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Transgender & Crossdressers Stories

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Engagement Sex

 — Surprise is revealed before Melissa & Bobby get engaged. by Luv2pleees09/15/074.41

England Pink

 — Sissy slut Tanya gets a cum coating for Mr Hull. by Stillherer12/23/123.98

Ensnared by a Corset

 — A closeted cross dresser is discovered and humiliated. by spinder02/14/144.10

Entertaining is Hard Work!

 — Dani has to entertain three black men at a private party. by Jemina00404/06/184.43


 — Squire Lyr becomes a sissy, thrall of the fae. by Sissyhalo11/03/174.30

Enticed and Humiliated Ch. 05

 — College boy explores cross dressing and maid service. by FantasizeAndRealize08/17/154.23

Entrance Exam

 — An unusual but much desired test. by MissYellowPanties05/04/194.46


 — A dickgirl housewife, home alone. by KuroshioX02/17/154.03


 — Young man experiences the ultimate feminine act. by Barno09/13/054.55HOT

Epiphany At An Epiphany Party

 — Discovering a change in desires. by cd_donna01/31/173.07

Erectile Dysfunction

 — Two friends work together to overcome erectile dysfunction. by chandler83109/22/184.65HOT

Eric's Dreams Pt. 01

 — Gay sex makes Eric feel like a girl. Should he become one? by Genevieve_Ohara04/11/174.36

Eric's Dreams Pt. 02

 — Eric transforms to have sex with a straight man. by Genevieve_Ohara04/19/174.53HOT

Eric's Dreams Pt. 03

 — Genevieve goes to a Halloween Party. by Genevieve_Ohara07/07/174.57HOT

Eric's Dreams Pt. 04

 — Eric becomes Genevieve while jacking off. by Genevieve_Ohara09/06/174.38

Eric's Dreams Pt. 05

 — To go on a date as a woman? Or a man? Eric must decide. by Genevieve_Ohara11/25/174.65HOT

Erica Goes to College

 — Fun is where we find it. by KirkEdwards05/04/094.33

Erin and the Shemale

 — Erin's roommate isn't what she appears to be. by kimberlykitten12/10/044.26


 — A beauty contestant who gives out the prize. by sr71plt05/23/134.31

Erotic Daydreams

 — Daydreaming while masturbating. by History Nut03/06/063.96


 — Girlie boy gets taken advantage of at a frat party. by Da_Vida02/25/094.28


 — A sissy makes an escape attempt from 'her' captor. by RainMaker9101/01/173.69

Escaping Curtis Brown

 — Bullied young man escapes his past and becomes something new. by JimBob4404/09/184.72HOT

Escapism: Nightingale

 — A reflection of a sissy's journey to womanhood. by chasingrisque02/14/174.33

Escapism: The Modern Man

 — Escapism can be a wonderful thing. by chasingrisque02/07/174.50HOT

Eternal Lovers at Last

 — She finds her other half after an eon of searching. by RedVixen06/27/122.94

European Vacation

 — A teenager goes to Europe for the beaches, in a bikini! by yr_sissy_toy05/09/104.30

Eva Steele 01

 — Eva Steele goes under the knife. by FutaWriter07/06/174.22

Eve Quest

 — A transvestite submits to his wife and her lesbian lover. by JJ Neal01/06/044.23

Eve Quest

 — A transvestite is dominated by two beautiful lesbians. by Sheila_TSSub07/22/174.18

