Trans Surprise Stories

136,543 results
Orientation
Length
Source
Infinite Scroll

The Dream Slut Chronicles

by Robopoop on Feb 20, 2017
Science Fiction

After a long day at work, you manage to complete your night time routines to crawl onto to bed. Tired from the day's events, you fall into a deep slumber the moment you rest your head on your pillow, drifting off to slowly fall into gestalt lands of endless possibilities both familiar and unknown. Either through some hidden carnal erotic coding deep within y...

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Writing Healthy Relationships

by yumeko on Sep 16, 2017
Reviews & Essays

I love written pornography. From the time I first discovered the written pornography in magazines when I was young, the written word has always been my favourite way to get off. And perhaps that should have been a clue to me, because I found out later that supposedly boys and men prefer visual material, but at the time I didn't much care. I only cared that r...

From a Husband to a Dutiful Sissy Ch. 15

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Fifteen: A Big Decision and Telling Mikel. Helen and I are dressed and ready to go to the ladies gym for a morning workout. I love this and dressing in my girlie workout clothes. Today I am going all black, a black leotard, black tights and black ladies shorts. I am going to contrast with my bright pink trainers. My now comfy long, just below my sho...

Lost Empire Ch. 44

by Pars001 on Sep 18, 2017
Non-Erotic

Ship # - name - prime 0001 - Tempro 0003 - Conner 0097 - Ace - Zimmel 0098 - Lucy 0101 - Shelby (mother ship) - Derrick 0125 - Lars 0200 - Ellen 0301 - Rodrick 0403 - Johnathon 0667 - Marco - Brown 0778 - Jan 0798 - Celeste - Shelby (human) 0908 - Tara - Mara 0999 - Zan 1000 - Sherry - Lucie (for the moment) Derrick calmly reached into his po...

How to Write Realistic Transsexual Characters

by TGirlNerd on Sep 1, 2017
How To

Table of Contents [1] Introduction: [2] Who are transsexuals? [3] Who are cross-dressers and transvestites? [4] What are cross-dressers and transvestites like? [5] How can I relate to my transsexual characters and get into their heads? [6] What terminology should I use? [7] What terminology should I avoid? [8.1] What do trans women look like naked?...

Butterfly

by NeoRisa on May 15, 2019
Transgender & Crossdressers

A/N: For all my struggling trans girls, I wrote this one for you. Keep on keepin' on, I believe in you! *** Waking up in the morning was the worst. Carla had known better than to take morning classes- this was her third year now, she was too mature for rookie mistakes like that- but fuck, she was not a morning person. Even though it couldn't have been mu...

Coming to Terms with It

by RexKitty on Apr 1, 2020
Fetish

Note: This writing contains scat, piss, and (because this is relevant and about my personal experience) is related to being transgender. If this isn't your cup of tea, no problem! It won't hurt to skip over this one. I briefly cover something that may trigger dysphoria in trans men. Also, this is my first post here (and first sex themed piece of writing in g...

Dakota's Surprise Pt. 03

by mfan2112 on Oct 5, 2020
Transgender & Crossdressers

Dear Readers, I hope you enjoy this piece. If you like it, please check out my other works. By the way, the dictionary defines a chapter as: a main division of a book, treatise, or the like, usually bearing a number or title or an important portion or division of anything. So, dear reader, if you have not read the first two chapters yet, what is stop...

Hung Trans Lesbians Fuck Two Ladyboys

by mrstanley on Jul 15, 2020
Transgender & Crossdressers

I haven't written a Trans story this year. In this story I try to describe more intimate intense scenarios with a wider variety of details. If you enjoy the story please vote and comment. Feel free to read my Fetish and Mature stories as well. Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, A...

Room for Mickie Ch. 04

by griffin57 on Sep 19, 2017
Transsexuals & Crossdressers

Well, I had to admit that could have gone better. Mickie and I were going to reveal to my parents that she was transgender, but my brother Ted discovered it before we ever had a chance to explain, and 'outed' her with a rather nasty homophobic rant. Mickie left the cabin crying and I was about to open a can of whoop ass on my brother, but my Dad intervened a...