Sissy Pornstar Stories

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Orientation
Length
Source
Infinite Scroll

Big U Pride Ch. 02: Going Deeper

by latinarita4 on Jun 2, 2020
Transgender & Crossdressers

Please read Chapter 1 to get the full experience and context! This chapter owes a lot to the SissifyYourself and SissyFactory content. You should check them both out! I also owe a lot to Drogon's hypno videos! ***** The 90-foot yacht cruised down the placid clear blue waters, making its lazy way past sun-specked islands. The Mediterranean waters were par...

Fantasy to Reality Ch. 02

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness My mind was pulsating from the excitement of a glorious dream, it involved a sissy kneeling subservient at the feet of her master, a single drop of cum dripped from her bottom lip and landed in the small puddle on the floor. The sissy's eyes looked up at the recently serviced glistening cock, thick and bulging from the hu...

Futa Island

by Kazza on Nov 18, 2019
Transsexual

This story is designed to be played as an interactive erotic adventure. For the best reading experience, please select the 'start game' button over on the right of the screen --> Futa Island was considered a myth for decades, a tall tale whispered amongst tipsy sailors in the dark corners of port taverns. The rumors spoke of a hidden island filled with...

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One of the Girls

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and the transsexual/cross-dressers niche. This is my first attempt at a story so go easy. ***** I couldn't believe my situation. I had signed up for porn, but I had not signed up for this. I was standing naked in the dressing room and the c...

The Wish of a Submissive Older Brother

by SubmissiveJosh on Dec 20, 2018
Fetish

Hello people, this is my first story, I am not a native English speaker, so the first chapters might have some mistakes. This was already posted up to chapter 14 in other sites so I am just porting the story over to the Chyoa format. I would like as much feedback as possible. Don't be afraid to lay hard on me what you think and how bad my writing is! I would...

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Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

Big U Pride Ch. 03: The Squad Forms

by latinarita4 on Jul 27, 2020
Transgender & Crossdressers

Remember to check on parts 1 and 2 before you read this! Also, please rate and review my stories! I love hearing feedback from readers! If you have suggestions, just send them right along! Maybe your suggestion will be featured in a future chapter... ________________ Most days at the campus health center were typically light affairs. Usually it's the rout...

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

Sam's Story Pt. 08

by Shadykingcolor on Jan 29, 2020
Fetish

As Mel and Steph leave the room only my caged cock is on my mind. It's burning like mad and balls are in agony from the cage. I try to massage my balls where the base ring is applying the most pressure. But having no joy. I get off of the bed, maybe a shower will help. I think to myself. As I start to leave the room I noticed a dildo on the floor. It mus...

Chrissy Gets Caught

by femininechrissy on Sep 18, 2017
Transsexuals & Crossdressers

I don't even know where to start. I've been cross dressing ever since I was a young girl, I mean boy. I have always been jealous of women. They get to wear the prettiest clothes. They get to wear makeup and make themselves look beautiful, as if they weren't born beautiful already. I have loved wearing panties and bras and dresses and makeup for as long as I...