Search
Literotica Video
On Demand

Related tags

tagStory Tagscrossdressing

Active Tags


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

Stories

Molly The Maid Boy

 — Enslaved by the oligarchs of Mars. by Otaku_Apologistin  Transsexuals & Crossdressers03/29/153.07NEW

Andy's Journey Ch. 04

 — Andy's delightful humiliation. by Borntolustin  Incest/Taboo03/28/154.22NEW

Lessons Learned

 — Sissy whore gets all pretty & then used by Mistress' friends. by MsCMin  BDSM03/28/154.12NEW

Cockatoo Pt. 01

 — Naive Englishman goes to Bangkok to get over his divorce. by nikkiesilkin  Transsexuals & Crossdressers03/27/154.32NEW

Introspection

 — Maddy turns Jack into a sissy slut. by edibles123in  Transsexuals & Crossdressers03/27/154.13NEW

The Date

 — Meeting my lover after a year apart. by 1Elizain  Transsexuals & Crossdressers03/26/153.90NEW

Andy's Journey Ch. 03

 — Their love expands, Alice reveals a secret. by Borntolustin  Incest/Taboo03/26/154.41NEW

Becoming Cassie Ch. 07

 — You were a cheerleader? by TGJamiein  Transsexuals & Crossdressers03/25/154.82HOTNEW

Becoming Cassie Ch. 06

 — Cassie visits Aunt Mary to decide. by TGJamiein  Transsexuals & Crossdressers03/17/154.68HOT

Caught For the Last Time Ch. 06

 — Jamie gets her name and his wife enjoys his feminine side. by TGJamiein  Transsexuals & Crossdressers03/15/154.62HOT

Andy's Journey Ch. 01

 — An abused sissy boy cast out by his wife comes home to Momma. by Borntolustin  Incest/Taboo03/10/154.41

Partners in Life

 — Surprise! by Dreamweaver594in  Transsexuals & Crossdressers03/09/150.00

Caught For the Last Time Ch. 05

 — You're definitely keeping that nightie. by TGJamiein  Transsexuals & Crossdressers03/06/154.62HOT

Piss Drinking Tranny Whore

 — Tranny has a wild night out at the adult movie theater. by nolimitstorytellerin  Fetish03/05/153.83

Becoming Cassie Ch. 04

 — Cassie learns more about her past. by TGJamiein  Transsexuals & Crossdressers03/04/154.63HOT

The Trouble with Roommates Ch. 07

 — Nick is caught taking advantage of Brian's absence. by KaylaGin  Transsexuals & Crossdressers03/03/154.51HOT

Easter Egg Hunt

 — A bottom is gang-banged at an Easter Party. by rikkitampa2014in  Anal03/03/152.98

Corssdressing at Pride Ch. 03

 — Amsterdam femboi reconnects with his older lover, moves in. by youngtwink19in  Transsexuals & Crossdressers03/03/154.78HOT

Master's Degree in Crossdressing Ch. 02

 — A grad student submits to his addiction to girly things. by wifetoyin  Transsexuals & Crossdressers02/27/154.45

Corssdressing at Pride Ch. 02

 — Further TRANSgressions, this time in a cruising club. by youngtwink19in  Transsexuals & Crossdressers02/26/154.56HOT

Caught For the Last Time Ch. 04

 — A new opportunity arises. by TGJamiein  Transsexuals & Crossdressers02/26/154.58HOT

Becoming Cassie Ch. 03

 — Seriously...you bought me heels? by TGJamiein  Transsexuals & Crossdressers02/25/154.75HOT

Foursome?

 — A gay threesome may add a fourth. by rikkitampa2014in  Gay Male02/25/154.00

Ethel and Gene, A New Life Ch. 06

 — Our connection with Jenny intensifies. by Borntolustin  Incest/Taboo02/25/150.00

The Trouble with Roommates Ch. 06

 — Nicole sinks deeper into submission. by KaylaGin  Transsexuals & Crossdressers02/24/154.67HOT

Corssdressing at Pride

 — Teen boy dresses up in drag, meets a handsome stranger. by youngtwink19in  Gay Male02/24/154.60HOT

Missing Morning Consequences

 — CD wife comes home to find husband waiting. by pushinmein  Transsexuals & Crossdressers02/24/154.00

My Life as a CD Wife

 — Three brief glimpses of sex with my husband. by pushinmein  Transsexuals & Crossdressers02/23/153.89

Dressing for a Latex Party

 — Cross dressed head to toe in latex for a fetish party. by latexlegsin  Fetish02/21/154.37

The Trouble with Roommates Ch. 05

 — Nick continues to test his boundaries and learns a lesson. by KaylaGin  Transsexuals & Crossdressers02/20/154.68HOT

Emmy's Iron Maiden Glory Hole

 — Emmy experiments further with Humphry's sexuality. by hummmphin  Fetish02/19/154.28

Becoming Cassie Ch. 02

 — Call me Cassie... by TGJamiein  Transsexuals & Crossdressers02/19/154.65HOT

Daddy Worships

 — Daddy fools Son into getting the best blowjob of his life. by StrappingStudin  Incest/Taboo02/19/154.23