Eve Quest Pt. 02

 — A transvestite gets an enema. by JJ Neal01/18/044.17

Eve Quest Pt. 03

 — The transformation is complete. by JJ Neal02/06/044.55HOT

Eve Quest Pt. 04

 — submissive transvestite lives happily ever after. by JJ Neal02/22/044.36

Eventful Birthday

 — Devious wife brings fantasy to life. by itchscratched08/20/144.18

Every Year

 — Imagine me. A slim eighteen year old boy. Dressed. by BethanyJ12/19/114.40

Everyone has a Freak Flag

 — Two stories from my crossdressing life. by Etaindarcy05/23/194.39

Evolution Ch. 01

 — Male to female transformation. by jamieengland101/16/153.98

Evolution of Keri

 — Kerry the boy becomes Keri the girl. by jackie_em08/19/194.50HOTNEW

Ex-Cellmate Looks Him Up

 — She's back for her bitch. by SugarandSalt10/16/124.55HOT

Except from Book

 — Francine recounts her first experiences. by KirkEdwards09/08/083.64

Executive Solutions Ch. 01

 — Jason Bourne-esque Tranny on the run adventure-plenty of sex. by MicheleNylons01/25/184.55HOT

Executive Solutions Ch. 02

 — Tranny on the run meets a bad man who takes advantage. by MicheleNylons01/26/184.69HOT

Executive Solutions Ch. 03

 — Tranny gives her pimp a blowjob while they search for her ID. by MicheleNylons01/28/184.64HOT

Executive Solutions Ch. 04

 — TS on the run with two boyfriends pays the price when caught. by MicheleNylons01/30/184.70HOT

Executive Solutions Ch. 05

 — Cassie has her memory back; good thing or bad thing for Nat? by MicheleNylons01/31/184.71HOT

Exhibition Fantasy

 — A fantasy played out with CD Lover. by beck130608/24/064.54HOT

Exhibitionism and its Consequences

 — Transvestite enjoys exhibitionism until caught. by HeatherMaureen10/30/184.35

Exhibitionism and the Sargent

 — The Sargent takes control and makes me embrace my femininity. by HeatherMaureen01/31/194.50HOT

Exit Strategy

 — Dominatrix seeks a way out of the industry. by sublocked08/15/164.31

Exotic Employment

 — A married couple looking for new things gets just that. by LadyDaisy09/30/163.63

Exotic Escapades Ch. 01

 — Will Tammy's sexcapades truly make her happy? by exroticdistant12/22/073.69

Exotic Escapades Ch. 02

 — Tammy meets a trucker and a third man. by exroticdistant12/31/074.03

Exotic Escapades Ch. 03

 — Tammy's adventures with a ladyboy and two men. by exroticdistant01/18/084.12

Expanding Boundaries

 — First time with a cross dresser. by CanadianM09/16/144.33

Expect The Unexpected

 — Man brings a surprise to a meeting. by seldomseen04/20/044.13

Experiencing Something New Ch. 01

 — When no one knows, you can try anything. by someoneyouknow09/08/134.70HOT

Experiencing Something New Ch. 02

 — Using and being used. by someoneyouknow09/27/134.78HOT

Explore the Inner Woman In You

 — Get girl advice, but watch out! by Tomsparty05/09/054.26

Exploring My Feelings Ch. 01

 — My first time exploring my feelings about men. by dave1967fun06/16/183.95

Exploring My Feelings Ch. 02

 — Getting to know what I like. by dave1967fun06/17/184.38

Exploring My Feelings Ch. 03

 — Finally. by dave1967fun06/18/184.17


 — A transman has to out himself to an interested cis-man. by sugarsync08/30/124.23

Extra Cheesy To-Go

 — Morgan just wants some pizza in the middle of the night. by PhantasyPen08/24/184.12


 — He meets his neighbor for the first time. by DaBlackMamba04/02/133.55

Extreme Crossdressing Experience

 — Wife dresses me in an extreme outfit, takes me out in public. by latexlegs02/15/154.31

F Is for Fiona

 — The First Day of the Rest of my Life. by BethanyJ02/27/124.46

F4: A Matter of Circumstance

 — A night of revelation for a transsexual prostitute. by slyc_willie05/10/144.58HOT

F4: Edge of Tomorrow

 — Sometimes, a girl's night out gets to be too much. by sr71plt05/10/144.30

F4: Life in Suspension

 — If you walk far enough, you come full circle. by MSTarot05/10/144.66HOT

Facing the Daddy

 — The final chapter in the story of the two lovers? by Buildaworld05/20/174.20

Fag Hag

 — Crossdressing to help her gay male friend was never so fun. by Krosis11/28/143.94

