sexstories.com
Transvestite
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Jeffry and Billy 6 by UndeniableUrges
«Becky apologizes and tries to make it up to poor Susie»
Rated 95.4%, Read 31461 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, 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 95.4%, Read 23034 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity -
Sister's Surprise_(0) by Achilles_Heel
Rated 95.4%, Read 856380 times, Posted Fri 8th of June 2012
Fiction , Consensual Sex, Incest, Romance, Teen Male / Female, Transvestite -
My young life by Stephon
«My introduction to crossdressing and sex»
Rated 95.3%, Read 111663 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite -
Taken by my neighbor by jen128
«Crossdreser taken for first time»
Rated 95.3%, Read 285807 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite -
caught in drag by picklewasher
Rated 95.3%, Read 507987 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite -
Kelly - Part 2 by xerxes10
Rated 95.3%, Read 141597 times, Posted Fri 23rd of December 2011
Fantasy , Anal, Oral Sex, Romance, Teen Male / Teen Male, Transgendered, Transvestite -
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 186312 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity -
I Hate Sneezing Ch. 3_(0) by jonialabaster
«Ryan gets caught peeping on his sister during her business ventures.»
Rated 95.3%, Read 45075 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite -
My first cock was a crossdressers by Sex conspiracy theorisit
Rated 95.3%, Read 193167 times, Posted Mon 10th of January 2011
True Story , Blowjob, Cum Swallowing, Oral Sex, Reluctance, 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 114546 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young -
Carl or Carla by Mystic47
Rated 95.2%, Read 139776 times, Posted Sun 29th of June 2014
Fiction , Incest, Lesbian, Male/Female, Transvestite, Written by women -
Cross-dressing camper by Satintex
«Wearing my favorite lingerie while camping and I get some unexpected visitors»
Rated 95.1%, Read 47853 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 95.1%, Read 55206 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young -
The Cinema_(0) by BangTidyUK
Rated 95.1%, Read 199953 times, Posted Tue 10th of April 2012
Fantasy , Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Gay, Group Sex, Hardcore, Oral Sex, Transvestite -
Kelly - Part 1 by xerxes10
Rated 95.1%, Read 158421 times, Posted Wed 21st of December 2011
Fantasy , Consensual Sex, Teen, Teen Male / Teen Male, Transgendered, Transvestite -
Meeting my on-line lover by dlcalguy
«Taking the leap from gay role-playing online to the real thing»
Rated 95%, Read 34437 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite -
First time_(15) by TheJessie
Rated 95%, Read 73164 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite -
Uncontrollable Pt. 2 by xerxes10
Rated 95%, Read 102138 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, 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 95%, Read 28014 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity -
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 94.9%, Read 150063 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite -
Jeffry and Billy 3 by UndeniableUrges
«Jeffry and Billy play even more sexy games»
Rated 94.9%, Read 56700 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, 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 94.8%, Read 119325 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young -
A Man's Play Thing by panty_sub
Rated 94.8%, Read 294051 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, Transvestite -
My first time with Joe _(0) by CD-Davina20
Rated 94.8%, Read 236514 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite -
Growing Up CH1 by GoatRavisher
«It started out as Babysitting»
Rated 94.7%, Read 69171 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, Transvestite -
Becoming Sadi by Beckyj1992
«Feminine crossdresser finally lives out his fantasy.»
Rated 94.7%, Read 207372 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity -
2 stories halloween parties by iminhose
Rated 94.6%, Read 50967 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Rite of Passage Ch.03 by XtinaSmith
«(Shemale x Male) Jamie's corruption furthers with help from his crush, Kelly.»
Rated 94.6%, Read 119778 times, Posted Fri 14th of April 2017
Fiction , Anal, Coercion, Consensual Sex, Domination/submission, Teen Male / Female, Transgendered, Transsexual, Transvestite, Written by women -
Jeffry and Billy 7 by UndeniableUrges
«The Siblings Invite Susie to a Party!»
Rated 94.6%, Read 56685 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young -
My Stepfather 2_(0) by Rutger5
Rated 94.6%, Read 182793 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, Transvestite -
My life as a woman by curiouscoupleinraleigh
Rated 94.6%, Read 330963 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 7 by Suzygurl
Rated 94.5%, Read 28035 times, Posted Wed 16th of July 2014
Fantasm , Blowjob, Slavery, Transgendered, Transsexual, Transvestite -
Wanting to be a girl by fuckmeanyway
Rated 94.5%, Read 157014 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, Incest, Transvestite -
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.5%, Read 285441 times, Posted Mon 11th of June 2012
Fiction , Blowjob, Consensual Sex, Cum Swallowing, Incest, Oral Sex, Romance, Teen Male / Female, Transgendered, Transsexual, Transvestite -
My Love for Daddy Transformed Me by willingwimp
Rated 94.5%, Read 247935 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity -
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.5%, Read 165318 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 Jane by maverick1989
«The story of a young man giving into his desires.»
