaits...will it be opened? by fantasywriterin  Transsexuals & Crossdressers11/26/114.46

The Awakening Of Gabrielle

 — A "gurl" searches for her place in this world. by fantasywriterin  Transsexuals & Crossdressers11/23/114.28

Working with Trista Ch. 02

 — Day 3 of working with Trista. by amberbmaidin  Transsexuals & Crossdressers11/18/114.41
Next
Page:123

Please, separate your tags with comma: anal orgasm, oral sex.

Read the Literotica Story Tag FAQ for more information on these tags.