Fair Is Fair Ch. 03

 — Husband finally gets what he deserves, or wants. by bgdddy_200012/23/134.70HOT

Fair Is Fair Ch. 04

 — Couple goes on a strange double date. by bgdddy_200012/09/144.66HOT

Fall of "91" Ch. 01

 — The fall I found passion. by larry7440311/10/154.52HOT

Fall of an Angel

 — A succubus encounters a naive angel and corrupts her. by GingerM12/24/124.59HOT


 — A story of Angels and Demons. by AmandaSwallows03/06/164.70HOT

Falling For My Roommate

 — You can tell it's fall again. by VTDarkAngel05/10/064.10

Falling For My Roommate Ch. 02

 — Things take an interesting turn. by VTDarkAngel06/04/064.48

Falling For My Roommate Ch. 03

 — The school year ends. by VTDarkAngel06/09/064.12

Falling into Being a Sissy

 — Sonny meets Josh at a reunion very quickly becomes Sunshine. by Sissyhalo12/08/184.54HOT

False Imprisonment

 — Tony a Transvestite finds himself in a women's prison. by Sirdar01/16/064.24

Family and Friends Ch. 02

 — Monique introduces father to different world. by SplitLicker6906/28/114.31

Family Issues Ch. 01

 — A futa girl forces an innocent young man to share her bed. by allthatisfuta11/30/174.59HOT

Family Issues Ch. 02

 — A futa girl forces an innocent young man to share her bed. by allthatisfuta12/18/174.67HOT

Family Issues Ch. 03

 — A futa girl forces an innocent young man to share her bed. by allthatisfuta01/17/184.76HOT

Family Issues Ch. 04

 — A futa girl forces an innocent young man to share her bed. by allthatisfuta01/24/184.86HOT

Family Issues Ch. 05

 — A futa girl forces an innocent young man to share her bed. by allthatisfuta03/02/184.86HOT

Family Issues Ch. 06

 — A futa girl forces an innocent young man to share her bed. by allthatisfuta04/13/184.87HOT

Family Issues Ch. 07

 — A futa girl forces an innocent young man to share her bed. by allthatisfuta06/05/184.76HOT

Family Issues Ch. 08

 — The Kingdom of God. by allthatisfuta06/28/184.85HOT

Family Issues Ch. 09

 — The Master and Margarita. by allthatisfuta06/30/184.88HOT

Family Issues Ch. 10

 — To Have and Have Not. by allthatisfuta07/25/184.85HOT

Family Issues Ch. 11

 — Ka-Bar. by allthatisfuta08/07/184.68HOT

Family Issues Ch. 12

 — The Sins of Our Fathers. by allthatisfuta09/06/184.75HOT

Family Issues Ch. 13

 — Final chapter. by allthatisfuta10/30/184.86HOT

Family Values

 — When her man shows up in a dress, drastic action is required. by thrillerauthor12/11/034.11

Fancy Dress Party

 — The best looking woman at the party was his tennis partner. by Travel_by_day04/08/084.50HOT

Fancy Dress Party

 — My first night out dressed as a maid!! by debbstv03/06/174.11

Fangs for the Mammaries

 — A vampire puts the bite on Billy. by sourdough99910/05/064.20

Fantasies Fulfilled

 — Tranny and her boyfriend fulfill fantasies. by Cindytranee04/10/114.22

Fantasy Becomes Real

 — Cross-dresser's dream becomes real. by Jerri_Raven04/26/063.78

Fantasy Cum to Life

 — Ryan's takes a leap with Alyssa. by Rfranco07/07/114.56HOT

Fantasy Oral Sex with TS Lisa Lawer

 — A story of oral sex session with Lisa Lawer. by fox-for-fun02/23/094.18

Fantasy Reversal

 — Sam last fantasy for his wife and then awakes changed. by cuirouswriter01/25/104.09

