sexstories.com
Transvestite
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My Summer as a Girl part 1 by allioops
«A young man is given the chance to stay with his cousin Christine and live as a girl.»
Rated 95.9%, Read 62322 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.8%, Read 182433 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite -
Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.7%, Read 396264 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
Straight to Bi by dlcalguy
«Discovering things I didn't imagine I would like»
Rated 95.6%, Read 80250 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, Transvestite -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.6%, Read 97710 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
caught in drag by picklewasher
Rated 95.6%, Read 594792 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
Carl or Carla by Mystic47
Rated 95.6%, Read 161118 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
Kelly - Part 2 by xerxes10
Rated 95.6%, Read 173385 times, Posted Fri 23rd of December 2011
Fantasy , Anal, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite -
My first cock was a crossdressers by Sex conspiracy theorisit
Rated 95.6%, Read 229242 times, Posted Mon 10th of January 2011
True Story , Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite -
Cross-dressing camper by Satintex
«Wearing my favorite lingerie while camping and I get some unexpected visitors»
Rated 95.6%, Read 114888 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.5%, Read 921678 times, Posted Fri 8th of June 2012
Fiction , Consensual Sex, Incest, Romance, Teen Male / Female, Transvestite -
Jeffry and Billy 4 by UndeniableUrges
«Billy and Jeffry get caught!»
Rated 95.5%, Read 102507 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young -
The Walk...continued (pt2) by charlotte69
Rated 95.4%, Read 38445 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 95.4%, Read 100686 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
Uncontrollable Pt. 2 by xerxes10
Rated 95.4%, Read 121338 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 95.3%, Read 95952 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 217515 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
Working 'Girl'_(1) by mrseven
«A teen boy works the park late at night to make money in the best way he knows how.»
Rated 95.3%, Read 66162 times, Posted Sat 20th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
My introduction to sex and sissyhood by FirstTimeSissy
«A true story on how I got into crossdressing and serving older men at a young age I'm very inexperienced with writing stories which is why I chose a true account to go off of but I apologise for my probably terrible style»
Rated 95.3%, Read 212811 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95.3%, Read 59361 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
Dressed To Thrill by PicturePainter
Rated 95.2%, Read 50787 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
The Cinema_(0) by BangTidyUK
Rated 95.2%, Read 227151 times, Posted Tue 10th of April 2012
Fantasy , Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Gay, Group Sex, Hardcore, Oral Sex, Transvestite -
A Man's Play Thing by panty_sub
Rated 95.2%, Read 345648 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, Transvestite -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 95.1%, Read 38673 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
Working 'Girl'_(0) by mrseven
«A teen boy works the park late at night to make money in the best way he knows how.»
Rated 95.1%, Read 154710 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
Valerie discovers me Part 1 by Satintex
«I enjoyed wearing panties to school and thought no one knew, but my friend Valerie was on to me.»
Rated 95.1%, Read 29022 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, Transvestite -
I’m Ed’s cross-dressing home help by Dave.Trudy2
«After being made redundant l needed something to keep me busy. I passed a charity shop and saw a card in the window asking for volunteers and that’s how l met Edward and the fun started.»
Rated 95.1%, Read 36504 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 95%, Read 170907 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 95%, Read 72477 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite -
Growing Up Chapter3 by GoatRavisher
«More adventures with the Rodgers women. I get to play a wide variety of roles, meet new friends and wear new outfits!»
Rated 95%, Read 35478 times, Posted Sat 1st of December 2018
Diary , Anal, Bi-sexual, Boy, Female / Girl, Fisting, Incest, Male / Older Female, Transvestite -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 95%, Read 60213 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
First time_(15) by TheJessie
Rated 95%, Read 83088 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
Kelly - Part 1 by xerxes10
Rated 94.9%, Read 186753 times, Posted Wed 21st of December 2011
Fantasy , Consensual Sex, Teen, Teen Male / Teen Male, Transgendered, Transvestite -
Wanting to be a girl by fuckmeanyway
Rated 94.9%, Read 182769 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
My first time with Joe _(0) by CD-Davina20
Rated 94.9%, Read 254439 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
ONE NIGHT IN A MOTEL by Miki-In-Panties
Rated 94.9%, Read 32460 times, Posted Wed 9th of May 2012
Fantasy , Blowjob, Oral Sex, Transvestite -
The Permissive Purity of Father Fontane [4] by NeonChameleon
«Deep in Dana's mouth»
Rated 94.9%, Read 24048 times, Posted Wed 1st of May 2019
Fiction , Blowjob, Boy, Cum Swallowing, Gay, Mature, Teen, Transgendered, Transvestite, Young -
sister throws a party, and catches brother by jonialabaster
Rated 94.8%, Read 66450 times, Posted Tue 19th of November 2013
Fantasy , Bi-sexual, Humiliation, Incest, Transvestite -
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.8%, Read 22212 times, Posted Tue 26th of May 2015
Fantasm , Coercion, Exhibitionism, Transgendered, Transvestite -
Growing Up Ch2 by GoatRavisher
«I get to be a big sister»
Rated 94.8%, Read 44991 times, Posted Sat 13th of October 2018
Diary , Cum Swallowing, First Time, Incest, Male / Older Female, Transvestite -
A Summer Ride by drivingallnight
«A young hitch-hiker winds up dressed as an attractive girl and comes to enjoy it very much while thinking of the events that in their life that led them to this point of self-discovery.»
