‘ladyboy’ stories

Active tags
shemale (52)transsexual (33)tranny (32)anal (23)transgender (13)crossdresser (11)gay (11)asian (9)transexual (8)oral (7)anal sex (7)lesbian (7)art (7)threesome (7)trans (6)transvestite (6)hermaphrodite (6)ass (6)thailand (5)crossdressing (5)cock (5)kathoey (5)dickgirl (5)first time (4)thai (4)sex (4)tgirl (4)forced (4)oral sex (4)bisexual (4)blowjob (4)gay sex (4)married man (4)creampie (4)futanari (4)t-girl (3)drawing (3)large cock (3)cum (3)slave (3)punishment (3)pain (3)threesomes (3)bondage (3)seduction (3)sissy (3)real life (3)he-she (3)forced bi (3)father (3)son (3)gay romance (3)massive cum shots (3)chastity belt (3)straight (3)one night stand (2)newhalf (2)orgasm denial (2)submission (2)futa (2)parody (2)androgyne (2)revenge (2)cuckold (2)painting (2)shower (2)orgy (2)humiliation (2)cum swallowing (2)wife (2)breasts (2)trap (2)huge cock (2)masturbation (2)alien (2)submissive (2)military (2)slut (2)bdsm (2)orgasms (2)domination (2)intersex (2)group sex (2)illustration (2)gay blowjob (2)surprise (2)mtf (2)sperm (2)shemale on male (2)erotic teasing (2)discipline (2)big cock (2)bras (1)androgyny (1)mature (1)bosom (1)slim (1)redhead (1)deepthroat (1)college student (1)master (1)fashion (1)character (1)drag queen (1)cuckoldry (1)attraction (1)dom (1)kimberly (1)tasha jones (1)lady boy (1)magazine (1)flogging (1)cane (1)strap on (1)roommate (1)bargirl (1)action (1)cocksucker (1)lingerie (1)orgasm (1)ladyboi (1)nonconsent (1)spank (1)gay virgin (1)sharing (1)korean (1)interracial (1)voyeur (1)whipping (1)gangbang (1)cocksucking (1)adventure (1)thong (1)cum covered (1)dick sucking (1)skirt (1)bisex (1)hot (1)triple penetrations (1)nipples (1)fuck (1)dominance (1)dominate shemale (1)large cocks (1)girly boy (1)quinn (1)watching (1)college (1)whore (1)double penetration (1)handcuffs (1)bi (1)hardcore (1)lesbian sex (1)futari (1)stripper (1)maid (1)army (1)nice t&a (1)cd romance (1)vigilante (1)romance (1)quayd (1)wilder (1)group (1)outdoors (1)cindrella (1)mmf threesome (1)cartoon (1)penis (1)dick-chick (1)mmp (1)breeding (1)photograph (1)tomerica (1)masculinity (1)wannabe woman (1)cum shots (1)philippines (1)vaginal sex (1)hoodwinked (1)fem top (1)hand job (1)striptease (1)tinder (1)aesthetic (1)bisexual sex (1)blonde (1)secret (1)wanking (1)massive ejaculations (1)double anal (1)paid (1)tits (1)safire (1)fem (1)brothers (1)mirror (1)soldier (1)boob (1)saphire (1)cheating (1)bangkok (1)drawings (1)egg laying (1)femininity (1)buttocks (1)incest (1)appreciation (1)big clits (1)banker (1)shemale anal (1)small penis (1)sketch (1)neighbor (1)black (1)jockstrap (1)tit-fuck (1)feminization (1)noncon (1)gay whore (1)bubble butt (1)blow job (1)heterosexual (1)butt plug (1)homosexual (1)nude (1)action adveture (1)penetration (1)transformation (1)dominant wife (1)nonconsensual (1)music (1)
ladyboy

Shemale Orgy

Ladyboy Mistress shares submissive with other shemale Doms.

Transsexuals & Crossdressers 11/05/2017

Lisa's Second Chance Pt. 08

Lisa has a busy two days.

