sexstories.com
Transvestite
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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 42906 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, 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 95.6%, Read 164931 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 95.6%, Read 214137 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 95.6%, Read 89046 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.5%, Read 898533 times, Posted Fri 8th of June 2012
Fiction , Consensual Sex, Incest, Romance, Teen Male / Female, Transvestite -
Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.5%, Read 342813 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
Kelly - Part 2 by xerxes10
Rated 95.5%, Read 160050 times, Posted Fri 23rd of December 2011
Fantasy , Anal, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.4%, Read 77901 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
Carl or Carla by Mystic47
Rated 95.4%, Read 152766 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
caught in drag by picklewasher
Rated 95.4%, Read 556983 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95.4%, Read 48030 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
Jeffry and Billy 4 by UndeniableUrges
«Billy and Jeffry get caught!»
Rated 95.4%, Read 80304 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.3%, Read 146097 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 95.3%, Read 205977 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
Straight to Bi by dlcalguy
«Discovering things I didn't imagine I would like»
Rated 95.3%, Read 48627 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, 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 95.2%, Read 46287 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
Uncontrollable Pt. 2 by xerxes10
Rated 95.2%, Read 111771 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 95.2%, Read 61959 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, 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 140379 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
Dressed To Thrill by PicturePainter
Rated 95.1%, Read 41121 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
The Walk...continued (pt2) by charlotte69
Rated 95.1%, Read 33357 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
A Man's Play Thing by panty_sub
Rated 95.1%, Read 323283 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 95%, Read 82878 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
The Cinema_(0) by BangTidyUK
Rated 95%, Read 216243 times, Posted Tue 10th of April 2012
Fantasy , Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Gay, Group Sex, Hardcore, Oral Sex, Transvestite -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 95%, Read 28341 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 95%, Read 78753 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
My first time with Joe _(0) by CD-Davina20
Rated 94.9%, Read 247173 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 94.9%, Read 162117 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 94.9%, Read 49014 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
First time_(15) by TheJessie
Rated 94.9%, Read 79188 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 94.8%, Read 21726 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, Transvestite -
Kelly - Part 1 by xerxes10
Rated 94.7%, Read 174648 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 171522 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, 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 94.7%, Read 34575 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.7%, Read 139194 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
My Stepfather 2_(0) by Rutger5
Rated 94.6%, Read 195915 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.6%, Read 154050 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
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 94.6%, Read 53118 times, Posted Sat 20th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, 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 87123 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 Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.6%, Read 242325 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
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 94.5%, Read 29316 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
sister throws a party, and catches brother by jonialabaster
Rated 94.5%, Read 60264 times, Posted Tue 19th of November 2013
Fantasy , Bi-sexual, Humiliation, Incest, Transvestite -
ONE NIGHT IN A MOTEL by Miki-In-Panties
Rated 94.5%, Read 29259 times, Posted Wed 9th of May 2012
Fantasy , Blowjob, Oral Sex, Transvestite -
my birthday gift_(1) by iminhose
Rated 94.5%, Read 133887 times, Posted Tue 7th of February 2012
True Story , Transvestite -
Internet Hookup Pioneer by Katie_Johnny
«A sissy spends an enchanting evening with a hot hunk»
Rated 94.4%, Read 11868 times, Posted Wed 22nd of March 2023
True Story , Blowjob, Cum Swallowing, Domination/submission, Drug, Oral Sex, Transsexual, Transvestite -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.4%, Read 176382 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.4%, Read 303510 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
2 stories halloween parties by iminhose
Rated 94.4%, Read 58035 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
My life as a woman by curiouscoupleinraleigh
Rated 94.4%, Read 361011 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, Chapter 3 by Achilles_Heel
Rated 94.4%, Read 177933 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 89343 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
My Love for Daddy Transformed Me by willingwimp
Rated 94.3%, Read 273738 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
Growing Up Ch2 by GoatRavisher
«I get to be a big sister»
Rated 94.2%, Read 38214 times, Posted Sat 13th of October 2018
Diary , Cum Swallowing, First Time, Incest, Male / Older Female, Transvestite -
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.2%, Read 19410 times, Posted Tue 26th of May 2015
Fantasm , Coercion, Exhibitionism, Transgendered, Transvestite -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 296823 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 113298 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, 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 64020 times, Posted Thu 7th of July 2016
Fiction , Anal, Blowjob, Body modification, Male/Teen Female, Oral Sex, Reluctance, Romance, Teen, Transgendered, Transsexual, Transvestite -
I Discover Jenna's Secret by Rutger5
Rated 94.1%, Read 107997 times, Posted Sat 4th of December 2010
Fiction , Anal, Ass to mouth, Coercion, Teen, Transvestite, Virginity -
Late Night In The Office by Heatround
Rated 94.1%, Read 109770 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, 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 94.1%, Read 29826 times, Posted Sat 1st of December 2018
Diary , Anal, Bi-sexual, Boy, Female / Girl, Fisting, Incest, Male / Older Female, Transvestite -
The Walk by charlotte69
Rated 94.1%, Read 30534 times, Posted Mon 6th of January 2014
Fantasy , Romance, Transgendered, 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 94.1%, Read 39189 times, Posted Sun 20th of May 2018
Fiction , Blowjob, Reluctance, Romance, Transvestite -
Jenny is Full of Secrets by Kingly
Rated 94%, Read 259725 times, Posted Thu 17th of April 2014
Fiction , Reluctance, Teen Male/Teen Female, Transgendered, Transsexual, Transvestite -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 94%, Read 177612 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young -
First Time pt 2 by trans_love
Rated 94%, Read 62523 times, Posted Mon 13th of February 2012
True Story , Exhibitionism, Gay, Teen, Transsexual, Transvestite -
Brother prostitute by sexyboytoy18
Rated 94%, Read 337875 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 461442 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 -
Kylee's Sauna Fantasies by Jess Romeo
«A hot rich teen named Kylee has a big surprise for the guy she brings back to her hotel room»
Rated 93.9%, Read 105285 times, Posted Thu 14th of January 2016
Fantasm , Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Toys, Transgendered, Transsexual, Transvestite, Young -
Sissy Hypno & The Fascinating Return To Porn Part 2 by Katie_Johnny
«For anyone reading this who hasn't read part one, you should! A brief recap ~ I had checked out of the porn world for several years, and upon my return, I discovered the exhilarating and fascinating "Sissy Hypno" genre.»
Rated 93.9%, Read 9351 times, Posted Thu 13th of April 2023
True Story , Anal, Blowjob, Cum Swallowing, Domination/submission, Drug, Hardcore, Transvestite -
The Auction_(0) by Phoenix Cinders
«Femboy gets tricked into being auctioned off as a slave»
Rated 93.9%, Read 147948 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