Fantasy Reversal Ch. 02

 — Sam realizes, being Katrina dream! by cuirouswriter02/05/104.53HOT

Fantasy Reversal Ch. 03

 — Sam, loses her virginity as Katrina! by cuirouswriter02/26/104.45

Fantasy Reversal Ch. 04

 — Katrina gets fucked, but by who? by cuirouswriter03/04/104.49

Fantasy Reversal Ch. 05

 — Katrina dances for Sam and others. by cuirouswriter03/14/104.64HOT

Fantasy Reversal Ch. 06

 — Katrina walks on the wild side. Will she ever return. by cuirouswriter04/19/104.60HOT

Fantasy Reversal Ch. 07

 — Katrina has her own adventures on her final day. by cuirouswriter06/30/104.35

Fantasy Reversal Ch. 08

 — Is this Katrina's final day as a woman. by cuirouswriter01/23/114.42

Fantasy to Reality

 — A sissy's fantasy becomes a reality. by CuckoldDesires04/20/124.20

Fantasy to Reality Ch. 02

 — A sissy's fantasy becomes a reality. by CuckoldDesires05/02/124.39

Farzana Khan of Ottawa

 — Indian transsexual meets a bisexual black man. by Samuelx08/12/173.63

Fast Friends

 — It's always nice when two people just seem to click. by sweet_lusciousdesire11/24/134.33

Fat Indian Crossdresser Slut Gangbang

 — A hot story of a sissy and fat crossdresser getting gangbang. by bottomgay03/15/134.03


 — He rendezvous with a force of nature. by griffin5710/17/124.73HOT

Fateful Jessica

 — An unexpected visit proves revealing. by Midnight_Ashwood03/18/073.89

Father-In-Law Shemale Adventure

 — He watches Dad blow a hot Latina. by greyhound_guy3003/22/054.45

Fatima and Steve in Ottawa

 — Bisexual Haitian guy meets Sudanese transsexual gal. by Samuelx04/24/18

Favourite Colour

 — A story inspired by a song. by Miah_H04/15/184.56HOT

Fear and Euphoria

 — Getting to know each other. by KimmyKari07/26/134.22


 — Felicity entertains. by wylite06/11/134.42

Fem School

 — Trained to be Fem. by bobellen10/02/134.36

Female For A Day?

 — A young man has a boob fetish. by Pudmeister06/17/094.33

Female Performs Oral on Shemale

 — She has an encounter with a shemale for the first time. by Tashas Baby05/31/023.99

Female Seduces a Shemale

 — She takes you while you chat. by Tashas Baby02/21/024.06

Female Seduces Shemale Ch. 2

 — They savor sex in the shower. by Tashas Baby02/24/024.26

Femberly's Special Night

 — A sissy has a special night out to fulfill her secret desire. by hobbnobb7712/06/174.20

Femboy Caught in Locker Room

 — An erotic story that I collaborated in on discord. by Femboy_Anna09/03/184.49

Femboy's Awakening

 — 19-year old squire is caught dressing up with the whores. by FlavioMatsunaga10/14/144.55HOT

Feminine Enough Ch. 01

 — Chris dresses to please a roommate. by oneironator11/15/124.38

Feminine Enough Ch. 02

 — Chris gets fucked. by oneironator11/22/124.56HOT

Feminine Enough Ch. 03

 — Dustin comes home unexpectedly. by oneironator12/19/124.58HOT

Feminine Fantasy Come True

 — Crossdresser has first experience with a man. by girlboybootsie09/19/044.51HOT

Feminine Fate Fulfilled

 — Eighteen year old boy gets in touch with his feminine side. by mattpantyhose12/22/184.22

Feminine Persuasion Pt. 01

 — Man made girly to lose weight by his neighbor. by rebeldoll08/06/074.52HOT

Femininity and Sucking Dick

 — Vaguely a story about a guy and his struggles with gender. by sadadadako09/16/133.89

