sexstories.com
Transvestite
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Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 95.6%, Read 49179 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
Kelly - Part 2 by xerxes10
Rated 95.4%, Read 135084 times, Posted Fri 23rd of December 2011
Fantasy , Anal, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite -
caught in drag by picklewasher
Rated 95.4%, Read 487068 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.4%, Read 99675 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, 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 95.4%, Read 14895 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.4%, Read 50766 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
First time_(15) by TheJessie
Rated 95.3%, Read 70746 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 177534 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.3%, Read 839868 times, Posted Fri 8th of June 2012
Fiction , Consensual Sex, Incest, Romance, Teen Male / Female, 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 95.3%, Read 86859 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young -
My first cock was a crossdressers by Sex conspiracy theorisit
Rated 95.3%, Read 186441 times, Posted Mon 10th of January 2011
True Story , Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite -
Jeffry and Billy 4 by UndeniableUrges
«Billy and Jeffry get caught!»
Rated 95.2%, Read 47697 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 95.2%, Read 270705 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
Carl or Carla by Mystic47
Rated 95.1%, Read 135264 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95.1%, Read 29781 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
Kelly - Part 1 by xerxes10
Rated 95.1%, Read 150468 times, Posted Wed 21st of December 2011
Fantasy , Consensual Sex, Teen, Teen Male / Teen Male, Transgendered, Transvestite -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 95%, Read 144885 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
Suzy Unleashed Chapter 9 by Suzygurl
Rated 95%, Read 17577 times, Posted Wed 27th of May 2015
Fantasy , Transgendered, Transvestite -
The Cinema_(0) by BangTidyUK
Rated 95%, Read 191937 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%, Read 38196 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite -
Cross-dressing camper by Satintex
«Wearing my favorite lingerie while camping and I get some unexpected visitors»
Rated 94.9%, Read 37098 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Uncontrollable Pt. 2 by xerxes10
Rated 94.9%, Read 98586 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
Rebecca Chapter 02 by RebeccaTG
Rated 94.9%, Read 38496 times, Posted Fri 2nd of March 2012
Fantasy , Ass to mouth, Cum Swallowing, First Time, Transgendered, Transvestite -
Jeffry and Billy 6 by UndeniableUrges
«Becky apologizes and tries to make it up to poor Susie»
Rated 94.9%, Read 27183 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, Transvestite, Young -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.7%, Read 114183 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
My first time with Joe _(0) by CD-Davina20
Rated 94.7%, Read 232956 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
My life as a woman by curiouscoupleinraleigh
Rated 94.7%, Read 311094 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 -
A Man's Play Thing by panty_sub
Rated 94.7%, Read 285153 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, 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 94.6%, Read 113613 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
2 stories halloween parties by iminhose
Rated 94.6%, Read 48423 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.5%, Read 277842 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.5%, Read 198354 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.5%, Read 121854 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
My Love for Daddy Transformed Me by willingwimp
Rated 94.5%, Read 237954 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 94.4%, Read 65037 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.4%, Read 160284 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 birthday gift_(1) by iminhose
Rated 94.4%, Read 125352 times, Posted Tue 7th of February 2012
True Story , Transvestite -
My Stepfather 2_(0) by Rutger5
Rated 94.4%, Read 177972 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, 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 94.3%, Read 25227 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.3%, Read 147444 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, 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 94.3%, Read 24570 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
The Auction_(0) by Phoenix Cinders
«Femboy gets tricked into being auctioned off as a slave»
Rated 94.3%, Read 119598 times, Posted Sat 25th of May 2019
Science-Fiction , Anal, Blowjob, Bondage and restriction, Boy, Consensual Sex, Cum Swallowing, Domination/submission, First Time, Girls domination, Group Sex, Oral Sex, Reluctance, Romance, Slavery, Spanking, Teen, Threesome, Transgendered, Transsexual, Transvestite, Voyeurism, Young -
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 94.3%, Read 76572 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
Wanting to be a girl by fuckmeanyway
Rated 94.3%, Read 152274 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
The Girl - Stories: Uncle Ben 2 by boardpin123
«The Girl gets an order to make her uncle fuck her. The problem is ... he likes boys.»
