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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 89.2%, Read 30645 times, Posted Mon 5th of February 2024
True Story , Anal, Blowjob, Consensual Sex, First Time, Mature, Teen, Transgendered, Transsexual, Transvestite, Young -
Camming Down the Rabbit Hole Ch5 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. but as i begun to fall down the warren of crossdressing I couldn't help but get lost in a world I would make my own.»
Rated 89.2%, Read 22224 times, Posted Tue 28th of September 2021
Fantasy , Anal, Bi-sexual, Cosplay, Exhibitionism, Male Solo, Masturbation, Prostitution, Transgendered, Transsexual, Transvestite -
Alexia at Charlie’s by markerss
«I had always thought about being with a tranny but never had to gut to meet one, but when the opportunity presented itself, i nervously took a chance.»
Rated 89.2%, Read 34626 times, Posted Sun 26th of December 2021
True Story , Anal, Blowjob, First Time, Gay, Transgendered, Transsexual, Transvestite -
Sam to Samantha_(1) by valkak
Rated 89.1%, Read 44877 times, Posted Thu 19th of November 2009
Fantasy , Anal, Blackmail, Reluctance, Transvestite, Young -
Fangs for the Mammaries by sourdough
Rated 89.1%, Read 32010 times, Posted Thu 2nd of December 2010
Fiction , Transgendered, Transvestite -
Sometimes short for Samuel pt. 1 by lavanne
«A young man's feminine side opens doors and more when he goes to college.»
Rated 89.1%, Read 19683 times, Posted Mon 14th of April 2025
Fiction , Anal, Bi-sexual, Blowjob, School, Teen Male / Teen Male, 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 -
Growing Up Chapter 7 by GoatRavisher
«Being a big brother/ house boy/ sex toy for a Sorority is pretty much the greatest job ever.»
Rated 89%, Read 17562 times, Posted Tue 17th of December 2019
Diary , Anal, Bi-sexual, Blowjob, Group Sex, Oral Sex, Teen Male/Teen Females, Threesome, Transvestite -
Step Daughter Figured It Out For Me by 50and7
«Step Daughter Convinces me that with my chest womens clothes are a way of life!»
Rated 89%, Read 16530 times, Posted Thu 23rd of August 2018
Fiction , First Time, Reluctance, Transvestite -
First time out in Woman's clothing by Mdcowboy01
Rated 89%, Read 35739 times, Posted Mon 26th of November 2012
Fiction , Anal, Ass to mouth, Gay, Transvestite -
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 -
My Unintentional Threesome Part One by Katie_Johnny
«What started as a normal hookup turned into my first ever threesome.»
Rated 88.9%, Read 29367 times, Posted Mon 7th of August 2023
True Story , Anal, Consensual Sex, Cum Swallowing, Drug, Gay, Threesome, Transvestite -
Hostile Takeover (James Bondage Quickies) by [James Bondage]
«An ambitious Latina Futanari senses opportunity when she learns the boss has a submissive femboy at home.»
Rated 88.9%, Read 16953 times, Posted Fri 7th of May 2021
Fiction , Anal, Blowjob, Consensual Sex, Domination/submission, Erotica, Female Domination, Hardcore, Job/Place-of-work, Latina, Masturbation, Oral Sex, Spanking, Threesome, Transsexual, Transvestite -
Hot Chocolate Ch.02_(0) by XtinaSmith
«Shahira comes back for more.»
Rated 88.8%, Read 35553 times, Posted Thu 15th of November 2018
Fiction , Blowjob, Cum Swallowing, Erotica, Romance, Transgendered, Transsexual, Transvestite, Written by women -
i got caught!!! by iminhose
Rated 88.7%, Read 73248 times, Posted Tue 7th of February 2012
True Story , Bi-sexual, Female Domination, Gay, Transvestite, Wife -
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 -
Lara & Jack to Melissa - part 3 by LesLara84
Rated 88.5%, Read 42573 times, Posted Fri 13th of January 2012
True Story , Anal, Blackmail, Body modification, Consensual Sex, Discipline, Domination/submission, Female Domination, Fisting, Latex fetish, Teen Male / Teen Male, Transsexual, Transvestite, Written by women -
Sisters Substitute by jmar93
Rated 88.5%, Read 63744 times, Posted Sun 29th of July 2012
True Story , Anal, Ass to mouth, Bi-sexual, Blowjob, Body modification, Boy, Cum Swallowing, Teen, Teen Female/Boy, Transvestite, Virginity, Young -
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 -
Superman-The Triad Chapter 2 by dperv1
Rated 88.3%, Read 30714 times, Posted Wed 28th of March 2012
Science-Fiction , Body modification, Fan fiction, Masturbation, Oral Sex, Transvestite -
A Night Not To Remember.... by sally slutton
«Dean fancies himself as a ladies man, work all week, fuck all weekend. The bigger the tits, the more he goes for them. Until he 'bumps' into Sally and gets more than he bargained for...»
