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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 95.8%, Read 56949 times, Posted Mon 2nd of August 2021
Fiction , First Time, Romance, Teen Male/Teen Female, Transvestite, Virginity
Straight to Bi by dlcalguy

«Discovering things I didn't imagine I would like»
Rated 95.7%, Read 65124 times, Posted Wed 22nd of September 2021
Fiction , Exhibitionism, Gay, Masturbation, Transvestite
Taken by my neighbor by jen128

«Crossdreser taken for first time»
Rated 95.7%, Read 381231 times, Posted Sun 27th of September 2015
Fiction , Anal, Blackmail, Blowjob, Coercion, Domination/submission, Erotica, Hardcore, Transvestite
caught in drag by picklewasher
Rated 95.6%, Read 586641 times, Posted Sun 6th of December 2009
True Story , Anal, Boy / Boy, Cum Swallowing, Gay, Masturbation, Transvestite
My young life by Stephon

«My introduction to crossdressing and sex»
Rated 95.6%, Read 166920 times, Posted Fri 23rd of November 2018
True Story , Anal, Blowjob, Boy / Boy, Cum Swallowing, First Time, Transvestite
Sister's Surprise_(0) by Achilles_Heel
Rated 95.6%, Read 917298 times, Posted Fri 8th of June 2012
Fiction , Consensual Sex, Incest, Romance, Teen Male / Female, Transvestite
Carl or Carla by Mystic47
Rated 95.5%, Read 159120 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 95.5%, Read 107532 times, Posted Thu 20th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, First Time, Gay, Oral Sex, Transvestite
Kelly - Part 2 by xerxes10
Rated 95.5%, Read 170115 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 95.5%, Read 225954 times, Posted Mon 10th of January 2011
True Story , Blowjob, Cum Swallowing, Oral Sex, Reluctance, Transvestite
Jeffry and Billy 4 by UndeniableUrges

«Billy and Jeffry get caught!»
Rated 95.4%, Read 95796 times, Posted Thu 3rd of September 2020
Fiction , Domination/submission, Incest, Teen Male / Teen Male, Teen Male/Teen Female, Transvestite, Young
Jeffry and Billy 7 by UndeniableUrges

«The Siblings Invite Susie to a Party!»
Rated 95.4%, Read 91116 times, Posted Wed 23rd of September 2020
Fiction , Boys/Teen Female, Incest, Teen Male / Teen Male, Teen Male/Teen Females, Transvestite, Young
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 204984 times, Posted Mon 17th of August 2020
True Story , Blowjob, Boy, First Time, Gay, Transvestite, Young
Jeffry and Billy 3 by UndeniableUrges

«Jeffry and Billy play even more sexy games»
Rated 95.3%, Read 92835 times, Posted Sun 30th of August 2020
Fiction , Domination/submission, Teen Male / Teen Male, Transvestite, Young
The Transformation of Jesse by JtellerMT
Rated 95.3%, Read 214929 times, Posted Sun 9th of February 2014
Fiction , Anal, Ass to mouth, Blowjob, Cum Swallowing, Gay, Romance, Transvestite, Virginity
Uncontrollable Pt. 2 by xerxes10
Rated 95.3%, Read 119532 times, Posted Sun 13th of February 2011
Fantasy , Anal, Cum Swallowing, Gay, Hardcore, Oral Sex, Romance, Teen Male / Teen Male, Transvestite
Brenda's First by brendajets

«A crossdresser takes the next step.»
Rated 95.2%, Read 35574 times, Posted Fri 12th of April 2019
Diary , Blowjob, First Time, 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 95.2%, Read 61257 times, Posted Sat 20th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young
The Walk...continued (pt2) by charlotte69
Rated 95.2%, Read 37344 times, Posted Wed 8th of January 2014
Fantasy , Bi-sexual, Cum Swallowing, Romance, Transgendered, Transvestite
Growing Up CH1 by GoatRavisher

«It started out as Babysitting»
Rated 95.2%, Read 92046 times, Posted Fri 21st of September 2018
Fiction , Boy, First Time, Teen Male / Female, 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 95.2%, Read 26763 times, Posted Fri 21st of May 2021
Fantasy , Blackmail, Male / Female Teens, School, Transvestite
A Man's Play Thing by panty_sub
Rated 95.2%, Read 341829 times, Posted Mon 28th of February 2011
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Domination/submission, Drug, First Time, Gay, Reluctance, Teen, 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 95.1%, Read 151098 times, Posted Fri 19th of January 2018
Fantasy , Blowjob, Boy, Gay, Prostitution, Transvestite, Young
Meeting my on-line lover by dlcalguy

