sexstories.com
Transvestite
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Tinder Tranny Hook Up by markerss
«This story took place many years ago after breaking up with a girlfriend of several years. I was feeling lost and felt I need to get out there. I started looking at porn online, and eventually searched the internet for dating site, and even casual sexual encounter sites.»
Rated 89%, Read 28968 times, Posted Mon 5th of February 2024
True Story , Anal, Blowjob, Consensual Sex, First Time, Mature, Teen, Transgendered, Transsexual, Transvestite, Young -
our walk part 1 & 2 by iminhose
Rated 92.2%, Read 28860 times, Posted Tue 7th of February 2012
True Story , Gay, Group Sex, Older Female / Males, Threesome, Transvestite, Wife -
My First Time by michelle6969
Rated 86.1%, Read 28755 times, Posted Thu 21st of November 2013
True Story , Transvestite -
sissyboy jake's first outing - part 1_(1) by culotte.de.dentelle
Rated 89.1%, Read 28440 times, Posted Sun 23rd of June 2013
Fiction , Anal, Domination/submission, Humiliation, Oral Sex, Transvestite -
Triplets by JW
Rated 72.1%, Read 28424 times, Posted Mon 3rd of January 2005
Fiction , Blowjob, Consensual Sex, Group Sex, Male / Females, Transvestite -
My Unintentional Threesome Part One by Katie_Johnny
«What started as a normal hookup turned into my first ever threesome.»
Rated 88.7%, Read 28305 times, Posted Mon 7th of August 2023
True Story , Anal, Consensual Sex, Cum Swallowing, Drug, Gay, Threesome, Transvestite -
Instructor Mike's Academy - Part 1 - Taking the First Step by qtaimee
«True story of my first real sexual experience.»
Rated 78.1%, Read 28242 times, Posted Wed 13th of July 2022
True Story , Asian, Authoritarian, BDSM, Boy, Cock & ball torture, Consensual Sex, Domination/submission, Exhibitionism, First Time, Gay, Interracial, Male Domination, Masturbation, School, Transvestite, Water Sports/Pissing, Young -
Nikki's special someone by nicholas-f1992
Rated 93.4%, Read 28149 times, Posted Wed 13th of August 2014
Fantasy , Anal, Authoritarian, Blackmail, Blowjob, Cum Swallowing, First Time, Male Domination, Mature, Transvestite, Virginity -
Biker Daddy Don - Story 1 by lisashinytights
Rated 88.6%, Read 28098 times, Posted Thu 1st of March 2012
True Story , Drug, Reluctance, Teen, Transvestite -
My Cum Filled Camping Trip Part One by CUM-LOVER
Rated 81.6%, Read 27909 times, Posted Mon 27th of February 2012
Fiction , Anal, Cum Swallowing, Domination/submission, 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 -
My first Time_(78) by iminhose
Rated 83.3%, Read 27822 times, Posted Tue 7th of February 2012
True Story , Bi-sexual, Threesome, Transvestite -
My changing fortunes - 04 by Luvagobfull
Rated 86.4%, Read 27486 times, Posted Wed 2nd of November 2011
Fiction , Anal, Blowjob, Coercion, Transvestite -
The Permissive Purity of Father Fontane [4] by NeonChameleon
«Deep in Dana's mouth»
Rated 94%, Read 27471 times, Posted Wed 1st of May 2019
Fiction , Blowjob, Boy, Cum Swallowing, Gay, Mature, Teen, Transgendered, Transvestite, Young -
Giving Up Control by cremieux23
«A dominant husband realizes some new urges. He decides to entertain them, but the crosses the line. When his finds out about his new found interest, she decides to give him just what he wanted.»
Rated 89.1%, Read 27318 times, Posted Thu 28th of October 2021
Fantasy , Authoritarian, BDSM, Bi-sexual, Cheating, Cock & ball torture, Cum Swallowing, Discipline, Domination/submission, Female Domination, Humiliation, Masturbation, Toys, Transvestite, Water Sports/Pissing -
Fuzzy Faced Allia: Yippy and the dog by TexanBelgianCutie
«An immature freckled faced cow-chick is caught off guard by a young bunny-girl and her loyal dog. The odd trio explore and satisfy their bizarre sexual needs.»