Rated 88.3%, Read 38985 times, Posted Mon 23rd of August 2021
Fiction , Anal, Male / Females, Oral Sex, Transsexual, 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 -
MY MAN AND I SHARE A LADYBOY. by CecilBCK
«In the afterglow of a recent wonderful sex session (just the two of us) I remarked that of all the sexual combinations we had enjoyed I had never seen Roger suck another man’s cock.»
Rated 88.2%, Read 61650 times, Posted Sun 16th of June 2019
True Story , Ass to mouth, BDSM, Bi-sexual, Blowjob, Cuckold, Exhibitionism, Male / Females, Oral Sex, Threesome, Transvestite, Written by women -
New Start pt2 (new job) by Dave.Trudy2
«This new start was going well, l had become better than good friends with my landlady and my new job as an odd-job man was better than l could ever imagine, l really did some odd-jobs at Willow Heights.»
Rated 88.2%, Read 14343 times, Posted Fri 12th of February 2021
Fantasy , Anal, Blowjob, Cum Swallowing, Older Female / Males, Transvestite -
Suzy's Daydream by Suzygurl
Rated 88.2%, Read 25497 times, Posted Sat 24th of November 2012
Fantasy , Domination/submission, Exhibitionism, Transsexual, Transvestite -
Fun during a sad time by CDKimberlyMaj
«A bit of family fun»
Rated 88.1%, Read 22671 times, Posted Mon 4th of December 2023
True Story , Anal, Consensual Sex, Cum Swallowing, Transsexual, Transvestite -
My little secret 3 by Ashley Coxx
Rated 88.1%, Read 60196 times, Posted Mon 29th of January 2007
Fantasy , Anal, Bi-sexual, Body modification, Transgendered, Transsexual, Transvestite -
Suzy Unleashed Chapter 12 by Suzygurl
«Suzy continues her journey into her new life as a cocksucking sissy whore and discovers just how much she enjoys it..»
Rated 88%, Read 11793 times, Posted Sat 30th of January 2021
Diary , Bi-sexual, Blowjob, Cum Swallowing, Domination/submission, Humiliation, Transsexual, Transvestite -
my friend came over by iminhose
Rated 88%, Read 31935 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
Our Only Hope, Chapter 05 by The_Technician
«The search for the Monty brothers leads W to Davenport Iowa»
Rated 87.9%, Read 11724 times, Posted Fri 20th of December 2019
Fiction , BDSM, Exhibitionism, Transsexual, Transvestite -
My first Time_(80) by iminhose
Rated 87.7%, Read 30654 times, Posted Tue 7th of February 2012
True Story , Transvestite -
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 -
Welcome surprize_(1) by caryli
«Long dry spell ends.»
Rated 87.5%, Read 29595 times, Posted Wed 27th of January 2016
True Story , Bi-sexual, Gay, Transvestite -
Paul and Jayne Part 1 by Piscean
Rated 87.5%, Read 20172 times, Posted Thu 1st of July 2010
Fiction , Domination/submission, Male/Female, Reluctance, Transvestite -
'My Beginning' by vanityfair
Rated 87.5%, Read 67230 times, Posted Sat 25th of September 2010
Fiction , Blowjob, Boy / Boy, Consensual Sex, Gay, Oral Sex, Transvestite -
Sometimes Short for Samuel pt. 2 by lavanne
«Settling into life in the dorm.»
Rated 87.5%, Read 7242 times, Posted Sat 3rd of May 2025
Fiction , Anal, Blowjob, Masturbation, School, Transsexual, Transvestite -
Forced to be a girl for a weekend by CDKimberlyMaj
«Lost a bet to a girl I just met»
Rated 87.4%, Read 21405 times, Posted Thu 11th of July 2024
True Story , Bi-sexual, Consensual Sex, Cum Swallowing, Transvestite -
Spicy Story - The rest of the fuckin story by TexanBelgianCutie
«Big dicked mommy, her submissive twink son, and the transformed daughter explore each other's bodies for days to come.»
Rated 87.3%, Read 39012 times, Posted Fri 1st of December 2017
Fantasy , Anal, Bi-sexual, Body modification, Boy, Domination/submission, Gay, Group Sex, Humiliation, Mature, Teen, Transgendered, Transsexual, Transvestite, Young -
Mistress Cruel Love - Chapter 2 - Total Commitment by [James Bondage]
«The feminization of Darius continues as he encounters dominant women at every turn.»