Feminized at Thirty-Three

 — A man in his thirties realizes the power of his inner woman. by Borntolust06/30/154.32

Feminized by a Black Thug

 — Closeted sissy gets turned out. by Tinydickthongboy8802/16/164.30

Feminized By Ch. 01: Myself

 — It all starts in the shower. by SilkeeSmooth108/07/194.04

Feminized By Ch. 02: My Stepsister

 — Back to the bathroom... by SilkeeSmooth108/15/194.62HOT

Feminized by My Girlfriend

 — The start of how she changed my life. by Trinni6909/21/114.25

Feminized by My Girlfriend Ch. 02

 — Feminization taken to a whole new level. by Trinni6912/30/114.40

Feminized By My Mother Ch. 01

 — Shemale mother makes son a sissy. by YANKEE DAN07/01/124.42

Feminized By My Mother Ch. 02

 — Son deals with his urges and unwanted male attention. by YANKEE DAN07/04/124.58HOT

Feminized My First Day at College

 — Sean becomes Stella on his first day at school. by putmeinadress07/21/174.27

Feminized to be Her Lesbian Girlfriend

 — A coercive neighbor forcibly feminizes me. by HerSubBoy9405/30/183.88

Femocil: Coping with Changes

 — Accidental exposure to a new drug transforms a man's body. by endymion_rex01/22/134.39

Fender Bender

 — Crossdressing teen has an accident. by SissyAndi04/12/104.54HOT

Fender Bender Ch. 02

 — Vicki is discovered by friends. by SissyAndi04/15/104.53HOT

Fender Bender Ch. 03

 — Vicki has more fun with Mark and Susan. by SissyAndi05/16/104.60HOT

Fender Bender Ch. 04

 — Vicki goes on her first date. by SissyAndi05/25/104.65HOT

Fender Bender Ch. 05

 — Vicki rewards the Mechanics. by SissyAndi06/12/104.62HOT

Fender Bender Ch. 06

 — Vicki Joins Mark and Susan and their friends. by SissyAndi08/06/104.70HOT

Fender Bender Ch. 07

 — Vicki and Gary get close. by SissyAndi08/31/104.69HOT

Fender Bender Ch. 08

 — Vicki Goes To A Party. by SissyAndi04/20/114.57HOT

Fender Bender Ch. 09

 — Vicki has fun with Julie and her Boyfriend. by SissyAndi08/04/114.59HOT

Fetish Factory

 — CD gets turned into a fetish doll. by shawnavinyltv02/20/194.65HOT

Few of My Ultra-Perverted Fantasies

 — Some of the juiciest stories you will ever encounter. by whiteboibbclicker02/07/172.29

Fifi La Femme: A Pansy at Last

 — First time with a man. by pris6969612/29/084.43

Fifi La Femme: A Pansy at Last Ch. 02

 — Missing Big Frank. by pris6969601/29/094.58HOT

Fifi's Long Wait

 — Fifi the maid needs to cum so badly. by Vertex03/12/124.63HOT

Fifties Housewife

 — Gerry becomes Gerilynn a housewife for his boyfriend. by Gerilynn6906/30/084.57HOT

Fifties Housewife After the Party

 — Gerilynn and Darren have costume sex. by Gerilynn6910/12/094.66HOT

Fifties Housewife The Next Day

 — Gerry goes to work and is confronted by his coworkers. by Gerilynn6907/31/084.61HOT