Rated 76.7%, Read 27228 times, Posted Sun 24th of December 2017
Fantasy , Bestiality, Bi-sexual, Body modification, Domination/submission, Drug, Girls / Female, Group Sex, Mind Control, Monster, Teen, Threesome, Transgendered, Transsexual, Transvestite, Young -
my walk with a sexy neighbor by iminhose
Rated 82.1%, Read 27096 times, Posted Tue 7th of February 2012
True Story , Transvestite -
My First Boyfriend 4 by Verytas
Rated 83.3%, Read 26916 times, Posted Thu 21st of April 2011
Fiction , Authoritarian, Cruelty, Foot or shoe fetish, Gay, Oral Sex, Transvestite -
My First Boyfriend 7 by Verytas
Rated 83.9%, Read 26862 times, Posted Wed 27th of April 2011
Fiction , Blowjob, Coercion, Cum Swallowing, Gay, Humiliation, Teen Male / Teen Male, Threesome, Transvestite -
Punished For My Crime by Ashcan2012
Rated 85.3%, Read 26670 times, Posted Thu 25th of October 2012
Fantasy , Incest, Oral Sex, Teen Male / Female, Transvestite -
hotel hookup by iminhose
Rated 86.4%, Read 26616 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
The commoner and the Prince pt 1 by Jenryu
Rated 87.8%, Read 26586 times, Posted Fri 28th of January 2011
Fantasy , Anal, Lesbian, Rape, Teen Female/Teen Female, Transvestite -
Francis to Frances by PieterM
Rated 88.2%, Read 26523 times, Posted Wed 15th of August 2012
Fantasy , Domination/submission, Female Domination, Male Domination, Transgendered, Transvestite -
The Office Chair by Katie_Johnny
«A suggestion from a fuck buddy ended up leading to the discovery of a new favorite way to get fucked»
Rated 85.3%, Read 26427 times, Posted Mon 19th of February 2024
True Story , Anal, Blowjob, Cum Swallowing, Transvestite -
Le Freak by Castlequeen
Rated 90.8%, Read 26397 times, Posted Sat 4th of April 2015
Fantasm , Anal, Ass to mouth, Bi-sexual, Consensual Sex, Cum Swallowing, Extreme, Group Sex, Oral Sex, Spanking, Transvestite -
BED AND BREAKFAST by iminhose
Rated 82.2%, Read 26223 times, Posted Tue 7th of February 2012
True Story , Threesome, Transvestite -
Suzy Unleashed Chapter 4 by Suzygurl
Rated 90.6%, Read 26181 times, Posted Fri 28th of June 2013
Fiction , Domination/submission, Interracial, Transsexual, Transvestite -
Growing up chapter 4 by GoatRavisher
«More adventures, maybe too far.»
Rated 93%, Read 26082 times, Posted Sun 20th of January 2019
Diary , Anal, Bi-sexual, Boy, Oral Sex, Rape, Teen, Transvestite -
im such a fag by iminhose
Rated 74.1%, Read 26043 times, Posted Tue 7th of February 2012
True Story , Male/Female, Threesome, Transvestite -
Amazing Night With A Sexy Crossdresser by markerss
«I wanted to be with a transsexual and as I looked on Craigslist for either a crossdresser or a transsexual to spend time with, of course before Casual Encounters was dropped, i came across a young lady that was not only attractive but seemed genuine too.»
