sexstories.com
Transvestite
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Sister's Surprise_(0) by Achilles_Heel
Rated 95.3%, Read 835812 times, Posted Fri 8th of June 2012
Fiction , Consensual Sex, Incest, Romance, Teen Male / Female, Transvestite -
caught in drag by picklewasher
Rated 95.3%, Read 479964 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 95.3%, Read 45891 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
Kelly - Part 2 by xerxes10
Rated 95.3%, Read 132717 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 95.3%, Read 183912 times, Posted Mon 10th of January 2011
True Story , Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite -
First time_(15) by TheJessie
Rated 95.3%, Read 69588 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, 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 95.2%, Read 78516 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 95.2%, Read 94299 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.2%, Read 174606 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
Kelly - Part 1 by xerxes10
Rated 95.2%, Read 147420 times, Posted Wed 21st of December 2011
Fantasy , Consensual Sex, Teen, Teen Male / Teen Male, Transgendered, Transvestite -
Carl or Carla by Mystic47
Rated 95.2%, Read 133737 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.1%, Read 47391 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.1%, Read 266925 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
Jeffry and Billy 4 by UndeniableUrges
«Billy and Jeffry get caught!»
Rated 95%, Read 45774 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95%, Read 27585 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 95%, Read 143397 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
Uncontrollable Pt. 2 by xerxes10
Rated 95%, Read 96834 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
The Cinema_(0) by BangTidyUK
Rated 95%, Read 189990 times, Posted Tue 10th of April 2012
Fantasy , Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Gay, Group Sex, Hardcore, Oral Sex, Transvestite -
Cross-dressing camper by Satintex
«Wearing my favorite lingerie while camping and I get some unexpected visitors»
Rated 95%, Read 35046 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Suzy Unleashed Chapter 9 by Suzygurl
Rated 94.9%, Read 16941 times, Posted Wed 27th of May 2015
Fantasy , Transgendered, Transvestite -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 94.8%, Read 36573 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite -
Rebecca Chapter 02 by RebeccaTG
Rated 94.8%, Read 37773 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 94.7%, Read 25959 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, Transvestite, Young -
My first time with Joe _(0) by CD-Davina20
Rated 94.7%, Read 231696 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 305424 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 -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.7%, Read 112302 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.6%, Read 195912 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
A Man's Play Thing by panty_sub
Rated 94.6%, Read 283128 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, 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 12183 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.5%, Read 275424 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, 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 94.5%, Read 112125 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
2 stories halloween parties by iminhose
Rated 94.5%, Read 47688 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.5%, Read 120006 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
My Brother's Girlfriend by justfordanniboi
«One boi's story of how an older brother's girlfriend awoke an identity.»
Rated 94.5%, Read 30090 times, Posted Fri 31st of July 2020
Diary , Gay, Incest, Teen Male / Teen Male, Transvestite -
The Auction_(0) by Phoenix Cinders
«Femboy gets tricked into being auctioned off as a slave»
Rated 94.5%, Read 116490 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 -
My Love for Daddy Transformed Me by willingwimp
Rated 94.5%, Read 235119 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 64140 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 158793 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 -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.4%, Read 145380 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
my birthday gift_(1) by iminhose
Rated 94.4%, Read 124722 times, Posted Tue 7th of February 2012
True Story , Transvestite -
My Stepfather 2_(0) by Rutger5
Rated 94.4%, Read 176853 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, 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 94.3%, Read 53163 times, Posted Thu 7th of July 2016
Fiction , Anal, Blowjob, Body modification, Male/Teen Female, Oral Sex, Reluctance, Romance, Teen, 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 94.2%, Read 75762 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 270510 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 -
Wanting to be a girl by fuckmeanyway
Rated 94.2%, Read 150996 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
Halloween with Kym_(0) by jackie offee
Rated 94.2%, Read 106845 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, Transvestite -
Jenny is Full of Secrets by Kingly
Rated 94.1%, Read 238422 times, Posted Thu 17th of April 2014
Fiction , Reluctance, Teen Male/Teen Female, Transgendered, Transsexual, 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 94.1%, Read 11742 times, Posted Mon 12th of July 2021
Fiction , Anal, Exhibitionism, Male/Teen Female, massage, Masturbation, Older Male / Female, Role-playing, Teen, Transvestite, Young -
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 94.1%, Read 24633 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 94.1%, Read 32307 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
Camming Down the Rabbit Hole Ch1 by Dani_does_Dallas
«The story of how during the pandemic of 2020 I was faced with the prospect of unemployment and turned to the world of camming as a way of making some money.»
Rated 94.1%, Read 16323 times, Posted Tue 24th of August 2021
Fiction , Bi-sexual, Exhibitionism, First Time, Male Solo, Masturbation, Prostitution, Transgendered, Transsexual, Transvestite -
Tricked became Enjoyed Part II by Sportslover
Rated 94.1%, Read 55665 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 73914 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite -
Suzy Unleashed Chapter 7 by Suzygurl
Rated 94.1%, Read 25761 times, Posted Wed 16th of July 2014
Fantasm , Blowjob, Slavery, Transgendered, 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%, Read 23907 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
The Walk...continued (pt2) by charlotte69
Rated 93.9%, Read 25125 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
James and Jenny Part 4 by Kingly
Rated 93.9%, Read 84261 times, Posted Thu 21st of August 2014
Fiction , Blowjob, Bondage and restriction, Consensual Sex, Pegging, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Sister's Surprise, Chapter 4 by Achilles_Heel
Rated 93.9%, Read 157365 times, Posted Thu 14th of June 2012
Fiction , Body modification, Consensual Sex, Incest, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 93.9%, Read 143886 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young -
Kim loses her virginity by jen128
Rated 93.9%, Read 162579 times, Posted Sun 19th of January 2014
Fantasy , Anal, Blowjob, Consensual Sex, First Time, Gay, Transgendered, Transsexual, Transvestite -
One With the Tribe pt1 by faringwayb
«A human washes up on the shore of a tribe of werewolves»
Rated 93.9%, Read 10521 times, Posted Fri 14th of January 2022
Fantasy , Gay, Humiliation, Monster, Transvestite -
Late Night In The Office by Heatround
Rated 93.9%, Read 97569 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, Transvestite -
Chloes Story by Skman
«My story of the emergency of Chloe»
Rated 93.9%, Read 18447 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, Transvestite -
The boy, boy toy by craigtv284
Rated 93.8%, Read 48366 times, Posted Thu 5th of February 2015
Fiction , Boy / Boy, Gay, Transvestite -
One Summer Day by hk124
Rated 93.8%, Read 254043 times, Posted Wed 27th of March 2013
Fiction , Anal, Consensual Sex, Transgendered, Transsexual, Transvestite -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 93.8%, Read 15933 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
Dressed To Thrill by PicturePainter
Rated 93.8%, Read 30810 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
An Accidental Woman by curiouscoupleinraleigh
Rated 93.7%, Read 425478 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 -
My Stepfather_(0) by Rutger5
Rated 93.7%, Read 414885 times, Posted Thu 25th of November 2010
Fiction , Anal, Gay, Non-consensual sex, Transsexual, Transvestite -
Brother prostitute by sexyboytoy18
Rated 93.7%, Read 310431 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