Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

My Brother, My Sister Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

I wrote this story originally under the title "Be Careful In the Park" about an older crossdresser who meets a street gang in a park and gets more than she bargained for. There was no incest in the original version. I like this version better as it includes all my peccadillos: incest, crossdressing, nylon fetish, and forced sex. A warning to those who find t...

The Private Transvestite Detective

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

The Private Transvestite Detective (Or The Undercover Dick) With apologies to the writers of the various movies from which I borrowed some inspiration (and a few good lines). Chapter One It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated m...

I should have Kept My Mouth Shut

by submissiveanne on Jan 28, 2019
Transgender & Crossdressers

This is a story that takes place years after the events of "Ramona Changed Me". *** Sometimes I have a big mouth and don't know when to not say something. This got me into trouble. I was 26, this was like 2005 and working at a job where I was assisting in the repair of plumbing damages. A vendor or someone goes into work on a home, they damage the sprinkl...

Lost My Cherry To A Tranny

by 7yearsitched on Sep 13, 2017
Transsexuals & Crossdressers

Well as you may have read, I got my first official facial that was big enough for me to get my first true taste of cum. And something that was not part of any plan that evening. I got barebacked by nice sized black cock in the process. The the first two were what I wanted and the third was still only a fantasy, but when I found myself sucking some strang...

How I Became A Filthy Tranny Slave Ch. 02

by beyondkink on Sep 13, 2017
Fetish

This is the continuation of the story "How I became a Filthy Tranny Slave" where a young man who lives out his fantasy of dressings as a transvestite and being defiled is abducted Ch. 02: Tranny Slave Is Imprisoned When I woke up from my drug induced coma it took a few minutes to adjust and analyze my new setting. It feels like I had been out for days, pos...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...

Tranny Night Out and One Kinky Session

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends. I knew something was wrong but never worked out what it was till one evening whilst dating a girl named Becky I had met on an online dati...

G Is for Gemma

by BethanyJ on Sep 14, 2017
Transsexuals & Crossdressers

*** Stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It all really started on a Monday. One bright sunny Monday, early summer, an unusually warm day for June in England. And it really was stupid thing to do. Sun-bathing in a bikini in my back garden, that is. I'd o...

The Virgin Tranny & the Bride Ch. 06

by yano on Sep 25, 2017
Transsexuals & Crossdressers

WOW!!! As I rewrote this episode the sheer sexiness of the occasion was so powerful. Another episode from Roberta before he went off to California on vacation. The following week was fraught with difficulties, none more so than my inability to contact Jodie. Calling her mobile on my way to and from college was always met by the message that it was switched...

Tranny Chasers: Bernie and Ron

by 1946EW on Sep 12, 2017
Transsexuals & Crossdressers

Bernie looked around as he entered the Cavalier d'Eon, checking out the patrons. Spying his friend Ron, he worked his way over to him. Ron was sitting at the bar, back to it, also checking out the patrons. "How's it hanging, Ron boy," Bernie asked, easing between Ron and the guy sitting next to him. "Low as usual, Bern," Ron replied, turning to his beer on...