Filipina Cuckolds Her Sissy Husband

 — A married couple have sex with black men. by nancyvasquez05/04/174.21


 — A life-long cd finally gets a taste. by worththewait03/29/104.28

Finally A Real Man

 — X dresser finds gay love. by maxman120s08/21/084.65HOT

Finally a Real Sissy

 — Treated like the sissy I want to be. by Parasissy04/25/194.39

Finally Ready

 — A young transwoman comes to love herself. by RavynsLand12/15/174.45

Find That Guy: Porn TV's TG Gameshow

 — Transgender gameshow for straight couples. by EyeSoreASite03/03/134.07

Find That Guy: Porn TV's TG Gameshow Round 02

 — Freddy & Sue compete on a transgender gameshow. by EyeSoreASite03/04/134.38

Find That Guy: Porn TV's TG Gameshow Round 03

 — Freddy and Sue play a transgender gameshow. by EyeSoreASite04/30/134.55HOT

Find the Cheerleader, Save the World

 — Holly's older brother Hayden becomes released. by Sissyhalo06/24/174.36

Finding A New Purpose Ch. 01

 — Losing innocence and gaining so much more. by RavagedDesires08/05/094.23

Finding A New Purpose Ch. 02

 — Take a step and growing up along the way. by RavagedDesires08/06/094.33

Finding A New Purpose Ch. 03

 — Rules are established. by RavagedDesires08/08/094.71HOT

Finding A New Purpose Ch. 04

 — He has a stressful day at work. by RavagedDesires08/09/094.48

Finding A New Purpose Ch. 05

 — An unexpected encounter threatens it all. by RavagedDesires08/10/094.56HOT

Finding A New Purpose Ch. 06

 — Her sister joins in for some kinky fun. by RavagedDesires08/11/094.60HOT

Finding Claire

 — Hayden goes deeper into becoming the sissy Claire. by Sissyhalo10/28/174.60HOT

Finding Dana

 — He met her at a reception, but had no idea who she was. by PedalPower01/06/164.53HOT

Finding Gabriel

 — A little gender play leads to love. by Lacessor08/16/164.56HOT

Finding Her Secret Emails Ch. 01

 — Wife feminises hubby at her mum's insistence. by Quietoldie03/18/174.49

Finding Her Secret Emails Ch. 02

 — Hubby gets spanked & reads more emails. by Quietoldie04/03/174.42

Finding Her Secret Emails Ch. 03

 — Wife's mum comes to stay, He submits to her. by Quietoldie06/15/174.50HOT

Finding My Dream Wo(man)

 — Never knew I wanted a tranny till I found one. by DixeenormousToo09/30/144.74HOT

Finding My Genie Ch. 01

 — Crossdresser finds a new girlfriend. by jealouscuck12/05/154.29

Finding My Genie Ch. 02

 — Panty wearing guy finds his soul mate. by jealouscuck01/08/164.52HOT

Finding My Genie Ch. 03

 — Hot couple continue panty play. by jealouscuck02/25/164.48

Finding My Place

 — Devin is abducted. by LarryToLaura11/15/184.16

Finding My Place Pt. 02

 — Devin gets renamed, put on hormones, starts therapy... by LarryToLaura11/22/184.55HOT

Finding My Place Pt. 03

 — Deziree's encounter with Noah continues, she makes a friend. by LarryToLaura11/29/184.42

Finding My Shemale Goddess Ch. 01

 — A young man finds his Shemale Goddess. by TheGuyInBlack03/07/154.43

Finding My Shemale Goddess Ch. 02

 — Tim meets Emma, then has fun with his Goddess and her friend. by TheGuyInBlack03/26/154.53HOT

Finding Our Heaven Ch. 00 - Prologue

 — A magic journal changes a couple's lives forever. by GoddessFrigga02/06/18

Finding Our Heaven Ch. 01

 — Christy comes home to her wife wanting some changes. by GoddessFrigga10/26/183.89

Finding Our Real Selves

 — Sammie and Britt's senior year (transmale x transfemale) by Certeis03/05/184.53HOT

Fine Tuning

 — Wife's cross-dressing game with husband opens new frontiers. by cathynylons06/06/18

Fine Tuning Ch. 02

 — Jane begins dating. by cathynylons08/30/18

Finishing School For Ladies Ch. 01

 — Transvestite hides in ladies finishing school, sex ensues. by MicheleNylons09/05/174.47

Finishing School For Ladies Ch. 02

 — Tranny teaches protegee how to crossdress and seduces her. by MicheleNylons09/07/174.68HOT

