sexstories.com
Transvestite
-
Jeffry and Billy 4 by UndeniableUrges
«Billy and Jeffry get caught!»
Rated 95.7%, Read 91176 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young -
Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.7%, Read 367362 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
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 95.6%, Read 51549 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.5%, Read 911181 times, Posted Fri 8th of June 2012
Fiction , Consensual Sex, Incest, Romance, Teen Male / Female, Transvestite -
caught in drag by picklewasher
Rated 95.5%, Read 574692 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
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 95.5%, Read 194145 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.5%, Read 158865 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite -
Carl or Carla by Mystic47
Rated 95.5%, Read 156927 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
My first cock was a crossdressers by Sex conspiracy theorisit
Rated 95.5%, Read 222411 times, Posted Mon 10th of January 2011
True Story , Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.5%, Read 86850 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
Uncontrollable Pt. 2 by xerxes10
Rated 95.4%, Read 116913 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
Cross-dressing camper by Satintex
«Wearing my favorite lingerie while camping and I get some unexpected visitors»
Rated 95.4%, Read 100089 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Kelly - Part 2 by xerxes10
Rated 95.4%, Read 166911 times, Posted Fri 23rd of December 2011
Fantasy , Anal, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 95.4%, Read 88995 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95.3%, Read 53715 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 95.3%, Read 54174 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 95.3%, Read 32859 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 211959 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
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 95.2%, Read 148056 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
Straight to Bi by dlcalguy
«Discovering things I didn't imagine I would like»
Rated 95.2%, Read 58845 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, Transvestite -
A Man's Play Thing by panty_sub
Rated 95.1%, Read 335592 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, Transvestite -
The Cinema_(0) by BangTidyUK
Rated 95.1%, Read 221865 times, Posted Tue 10th of April 2012
Fantasy , Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Gay, Group Sex, Hardcore, Oral Sex, Transvestite -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 95.1%, Read 66795 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 95.1%, Read 87468 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
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%, Read 57618 times, Posted Sat 20th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
The Walk...continued (pt2) by charlotte69
Rated 95%, Read 36033 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 95%, Read 166491 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, 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%, Read 32466 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
Dressed To Thrill by PicturePainter
Rated 94.9%, Read 47760 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
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 94.9%, Read 24810 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, Transvestite -
First time_(15) by TheJessie
Rated 94.9%, Read 81237 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
My first time with Joe _(0) by CD-Davina20
Rated 94.9%, Read 251070 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
Kelly - Part 1 by xerxes10
Rated 94.9%, Read 180702 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 94.7%, Read 177459 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
2 stories halloween parties by iminhose
Rated 94.7%, Read 60084 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
One With the Tribe pt1 by faringwayb
«A human washes up on the shore of a tribe of werewolves»
Rated 94.7%, Read 19020 times, Posted Fri 14th of January 2022
Fantasy , Gay, Humiliation, Monster, Transvestite -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.7%, Read 259710 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
My Stepfather 2_(0) by Rutger5
Rated 94.6%, Read 200601 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
ONE NIGHT IN A MOTEL by Miki-In-Panties
Rated 94.6%, Read 30822 times, Posted Wed 9th of May 2012
Fantasy , Blowjob, Oral Sex, 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 94.6%, Read 53460 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
my birthday gift_(1) by iminhose
Rated 94.6%, Read 136221 times, Posted Tue 7th of February 2012
True Story , Transvestite -
Growing Up Ch2 by GoatRavisher
«I get to be a big sister»
Rated 94.5%, Read 40971 times, Posted Sat 13th of October 2018
Diary , Cum Swallowing, First Time, Incest, Male / Older Female, Transvestite -
Internet Hookup Pioneer by Katie_Johnny
«A sissy spends an enchanting evening with a hot hunk»
Rated 94.5%, Read 18540 times, Posted Wed 22nd of March 2023
True Story , Blowjob, Cum Swallowing, Domination/submission, Drug, Oral Sex, Transsexual, Transvestite -
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 94.5%, Read 36834 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
First Time pt 2 by trans_love
Rated 94.5%, Read 66717 times, Posted Mon 13th of February 2012
True Story , Exhibitionism, Gay, Teen, Transsexual, Transvestite -
Joey Fucks Teach by MightBeRealz
«A senior gets more than he bargained for when he tries to seduce the shop teacher.»
Rated 94.5%, Read 90069 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.4%, Read 165168 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
sister throws a party, and catches brother by jonialabaster
Rated 94.4%, Read 63402 times, Posted Tue 19th of November 2013
Fantasy , Bi-sexual, Humiliation, Incest, Transvestite -
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.4%, Read 182886 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 -
My Love for Daddy Transformed Me by willingwimp
Rated 94.4%, Read 283359 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.4%, Read 145242 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
The Permissive Purity of Father Fontane [4] by NeonChameleon
«Deep in Dana's mouth»
Rated 94.4%, Read 21522 times, Posted Wed 1st of May 2019
Fiction , Blowjob, Boy, Cum Swallowing, Gay, Mature, Teen, Transgendered, Transvestite, Young -
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 94.4%, Read 32202 times, Posted Sat 1st of December 2018
Diary , Anal, Bi-sexual, Boy, Female / Girl, Fisting, Incest, Male / Older Female, Transvestite -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.4%, Read 310215 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.4%, Read 184677 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.4%, Read 20634 times, Posted Tue 26th of May 2015
Fantasm , Coercion, Exhibitionism, Transgendered, 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 93825 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
My life as a woman by curiouscoupleinraleigh
Rated 94.3%, Read 368988 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 Sadi: Part 3 by Beckyj1992
«Sadi takes a big risk and is then faced with a decision that will change her life forever!»
Rated 94.3%, Read 67305 times, Posted Thu 7th of July 2016
Fiction , Anal, Blowjob, Body modification, Male/Teen Female, Oral Sex, Reluctance, Romance, Teen, Transgendered, Transsexual, 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 94.2%, Read 40761 times, Posted Sun 20th of May 2018
Fiction , Blowjob, Reluctance, Romance, Transvestite -
Halloween with Kym_(0) by jackie offee
Rated 94.2%, Read 114783 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, Transvestite -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 303210 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 -
Jeffry and Billy 6 by UndeniableUrges
«Becky apologizes and tries to make it up to poor Susie»
Rated 94.1%, Read 46863 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, Transvestite, Young -
Late Night In The Office by Heatround
Rated 94.1%, Read 114171 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, Transvestite -
Growing Up Chapter 11 by GoatRavisher
«College Life goes on!»
Rated 94.1%, Read 10314 times, Posted Mon 13th of July 2020
Diary , Anal, BDSM, Bi-sexual, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 94.1%, Read 186552 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young -
Brother prostitute by sexyboytoy18
Rated 94%, Read 344412 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%, Read 471297 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 -
Pleasing Bill: A Crossdressing Story #3 by JessRider
«]I woke up early the morning after my first day of being Bill’s live in slut. I got up to listen and hear my dad and siblings leaving for work around 7. I was going to wait for all of them to leave before I dress and go back to Bill’s at 12.»
Rated 94%, Read 33507 times, Posted Tue 29th of November 2016
Fantasm , Anal, Blowjob, Discipline, Domination/submission, Slavery, Transgendered, Transsexual, Transvestite -
Suzy Unleashed Chapter 11 by Suzygurl
«Suzy continues her journey as she learns to accept her feminity»
Rated 94%, Read 10554 times, Posted Fri 8th of January 2021
Diary , Bi-sexual, Transsexual, Transvestite