sexstories.com
Transvestite
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Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.7%, Read 385848 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 58587 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
Straight to Bi by dlcalguy
«Discovering things I didn't imagine I would like»
Rated 95.6%, Read 69213 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, Transvestite -
caught in drag by picklewasher
Rated 95.6%, Read 591072 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 160101 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.6%, Read 170289 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.6%, Read 919719 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 95.6%, Read 98268 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young -
Kelly - Part 2 by xerxes10
Rated 95.5%, Read 171774 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 95.5%, Read 227826 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 95.5%, Read 109581 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.5%, Read 93174 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 95.4%, Read 95832 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 95.4%, Read 63159 times, Posted Sat 20th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
The Walk...continued (pt2) by charlotte69
Rated 95.3%, Read 37890 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 216348 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 95.3%, Read 207654 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young -
Uncontrollable Pt. 2 by xerxes10
Rated 95.3%, Read 120351 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 95.3%, Read 36513 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 95.2%, Read 93273 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 95.2%, Read 57369 times, Posted Sat 13th of February 2021
Fiction , Gay, 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 152208 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 95.1%, Read 58065 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
Dressed To Thrill by PicturePainter
Rated 95.1%, Read 50070 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
The Cinema_(0) by BangTidyUK
Rated 95.1%, Read 226092 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 95.1%, Read 343893 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, Transvestite -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 95%, Read 170064 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
First time_(15) by TheJessie
Rated 95%, Read 82758 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, 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 27501 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, 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 94.9%, Read 34068 times, Posted Sat 1st of December 2018
Diary , Anal, Bi-sexual, Boy, Female / Girl, Fisting, Incest, Male / Older Female, Transvestite -
Kelly - Part 1 by xerxes10
Rated 94.9%, Read 185550 times, Posted Wed 21st of December 2011
Fantasy , Consensual Sex, Teen, Teen Male / Teen Male, Transgendered, Transvestite -
My first time with Joe _(0) by CD-Davina20
Rated 94.9%, Read 253791 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
Wanting to be a girl by fuckmeanyway
Rated 94.9%, Read 181815 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 94.9%, Read 70608 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, 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 94.9%, Read 34878 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
ONE NIGHT IN A MOTEL by Miki-In-Panties
Rated 94.8%, Read 32151 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 94.8%, Read 57123 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
My Stepfather 2_(0) by Rutger5
Rated 94.8%, Read 204180 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.7%, Read 21942 times, Posted Tue 26th of May 2015
Fantasm , Coercion, Exhibitionism, Transgendered, Transvestite -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.7%, Read 175362 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
sister throws a party, and catches brother by jonialabaster
Rated 94.7%, Read 65838 times, Posted Tue 19th of November 2013
Fantasy , Bi-sexual, Humiliation, Incest, Transvestite -
Growing Up Ch2 by GoatRavisher
«I get to be a big sister»
Rated 94.7%, Read 43164 times, Posted Sat 13th of October 2018
Diary , Cum Swallowing, First Time, Incest, Male / Older Female, Transvestite -
my birthday gift_(1) by iminhose
Rated 94.6%, Read 137988 times, Posted Tue 7th of February 2012
True Story , Transvestite -
The Permissive Purity of Father Fontane [4] by NeonChameleon
«Deep in Dana's mouth»
Rated 94.6%, Read 23034 times, Posted Wed 1st of May 2019
Fiction , Blowjob, Boy, Cum Swallowing, Gay, Mature, Teen, Transgendered, Transvestite, Young -
Jeffry and Billy 6 by UndeniableUrges
«Becky apologizes and tries to make it up to poor Susie»
Rated 94.6%, Read 50283 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, Transvestite, Young -
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 92631 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.5%, Read 151818 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
2 stories halloween parties by iminhose
Rated 94.5%, Read 61725 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Growing Up Chapter 11 by GoatRavisher
«College Life goes on!»
Rated 94.4%, Read 11127 times, Posted Mon 13th of July 2020
Diary , Anal, BDSM, Bi-sexual, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.4%, Read 271398 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
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 97215 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, 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 94.4%, Read 42120 times, Posted Sun 20th of May 2018
Fiction , Blowjob, Reluctance, Romance, Transvestite -
My life as a woman by curiouscoupleinraleigh
Rated 94.4%, Read 374712 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 -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.3%, Read 314907 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 94.3%, Read 195717 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
My Love for Daddy Transformed Me by willingwimp
Rated 94.3%, Read 291156 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
Late Night In The Office by Heatround
Rated 94.3%, Read 118119 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, Transvestite -
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.3%, Read 186090 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 -
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 94.2%, Read 38508 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 307923 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 115938 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, Transvestite -
Internet Hookup Pioneer by Katie_Johnny
«A sissy spends an enchanting evening with a hot hunk»
Rated 94.1%, Read 23031 times, Posted Wed 22nd of March 2023
True Story , Blowjob, Cum Swallowing, Domination/submission, Drug, Oral Sex, Transsexual, Transvestite -
the next step on the road to being a slut by NewSubmissiveSlut
Rated 94.1%, Read 95814 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 -
I Discover Jenna's Secret by Rutger5
Rated 94.1%, Read 112614 times, Posted Sat 4th of December 2010
Fiction , Anal, Ass to mouth, Coercion, Teen, Transvestite, Virginity -
My Brother's Girlfriend by justfordanniboi
«One boi's story of how an older brother's girlfriend awoke an identity.»
Rated 94.1%, Read 44985 times, Posted Fri 31st of July 2020
Diary , Gay, Incest, Teen Male / Teen Male, Transvestite -
Chloes Story by Skman
«My story of the emergency of Chloe»
Rated 94.1%, Read 26232 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, Transvestite -
Brother prostitute by sexyboytoy18
Rated 94.1%, Read 348756 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 -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 94.1%, Read 192441 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young -
The Walk by charlotte69
Rated 94.1%, Read 33816 times, Posted Mon 6th of January 2014
Fantasy , Romance, Transgendered, Transvestite -
An Accidental Woman by curiouscoupleinraleigh
Rated 94%, Read 477528 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