Finishing School For Ladies Ch. 03

 — Valerie attends her interview to be inducted into the school. by MicheleNylons09/13/174.58HOT

Finishing School For Ladies Ch. 04

 — Transvestite at finishing school is molested. by MicheleNylons09/16/174.61HOT

Finishing School For Ladies Ch. 05

 — Tranny at school dance gets fucked by young lad. by MicheleNylons09/17/174.70HOT

Finishing School For Ladies Ch. 06

 — Sally and Valerie invite Emily into their bed and sparks fly. by MicheleNylons09/20/174.65HOT

Finishing School For Ladies Ch. 08

 — Two transvestites make a lifetime commitment. by MicheleNylons09/26/174.68HOT

Finishing School For Ladies Ch. 09

 — Tranny gets her girlfriend to seduce the deputy headmaster. by MicheleNylons09/29/174.64HOT

Finishing School For Ladies Ch. 10

 — TV seduces deputy headmistress so girls can fuck for money. by MicheleNylons10/03/174.57HOT

Finishing School For Ladies Ch. 11

 — Final chapter - will they live happy ever after? by MicheleNylons10/04/174.64HOT

Finishing School for Shemales

 — David is turned into the ultimate sex toy. by Imogen_TS_202005/12/114.66HOT

Finishing School for Shemales Ch. 02

 — Davina carries on her training. by Imogen_TS_202010/05/114.77HOT

Finishing School for Shemales Ch. 03

 — From paradise to hell. by Imogen_TS_202004/11/134.77HOT

Firehouse Sissy

 — Sissy Hillary's dressing escalates to an unhealthy level. by hillaryrose6908/20/134.08

First Blowjob

 — First blowjob experience. by ashleighswift11/10/174.28

First Date

 — TG gets some snuggle time. by Tanace07/13/054.00

First Dawn

 — Transvestite loses her virginity to her Mistress. by Winterloverm03/30/164.13

First Gay Experience

 — Anal Sex With a Black Tranny in L.A. by Friske_one106/01/114.58HOT

First Moves

 — First date, in the woods. by LoJacked09/06/114.17

First Multiple Sissygasm Today

 — I dress up and have my very first multiple sissygasm. by JessC04/12/174.35

First Night Nerves

 — Tim becomes Tina, & loses her virginity. by TinaTim11/30/034.63HOT

First Night Nerves Ch. 02

 — Tina and Barry arrange to meet without the girls. by TinaTim12/11/034.53HOT

First Night Out

 — Sex, spiders, and blowjobs. by Raizal03/07/043.99

First Outdoor Fuck

 — My first time in the woods with a horny guy. by Sweetlisatv12/15/124.29

First Panty Sex Experience

 — Having told my girlfriend I have a fetish for panties. by AndrogynousMind12/13/164.08

First Sexual Crossdress Experience

 — A crossdressing tale. by marshall1111110/28/114.70HOT

First Time

 — Party in college changes his life. by nikki_cd106/19/054.33

First time

 — Submission to Her for the first time. by maliToHim12/05/082.97

First Time

 — My first time begins with a gang bang. by cdandie07/30/094.46

First Time

 — First time with a TS escort. by TheCherub05/27/164.46

First Time

 — A crossdresser takes her first venture in a group encounter. by eroticARTa07/21/164.16

First Time

 — Very close to the truth about first trans experience. by tgirl_Mary11/02/164.64HOT

First Time as a Cum Slut

 — First encounter with a guy. by kager09/01/044.21

First Time as a Cum Slut Ch. 02

 — First time with three guys. by kager10/11/044.53HOT

First Time as a Cum Slut Ch. 03

 — His third time. by kager04/29/054.64HOT

First Time as Sissy

 — My story visiting a dominatrix and dressing as a woman. by twofish7301/14/174.37

First Time at Work

 — Man at work gets surprise from sexy shemale. by Downforeverything02/26/134.57HOT

First Time at Work Ch. 02

 — Continuing adventures from first time at work. by Downforeverything03/04/134.71HOT