Rated 94.5%, Read 126843 times, Posted Fri 2nd of September 2016
Fantasy , Transgendered, Transsexual, Transvestite -
Tricked became Enjoyed Part II by Sportslover
Rated 94.4%, Read 57780 times, Posted Wed 15th of May 2013
Fantasy , Blowjob, Boy, Cum Swallowing, Gay, Job/Place-of-work, Mature, Oral Sex, 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 94.4%, Read 11061 times, Posted Mon 11th of October 2021
Fiction , Anal, Bi-sexual, Cum Swallowing, Exhibitionism, Male Solo, Masturbation, Pegging, Prostitution, Transgendered, Transsexual, Transvestite -
Brenda's First by brendajets
«A crossdresser takes the next step.»
Rated 94.4%, Read 18222 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, Transvestite -
Suzy Unleashed Chapter 9 by Suzygurl
Rated 94.4%, Read 20046 times, Posted Wed 27th of May 2015
Fantasy , Transgendered, Transvestite -
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.4%, Read 154140 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite -
my birthday gift_(1) by iminhose
Rated 94.4%, Read 127512 times, Posted Tue 7th of February 2012
True Story , Transvestite -
James to Jamie by Lucitta
«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 94.3%, Read 36018 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young -
Joey Fucks Teach by MightBeRealz
«A senior gets more than he bargained for when he tries to seduce the shop teacher.»
Rated 94.3%, Read 77454 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 Brother's Girlfriend by justfordanniboi
«One boi's story of how an older brother's girlfriend awoke an identity.»
Rated 94.3%, Read 34158 times, Posted Fri 31st of July 2020
Diary , Gay, Incest, Teen Male / Teen Male, Transvestite -
Dressed To Thrill by PicturePainter
Rated 94.3%, Read 32619 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite -
The Auction_(0) by Phoenix Cinders
«Femboy gets tricked into being auctioned off as a slave»
Rated 94.3%, Read 128682 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 -
The Walk...continued (pt2) by charlotte69
Rated 94.3%, Read 26454 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite -
The Permissive Purity of Father Fontane [3] by NeonChameleon
«Twenty miles»
Rated 94.3%, Read 19485 times, Posted Fri 26th of April 2019
Fiction , Bi-sexual, Blowjob, Boy, Cum Swallowing, Gay, Incest, Mature, Transvestite, 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 79629 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite -
Rebecca Chapter 02 by RebeccaTG
Rated 94.3%, Read 40164 times, Posted Fri 2nd of March 2012
Fantasy , Ass to mouth, Cum Swallowing, First Time, Transgendered, Transvestite -
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 278976 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 -
Jenny is Full of Secrets by Kingly
Rated 94.1%, Read 246057 times, Posted Thu 17th of April 2014
Fiction , Reluctance, Teen Male/Teen Female, Transgendered, Transsexual, Transvestite -
Halloween with Kym_(0) by jackie offee
Rated 94.1%, Read 108891 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, 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 94.1%, Read 20412 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite -
Straight to Bi by dlcalguy
«Discovering things I didn't imagine I would like»
Rated 94.1%, Read 33564 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, 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%, Read 12708 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, Transvestite -
Suzy Unleashed Chapter 2 by Suzygurl
Rated 93.9%, Read 43419 times, Posted Thu 7th of June 2012
Fiction , Slavery, Transgendered, Transsexual, Transvestite -
Auntie Turned Me into Her Little Boy Slut by willingwimp
Rated 93.9%, Read 154485 times, Posted Mon 2nd of February 2015
Fiction , Domination/submission, Incest, Transsexual, Transvestite, Young -
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 93.9%, Read 27984 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism -
Brother prostitute by sexyboytoy18
Rated 93.9%, Read 318432 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 -
James and Jenny Part 4 by Kingly
Rated 93.9%, Read 87825 times, Posted Thu 21st of August 2014
Fiction , Blowjob, Bondage and restriction, Consensual Sex, Pegging, Teen Male / Female, Transgendered, Transsexual, Transvestite -
An Accidental Woman by curiouscoupleinraleigh
Rated 93.8%, Read 436386 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 -
One Summer Day by hk124
Rated 93.8%, Read 258264 times, Posted Wed 27th of March 2013
Fiction , Anal, Consensual Sex, Transgendered, Transsexual, Transvestite -
Sister's Surprise, Chapter 4 by Achilles_Heel
Rated 93.8%, Read 161124 times, Posted Thu 14th of June 2012
Fiction , Body modification, Consensual Sex, Incest, Romance, Teen Male / Female, 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 22044 times, Posted Wed 9th of June 2021
True Story , Anal, Blowjob, Consensual Sex, Gay, Transgendered, Transsexual, Transvestite, Young -
Chloes Story by Skman
«My story of the emergency of Chloe»
Rated 93.7%, Read 20475 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, Transvestite -
Pleasing Bill: A Crossdressing Story #1 by JessRider
«A closeted crossdresser is home while two men walk in and take a liking to him/her»
Rated 93.7%, Read 49257 times, Posted Fri 11th of December 2015
Fiction , Anal, Blowjob, Domination/submission, First Time, Group Sex, Reluctance, Transgendered, Transsexual, Transvestite