Trans Surprise Stories

136,543 results
Orientation
Length
Source
Infinite Scroll

Sin

by KallieHF on Feb 6, 2018
Transsexuals & Crossdressers

She wouldn't cry again, Ji-Ha told herself, as she walked hurriedly down the dark, deserted, snow-covered street. Huddled in her oversized coat, she was hurrying to keep warm, not because she was going somewhere. She had nowhere to go. Nowhere at all. But she wouldn't cry. She had shed enough tears tonight. Enough for a lifetime. She wasn't going to shed an...

Chasing Waves Ch. 04

by dourdan on Feb 26, 2019
Transgender & Crossdressers

Ten years later; Msgt Diego Quinto's life was a barrage of bullets, deployments, violent arguments with his wife, and chemo- a seemingly endless round of chemo for his, now thirteen-year-old, son Cam. His only light was his little daughter, five-year-old Jenessa. (His wife called her Jenny, but to him, she was Jen.) Little Jen lived as an organ and tissue do...

Christmas Ewe

by Karinie on Dec 24, 2019
Transgender & Crossdressers

Please be aware that this story includes animal transformation, furry elements, and two lovely trans ladies. Please enjoy! ~ "Th-th-there!" The last batch of cookies finally came out of the oven. A dozen sugary brown circles sat on the undersized baking sheet, and to Amber's relief, none of them had accidentally expanded into another one and fused togeth...

My First Trans Woman

by Indianaboy6555 on Sep 23, 2019
First Time

One of my favorite fantasies has always been shemales. I kept it a secret for a long time, but finally I had to explore it. I loved the videos I saw. Long hair, big tits, feminine features and a hard cock. I used to joke that they were the best of both worlds. I never pursued any though. They remained a secret fantasy until eventually I basically forgot ab...

Jaime and Mike Pt. 01

by LadyMelodyDarkheart on Nov 20, 2018
Transgender & Crossdressers

This is my first story but not my last. More to come in this saga. *** It was 3 days before Halloween, and as usual, being a chef, I was going to have to work that night. Fortunately, there was a party this evening at a local club and I was set to go. I had found an old tux with tails in a second hand shop and after I'd done my sugar skull make up, I was...

Diva Las Vegas Pt. 01

by tgirl_Mary on Sep 12, 2017
Transsexuals & Crossdressers

My wife Rona was sitting on the sofa with her popcorn as I finished up the supper dishes. "Hal! Hurry up Hal, it's about to start," my excited wife beckoned. "One second honey. I'm almost finished," I answered while putting away the last plate. My twenty-six year old bride of three years had a tendency to get intense when her favorite show came on TV. She w...

The Sub Club: Buffet Night

by TheWolfNose on Dec 17, 2018
BDSM

The Hostess' smile radiated a sort of vulpine cleverness, with teeth so white they were on the verge of inventing a new color for them, called Pristine Truth. He'd heard of her, of course; it was said her beauty was etched onto the mind of every person who entered The Club, and if you were lucky, she forced you to your knees to worship her. He hoped he would...

The New Lodger Ch. 02

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

For some weeks Marc and me constantly headed up the town on the pull for guys mostly but to my surprise Marc had been interested in my Trans partner and how we met and of course my other Trans friends that were always out and about in the pubs and clubs of our home town. It wasn't until late one night after a drinking session with friends and no sign of a s...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

Leftovers

by LittleBrain on Dec 3, 2019
Romance

I decided to put this in its correct category. Chapter 1 At the age of nearly 30 I would have preferred not to bring a stranger into my house to live on a semi-permanent basis but unfortunately it was a case of 'needs must'. My ex-girlfriend (I would like to point out that she was not 'ex' at the time that we did the deed as that would have been too stupi...