Rated 82.7%, Read 26013 times, Posted Mon 27th of June 2022
True Story , Anal, Blowjob, Consensual Sex, Gay, Transgendered, Transsexual, Transvestite -
Suzy Unleashed Chapter 6 by Suzygurl
Rated 93.4%, Read 25704 times, Posted Wed 23rd of April 2014
Fiction , Blowjob, Domination/submission, Transsexual, 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 91.9%, Read 25593 times, Posted Mon 12th of July 2021
Fiction , Anal, Exhibitionism, Male/Teen Female, massage, Masturbation, Older Male / Female, Role-playing, Teen, Transvestite, Young -
Suzy's Daydream by Suzygurl
Rated 88.2%, Read 25497 times, Posted Sat 24th of November 2012
Fantasy , Domination/submission, Exhibitionism, Transsexual, Transvestite -
The Girl - Stories: Uncle Ben 3 by boardpin123
«The Girl gets an order to make her uncle fuck her. The problem is ... he likes boys.»
Rated 89.4%, Read 25476 times, Posted Mon 12th of July 2021
Fiction , Anal, Ass to mouth, Coercion, Exhibitionism, Male/Teen Female, Masturbation, Older Male / Female, Rape, Reluctance, Role-playing, Teen, Transvestite, Young -
A fantasy of a closeted CD by victoriaD1121
Rated 81.7%, Read 25308 times, Posted Mon 2nd of February 2015
Fantasy , Blowjob, First Time, Transgendered, Transsexual, Transvestite -
guy in heels takes it all at the temple by jerseyporn
Rated 69.6%, Read 25185 times, Posted Fri 27th of July 2012
True Story , Anal, Bi-sexual, Black, Extreme, Interracial, School, Transvestite -
New identity by luv 2 wear cotton panties
«A man goes out in drag for the first time to see how people react.»
Rated 85.7%, Read 25173 times, Posted Sat 15th of July 2017
Fiction , Anal, Interracial, Oral Sex, Transvestite -
Little Red Riding Fag by LatexXdress
Rated 68.3%, Read 25032 times, Posted Wed 21st of September 2011
Fantasy , Transgendered, Transvestite -
Danny becomes Danni by Danni8585
«A young man become a crossdresser...astory..and learns about his female side finding out his aunt is a lesbian and finding her lesbian friend's kids his age are there to Danny through his experimentation. .Part 1»
Rated 78.9%, Read 24984 times, Posted Mon 13th of May 2019
Essay , Cum Swallowing, Female solo, Female/Female, First Time, Lesbian, Toys, Transvestite -
I own you now! by aryalez
«Just a random encounter in a bar, like many other. Or maybe not.»
Rated 87.4%, Read 24978 times, Posted Sun 27th of December 2020
Fiction , Anal, Blowjob, Consensual Sex, Cum Swallowing, First Time, Oral Sex, Transgendered, Transsexual, Transvestite -
King of the hill : the sexual adventures in the alley by Pokemon2
Rated 56.8%, Read 24846 times, Posted Thu 7th of March 2013
Fantasy , Bi-sexual, Boy, Fan fiction, Gay, Incest, Transvestite -
TRISH ON THURSDAY. by CecilBCK
«After a very sexy foursome on the weekend I have arranged to meet Trish for a lesbian experience on the following Thursday.»
Rated 81.4%, Read 24846 times, Posted Sun 10th of May 2020
True Story , Ass to mouth, Bi-sexual, Cheating, Consensual Sex, Erotica, Exhibitionism, Hardcore, Lesbian, Masturbation, Mature, Oral Sex, Threesome, Transvestite, Voyeurism, Written by women -
Cadogan Street Carpark - Crossing The Line by PicturePainter
Rated 88.9%, Read 24798 times, Posted Tue 15th of June 2010
Fantasy , Anal, Authoritarian, Bi-sexual, Blowjob, Cum Swallowing, Domination/submission, Gay, Transvestite -
SYLVIA EXTENDS HER SEXUAL FANTASIES. by CecilBCK
«I am Sylvia a forty-five year old widow after my much older husband died three years ago. I am on a mission to extend my sexual fantasies.»