«Taking the leap from gay role-playing online to the real thing»
Rated 95.1%, Read 56550 times, Posted Sat 13th of February 2021
Fiction , Gay, Transvestite
The Cinema_(0) by BangTidyUK
Rated 95.1%, Read 225042 times, Posted Tue 10th of April 2012
Fantasy , Anal, Bi-sexual, Consensual Sex, Cum Swallowing, Gay, Group Sex, Hardcore, Oral Sex, Transvestite
Dressed To Thrill by PicturePainter
Rated 95.1%, Read 49386 times, Posted Thu 1st of July 2010
Fantasy , Bondage and restriction, Male Solo, Masturbation, Spanking, Transvestite
James to Jamie by Lucitta

«James experiments with hsi sisters clothing, before getting caught red hnaded.»
Rated 95.1%, Read 57114 times, Posted Sat 18th of July 2020
Fiction , Boys/Teen Female, Incest, Masturbation, Teen Male Solo, Transvestite, Young
I Hate Sneezing Ch. 3_(0) by jonialabaster

«Ryan gets caught peeping on his sister during her business ventures.»
Rated 95%, Read 69816 times, Posted Mon 24th of September 2018
Fiction , Bi-sexual, Blackmail, Blowjob, Coercion, Cum Swallowing, Incest, Pegging, Prostitution, Transvestite
Sister's Surprise, Chapter 5 by Achilles_Heel
Rated 95%, Read 169134 times, Posted Fri 4th of January 2013
Fantasy , Bi-sexual, Erotica, Incest, Male/Female, Oral Sex, Romance, Teen Male/Teen Female, Transgendered, Transvestite
First time_(15) by TheJessie
Rated 95%, Read 82362 times, Posted Thu 21st of February 2013
Fiction , First Time, Lesbian, Transvestite
Kelly - Part 1 by xerxes10
Rated 94.9%, Read 184254 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 253230 times, Posted Wed 29th of August 2012
True Story , Gay, Hardcore, Oral Sex, Transvestite
Wanting to be a girl by fuckmeanyway
Rated 94.9%, Read 180807 times, Posted Mon 22nd of February 2010
Fiction , Blowjob, Cum Swallowing, First Time, Gay, 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 94.8%, Read 34251 times, Posted Sat 24th of October 2020
Fantasy , Anal, Blowjob, Role-playing, Transvestite
My Stepfather 2_(0) by Rutger5
Rated 94.7%, Read 203169 times, Posted Sun 28th of November 2010
Fiction , Anal, Domination/submission, Gay, 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 94.7%, Read 56040 times, Posted Thu 29th of April 2021
Fiction , Blowjob, First Time, Teen, Transgendered, Transvestite, Virginity
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 94.7%, Read 33456 times, Posted Sat 1st of December 2018
Diary , Anal, Bi-sexual, Boy, Female / Girl, Fisting, Incest, Male / Older Female, Transvestite
ONE NIGHT IN A MOTEL by Miki-In-Panties
Rated 94.6%, Read 31743 times, Posted Wed 9th of May 2012
Fantasy , Blowjob, Oral Sex, Transvestite
sister throws a party, and catches brother by jonialabaster
Rated 94.6%, Read 65184 times, Posted Tue 19th of November 2013
Fantasy , Bi-sexual, Humiliation, Incest, Transvestite
Growing Up Ch2 by GoatRavisher

«I get to be a big sister»
Rated 94.6%, Read 42534 times, Posted Sat 13th of October 2018
Diary , Cum Swallowing, First Time, Incest, Male / Older Female, Transvestite
my birthday gift_(1) by iminhose
Rated 94.6%, Read 137547 times, Posted Tue 7th of February 2012
True Story , Transvestite
Suzy Unleashed Chapter 8 by Suzygurl
Rated 94.6%, Read 21480 times, Posted Tue 26th of May 2015
Fantasm , Coercion, Exhibitionism, Transgendered, 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 148785 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 94.6%, Read 170352 times, Posted Fri 2nd of September 2016
Fantasy , 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 94.6%, Read 91797 times, Posted Tue 19th of June 2018
Fantasy , Authoritarian, Consensual Sex, Cum Swallowing, Discipline, Gay, Job/Place-of-work, Mature, School, Spanking, Teen, Transvestite
The Permissive Purity of Father Fontane [4] by NeonChameleon

