sexstories.com
Transvestite
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caught in drag by picklewasher
Rated 95.4%, Read 466569 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.3%, Read 41772 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.3%, Read 827328 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 95.3%, Read 41928 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 258771 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
Kelly - Part 2 by xerxes10
Rated 95.2%, Read 128910 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 95.2%, Read 178989 times, Posted Mon 10th of January 2011
True Story , Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.2%, Read 85860 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 95.1%, Read 170307 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
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 95.1%, Read 64866 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young -
Carl or Carla by Mystic47
Rated 95.1%, Read 130728 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
First time_(15) by TheJessie
Rated 95%, Read 67806 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
Jeffry and Billy 6 by UndeniableUrges
«Becky apologizes and tries to make it up to poor Susie»
Rated 95%, Read 23697 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, Transvestite, Young -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 95%, Read 41592 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 95%, Read 140877 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
Cross-dressing camper by Satintex
«Wearing my favorite lingerie while camping and I get some unexpected visitors»
Rated 94.9%, Read 30489 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Kelly - Part 1 by xerxes10
Rated 94.9%, Read 142371 times, Posted Wed 21st of December 2011
Fantasy , Consensual Sex, Teen, Teen Male / Teen Male, Transgendered, Transvestite -
The Cinema_(0) by BangTidyUK
Rated 94.9%, Read 186288 times, Posted Tue 10th of April 2012
Fantasy , Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Gay, Group Sex, Hardcore, Oral Sex, Transvestite -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 94.8%, Read 25119 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
Uncontrollable Pt. 2 by xerxes10
Rated 94.8%, Read 94755 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
My first time with Joe _(0) by CD-Davina20
Rated 94.8%, Read 229398 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 295143 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 by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.7%, Read 190311 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
Suzy Unleashed Chapter 9 by Suzygurl
Rated 94.7%, Read 16023 times, Posted Wed 27th of May 2015
Fantasy , Transgendered, Transvestite -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.6%, Read 114900 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
The Auction_(0) by Phoenix Cinders
«Femboy gets tricked into being auctioned off as a slave»
Rated 94.6%, Read 109983 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 94.6%, Read 229893 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 94.6%, Read 34434 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.6%, Read 109680 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
Rebecca Chapter 02 by RebeccaTG
Rated 94.5%, Read 36822 times, Posted Fri 2nd of March 2012
Fantasy , Ass to mouth, Cum Swallowing, First Time, Transgendered, Transvestite -
A Man's Play Thing by panty_sub
Rated 94.5%, Read 279198 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, Transvestite -
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 94.5%, Read 13605 times, Posted Tue 24th of August 2021
Fiction , Bi-sexual, Exhibitionism, First Time, Male Solo, Masturbation, Prostitution, 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 108804 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
Suzy Unleashed Chapter 7 by Suzygurl
Rated 94.5%, Read 24351 times, Posted Wed 16th of July 2014
Fantasm , Blowjob, Slavery, Transgendered, Transsexual, Transvestite -
2 stories halloween parties by iminhose
Rated 94.5%, Read 46455 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.5%, Read 270945 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 94.5%, Read 61806 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.3%, Read 141531 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.3%, Read 156111 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 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 74022 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
my birthday gift_(1) by iminhose
Rated 94.3%, Read 123534 times, Posted Tue 7th of February 2012
True Story , Transvestite -
My Stepfather 2_(0) by Rutger5
Rated 94.3%, Read 174897 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 267129 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 -
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 94.2%, Read 51423 times, Posted Thu 7th of July 2016
Fiction , Anal, Blowjob, Body modification, Male/Teen Female, Oral Sex, Reluctance, Romance, Teen, Transgendered, Transsexual, Transvestite -
My Brother's Girlfriend by justfordanniboi
«One boi's story of how an older brother's girlfriend awoke an identity.»