NonHuman 10/25/2017

Lisa's Second Chance Pt. 06

Lisa helps out a newbie with a little secret.

NonHuman 10/16/2017

Cockatoo Pt. 37

Shane and Nin get together. Jamie gets ready for the party.

Transsexuals & Crossdressers 09/23/2017

Cockatoo Pt. 36

James gets ready to go to Kritsada's party as Jamie.

Transsexuals & Crossdressers 09/14/2017

Meat

A man takes home the waitress from his favorite steak house.

Transsexuals & Crossdressers 08/31/2017

Agnes Dourville Ch. 12

Anton and Antonia.

Transsexuals & Crossdressers 07/01/2017

I have a Confession to Make

After a fight with the wife, a man helps a college girl/boy.

Transsexuals & Crossdressers 06/09/2017

The Training of a Ladyboy

Best friend makes me his personal Ladyboy.

Gay Male 05/16/2017

A Prisoner to the Middle Sex

One man in Bangkok, and his ladyboy prisoners.

NonConsent/Reluctance 02/26/2017

Addicted to Pream's Cream

A man's first TS encounter at a massage parlor.

Transsexuals & Crossdressers 01/27/2017

Promiscuous Parents and Sons

Neighborhood parents get close as do gay and bisexual sons.

Novels and Novellas 12/31/2016

Fem Firm Ch. 01: Character Intro

Introduction to characters.

Transsexuals & Crossdressers 12/02/2016

Transsexual Journey 01

Single stud meets a lady boy on a Trans Atlantic cruise.

Transsexuals & Crossdressers 11/20/2016

The Misadventures of Amelia Pt. 02

Amelia goes to work with her new friend!

Transsexuals & Crossdressers 10/02/2016

My Treasure

My first time encounter with a ladyboy.

Transsexuals & Crossdressers 05/14/2016

Encounter of the First Kind

First ladyboy experience.

Transsexuals & Crossdressers 03/17/2016

Letter from Jefferson City

Licia, dominant wife!

BDSM 01/18/2016

Letter from Ravenswood Bluff

Mistress Jessamyn tells all.

BDSM 01/09/2016

Letter from Dayton

From a Young Male Master of Naughty Boys!

BDSM 01/01/2016

Cockatoo Pt. 17

James returns from Bangkok with news for Alex and Areeya.

Transsexuals & Crossdressers 11/28/2015

Futagear

A futa story.

Sci-Fi & Fantasy 08/18/2015

Cummy Panties

Erotic encounter at a bar.

Transsexuals & Crossdressers 08/15/2015

My First Thai Holliday

Young man gets fucked by horny shemales.

Transsexuals & Crossdressers 08/08/2015

Cockatoo Pt. 05

Naive Englishman gets more involved with old friend.

Transsexuals & Crossdressers 04/10/2015

Quinn

A young cross dresser transforms.

Transsexuals & Crossdressers 04/09/2015

That Helpless Moment

Story on how I found myself helpless against two Asian ladyboys.

Transsexuals & Crossdressers 03/13/2015

My Cleaner Ch. 03

Married man and ladyboy.

Transsexuals & Crossdressers 01/22/2015

Wild Asian Adventure Ch. 05

Final chapter of a wild trip gets wilder.

Group Sex 01/20/2015

Banker's First Encounter

Banker seduced by ladyboy customer.

Transsexuals & Crossdressers 01/19/2015

My Sexy Changes Ch. 04.2

Make embraces his feminine side.

Transsexuals & Crossdressers 11/04/2014

My Sexy Changes Ch. 04

Male discovers his female-self.

Transsexuals & Crossdressers 10/23/2014

Catching Up with Susan

Lady-boy Susan confesses her top fantasy.

Transsexuals & Crossdressers 10/21/2014

T-girl's Double Date

She used to be a boy but she's all woman now.

Transsexuals & Crossdressers 08/15/2014

My Cleaner Ch. 02

Married man seduced by ladyboy.

Transsexuals & Crossdressers 08/14/2014

My Cleaner

Married man seduced by ladyboy.

