sexstories.com
Transvestite
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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 95.8%, Read 45096 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.8%, Read 237903 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite -
caught in drag by picklewasher
Rated 95.6%, Read 594792 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 95.6%, Read 114975 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
Kelly - Part 2 by xerxes10
Rated 95.6%, Read 173385 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 95.6%, Read 229242 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 138984 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.5%, Read 430197 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 95.5%, Read 109551 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
The Walk...continued (pt2) by charlotte69
Rated 95.4%, Read 38445 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
Uncontrollable Pt. 2 by xerxes10
Rated 95.4%, Read 121338 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 217515 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 234891 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young -
Dressed To Thrill by PicturePainter
Rated 95.2%, Read 50787 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
Straight to Bi by dlcalguy
«Discovering things I didn't imagine I would like»
Rated 95.2%, Read 110859 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, 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 95.2%, Read 166380 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
The Cinema_(0) by BangTidyUK
Rated 95.2%, Read 227151 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 95.2%, Read 345648 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, 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 95.1%, Read 36858 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, Transvestite -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95.1%, Read 67185 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
First time_(15) by TheJessie
Rated 95%, Read 83088 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
Kelly - Part 1 by xerxes10
Rated 94.9%, Read 186753 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 254439 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
Growing Up Chapter 11 by GoatRavisher
«College Life goes on!»
Rated 94.9%, Read 15018 times, Posted Mon 13th of July 2020
Diary , Anal, BDSM, Bi-sexual, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite -
ONE NIGHT IN A MOTEL by Miki-In-Panties
Rated 94.9%, Read 32460 times, Posted Wed 9th of May 2012
Fantasy , Blowjob, Oral Sex, 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 94.8%, Read 72831 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.8%, Read 22212 times, Posted Tue 26th of May 2015
Fantasm , Coercion, Exhibitionism, Transgendered, 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 94.7%, Read 73452 times, Posted Sat 20th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
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 94.7%, Read 68745 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
my birthday gift_(1) by iminhose
Rated 94.7%, Read 138471 times, Posted Tue 7th of February 2012
True Story , Transvestite -
My Stepfather 2_(0) by Rutger5
Rated 94.6%, Read 205026 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
Hard Evidence by AnalLover42069
«Femboy stripper Rikki Ryder gets interrogated by Officer Maxine Steele, who fucks her in the ass.»
Rated 94.6%, Read 6654 times, Posted Fri 20th of June 2025
Fiction , Anal, Blowjob, Consensual Sex, Job/Place-of-work, 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 94.6%, Read 47028 times, Posted Sun 20th of May 2018
Fiction , Blowjob, Reluctance, Romance, Transvestite -
2 stories halloween parties by iminhose
Rated 94.5%, Read 62127 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Joey Fucks Teach by MightBeRealz
«A senior gets more than he bargained for when he tries to seduce the shop teacher.»
Rated 94.5%, Read 101184 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite -
My life as a woman by curiouscoupleinraleigh
Rated 94.4%, Read 376566 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 -
Growing Up chapter 5 1/2 by GoatRavisher
«I totally got this out of order! Cindy and Christine hook up before chapter 6.»
Rated 94.4%, Read 19524 times, Posted Tue 23rd of July 2019
Diary , Girls domination, Teen Male/Teen Females, Threesome, Transvestite -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.3%, Read 194571 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
The Walk by charlotte69
Rated 94.2%, Read 34242 times, Posted Mon 6th of January 2014
Fantasy , Romance, Transgendered, Transvestite -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.2%, Read 288081 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
the next step on the road to being a slut by NewSubmissiveSlut
Rated 94.2%, Read 96588 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 -
Chloes Story by Skman
«My story of the emergency of Chloe»
Rated 94.1%, Read 30678 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, 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 94.1%, Read 106569 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.1%, Read 163692 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
The Permissive Purity of Father Fontane [4] by NeonChameleon
«Deep in Dana's mouth»
Rated 94.1%, Read 28479 times, Posted Wed 1st of May 2019
Fiction , Blowjob, Boy, Cum Swallowing, Gay, Mature, Teen, Transgendered, Transvestite, Young -
An Accidental Woman by curiouscoupleinraleigh
Rated 94.1%, Read 479100 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 -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 94%, Read 43404 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
I Discover Jenna's Secret by Rutger5
Rated 94%, Read 113037 times, Posted Sat 4th of December 2010
Fiction , Anal, Ass to mouth, Coercion, Teen, Transvestite, Virginity -
Rebecca Chapter 02 by RebeccaTG
Rated 93.9%, Read 47172 times, Posted Fri 2nd of March 2012
Fantasy , Ass to mouth, Cum Swallowing, First Time, Transgendered, Transvestite -
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 15696 times, Posted Thu 13th of April 2023
True Story , Anal, Blowjob, Cum Swallowing, Domination/submission, Drug, Hardcore, Transvestite -
Tricked became Enjoyed Part II by Sportslover
Rated 93.9%, Read 64833 times, Posted Wed 15th of May 2013
Fantasy , Blowjob, Boy, Cum Swallowing, Gay, Job/Place-of-work, Mature, Oral Sex, Transvestite -
First Time pt 2 by trans_love
Rated 93.9%, Read 70113 times, Posted Mon 13th of February 2012
True Story , Exhibitionism, Gay, Teen, Transsexual, Transvestite -
Late Night In The Office by Heatround
Rated 93.8%, Read 118962 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, Transvestite -
Visiting Nikki, A Filipino Ladyboy by markerss
«When I met a girl online through one of those paid web-cam site, i knew she was more than just a girl. She went by the name of Nicole and I knew she was a transsexual, because at the time I was very curious about being with one. She was a very attractive, and passable girl with a great body.»
