sexstories.com
Transvestite
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Deep in California by JtellerMT
Rated 58.8%, Read 1313892 times, Posted Fri 12th of December 2014
Fiction , Anal, Blowjob, Cum Swallowing, Erotica, Extreme, Gay, Hardcore, Transgendered, Transsexual, 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 -
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 -
Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.5%, Read 430194 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, 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 -
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 -
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 -
Playing Wifey by panty_sub
Rated 92.8%, Read 280728 times, Posted Mon 13th of June 2011
Fantasy , Blowjob, Cum Swallowing, Gay, Oral Sex, Transvestite, Wife -
Your tansgender girlfriend by TheTVonthecorner
Rated 93.6%, Read 278292 times, Posted Wed 5th of January 2011
True Story , 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 -
Dressed to Thrill (Part 1) by PicturePainter
Rated 92.5%, Read 262308 times, Posted Thu 14th of January 2010
Fantasy , Bi-sexual, Domination/submission, Female Domination, Masturbation, Transvestite, Wife -
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 -
My little secret by Ashley Coxx
Rated 88.3%, Read 249658 times, Posted Mon 22nd of January 2007
Fantasy , Anal, Bi-sexual, Boy / Boy, Transgendered, Transsexual, 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 -
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 -
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 -
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 -
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 -
Tricked became enjoyed by Sportslover
Rated 92.8%, Read 216609 times, Posted Mon 23rd of February 2009
Fiction , Anal, Blowjob, Gay, Reluctance, Teen Male / Teen Male, 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 -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.3%, Read 194568 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, 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 -
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 encounter_(4) by sissyboytom
Rated 92.3%, Read 177861 times, Posted Wed 25th of February 2009
True Story , Ass to mouth, Blowjob, Consensual Sex, Cum Swallowing, Gay, Transgendered, Transvestite, Virginity -
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 -
The Auction_(0) by Phoenix Cinders
«Femboy gets tricked into being auctioned off as a slave»
Rated 93.3%, Read 171642 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 -
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 -
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 -
My Favorite Aunt Fantasy by G. Snave
Rated 87.7%, Read 147325 times, Posted Mon 26th of September 2005
Fantasy , Authoritarian, Cum Swallowing, Domination/submission, Female Domination, Transvestite -
Making him into my little girl by totallydude01
Rated 91.7%, Read 142686 times, Posted Mon 6th of April 2009
Fiction , Anal, Boy, Consensual Sex, Cum Swallowing, Gay, 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 -
my birthday gift_(1) by iminhose
Rated 94.7%, Read 138471 times, Posted Tue 7th of February 2012
True Story , Transvestite -
Caught by the Boy Next-door! by UndeniableUrges
«Mike Miller is caught wearing panties by the boy-next-door. What canl he do to make Kevin forget what he saw?»
Rated 86.7%, Read 123513 times, Posted Sun 27th of June 2021
Fiction , Blackmail, Blowjob, Gay, Humiliation, 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 -
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 -
Late Night In The Office by Heatround
Rated 93.8%, Read 118962 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, Transvestite -
A New Waitress in Town by G. Snave
Rated 91.8%, Read 116286 times, Posted Mon 24th of April 2006
Fiction , Anal, Bi-sexual, Blowjob, Cum Swallowing, Transvestite -
My Sissy Roommate by Wolf Hunt
«My roommate gets sissified and gets his ass pounded by me»
Rated 92.9%, Read 116283 times, Posted Tue 19th of November 2019
Science-Fiction , Anal, Ass to mouth, Coercion, Consensual Sex, Gay, Male Domination, Reluctance, Teen Male / Teen Male, Transgendered, Transvestite, Virginity -
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 -
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 -
AuntSammy by ShEhEmAlE
Rated 77.9%, Read 112763 times, Posted Tue 22nd of August 2006
True Story , Anal, Blowjob, Cum Swallowing, Transgendered, Transsexual, Transvestite -
Halloween_(1) by Heatround
Rated 83.7%, Read 111674 times, Posted Wed 11th of May 2005
True Story , Bi-sexual, Domination/submission, First Time, Gay, Hardcore, 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 -
My Stepfather Part 3 by Rutger5
Rated 91.7%, Read 110463 times, Posted Mon 29th of November 2010
Fiction , Anal, Authoritarian, Domination/submission, Gay, Spanking, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 95.5%, Read 109548 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, 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 -
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 -
Room Serviced by dlcalguy
«First time real gay sex for a man who has been fantasizing about it.»
