Sissy Pornstar Stories

7,967 results
Orientation
Length
Source
Infinite Scroll

My Wife Is The Boss

by Laurasbitch on Sep 17, 2017
Loving Wives

Laura is my goddess! At home she is a great wife and helps me out in every way. In the bedroom, she's ruthless. She talks to me as if I'm insignificant, and I love it. I shake I'm so excited. She confessed her bi-sexuality years ago, so I let loose with my fantasies and she obliges. Laura is in her early 30's, D cup and thick where she needs to be. She's b...

A Little Bit Feminine

by ThatGuyMan on May 12, 2020
Transgender & Crossdressers

"Are you sure I can't help?" The reply was cut short by the sound of Jason retching once again. The sound came from their bathroom at the end of the bed, where it had for the last five minutes. Tammy leaned up in bed, concern on her face, as she made to kick the sheets off and go help her husband. Jason, ears like a hawk despite currently revisiting last n...

The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

Becoming Sarah Pt. 01

by sissy_sarah_09 on Jul 31, 2019
Transgender & Crossdressers

I used to write these on Tumblr, now on Fetlife, so I have a few to post quickly, then I'll be adding new ones as I write them * Walking up the drive from work, I put the key in the door and pulled the post from the inside of the door. It had been a long day, but it was finally the weekend and I was ready to relax. I always got home before my wife, Katie,...

Girl's Night Pt. 04

by DifferentBreed on Sep 14, 2017
Fetish

"You want to cum too, don't you bitch?" Sophie said. "But pleasure is only reserved for Mistresses and Dommes. Not sissy whores like you." Sophie looked down at him, grinning evilly, turned on by the lips descending her body and the sight of him kneeling there in sexual servitude and agony. She let her hand fall lightly on the back of Jenny's head as she fel...

Black Femdom POV (Takeesha) Ch. 01

by Dunn81 on Sep 12, 2018
Fetish

This is new for me; I'm going to write a story into the Black Dom POV. We'll see how it goes. I hope you enjoy and again, I can't please anyone but I know I've got lots of readers so thanks for your message. I really enjoy it and enjoy your recommendations and idea of how you would proceed with one story in particular. After this one, I'll stop creating new...

Caught in a New Life Pt. 01

by Fibaro on Apr 20, 2020
Transgender & Crossdressers

(Hello everyone, this is a story that has been written for a very special reader of mine.) Intro Monroe Smith had everything pretty well figured out for himself. He was 43, his hair was brown and slightly greying, but his hairline hadn't really receded thanks to the hair implants he had done about a year back. He had never been a big guy when it came to mu...

Neighbourhood Terror to Sissy Pt. 18

by Fibaro on Mar 10, 2020
Transgender & Crossdressers

Chapter 20 Marcy had a wonderful night's sleep while she didn't realise it, the only reason she had a quiet night was because Lisa had demanded it. What he also didn't realise was that while he was sleeping peacefully John was setting up a website, turning him into a real pornstar. Once it was online John hoped he would make a good amount of money off his s...