The Trouble with Roommates Ch. 04

 — Nick's relationship with Brian takes a turn for the physical. by KaylaGin  Transsexuals & Crossdressers02/19/154.70HOT

Caught For the Last Time Ch. 03

 — A Tshirt bra and more. by TGJamiein  Transsexuals & Crossdressers02/18/154.60HOT

The Trouble with Roommates Ch. 03

 — Nick reluctantly takes a humiliating trip out with Brian. by KaylaGin  Transsexuals & Crossdressers02/18/154.59HOT

The Trouble with Roommates Ch. 02

 — An accidental slip-up leads Nick to the next penalty. by KaylaGin  Transsexuals & Crossdressers02/17/154.41

Milk Laden Mistress

 — A lost memory stick leads to his enslavement. by dr13bonein  BDSM02/17/154.12

The Trouble with Roommates Ch. 01

 — Nick is forcibly feminized by his dominating roommate Brian. by KaylaGin  Transsexuals & Crossdressers02/16/154.34

Sexless in Seattle

 — One of life's misfits; a dickgirl who can't find Mr. Right. by KuroshioXin  Transsexuals & Crossdressers02/15/153.52

Sissy Cuckold Husband

 — A fantasy that I wish would happen to me. by bisissystepheniein  Fetish02/14/153.72

Becoming Cassie Ch. 01

 — Babysitting was more than money. by TGJamiein  Transsexuals & Crossdressers02/13/154.31

Caught For the Last Time Ch. 02

 — Wife suggests some new things. by TGJamiein  Transsexuals & Crossdressers02/12/154.35

The Rough Road Pt. 01

 — Husband crossdresses to please wife, rest follows. by aausahebin  Transsexuals & Crossdressers02/11/153.21

Narcissa

 — Self-indulgence; the joy of cross-dressing. by sydianin  Transsexuals & Crossdressers02/06/153.35

Caught For the Last Time Ch. 01

 — Wife finds his stash of panties...again. by TGJamiein  Transsexuals & Crossdressers02/05/153.97

Rest Stop Romance Ch. 03

 — Rose and Dave make a stop on their "cross-country" trip. by Dark_Rose90in  Transsexuals & Crossdressers01/30/154.23

And When I Return Ch. 06

 — Anna exposed to public, loses virginity. by sublockedin  Transsexuals & Crossdressers01/24/154.50HOT

In For a Penny... Ch. 02

 — The further adventures of a horny husband. by TheHellWasIThinkingin  Fetish01/23/154.37

And When I Return Ch. 05

 — Rules built and expectations raised. Feminization begins. by sublockedin  Transsexuals & Crossdressers01/21/154.64HOT

The Blue Life Ch. 05: After Jillian

 — Revelations about Jillian, plus spanking & butt-fucking Mom. by GrantLeeStonein  Incest/Taboo01/18/154.41

The Entertainment Ch. 01

 — A sissy maid prepares to entertain his owners' guests. by econutin  Fetish01/11/154.31

A Father's Kiss Ch. 01

 — A young transgendered son has his fantasy come true. by DaveLane2014in  Incest/Taboo01/04/154.20

Helping a Butterfly

 — 'Daddy' helps a lonely boy break free. by JimBob44in  Transsexuals & Crossdressers01/03/154.56HOT

CD Fun Ch. 03

 — Stepping it up. by 62_gooin  Transsexuals & Crossdressers01/03/154.27

Weekend Slut for a Huge Cock

 — I cross dress for a huge white dick for the weekend. by MarkLazerin  Transsexuals & Crossdressers01/02/154.34

Rebecca and Rob Pt. 02

 — Later that day, I discover I have been discovered. by marissacdin  Transsexuals & Crossdressers12/27/144.55HOT

Kerwin's Decision

 — Does he want to be his wife's tranny cuckold? by colonellunchmeatin  Transsexuals & Crossdressers12/21/143.51

My Real Life Crossdressing Experience

 — A Lovemaking Session. by TammyPantyin  Transsexuals & Crossdressers12/18/144.07

I Call Him Mama

 — A butch girl is taught a lesson by a male mommy. by MadeiraDin  BDSM12/15/143.56

An Engagement Ch. 01

 — How to become a Man while Dressing as a Woman. by pocketrocketin  Novels and Novellas12/14/144.50

Fair Is Fair Ch. 04

 — Couple goes on a strange double date. by bgdddy_2000in  Transsexuals & Crossdressers12/09/144.49

Becoming Black Owned Pt. 03

 — Delia and Carl get marked. by JerseyGirlBcomin  BDSM12/04/144.44

CD Fun Ch. 02

 — Caz and Mikki find new friends to play with. by 62_gooin  Transsexuals & Crossdressers12/04/144.41

Our Secrets Ch. 02

 — A mother confronts her crossdressing son. by ShyTammyin  Incest/Taboo12/03/144.50HOT

Daddy's CD Waitress

 — Young crossdresser learns to love living as a woman. by pantycladladin  Transsexuals & Crossdressers12/03/144.69HOT