Rated 87.3%, Read 22863 times, Posted Fri 11th of September 2020
Fiction , Anal, Authoritarian, BDSM, Black, Body modification, Bondage and restriction, Consensual Sex, Cum Swallowing, Discipline, Domination/submission, Female Domination, Hardcore, Humiliation, Interracial, Job/Place-of-work, Pegging, Plumper, Reluctance, Spanking, Toys, Transvestite -
Surprise comes along with seeing friend's brother by jx88
«I went to visit my best friend all the time at his house - but this time only his older brother was home.»
Rated 87.2%, Read 19800 times, Posted Mon 26th of March 2018
True Story , Anal, Ass to mouth, Blowjob, First Time, Gay, Male Domination, Transvestite -
Walking home in South Dakota - Ch 1 by dpga4625
«My introduction to sex, girls, guys, and cross-dressing in my early years. While it started out forced it soon became a distinct pleasure as I found out about both sexes.»
Rated 87.2%, Read 18321 times, Posted Fri 7th of August 2020
True Story , Anal, Bi-sexual, Bondage and restriction, Boy / Boy, Boys/Teen Female, Domination/submission, First Time, Oral Sex, Transvestite -
Tom Confesses by Fred
Rated 87.2%, Read 63019 times, Posted Sat 9th of July 2005
Fiction , Anal, Blowjob, Oral Sex, Romance, Transsexual, Transvestite -
Kalynns Ass part two_(1) by Kalynn
Rated 87.2%, Read 22128 times, Posted Sun 2nd of June 2013
True Story , Transvestite -
DNA Chapter 4 by Zenythmon
Rated 87.2%, Read 47726 times, Posted Fri 26th of October 2007
Fantasy , Pregnant, Transgendered, Transsexual, Transvestite -
Sweet Pick Up by Regina10
Rated 87.1%, Read 24291 times, Posted Sun 3rd of May 2009
Fantasy , Transvestite -
I own you now! by aryalez
«Just a random encounter in a bar, like many other. Or maybe not.»
Rated 87%, Read 25578 times, Posted Sun 27th of December 2020
Fiction , Anal, Blowjob, Consensual Sex, Cum Swallowing, First Time, Oral Sex, Transgendered, Transsexual, Transvestite -
The Girl - Stories: Uncle Ben 5 by boardpin123
«The Girl gets an order to make her uncle fuck her. The problem is ... he likes boys.»
Rated 87%, Read 20379 times, Posted Mon 12th of July 2021
Fiction , Anal, Ass to mouth, Authoritarian, BDSM, Bondage and restriction, Domination/submission, Humiliation, Male/Teen Female, Older Male / Female, Role-playing, Slavery, Teen, Toys, Transvestite, Young -
MY NEW LADY AND HER FRIENDS. by CecilBCK
«I am Simon, a well-presented forty-year old divorced male in professional employment and I have just met a new lady.»
Rated 86.9%, Read 21858 times, Posted Mon 25th of October 2021
True Story , Ass to mouth, BDSM, Bi-sexual, Blowjob, Cheating, Consensual Sex, Cuckold, Cum Swallowing, Erotica, Exhibitionism, Extreme, Female exhibitionist, Group Sex, Hardcore, Lesbian, Masturbation, Oral Sex, Spanking, Threesome, Transvestite -
My Stepfather 2_(1) by Rutger5
Rated 86.8%, Read 59031 times, Posted Sun 9th of January 2011
Fiction , Anal, Domination/submission, Teen, 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 -
A story of my CD friend and I by biguy1984
«I tell the story of meeting my new crossdresser playmate and the time that he flipped the *********** on me.»
Rated 86.7%, Read 10944 times, Posted Wed 2nd of June 2021
True Story , Anal, Asian, Consensual Sex, Gay, Oral Sex, Transvestite -
MARRIED COUPLE DISCOVER TRANNY SEX by CecilBCK
«I am Allie, I want to tell you about how my husband and I had sex with with a drop, dead, gorgeous tranny, something we had been fantasizing about for a while and fantasizing about for long enough to make it even more exciting for both of us.»
Rated 86.7%, Read 12339 times, Posted Thu 28th of March 2024
True Story , Ass to mouth, Ass to pussy, Bi-sexual, Blowjob, Consensual Sex, Cuckold, Erotica, Exhibitionism, Hardcore, Masturbation, Oral Sex, Transvestite, Voyeurism, Written by women -
sissyboy jake's first outing - part 1_(0) by culotte.de.dentelle
Rated 86.7%, Read 20178 times, Posted Fri 28th of June 2013
Fiction , Anal, Domination/submission, Humiliation, Oral Sex, 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 -
Friday night crossdressing fun part two by Lisa's panties
«A continuation. Having fun at a friend's house while I'm dressed in woman's clothing and caged in chastity.»
