Sissy Prostitute Stories

12,544 results
Orientation
Length
Source
Infinite Scroll

Brad's Return Ch. 01

by grizzley123 on Sep 29, 2020
Loving Wives

Brad's Return, Chapter 1 ****************************************************** This is a continuation of the "Brad's Suggestion" stories I wrote a while back. It has similar cuckold and bisexuality themes, along with some lesbian and light BDSM fun thrown in. It emerged from my never-ending desire to put off the real work I should be doing. I hope you enj...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

Open in Reader

His Online Presence

by justincbenedict on Sep 23, 2019
BDSM

Norma Fishbein turned on her computer...and yes, look who was waiting! Norma shook back her long ash blonde hair, refreshed her lip plumper and became Mistress Merlyn. Crackers's webcam opened, and there he was, looking somewhat hopeful. Naked, and look at that frustrated dong. What Merlyn loved about Crackers was, he was an honor system guy who actually w...

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...

Sexual Harassment Ch. 02

by Cute Little Thing on Sep 18, 2017
Fetish

My instructions were explicit. I was to go home for the weekend and prepare myself for Mr. Anderson on Monday. I was to remove all obvious traces of my masculinity 'excluding your faggot sissy-stick of course' in order to prepare myself to be his fuck toy. This meant shaving my body hair, clipping and painting my nails, sanding my calluses, and waxing my eye...

Jesse's Journey Down a Rabbit Hole Ch. 10

by Rebeccasm on Sep 19, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccasm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to t...

A Loving Wife's Story Ch. 02

by diagones on Sep 11, 2017
Loving Wives

During the days that followed I felt an odd buoyant happiness. I could not get that night of our fantasy sharing out of my mind. Such a powerful experience! So new and exciting! Something that came from a round the curve view of a now seedy motel on a hill side. A view I had countless times over recent years, which never triggered a thought of Ken my mature...

Candi's Conversion Ch. 04

by CandiCumminz on Oct 24, 2018
Transgender & Crossdressers

It was early afternoon when we pulled up at the mall. Mistress Luna had me drape myself sluttily over her car while she took some photos for my Instagram. I was still dressed as a sissy bimbo doll, having been styled by Crystal, a much more experienced sissy in servitude to another dominant, Goddess Furia. Mistress had given me a lollipop to wrap my glos...

Adult Arcade Sissy

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

Dwayne started hanging out with us when I was 18. He was older than us - 28 - but he came across as someone our age. Because he was older a lot of us guys sort of hero- worshipped him - me included. So naturally I was flattered when he began to spend a lot of attention on me in particular. The guys I hung out with were a little wary of Dwayne, because he w...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...