Transsexuals & Crossdressers 07/07/2014

Ts Tasha Jones Takes Huge Cock

An encounter when I was a stripper.

Transsexuals & Crossdressers 04/12/2014

Hero's Welcome

A soldier comes home to meet a new friend.

Gay Male 12/12/2013

My First Ladyboy

Looking for something new I meet with a my first ladyboy.

Transsexuals & Crossdressers 10/04/2013

Ladyboy Maid

A seductive ladyboy changes a married man's life.

Transsexuals & Crossdressers 09/24/2013

Lin

A trip to Thailand for some forbidden fun.

Fetish 07/24/2013

The Club

They thought they were just going to watch...

Transsexuals & Crossdressers 07/15/2013

His Best College Roommate Ever

He engages in bi-sex with his gay college roomate.

Gay Male 07/05/2013

In The Moment, Things Change

Who cares what she's working with - bring it on!

Transsexuals & Crossdressers 07/01/2013

The Vicar's Wife Ch. 25

A new outfit for Sarah.

Group Sex 06/30/2013

Girls Vegas-Style

Lonely man in Vegas hooks up with a fine looking "lady".

Transsexuals & Crossdressers 06/10/2013

Bizarre Bras Ch. 02

They're weird and funny, but they have a purpose, too.

Reviews & Essays 05/15/2013

A Night to Remember

That unforgettable night, when he first met her...

Transsexuals & Crossdressers 05/12/2013

A Thrilla in Manila

My Affair With a Ladyboy.

Transsexuals & Crossdressers 02/20/2013

Dictation

Dictation: it's not just for secretaries anymore!

Transsexuals & Crossdressers 11/08/2012

Ladyboy DP for Thai Wife

Sexy Thai gf agrees to share her Ladyboy lover with hubby .

Transsexuals & Crossdressers 08/31/2012

What Happens in Bangkok

Two brothers and a Thai hooker.

Incest/Taboo 08/26/2012

Cindrellas Kiss Ch. 02

She gets more than just a kiss.

Transsexuals & Crossdressers 07/26/2012

Ladyboy for my Thai Wife

I enjoy watching my Thai wife have sex with a ladyboy.

Transsexuals & Crossdressers 06/25/2012

TG Treats

How (and why) do I love them? Let me count the ways!

Reviews & Essays 04/10/2012

Bobbyluv: A National Treasure

His shemale art will melt your heart!

Reviews & Essays 03/12/2012

Porn Makes Connoisseurs of Us All

Another reason to be thankful for porn!

Reviews & Essays 03/05/2012

Danielle's First Time

Daniel, a straight man discovers that he's a transsexual.

Transsexuals & Crossdressers 01/31/2012

Brainwashing for Small Cocks Ch. 01

He's captured and mind-fucked into becoming gay.

Mind Control 01/09/2012

Images of Kimberly

Portraits of the artist as a young ladyboy.

Reviews & Essays 09/21/2011

The Bottom Tier: Ari and Cato

A new pair of lovers in a broken world.

Gay Male 09/04/2011

Five Ring Circus

An evil crime and extreme retribution for tranny fans.

NonConsent/Reluctance 07/27/2011

Recruited Ch. 01

A ladyboy scouted and recruited to service men in the army.

Transsexuals & Crossdressers 06/01/2011

The Neighborhood Ladyboy Ch. 02

Local Asian crossdresser gets invited to the neighborhood.

Transsexuals & Crossdressers 05/30/2011

The Neighborhood Ladyboy Ch. 01

Local asian crossdresser taken behind the supermarket.

Transsexuals & Crossdressers 05/23/2011

The Bottom Tier Revisited

An epilogue to the Bottom Tier.

Gay Male 04/22/2011

My Experience So Far

It's just a blowjob.

Transsexuals & Crossdressers 04/12/2011

The Bottom Tier

In a world divided unfairly, the victims find love.

Gay Male 03/22/2011

Sulka: A Vintage Shemale

Trannies were sweet treats back in the day, too.