Rated 86.6%, Read 11016 times, Posted Sun 8th of January 2023
Fantasy , Anal, Blowjob, Cum Swallowing, Gay, Transvestite -
Symone's gang bang by paddler20
«A young man is dressed as a young woman by a group of women and sent to satisfy a group of young men.»
Rated 86.6%, Read 12963 times, Posted Fri 7th of February 2025
True Story , Anal, Bi-sexual, Blowjob, Consensual Sex, Cum Swallowing, Female Domination, Group Sex, Interracial, Transvestite -
Making my slut fantasies become real by pinkybrown666
«TS Mistress puts her weekend CD sissy slut to work placing ads and making sure she is fully used by men, women, trans and groups getting her higher and higher which makers her sluttier and sluttier.»
Rated 86.4%, Read 17994 times, Posted Sat 15th of May 2021
Fantasy , Bi-sexual, Cum Swallowing, Drug, Erotica, Female Domination, Group Sex, Interracial, Mind Control, Oral Sex, Prostitution, Threesome, Transsexual, Transvestite -
My changing fortunes - 04 by Luvagobfull
Rated 86.4%, Read 27486 times, Posted Wed 2nd of November 2011
Fiction , Anal, Blowjob, Coercion, 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 86.4%, Read 25926 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 -
Cumming up Trumps Part 5 by Fisher King
«Trump hunts Manning down to an exhibition of cricket»
Rated 86.4%, Read 13842 times, Posted Sat 23rd of April 2016
Fiction , Anal, Ass to mouth, Authoritarian, Bi-sexual, Blowjob, Consensual Sex, Cum Swallowing, Erotica, Gay, Lesbian, Masturbation, Oral Sex, Transvestite, Water Sports/Pissing -
hotel hookup by iminhose
Rated 86.4%, Read 26616 times, Posted Tue 7th of February 2012
True Story , Gay, Transvestite -
MORGANA AND RAELINE by CecilBCK
«My lady Morgana and me both have a high sex drive and thrive on sexual excitement. We are both in our late thirties, attractive business professionals, sexually sophisticated, and gender fluid, bi-sexual.»
Rated 86.2%, Read 4599 times, Posted Tue 20th of May 2025
True Story , Ass to mouth, Bi-sexual, Blowjob, Erotica, Exhibitionism, Female/Female, Group Sex, Hardcore, Lesbian, Male / Older Female, Oral Sex, Transvestite, Voyeurism -
The Sissygasm Bet by Loupy
«A sissy has arranged to finally lose her cherry to a sexy older man she met online, and they have agreed to a little bet.»
Rated 86.2%, Read 24756 times, Posted Wed 29th of January 2025
Fiction , Anal, Authoritarian, Blowjob, Consensual Sex, First Time, Gay, Transsexual, Transvestite, Virginity, Young -
My First Time!_(3) by Eonasha
«Thanks for reading my first story!»
Rated 86.2%, Read 54744 times, Posted Sat 26th of November 2016
True Story , Anal, Asian, Blowjob, Boy / Boy, Consensual Sex, First Time, Gay, Teen Male / Teen Male, Transgendered, Transsexual, Transvestite -
My First Time by michelle6969
Rated 86.1%, Read 28755 times, Posted Thu 21st of November 2013
True Story , Transvestite -
Camming Down the Rabbit Hole Ch.12 by Dani_does_Dallas
«It’s all getting messy for our cam gurl, being pulled in so many directions, but a decision must be made. how will he/she come to a conclusion?»
Rated 86.1%, Read 12825 times, Posted Thu 5th of May 2022
Fiction , Bi-sexual, Blowjob, Cum Swallowing, Masturbation, Transgendered, Transsexual, Transvestite -
Camming Down the Rabbit Hole Ch10 by Dani_does_Dallas
«My continued journey into the crossdressing cam world. A gift arrives, that takes me to new heights but at what cost.»
Rated 85.8%, Read 15849 times, Posted Sun 10th of April 2022
Fiction , Cum Swallowing, Exhibitionism, Masturbation, Pegging, Transgendered, Transsexual, 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 -
t-girl girlfriend by caryli
Rated 85.7%, Read 64032 times, Posted Mon 17th of March 2014
True Story , Bi-sexual, Transgendered, Transsexual, 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 25608 times, Posted Sat 15th of July 2017
Fiction , Anal, Interracial, Oral Sex, Transvestite