Rated 87.5%, Read 24672 times, Posted Thu 19th of August 2021
True Story , Ass to mouth, Bi-sexual, Blowjob, Body modification, Cheating, Consensual Sex, Cuckold, Cum Swallowing, Erotica, Exhibitionism, Female exhibitionist, Female/Female, Group Sex, Lesbian, Oral Sex, Threesome, Transvestite, Voyeurism, Written by women -
Michael to Michelle Part 5 The Gay Sauna by SonicRush66
«The transition into a sissy continues when I get the experience of my life at a gay sauna»
Rated 87.4%, Read 24609 times, Posted Tue 25th of April 2023
Diary , Anal, BDSM, Bi-sexual, Blowjob, Bondage and restriction, Boy / Boy, Cum Swallowing, Domination/submission, Extreme, Gay, Group Sex, Humiliation, Male Domination, Mature, Non-consensual sex, Rape, Transgendered, Transsexual, Transvestite -
Cardogan Street Car Park by PicturePainter
Rated 80%, Read 24606 times, Posted Wed 21st of April 2010
Fantasy , Bi-sexual, Blowjob, Cum Swallowing, Domination/submission, Transvestite -
Tamina the thick goblin seductress: Finding a playmate for the alpha wolf by TexanBelgianCutie
«Tami, a busty goblin chick morphs a young lad into a defenseless sheep girl. A large strong wolf finds them and forces the two into submission.»
Rated 86.7%, Read 24480 times, Posted Wed 29th of November 2017
Fantasy , Anal, Bestiality, Bi-sexual, Black, Blowjob, Body modification, Cuckold, Drug, Gay, Humiliation, Male / Females, Rape, Teen, Transgendered, Transsexual, Transvestite, Young -
Sweet Pick Up by Regina10
Rated 87.1%, Read 24291 times, Posted Sun 3rd of May 2009
Fantasy , Transvestite -
JUDITH X. by CecilBCK
«Judith and I share a man full of surprises.»
Rated 81.9%, Read 24084 times, Posted Thu 21st of February 2019
Diary , Ass to mouth, BDSM, Bi-sexual, Blowjob, Exhibitionism, Hardcore, Lesbian, Male/Female, Masturbation, Older Female / Males, Oral Sex, Threesome, Transvestite, Voyeurism, Written by women -
One With the Tribe pt1 by faringwayb
«A human washes up on the shore of a tribe of werewolves»
Rated 92.4%, Read 23979 times, Posted Fri 14th of January 2022
Fantasy , Gay, Humiliation, Monster, Transvestite -
Suzy Unleashed Chapter 9 by Suzygurl
Rated 93.3%, Read 23778 times, Posted Wed 27th of May 2015
Fantasy , Transgendered, Transvestite -
Becoming Cara's Sissy_(1) by jonialabaster
«Here is a story about my ex and her husband, and myself. The first part is true. Where her husband enters the picture is fantasy. Names changed for anonymity of course.»
Rated 91.5%, Read 23775 times, Posted Tue 19th of June 2018
Fiction , Bi-sexual, Blowjob, Female Domination, Transvestite -
Camming Down the Rabbit Hole Ch6 by Dani_does_Dallas
«The continued journey into a guy becoming a cam girl - New outfits and a trip to the shops with an unexpected bonus.»
Rated 92.7%, Read 23694 times, Posted Mon 11th of October 2021
Fiction , Anal, Bi-sexual, Cum Swallowing, Exhibitionism, Male Solo, Masturbation, Pegging, Prostitution, Transgendered, Transsexual, Transvestite -
Its never too late part 1 by gandalf8472
Rated 85.7%, Read 23430 times, Posted Thu 3rd of May 2012
Fiction , Anal, Blowjob, Cum Swallowing, Incest, Transvestite -
Tamani the thick goblin seductress: Drugging the shy centaur girl, Vix by TexanBelgianCutie
«Vix, a timid lesbian takes a lust pill and opens herself up to everyone. Accompanied by a cock-hungry goblin, the drugged up girls make new friends with the sex-fueled ravenous townsfolk.»