«Deep in Dana's mouth»
Rated 94.5%, Read 22554 times, Posted Wed 1st of May 2019
Fiction , Blowjob, Boy, Cum Swallowing, Gay, Mature, Teen, Transgendered, 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 94.5%, Read 96246 times, Posted Fri 13th of May 2016
Fiction , Anal, Blowjob, Cum Swallowing, Gay, Mature, Oral Sex, Romance, Transgendered, Transsexual, Transvestite
Becoming Daddy's Halloween Princess by willingwimp
Rated 94.5%, Read 193761 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Incest, Romance, Teen, Transsexual, Transvestite
Becoming Sadi by Beckyj1992

«Feminine crossdresser finally lives out his fantasy.»
Rated 94.4%, Read 269586 times, Posted Mon 2nd of May 2016
Fiction , Anal, Blowjob, First Time, Gay, Mature, Oral Sex, Reluctance, Romance, Transgendered, Transsexual, Transvestite, Virginity
Growing Up Chapter 11 by GoatRavisher

«College Life goes on!»
Rated 94.4%, Read 10884 times, Posted Mon 13th of July 2020
Diary , Anal, BDSM, Bi-sexual, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite
2 stories halloween parties by iminhose
Rated 94.4%, Read 61344 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite
Jeffry and Billy 6 by UndeniableUrges

«Becky apologizes and tries to make it up to poor Susie»
Rated 94.4%, Read 49002 times, Posted Tue 22nd of September 2020
Fiction , Incest, Male / Female Teens, Teen Male/Teen Female, Transvestite, Young
Sister's Surprise, Capter 2 by Achilles_Heel
Rated 94.4%, Read 313575 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 94.4%, Read 289317 times, Posted Mon 24th of August 2015
Fiction , Consensual Sex, Erotica, First Time, Incest, Transsexual, Transvestite, Virginity
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 94.4%, Read 41712 times, Posted Sun 20th of May 2018
Fiction , Blowjob, Reluctance, Romance, Transvestite
My life as a woman by curiouscoupleinraleigh
Rated 94.3%, Read 373200 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
Late Night In The Office by Heatround
Rated 94.3%, Read 116859 times, Posted Tue 13th of August 2013
Fantasy , Hardcore, Transgendered, Transsexual, Transvestite
Sister's Surprise, Chapter 3 by Achilles_Heel
Rated 94.2%, Read 185301 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
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 94.2%, Read 38196 times, Posted Mon 16th of April 2018
Fiction , Blowjob, Incest, Transvestite, Voyeurism
Halloween with Kym_(0) by jackie offee
Rated 94.2%, Read 115644 times, Posted Thu 16th of June 2011
Fiction , Exhibitionism, Incest, Transvestite
Sister's Surprise, Chapter 6: The Slumber Party by Achilles_Heel
Rated 94.2%, Read 306495 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
Suzy Unleashed Chapter 11 by Suzygurl

«Suzy continues her journey as she learns to accept her feminity»
Rated 94.1%, Read 11424 times, Posted Fri 8th of January 2021
Diary , Bi-sexual, Transsexual, Transvestite
the next step on the road to being a slut by NewSubmissiveSlut
Rated 94.1%, Read 94980 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
I Discover Jenna's Secret by Rutger5
Rated 94.1%, Read 112119 times, Posted Sat 4th of December 2010
Fiction , Anal, Ass to mouth, Coercion, Teen, Transvestite, Virginity
The Walk by charlotte69
Rated 94.1%, Read 33399 times, Posted Mon 6th of January 2014
Fantasy , Romance, Transgendered, Transvestite
Brother prostitute by sexyboytoy18
Rated 94.1%, Read 347664 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
Suzy Unleashed Chapter 9 by Suzygurl
Rated 94.1%, Read 23445 times, Posted Wed 27th of May 2015
Fantasy , Transgendered, Transvestite
Chloes Story by Skman

«My story of the emergency of Chloe»
Rated 94%, Read 25896 times, Posted Wed 11th of November 2020
True Story , Anal, Blowjob, Consensual Sex, Gay, Transvestite
Internet Hookup Pioneer by Katie_Johnny

«A sissy spends an enchanting evening with a hot hunk»
Rated 94%, Read 22320 times, Posted Wed 22nd of March 2023
True Story , Blowjob, Cum Swallowing, Domination/submission, Drug, Oral Sex, Transsexual, Transvestite
An Accidental Woman by curiouscoupleinraleigh
Rated 94%, Read 475770 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