Sissy Pornstar Stories

7,967 results
Orientation
Length
Source
Infinite Scroll

Sissy Gets His Wish

by Tinydickthongboy88 on Sep 18, 2017
Transsexuals & Crossdressers

I should've guessed something was up when my boss Victoria winked at me on our way into the office. She's about 5'9", 130lbs, she just got a boob job last winter, and as she walks by her ass bounces in the sexiest way I've ever seen. Work started normal enough. Our company was in the testing phase of software for a military application. I wasn't clear on i...

Camp Queerbait

by GoddessCompels on Sep 28, 2020
BDSM

The camp counselor uniform piqued her interest. Jessica had stopped for gas along a lonely road, and decided to enter the convenience store to get food for the last leg of her journey after filling up. She spotted him immediately upon entering. She hadn't ever seen shorts that short or tight, at least on a man. The knee high, striped socks and running shoes...

Michelle My Hotwife Ch. 02

by KINKYCanada on Sep 13, 2017
Group Sex

When I awoke the next day, I was amazed at how relaxed I was. I looked over at Michelle and saw that she was sleeping soundly, as she usually was as I got up three hours before her most days. In the shower, I jerked myself to one of the best finishes ever. I had a hard on all the while I ate breakfast and made my lunch. I went and got dressed and looked at m...

Marilyn: Going Your Way

by BrettLynn on Sep 13, 2017
Transsexuals & Crossdressers

Welcome to the latest installment of my tales of pure, unadulterated lust. Wait a sec, I’ve just adulterated it. Oh well. I’ll keep it short and sweet. After all, I have enough problems with people bashing my work. No disclaimers. If you don’t have the good sense to realize that this my work, and that if you’re gonna make money off of it, it is my legal righ...

Portlandia Episode: Racquel Darrian

by Deckard6969 on Sep 17, 2017
Celebrities & Fan Fiction

50's retro-diner: Racquel Darrian is alone at a table looking around for her date that is apparently running several minutes late. She is wearing a white latex mini-skirt with matching knee-high boots and a black jacket. Her brunette hair is streaked with blonde and she is wearing her famous gold hoop earrings. In other words --incredible. Carrie and Fred ar...

Mindy Main's Traffic Stop

by maniaxxxe on Sep 14, 2017
Celebrities & Fan Fiction

Mindy Main was happy, and it wasn't just because half an 8- ball had found its way up her nose this afternoon. She was finally quitting the porn business once and for all. Like most women she had gone from being a stripper to a sometime hooker right to taking hard cock on film. The transition had been both seamless and degrading. Now she was getting married,...

Big Book of Wrestling Babes Ch. 05

by daxg2001 on Jun 8, 2020
Celebrities & Fan Fiction

WARNING: The following is a work of erotic fan fiction. The events of which are completely made up and did not happen, and is no true reflection of the characters, promotions, wrestlers, events etc depicted or referenced within. Fantasy is legal. This material is unsuitable to be viewed by those under the legal age limit of viewing pornographic material in y...

Spectacular Spider-Man Vol. 01.1

by Thatguy12A on Sep 28, 2020
Celebrities & Fan Fiction

Disclaimer: All characters are 18 and up. Later Volumes And Issues Will Be Released In Time. Please Give Me Feedback, I'd Greatly Appreciate It. Spectacular Spider-Man Vol 1: In The Wake Of Tragedy Issue 1: So It Begins Part 1 PETER PARKER (Faceclaim: Josh Hutcherson) It was a rainy day for the city of New York with puddles being made in the streets...

Working Relationships: Jodi, Ch. 08

by insatiablerob8 on Dec 25, 2019
Group Sex

I was wearing running shorts and I guess it was impossible to miss the bulge. I remember thinking about spending the evening with Jo and Pete; what can I say...I got worked up. He grinned, "You know...I've seen a few impressive dicks, but the outline in those shorts is fucking pornstar, dude." "You know, in high school, I would sneak glances at this guy, i...

Alex Through The Pornoglass Ch. 01

by SirSinn on Sep 11, 2017
Sci-Fi & Fantasy

This is filed under Sci-Fi & Fantasy because it's set in an alternate world. It will, though, heavily feature incest, big tits and big dicks like most of my stuff. And, as always, everyone involved is at least 18. This is a direct sequel to my story Alex in Pornoland. † † † † † My name is Alex Taylor. I had an accident and woke up in a world where I was a...