A Roleplay Gone Awry

 — What was supposed to be a prank against a dorky girl within. by ronald81in  BDSM11/29/143.84

Fag Hag

 — Crossdressing to help her gay male friend was never so fun. by Krosisin  Transsexuals & Crossdressers11/28/143.85

Albicania Ch. 01: King of Cujra

 — Meet the incestuous ruling family of the Cujra Kingdom. by Albicaniain  Sci-Fi & Fantasy11/26/143.84

Public Cross Dressing Experience Ch. 03

 — Don (Donna) is used for pleasure at a lesbian club. by sublockedin  Transsexuals & Crossdressers11/25/144.48

CD Fun

 — Michael becomes Mikki and is married to Caz. by 62_gooin  Transsexuals & Crossdressers11/25/144.31

Our Secrets Ch. 01

 — A loving mom follows her son and discovers his crossdressing. by ShyTammyin  Incest/Taboo11/23/144.21

Ethel and Gene, A New Life Ch. 05

 — Gina gives her virginity to Eloise. by Borntolustin  Incest/Taboo11/21/140.00

The Contract Ch. 02

 — Consensual slavery initiation. by sublockedin  Transsexuals & Crossdressers11/19/144.21

The Piano Tuner

 — A cuckold bottoms for his wife's horny lover. by rikkitampa2014in  Gay Male11/18/143.93

Rebecca and Rob

 — I fall into a sexy trap set by Rebecca, with Rob as bait. by marissacdin  Transsexuals & Crossdressers11/18/144.38

In For a Penny...

 — The lengths to which a horny husband will go. by TheHellWasIThinkingin  Fetish11/17/144.51HOT

Transexual Encounter Ch. 01

 — Real Life TS encounter. by SluttyValeriein  Transsexuals & Crossdressers11/17/144.52HOT

Ethel and Gene, A New Life Ch. 04

 — We meet Jenny. by Borntolustin  Incest/Taboo11/13/140.00

Playtime with Pets

 — Miss Alex has her pets switch roles. by subfellowin  Fetish11/08/144.33

Ethel and Gene, A New Life Ch. 03

 — We consumate our union. by Borntolustin  Incest/Taboo11/06/140.00

Man Disciplines Sissy Ch. 02

 — The punishment continues; and oral submission. by LanaBehavein  Transsexuals & Crossdressers10/28/144.41

Ethel and Gene, A New Life Ch. 02

 — Foreplay and feminization. by Borntolustin  Incest/Taboo10/26/140.00

A Lot of First for Me

 — New neighbor introduces me to my first kiss and so much more. by amygurlin  Transsexuals & Crossdressers10/23/144.52HOT

The Rendezvous Ch. 03

 — Nikki finally accepts herself and accepts her new Daddy. by CassidyCainein  Transsexuals & Crossdressers10/23/144.63HOT

My Sexy Changes Ch. 04

 — Male discovers his female-self. by TaraJadenin  Transsexuals & Crossdressers10/23/143.62

The Rendezvous Ch. 02

 — Nikki gets to play with two new play mates while shopping. by CassidyCainein  Transsexuals & Crossdressers10/22/144.59HOT

The Rendezvous Ch. 01

 — A crossdresser gets coerced into being another man's sissy. by CassidyCainein  Transsexuals & Crossdressers10/21/144.41

Sam Steals Neighbor's Panties

 — Sam has a bad day. It soon becomes a nightmare. by jadedappetitein  Fetish10/17/144.11

Ellie's Room

 — Fun time in Ellie' Closet. by lisaluvslacein  NonConsent/Reluctance10/16/143.58

Femboy's Awakening

 — 19-year old squire is caught dressing up with the whores. by FlavioMatsunagain  Transsexuals & Crossdressers10/14/144.61HOT

Zombie Sex

 — Two male zombies become a man's sex partners. by rikkitampa2014in  Gay Male10/14/143.84

Just a Game Ch. 03

 — Roommates finally go for it. Everybody wins. by tamgreenin  Gay Male10/12/144.54HOT

Thrift Store Sissy

 — MTF trans girl has a chance meeting with a kindred spirit. by sissywendiin  Transsexuals & Crossdressers10/05/144.26

Initial Crossdressing Adventures

 — First time dressing up. by vjak19in  Transsexuals & Crossdressers10/05/144.47

Teased, Denied and Sissified Ch. 04

 — Ashley further emasculates me while. by subbiemanin  Fetish09/25/144.47

Kallie

 — You want society to accept you but you can't accept yourself. by Tara_Nealein  Transsexuals & Crossdressers09/22/144.06

My Wife's Sunday Bikeride

 — A cuckold seeks pleasure with his adult daughter. by rikkitampa2014in  Incest/Taboo09/16/143.07

Last Time Cross Dressing

 — Simple date turns into an unwanted gangbang. by vjak19in  Transsexuals & Crossdressers09/12/144.29

A Learning Experience Ch. 07

 — A story of redemption & a rescue from hell. by Joscelyn2tgin  Transsexuals & Crossdressers09/09/144.75HOT
Next
Page:123

Active Tags


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

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

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