Rated 94.2%, Read 12276 times, Posted Mon 12th of July 2021
Fiction , Anal, Exhibitionism, Male/Teen Female, massage, Masturbation, Older Male / Female, Role-playing, Teen, Transvestite, Young -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 272508 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 -
Jenny is Full of Secrets by Kingly
Rated 94.2%, Read 240135 times, Posted Thu 17th of April 2014
Fiction , Reluctance, Teen Male/Teen Female, Transgendered, Transsexual, Transvestite -
Halloween with Kym_(0) by jackie offee
Rated 94.2%, Read 107334 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, Transvestite -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 94.2%, Read 33243 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
My Brother's Girlfriend by justfordanniboi
«One boi's story of how an older brother's girlfriend awoke an identity.»
Rated 94.2%, Read 31293 times, Posted Fri 31st of July 2020
Diary , Gay, Incest, Teen Male / Teen Male, Transvestite -
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 94.1%, Read 53967 times, Posted Thu 7th of July 2016
Fiction , Anal, Blowjob, Body modification, Male/Teen Female, Oral Sex, Reluctance, Romance, Teen, Transgendered, Transsexual, Transvestite -
Tricked became Enjoyed Part II by Sportslover
Rated 94.1%, Read 56070 times, Posted Wed 15th of May 2013
Fantasy , Blowjob, Boy, Cum Swallowing, Gay, Job/Place-of-work, Mature, Oral Sex, Transvestite -
Joey Fucks Teach by MightBeRealz
«A senior gets more than he bargained for when he tries to seduce the shop teacher.»
Rated 94.1%, Read 74766 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite -
One With the Tribe pt1 by faringwayb
«A human washes up on the shore of a tribe of werewolves»
Rated 94.1%, Read 11169 times, Posted Fri 14th of January 2022
Fantasy , Gay, Humiliation, Monster, Transvestite -
Suzy Unleashed Chapter 7 by Suzygurl
Rated 94.1%, Read 26244 times, Posted Wed 16th of July 2014
Fantasm , Blowjob, Slavery, Transgendered, Transsexual, Transvestite -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 94%, Read 146391 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young -
The Walk...continued (pt2) by charlotte69
Rated 94%, Read 25356 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
Chloes Story by Skman
«My story of the emergency of Chloe»
Rated 94%, Read 18912 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, Transvestite -
Dressed To Thrill by PicturePainter
Rated 93.9%, Read 31212 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
Sister's Surprise, Chapter 4 by Achilles_Heel
Rated 93.9%, Read 158271 times, Posted Thu 14th of June 2012
Fiction , Body modification, Consensual Sex, Incest, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 93.9%, Read 16362 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
James and Jenny Part 4 by Kingly
Rated 93.8%, Read 85182 times, Posted Thu 21st of August 2014
Fiction , Blowjob, Bondage and restriction, Consensual Sex, Pegging, Teen Male / Female, Transgendered, Transsexual, Transvestite -
One Summer Day by hk124
Rated 93.8%, Read 254895 times, Posted Wed 27th of March 2013
Fiction , Anal, Consensual Sex, Transgendered, Transsexual, Transvestite -
An Accidental Woman by curiouscoupleinraleigh
Rated 93.8%, Read 428019 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 -
Brother prostitute by sexyboytoy18
Rated 93.8%, Read 312111 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 -
My Stepfather_(0) by Rutger5
Rated 93.7%, Read 417483 times, Posted Thu 25th of November 2010
Fiction , Anal, Gay, Non-consensual sex, Transsexual, Transvestite -
Camming Down the Rabbit Hole Ch6 by Dani_does_Dallas
«The continued journey into a guy becoming a cam girl - New outfits and a trip to the shops with an unexpected bonus.»
Rated 93.7%, Read 8478 times, Posted Mon 11th of October 2021
Fiction , Anal, Bi-sexual, Cum Swallowing, Exhibitionism, Male Solo, Masturbation, Pegging, Prostitution, Transgendered, Transsexual, Transvestite -
The Permissive Purity of Father Fontane [3] by NeonChameleon
«Twenty miles»
Rated 93.7%, Read 17484 times, Posted Fri 26th of April 2019
Fiction , Bi-sexual, Blowjob, Boy, Cum Swallowing, Gay, Incest, Mature, Transvestite, Young -
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 93.7%, Read 18192 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
Kim loses her virginity by jen128
Rated 93.7%, Read 164001 times, Posted Sun 19th of January 2014
Fantasy , Anal, Blowjob, Consensual Sex, First Time, Gay, Transgendered, Transsexual, Transvestite