Rated 92.3%, Read 99495 times, Posted Mon 28th of November 2016
Fiction , Anal, First Time, Gay, Interracial, Transvestite -
The Story of Tim to Jennifer Part 3 by jen128
Rated 92.8%, Read 97902 times, Posted Sun 16th of October 2011
Fiction , Bi-sexual, Cuckold, Hardcore, Threesome, Transgendered, Transsexual, Transvestite -
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 -
Christmas party fun by iminhose
Rated 92%, Read 93834 times, Posted Tue 7th of February 2012
True Story , Bi-sexual, Exhibitionism, Humiliation, Oral Sex, Transvestite, Wife -
Exactly What It Looks Like by into_everything
Rated 92.5%, Read 92154 times, Posted Mon 23rd of January 2012
Fiction , Ass to mouth, Bi-sexual, Blackmail, Female Domination, Girls domination, Humiliation, Male/Teen Female, Transvestite -
First Contact_(1) by snipe
Rated 86.6%, Read 91510 times, Posted Tue 5th of September 2006
True Story , Anal, Blowjob, Cum Swallowing, Transsexual, Transvestite -
Mama's Girl by Phoenix Cinders
«In order to survive in the projects, white boy had to become an ebony woman's sissy bitch and take her big black dick.»
Rated 93.2%, Read 88119 times, Posted Sat 9th of March 2019
Science-Fiction , Anal, Ass to mouth, Black, Blowjob, Consensual Sex, Domination/submission, Erotica, Oral Sex, Romance, Teen, Transgendered, Transsexual, Transvestite -
What I wanted... Part 1 by Ashley Cox
Rated 79.6%, Read 86785 times, Posted Fri 20th of January 2006
True Story , First Time, Transgendered, Transsexual, Transvestite, Virginity -
Nerves, Shivers, Cum by tina_b_girl
Rated 91.9%, Read 86721 times, Posted Tue 7th of September 2010
True Story , Anal, Transsexual, Transvestite -
The Maid in me by Ashley Coxx
Rated 75.1%, Read 85881 times, Posted Wed 10th of January 2007
Fantasy , Anal, Bi-sexual, Cum Swallowing, Transgendered, Transsexual, Transvestite -
Teenage boy blackmailed by neighbors Part 1 by confusedchloe3
Rated 90.9%, Read 85656 times, Posted Mon 7th of October 2013
Fantasy , Girls domination, Teen Male / Female, Toys, Transgendered, Transsexual, Transvestite -
Cock sucking Crossdresser by craigtv284
«Young man learns to love cock»
Rated 91.8%, Read 84957 times, Posted Mon 21st of September 2015
Fantasy , Gay, Transvestite -
Mom's wild sex life by Jayokegbe
«Jake and his step mom are closer now and she begins to share with him, and to Jake's shock he was about to hear something wild»
Rated 92.6%, Read 84612 times, Posted Sun 7th of March 2021
Fiction , Asian, Ass to mouth, Ass to pussy, Bi-sexual, Blowjob, Consensual Sex, Cum Swallowing, Gay, Group Sex, Oral Sex, Pegging, Prostitution, Transsexual, Transvestite, Wife -
Bondage Obsession by ELLEN
Rated 53.9%, Read 83911 times, Posted Sat 2nd of October 2004
True Story , BDSM, Cock & ball torture, Cum Swallowing, Female Domination, Humiliation, Transvestite -
Halloween Surprise pt1 by trans_love
Rated 93%, Read 83316 times, Posted Tue 29th of October 2013
Fiction , Anal, Oral Sex, Transgendered, Transsexual, Transvestite, Young -
What I wanted... Part 2 by Ashley Cox
Rated 89.7%, Read 83189 times, Posted Sat 21st of January 2006
True Story , First Time, Transgendered, Transsexual, Transvestite, Virginity -
First time_(15) by TheJessie
Rated 95%, Read 83088 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
My little secret 2 by Ashley Coxx
Rated 85.8%, Read 82808 times, Posted Thu 25th of January 2007
Fantasy , Anal, Bi-sexual, Enema, Transgendered, Transsexual, Transvestite -
Neighbors Pt. 1 by Phoenix Cinders
«The Lesbian Neighbors help a femboy blossom out of his shell.»
Rated 91.9%, Read 80985 times, Posted Sat 28th of December 2019
Science-Fiction , Anal, Black, Blowjob, Consensual Sex, Cum Swallowing, Erotica, First Time, Interracial, Latina, Male / Females, Oral Sex, Pegging, Reluctance, Romance, Teen, Teen Male / Female, Threesome, Transgendered, Transsexual, Transvestite, Virginity -
DNA Chapter 1 by Zenythmon
Rated 91.2%, Read 80377 times, Posted Mon 15th of October 2007
Fantasy , Cheating, Job/Place-of-work, Masturbation, Transgendered, Transvestite -
Sex with a crossdressing in a public toilet by srlvictoria
Rated 91.9%, Read 79122 times, Posted Mon 19th of November 2012
True Story , Anal, Oral Sex, Teen, Transgendered, Transvestite, Young -
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 -
Denver and Alex by younganhung1889
Rated 93%, Read 77202 times, Posted Mon 25th of April 2011
Fiction , Blowjob, Transgendered, Transsexual, Transvestite