First Time at Work Ch. 03

 — The third installment of First Time at Work. by Downforeverything07/30/134.41

First Time Being a Woman

 — Crossdresser experiences being a woman. by regina_allen5508/06/054.32

First Time Bi

 — Panty wearer is discovered and forced to perform. by First_time_bi10/26/084.33

First Time Bi

 — Going from bi-curious to bisexual. by f_stop08/31/164.43

First Time Buttslut

 — CD gets first taste of cock. by missyminx05/18/044.20

First Time Dressing Up

 — Hung black teen crossdresses. by CaramelBlack01/13/184.27

First Time Fantasy

 — What he dreams it will be like. by Fantasycd11/10/054.56HOT

First Time for Daddy's Girl

 — Young, Sissy CD's First Time with her Daddy. by JennaJay91912/13/184.38

First Time for Everything

 — First time turns into a group affair. by bootwhore66601/28/104.27

First Time Fucking A Trans Man

 — Gay guy finds a trans guy and hot sex ensues. by silver_midi01/01/174.27

First Time Fully Caught Dressed Outdoor

 — Dressed outdoors first time and propositioned. by Andreacdxxxx05/15/184.33

First Time Hotel meet

 — After a cam session a first time meeting was arranged. by sammysamson403/12/194.31

First Time I Fucked as a Girl

 — My first time dressed and fucked like a girl. by ambercumz02/16/184.46

First Time In Panties

 — Story about the first time he wore panties. by shylexigirl07/18/103.80

First Time in the City

 — Michael meets a powerful man and becomes Julia. by becca198302/06/174.56HOT

First Time Is A Great Time!!

 — Jeff dresses up and get an unexpected visitor! by slimwun8103/15/124.42

First Time Meeting Master Gene

 — First time meeting and being submissive with a Master. by sissysubTiffany05/24/184.30

First Time Out

 — True account of my latest adventure. by Fairy_Nancy08/24/084.35

First Time S & M Whore

 — TG pain-slut is whored out. by slutty_jannelle05/17/094.24

First Time Sissy at the Gloryhole

 — I wanted to be seen in my frilly things, but I got more. by Stephen_Heathcote05/11/164.07

First Time Sissy Maid

 — He is turned into a slutty maid by a dominant couple. by bart207703/01/114.24

First Time Together

 — Gabrielle is more than she appears. by Buildaworld05/03/174.25

First Time Tranny Loving

 — A young man pursues his transgender affection. by The_Good_Doctor01/09/184.45

First Time With A Dominant

 — And what a time. by ElijahSnow02/04/074.44

First Time With A Guy Ch. 02

 — Bootsie continues first experience with two hunky men. by girlboybootsie09/24/074.45

First Time with a Male

 — He has encounter with a guy who's part woman. by DarkAvenger4909/18/083.28

First Time with a Male Ch. 02

 — This the second part of the story. by DarkAvenger4901/30/094.07

First Time with a Shemale

 — He has his first experience with a shemale. by BigAndy92201/26/124.35

First Time With A TS

 — A Businessman takes the plunge with sexy Sylvia. by Pussrider09/28/154.48

First Time with Chris

 — Jamie comes out to old high school classmate. by Sissyhalo02/14/184.44

First Time with Jessica

 — Rob takes first step towards living out his fantasy. by magicrub04/04/053.95

First Time With My Best Friend Ch. 01

 — His best friend discovers him in panties. by girlboybootsie05/02/034.49

First Time with Sam in the Car

 — First time hookup with my FTM lover in my car during the day. by maxsmithdfw1310/23/184.69HOT

First Time with TS

 — My first wild ride on shemale cock. by hasnoalias05/31/154.41

First Time, From A Window

 — I want your feminised body and the dildo, in that order. by purekink04/07/114.37

First Times

 — His first time with a man. by MichelleWhoIs03/14/074.48

First TS Ass

 — My first full encounter with a TS. by TheWoot3308/29/063.96

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