Rated 94.7%, Read 59493 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
Jeffry and Billy 6 by UndeniableUrges
«Becky apologizes and tries to make it up to poor Susie»
Rated 94.7%, Read 52344 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, Transvestite, Young -
my birthday gift_(1) by iminhose
Rated 94.7%, Read 138471 times, Posted Tue 7th of February 2012
True Story , Transvestite -
My Stepfather 2_(0) by Rutger5
Rated 94.6%, Read 205026 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
Joey Fucks Teach by MightBeRealz
«A senior gets more than he bargained for when he tries to seduce the shop teacher.»
Rated 94.6%, Read 94230 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite -
Growing Up Chapter 11 by GoatRavisher
«College Life goes on!»
Rated 94.6%, Read 11754 times, Posted Mon 13th of July 2020
Diary , Anal, BDSM, Bi-sexual, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite -
2 stories halloween parties by iminhose
Rated 94.5%, Read 62127 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Sister's Dress Up Doll - revised_(1) by jonialabaster
«A new doll is all the rage with older girls. Kimmy can't afford one, but her brother looks like he could fit her clothes»
Rated 94.5%, Read 42978 times, Posted Sun 20th of May 2018
Fiction , Blowjob, Reluctance, Romance, Transvestite -
Internet Hookup Pioneer by Katie_Johnny
«A sissy spends an enchanting evening with a hot hunk»
Rated 94.4%, Read 25224 times, Posted Wed 22nd of March 2023
True Story , Blowjob, Cum Swallowing, Domination/submission, Drug, Oral Sex, Transsexual, Transvestite -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.4%, Read 154308 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
My life as a woman by curiouscoupleinraleigh
Rated 94.4%, Read 376566 times, Posted Mon 19th of July 2010
Fiction , Anal, Bi-sexual, Blowjob, Cheating, Consensual Sex, Cum Swallowing, First Time, Group Sex, Oral Sex, Transgendered, Transsexual, Transvestite, Written by women, Young -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.4%, Read 183795 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
Becoming Sadi: Part 2 by Beckyj1992
«Sadi goes over to Garets place with a bag full of sexy clothes for the night. I like where this is going!»
Rated 94.4%, Read 99231 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.3%, Read 275379 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
My Love for Daddy Transformed Me by willingwimp
Rated 94.3%, Read 293181 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
I hate Sneezing!_(0) by jonialabaster
«Ryan is a voyeur, a pervert, and a younger. He's discovered in his sister's closet while she's working.»
Rated 94.3%, Read 39384 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.3%, Read 186915 times, Posted Wed 13th of June 2012
Fiction , Blowjob, Consensual Sex, Female solo, Incest, Male Solo, Masturbation, Romance, Teen Male / Female, Toys, Transgendered, Transsexual, Transvestite, Voyeurism, Young -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.3%, Read 315888 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 309009 times, Posted Sun 2nd of June 2013
Fiction , Anal, Female/Female, Group Sex, Incest, Lesbian, Male / Females, Pegging, Romance, Threesome, Toys, Transgendered, Transsexual, Transvestite, Virginity -
Halloween with Kym_(0) by jackie offee
Rated 94.2%, Read 116166 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, Transvestite -
The Walk by charlotte69
Rated 94.2%, Read 34242 times, Posted Mon 6th of January 2014
Fantasy , Romance, Transgendered, Transvestite -
Chloes Story by Skman
«My story of the emergency of Chloe»
Rated 94.2%, Read 26985 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, Transvestite -
the next step on the road to being a slut by NewSubmissiveSlut
Rated 94.2%, Read 96588 times, Posted Tue 29th of November 2011
True Story , Anal, Bi-sexual, Blowjob, Boy / Boy, Domination/submission, Drug, Exhibitionism, Gay, Masturbation, Mature, Older Female / Males, Oral Sex, Transvestite -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 94.1%, Read 193989 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young -
Kylee's Sauna Fantasies by Jess Romeo
«A hot rich teen named Kylee has a big surprise for the guy she brings back to her hotel room»
Rated 94.1%, Read 114159 times, Posted Thu 14th of January 2016
Fantasm , Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Toys, Transgendered, Transsexual, Transvestite, Young -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.1%, Read 196929 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
My Brother's Girlfriend by justfordanniboi
«One boi's story of how an older brother's girlfriend awoke an identity.»
Rated 94.1%, Read 45942 times, Posted Fri 31st of July 2020
Diary , Gay, Incest, Teen Male / Teen Male, Transvestite -
Brother prostitute by sexyboytoy18
Rated 94.1%, Read 349746 times, Posted Thu 24th of January 2013
Fantasy , Blowjob, Boy / Boy, Consensual Sex, Cum Swallowing, First Time, Gay, Incest, Male Solo, Masturbation, Oral Sex, Prostitution, Teen Male / Teen Male, Transvestite, Virginity, Young -
An Accidental Woman by curiouscoupleinraleigh
Rated 94.1%, Read 479100 times, Posted Tue 3rd of August 2010
Fiction , Bi-sexual, Blowjob, Body modification, Coercion, Cum Swallowing, Female / Girl, First Time, Hardcore, Mind Control, Oral Sex, Reluctance, Teen, Transgendered, Transsexual, Transvestite, Written by women, Young -
I Discover Jenna's Secret by Rutger5
Rated 94%, Read 113037 times, Posted Sat 4th of December 2010
Fiction , Anal, Ass to mouth, Coercion, Teen, Transvestite, Virginity