Sissy Pornstar Stories

7,967 results
Orientation
Length
Source
Infinite Scroll

Afro Stress Relief Ch. 08

by llts1970 on Nov 11, 2019
Transgender & Crossdressers

It was Monday evening, again, and I hurried home from work to get ready for my shift at 'Babes With Asstitude' (BWA). My new Afro-boyfriend, Drake, rang to chat about our new venture as soon-to-be Brothel-keepers and tell me not to work 'too hard' on my shift as a whore at Drake's uncle, Leroy's, place, BWAs! Drake wanted to come over but I said I wouldn't b...

Girl's Night Pt. 07

by DifferentBreed on Sep 14, 2017
Fetish

This a continuation from an earlier story. It contains fetish themes of forced feminization, public humiliation and other erotic themes that may not be to everyone's taste. If you enjoy these, please read on and leave comments as to how you'd like the story to evolve or what you like. Enjoy. - DB ***** Fisher slid across the passenger seat of his Jeep, man...

Spence The Pornstar Ch. 01

by DickThePimp on Dec 3, 2018
Celebrities & Fan Fiction

This is a perverted sleazy fucktastic parody series... It ain't real Stars Of This Story : James (Me) Kim Kardashian (Herself) Beyonce (Herself) Spence (Spence Ulchin Of The Sitcom King Of Queens) Professor Gaia (Herself) Christy Canyon (Herself) "Babe, will you and Beyonce please go to the Adult Convention in San Diego with Spence and try to help...

Date a pornstar

by pipster2927 on Feb 23, 2019
Amateur

Please add to this story if you want to. I will add whenever I have inspiration. Thanks. EDIT: This story takes place in an alternate universe in 2020 and therefore all main characters are 18 years or older. You are John Smith. You have just received an email from Pornstar Services congratulating you on winning a date with a pornstar. The email reads: Dear J...

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A Frustrated Wife Ch. 03

by skadoo on Sep 12, 2017
Loving Wives

I'm glad many of you have enjoyed the adventures of Stacy so far, and I greatly appreciate all the feedback that I have received so far. What I would love to get in the form of feedback is to tell me how you want the story to continue, what you like or don't like. I would love a little more detail to your feedback, it would both help my writing and help deve...

A Frustrated Wife Ch. 04

by skadoo on Sep 12, 2017
Group Sex

This is the fourth chapter in the series, hopefully you have read the previous other chapters, if not then do it NOW! Just kidding. It would help you to read the previous other chapters to get the back story on Stacy and the rest of the characters. I hope this new chapter will not disappoint. So please read, enjoy, and as always give me your feedback. Stacy...

Spence The Wannabe Pornstar

by DickThePimp on Jul 6, 2020
Celebrities & Fan Fiction

Spence The Wannabe Pornstar By : DickThePimp A short story about Spence, Carrie, Kelly... and Doug's mom Janet... from the sitcom King Of Queens Cast : Spence Ulchin (Patton Oswalt) Carrie Heffernan (Leah Remini) Kelly Palmer (Merrin Dungey) And Janet Heffernan (Jenny O'Hara) "Carrie, can I talk to you for a minute?" "Make it quick, Spence. I've go...

You're Like a Little Boy at Times Ch. 05

by Myneed on Oct 13, 2017
Fetish

This is a slightly twisted femdom love story of James and Mel, his Mistress. It will make most sense if the chapters are read in order. In the last chapter, Mel's boyfriend, Tim, left the costume party with Tiffany. Mel made James, who is dressed as a girl, cum in public. I hope you are enjoying the series. All characters are over 18. ***** The party co...

A New Adventure... Ch. 03

by johnjinglez1 on Jun 19, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. About a month had gone by since my last little encounter with a CD; I'd been on some dates and had some things lined up but nothing was looking too promising. One night while I w...

Detective Pornstar Ch. 06: Babee Driver

by SZENSEI on Nov 19, 2018
Exhibitionist & Voyeur

"Oh Come on!" Calliope Cruz was worn out enough without fighting a vending machine this early in the morning. All she wanted was a cream cheese danish. Having been snuck in the back entrance not many of the morning shift Officers were here yet. The lingering night shift busy finalizing their own night of reports. This gave her time for breakfast before sta...