Rated 93.8%, Read 44382 times, Posted Wed 9th of June 2021
True Story , Anal, Blowjob, Consensual Sex, Gay, Transgendered, Transsexual, Transvestite, Young -
Neck Deep Ch.02 by XtinaSmith
«Jay advances his position with the enabled twins.»
Rated 93.8%, Read 77148 times, Posted Fri 6th of October 2017
Fantasy , Anal, Blowjob, Consensual Sex, Cum Swallowing, Oral Sex, Threesome, Transgendered, Transsexual, Transvestite, Written by women -
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 93.8%, Read 75984 times, Posted Thu 7th of July 2016
Fiction , Anal, Blowjob, Body modification, Male/Teen Female, Oral Sex, Reluctance, Romance, Teen, Transgendered, Transsexual, Transvestite -
Internet Hookup Pioneer by Katie_Johnny
«A sissy spends an enchanting evening with a hot hunk»
Rated 93.8%, Read 31140 times, Posted Wed 22nd of March 2023
True Story , Blowjob, Cum Swallowing, Domination/submission, Drug, Oral Sex, Transsexual, Transvestite -
Michael to Michelle by SonicRush66
«This is the story how Michael turned into the sissy slut Michelle»
Rated 93.8%, Read 78021 times, Posted Mon 21st of March 2022
Fantasy , Anal, Bi-sexual, Blowjob, Boy / Boy, Cum Swallowing, Gay, Group Sex, Transsexual, Transvestite -
Growing Up Chapter 13 by GoatRavisher
«More fun in college with my Sorority "Sisters"»
Rated 93.8%, Read 9210 times, Posted Fri 26th of March 2021
Diary , Bi-sexual, Blowjob, Cum Swallowing, Male / Females, Masturbation, Teen Male/Teen Female, Transvestite -
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 93.7%, Read 123075 times, Posted Thu 14th of January 2016
Fantasm , Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Toys, Transgendered, Transsexual, Transvestite, Young -
Kalynns Ass part two_(0) by Kalynn
Rated 93.7%, Read 41253 times, Posted Sun 2nd of June 2013
True Story , Transvestite -
Three Firsts In One Hazy, Crystal Clear Night by Katie_Johnny
«Two friends explore their sexuality at the end of the night for the first time. This is a true story about the first time I was caught wearing panties, which turned into the first time I ever kissed a guy, which led to the first time I ever orally serviced a guy.»
Rated 93.6%, Read 24369 times, Posted Fri 27th of January 2023
True Story , Blowjob, Cum Swallowing, Drug, First Time, Gay, Transvestite -
Your tansgender girlfriend by TheTVonthecorner
Rated 93.6%, Read 278292 times, Posted Wed 5th of January 2011
True Story , Transgendered, Transsexual, Transvestite -
Growing Up chapter 10 by GoatRavisher
«Summer Break. What shall i do, go home to Mom and Dad? Hell no!»
Rated 93.6%, Read 12405 times, Posted Sat 4th of April 2020
Diary , Anal, Bi-sexual, Bondage and restriction, Cum Swallowing, Male/Teen Female, Masturbation, Teen Male/Teen Females, Threesome, Transvestite -
Explicit powers Chapter 3 by Curious_George
Rated 93.5%, Read 32244 times, Posted Thu 1st of May 2014
Fantasy , Blowjob, Body modification, Cum Swallowing, Female/Female, Lesbian, Oral Sex, Teen Female/Teen Female, Toys, Transgendered, Transsexual, Transvestite -
One Summer Day by hk124
Rated 93.5%, Read 273678 times, Posted Wed 27th of March 2013
Fiction , Anal, Consensual Sex, Transgendered, Transsexual, Transvestite -
What If I Told Him I Wanted To Give Him A Blow Job? by Miki-In-Panties
Rated 93.5%, Read 27885 times, Posted Mon 7th of May 2012
Fantasy , Bi-sexual, Blowjob, Oral Sex, Transvestite -
The story of Tim to Jennifer Part 6 by jen128
Rated 93.5%, Read 45459 times, Posted Tue 15th of November 2011
Fiction , Anal, Blowjob, Cum Swallowing, Hardcore, Oral Sex, Transgendered, Transsexual, Transvestite -
Bunking Off by student111
Rated 93.5%, Read 33819 times, Posted Mon 10th of February 2014
Fiction , First Time, Group Sex, Transvestite -
Kim loses her virginity by jen128
Rated 93.5%, Read 186957 times, Posted Sun 19th of January 2014
Fantasy , Anal, Blowjob, Consensual Sex, First Time, Gay, Transgendered, Transsexual, Transvestite