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 95.7%, Read 44217 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 95.5%, Read 168432 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 95.5%, Read 215307 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 90813 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite -
Jeffry and Billy 4 by UndeniableUrges
«Billy and Jeffry get caught!»
Rated 95.5%, Read 81888 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.5%, Read 900135 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 344967 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
caught in drag by picklewasher
Rated 95.4%, Read 558861 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
Carl or Carla by Mystic47
Rated 95.4%, Read 153195 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
Kelly - Part 2 by xerxes10
Rated 95.4%, Read 160980 times, Posted Fri 23rd of December 2011
Fantasy , Anal, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.4%, Read 147597 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite -
Straight to Bi by dlcalguy
«Discovering things I didn't imagine I would like»
Rated 95.3%, Read 49806 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 206757 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
The Walk...continued (pt2) by charlotte69
Rated 95.3%, Read 33726 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
Uncontrollable Pt. 2 by xerxes10
Rated 95.3%, Read 112251 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95.3%, Read 48714 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 95.3%, Read 62778 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 95.2%, Read 79320 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
Dressed To Thrill by PicturePainter
Rated 95.2%, Read 41571 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, 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 141213 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 95.1%, Read 83553 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
A Man's Play Thing by panty_sub
Rated 95.1%, Read 324762 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, 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 95.1%, Read 47361 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
The Cinema_(0) by BangTidyUK
Rated 95%, Read 216891 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 28773 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 95%, Read 49518 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 94.9%, Read 162645 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
My first time with Joe _(0) by CD-Davina20
Rated 94.9%, Read 247653 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
First time_(15) by TheJessie
Rated 94.9%, Read 79440 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 94.9%, Read 80364 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young -
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 22086 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, Transvestite -
Internet Hookup Pioneer by Katie_Johnny
«A sissy spends an enchanting evening with a hot hunk»
Rated 94.7%, Read 12894 times, Posted Wed 22nd of March 2023
True Story , Blowjob, Cum Swallowing, Domination/submission, Drug, Oral Sex, Transsexual, Transvestite -
Kelly - Part 1 by xerxes10
Rated 94.7%, Read 175350 times, Posted Wed 21st of December 2011
Fantasy , Consensual Sex, Teen, Teen Male / Teen Male, Transgendered, 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 34944 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
Wanting to be a girl by fuckmeanyway
Rated 94.7%, Read 172272 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.7%, Read 140355 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
Becoming Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.7%, Read 155643 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 94.7%, Read 53646 times, Posted Sat 20th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
My Stepfather 2_(0) by Rutger5
Rated 94.6%, Read 196458 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
Joey Fucks Teach by MightBeRealz
«A senior gets more than he bargained for when he tries to seduce the shop teacher.»
Rated 94.6%, Read 87534 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, 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 94.6%, Read 29655 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.6%, Read 243363 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
sister throws a party, and catches brother by jonialabaster
Rated 94.5%, Read 60612 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 29466 times, Posted Wed 9th of May 2012
Fantasy , Blowjob, Oral Sex, Transvestite -
my birthday gift_(1) by iminhose
Rated 94.5%, Read 134178 times, Posted Tue 7th of February 2012
True Story , Transvestite -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.4%, Read 177606 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
2 stories halloween parties by iminhose
Rated 94.4%, Read 58218 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.4%, Read 304194 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.4%, Read 178545 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 -
The Walk by charlotte69
Rated 94.4%, Read 30759 times, Posted Mon 6th of January 2014
Fantasy , Romance, Transgendered, Transvestite -
Growing Up Ch2 by GoatRavisher
«I get to be a big sister»
Rated 94.3%, Read 38499 times, Posted Sat 13th of October 2018
Diary , Cum Swallowing, First Time, Incest, Male / Older 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 94.3%, Read 89706 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 274722 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
My life as a woman by curiouscoupleinraleigh
Rated 94.3%, Read 361866 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 -
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.2%, Read 19527 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 297606 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 113466 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 94.2%, Read 64455 times, Posted Thu 7th of July 2016
Fiction , Anal, Blowjob, Body modification, Male/Teen Female, Oral Sex, Reluctance, Romance, Teen, Transgendered, Transsexual, Transvestite -
Late Night In The Office by Heatround
Rated 94.1%, Read 110196 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 30138 times, Posted Sat 1st of December 2018
Diary , Anal, Bi-sexual, Boy, Female / Girl, Fisting, Incest, Male / Older Female, 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 39351 times, Posted Sun 20th of May 2018
Fiction , Blowjob, Reluctance, Romance, Transvestite -
Jenny is Full of Secrets by Kingly
Rated 94.1%, Read 260289 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 178638 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, 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 94%, Read 105837 times, Posted Thu 14th of January 2016
Fantasm , Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Toys, Transgendered, Transsexual, Transvestite, Young -
First Time pt 2 by trans_love
Rated 94%, Read 62859 times, Posted Mon 13th of February 2012
True Story , Exhibitionism, Gay, Teen, Transsexual, 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 94%, Read 9750 times, Posted Thu 13th of April 2023
True Story , Anal, Blowjob, Cum Swallowing, Domination/submission, Drug, Hardcore, Transvestite -
An Accidental Woman by curiouscoupleinraleigh
Rated 94%, Read 462582 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 -
Brother prostitute by sexyboytoy18
Rated 94%, Read 338586 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 -
Growing Up Chapter 11 by GoatRavisher
«College Life goes on!»
Rated 93.9%, Read 9396 times, Posted Mon 13th of July 2020
Diary , Anal, BDSM, Bi-sexual, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite -
The Permissive Purity of Father Fontane [4] by NeonChameleon
«Deep in Dana's mouth»
Rated 93.9%, Read 19512 times, Posted Wed 1st of May 2019
Fiction , Blowjob, Boy, Cum Swallowing, Gay, Mature, Teen, Transgendered, Transvestite, Young