Reviews & Essays 01/23/2011

NOT Waiting For Godot XXX

Thai Ladyboy edition, a porn parody.

Humor & Satire 01/18/2011

A Pinch of Pain

Give him an inch, and. . . .

Transsexuals & Crossdressers 01/02/2011

Bagging a Bitch with Balls

Which ladyboy, Thai or Filipina, is apt to please best?

Transsexuals & Crossdressers 12/07/2010

Modified Covers

A transformation devoutly to be desired.

Reviews & Essays 10/08/2010

Transgender Art: A Sampler

Uh, it's transgender art and it's a, uh, sampler, sort of.

Reviews & Essays 10/01/2010

Gargantua Ch. 02

A homoerotic genre.

Reviews & Essays 09/22/2010

Another Day, Different Office

A night alone in Amsterdam.

Transsexuals & Crossdressers 09/19/2010

Tilted Kilt Ch. 04

Danika experiences a Japanese Encounter.

Transsexuals & Crossdressers 08/10/2010

Gargantua

In dickgirl art, bigger is better.

Reviews & Essays 04/26/2010

A Slut Awakens

Girly boy is found out by his Black neighbor.

Transsexuals & Crossdressers 02/23/2010

Shemale First Time

Shemale male first time sex.

Transsexuals & Crossdressers 02/16/2010

Punish the Freak

Marie needs to be punished for what she is.

Transsexuals & Crossdressers 02/09/2010

Catalogue of Desire Pt. 03

Sex--what does is suggest about human nature?

Reviews & Essays 12/12/2009

Shemales: An Appreciation Pt. 03

Why are shemales so damned hot? Here's another reason. . .

Reviews & Essays 09/30/2009

Melody and Harmony

These songbirds gave new meaning to song!

Transsexuals & Crossdressers 09/03/2009

Transsexual Neighbors Ch. 05

Brooke meets the ladyboys.

Transsexuals & Crossdressers 06/22/2009

Looking-Glass Ladyboy

Sometimes, a mirror reflects both the body and the soul.

Transsexuals & Crossdressers 03/11/2009

Romeo, Where Art Thou Going in Life? Ch. 03

Romeo accepts Marcel's offer to become a ladyboy.

Gay Male 02/21/2009

Amethyst: a Story of Fulfilment

Amethyst finds he's - err, she's leading an ideal life.

Transsexuals & Crossdressers 01/23/2009

Everybody's Somebody Sometime

What goes around, comes around. -- Anonymous

Transsexuals & Crossdressers 01/19/2009

Sex with Shonda

Clint picks up a hot shemale from the local club.

Transsexuals & Crossdressers 10/19/2008

Guilty Pleasures

A drag queen submits to her boyfriend's perverted urges.

Transsexuals & Crossdressers 07/24/2008

Twisted

Dallas and Eve put on a live performance at a ladyboy bar.

Transsexuals & Crossdressers 03/27/2008

Exotic Escapades Ch. 03

Tammy's adventures with a ladyboy and two men.

Transsexuals & Crossdressers 01/18/2008

Bangkok Bar Girl

Businesman gets a surprise in a Thai bar.

Transsexuals & Crossdressers 06/21/2007

Beefy Buns

Shemale employee adds herself to the fast food menu.

Transsexuals & Crossdressers 05/30/2007

Pygmalion

The Perfect Woman isn't made of stone.

Transsexuals & Crossdressers 05/23/2007

Shemales: An Appreciation

Why are shemales so damned hot?

Reviews & Essays 05/15/2007

Tomeric: The Kiss

He discovers hidden talents through an accidental kiss.

Transsexuals & Crossdressers 09/14/2006

Shemale Art and Artists

Tranny toons.

Reviews & Essays 07/26/2006

A Cyber-Awakening

Online chat with mysterious lady leads to unexpected desire.

Transsexuals & Crossdressers 03/28/2005
Active tags
ladyboy
Separate tags with commas. More info in the FAQ
Related Tags