Rated 94.2%, Read 28308 times, Posted Fri 31st of July 2020
Diary , Gay, Incest, Teen Male / Teen Male, Transvestite -
Halloween with Kym_(0) by jackie offee
Rated 94.2%, Read 106023 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, Transvestite -
Wanting to be a girl by fuckmeanyway
Rated 94.1%, Read 148644 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
Jenny is Full of Secrets by Kingly
Rated 94%, Read 235671 times, Posted Thu 17th of April 2014
Fiction , Reluctance, Teen Male/Teen Female, Transgendered, 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%, Read 72594 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite -
Tricked became Enjoyed Part II by Sportslover
Rated 94%, Read 54756 times, Posted Wed 15th of May 2013
Fantasy , Blowjob, Boy, Cum Swallowing, Gay, Job/Place-of-work, Mature, Oral Sex, Transvestite -
The Walk...continued (pt2) by charlotte69
Rated 93.9%, Read 24702 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, 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 93.9%, Read 23580 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
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 93.9%, Read 10470 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
Suzy Unleashed Chapter 2 by Suzygurl
Rated 93.9%, Read 40437 times, Posted Thu 7th of June 2012
Fiction , Slavery, Transgendered, Transsexual, Transvestite -
Sister's Surprise, Chapter 4 by Achilles_Heel
Rated 93.8%, Read 155859 times, Posted Thu 14th of June 2012
Fiction , Body modification, Consensual Sex, Incest, Romance, Teen Male / Female, 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 93.8%, Read 22641 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
One Summer Day by hk124
Rated 93.8%, Read 252222 times, Posted Wed 27th of March 2013
Fiction , Anal, Consensual Sex, Transgendered, Transsexual, Transvestite -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 93.8%, Read 30732 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
Kim loses her virginity by jen128
Rated 93.8%, Read 160290 times, Posted Sun 19th of January 2014
Fantasy , Anal, Blowjob, Consensual Sex, First Time, Gay, Transgendered, Transsexual, Transvestite -
James and Jenny Part 4 by Kingly
Rated 93.8%, Read 82899 times, Posted Thu 21st of August 2014
Fiction , Blowjob, Bondage and restriction, Consensual Sex, Pegging, Teen Male / Female, Transgendered, Transsexual, Transvestite -
The boy, boy toy by craigtv284
Rated 93.8%, Read 46896 times, Posted Thu 5th of February 2015
Fiction , Boy / Boy, Gay, 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 93.8%, Read 10521 times, Posted Mon 12th of July 2021
Fiction , Anal, Exhibitionism, Male/Teen Female, massage, Masturbation, Older Male / Female, Role-playing, Teen, Transvestite, Young -
An Accidental Woman by curiouscoupleinraleigh
Rated 93.7%, Read 420606 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 -
Camming Down the Rabbit Hole Ch3 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 93.7%, Read 10503 times, Posted Tue 24th of August 2021
Fiction , Anal, Bi-sexual, Body modification, Bondage and restriction, Coercion, Erotica, Exhibitionism, Male Solo, Masturbation, Prostitution, Role-playing, Toys, Transgendered, Transsexual, Transvestite -
Late Night In The Office by Heatround
Rated 93.7%, Read 95808 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, Transvestite -
Brother prostitute by sexyboytoy18
Rated 93.7%, Read 307296 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 -
Chloes Story by Skman
«My story of the emergency of Chloe»
Rated 93.7%, Read 17580 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, Transvestite -
My Stepfather_(0) by Rutger5
Rated 93.6%, Read 409980 times, Posted Thu 25th of November 2010
Fiction , Anal, Gay, Non-consensual sex, Transsexual, Transvestite -
Wartime Comfort House Diary - Day 8 Shemale by rojac29
«A wartime General found his comfort in a captured young local beauty, converted and trained by his Japanese lover in occupied land.»
Rated 93.6%, Read 15543 times, Posted Mon 11th of October 2021
Fiction , Anal, Asian, Authoritarian, BDSM, Bi-sexual, Blowjob, Body modification, Bondage and restriction, Cruelty, Cum Swallowing, Discipline, Domination/submission, Extreme, Group Sex, Hardcore, Lactation, Male / Females, Male Domination, Mind Control, Oral Sex, Slavery, Threesome, Transgendered, Transsexual, Transvestite, Violence -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 93.6%, Read 139356 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young