Rated 77.3%, Read 23373 times, Posted Wed 29th of November 2017
Fantastic , Alien, Anal, Bestiality, Bi-sexual, Body modification, Cuckold, Cum Swallowing, Domination/submission, Drug, Female / Girl, Gay, Group Sex, Job/Place-of-work, Mind Control, Monster, Rape, Teen, Transgendered, Transsexual, Transvestite, Young -
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 93.8%, Read 23349 times, Posted Fri 27th of January 2023
True Story , Blowjob, Cum Swallowing, Drug, First Time, Gay, Transvestite -
Cousin David by mazeyj
«David frustion led him to call on me»
Rated 80.4%, Read 23307 times, Posted Wed 16th of August 2017
Diary , Gay, Transvestite -
My Initiation Into BBC by Tranedrvr247
«My First introduction to BBC»
Rated 80.7%, Read 23229 times, Posted Mon 17th of June 2019
Fiction , Black, Boy, Consensual Sex, First Time, Transvestite -
Me and Alice Part 2 by gblover
Rated 84.9%, Read 23088 times, Posted Thu 4th of March 2010
True Story , Anal, Ass to mouth, BDSM, Bi-sexual, Blowjob, Bondage and restriction, Consensual Sex, Cum Swallowing, Domination/submission, Female Domination, First Time, Foot or shoe fetish, Girls domination, Plumper, Reluctance, Teen Male/Teen Female, Toys, Transvestite, Virginity -
Auntie’s home tuition (pt3) by Dave.Trudy2
«Auntie wasn’t the only one that wanted me because while she was in hospital my uncle Robert let his friends use me for their pleasure, but once auntie Silvia was home me being used as an abused whore stopped.»
Rated 79.5%, Read 23034 times, Posted Tue 1st of October 2019
Fiction , Anal, Cum Swallowing, Interracial, Males / Females, Transvestite, Water Sports/Pissing -
Melanie Catches Me Wearing Her Panties by Rangerfan6165
«I had been using my sister's panties to jerk off with for a while. I started to wear them and cumming in them a few weeks ago. She caught me. Things took an unexpected turn, and I discovered my true inner-self.»
Rated 91.3%, Read 22977 times, Posted Tue 19th of August 2025
Fiction , Blowjob, Domination/submission, Female Domination, Foot or shoe fetish, Incest, Male / Female Teens, Masturbation, Oral Sex, Teen, Transvestite, Young -
The First Time Part (one) by Arianna401971
Rated 75%, Read 22974 times, Posted Thu 24th of October 2013
Fantasy , Transgendered, Transsexual, Transvestite -
Realising Our Fantasies Together part 2 by Beezlebubzzz
«Steve is introduced to the paddle and the nightclub»
Rated 91.8%, Read 22893 times, Posted Mon 15th of February 2016
Fiction , Anal, Authoritarian, Discipline, Domination/submission, Transvestite, Wife -
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 92.3%, Read 22518 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 -
Superman-The Triad Chapter 3 by dperv1
Rated 77.3%, Read 22281 times, Posted Mon 2nd of April 2012
Science-Fiction , Bi-sexual, Drug, Female Domination, Female solo, Female/Female, Male/Female, Mind Control, Transvestite, Written by women -
Lisa gets more than what she thought she would by toddh1970
Rated 84.5%, Read 22227 times, Posted Sun 16th of November 2014
Fiction , Blowjob, Cum Swallowing, Transvestite -
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.8%, Read 22212 times, Posted Tue 26th of May 2015
Fantasm , Coercion, Exhibitionism, Transgendered, Transvestite -
Kalynns Ass part two_(1) by Kalynn
Rated 87.2%, Read 22128 times, Posted Sun 2nd of June 2013
True Story , Transvestite -
Phat Ass White Boy by Unknown user
Rated 78.9%, Read 22008 times, Posted Fri 23rd of August 2013
Fantasy , Anal, Ass to mouth, Bi-sexual, Blackmail, Blowjob, Cum Swallowing, Domination/submission, Gay, Hardcore, Male Domination, massage, Oral Sex, Spanking, Transvestite -
Fun during a sad time by CDKimberlyMaj
«A bit of family fun»
Rated 87.6%, Read 21987 times, Posted Mon 4th of December 2023
True Story , Anal, Consensual Sex, Cum Swallowing, Transsexual, Transvestite