Sissy Whore Stories

50,992 results
Orientation
Length
Source
Infinite Scroll

A Sissy's Joy in Being Fucked

by MissDeeLiscious on Sep 16, 2017
Transsexuals & Crossdressers

We were in the back room of our local drag club, "Miss Thing's", a very special place where only the seasoned and initiated drag queens and sissies are allowed after hours when the queens have finished performing. As one might imagine putting on an erotic performance going as far as the law will allow all painted up in all their glory makes them aroused in d...

The Prostate Exam Pt. 06

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

"Just as it should be, now walk to quickly to the Langham hotel. Make sure you keep the bag out in full view, for all to see, it cannot go in your back pack. I want anyone who sees you to know what a slut you are.." "Go straight to the bar and order a triple G&T and 3 shots of good tequila. If the bar man asks you what you're doing you will tell him that yo...

Girl's Night Pt. 10

by DifferentBreed on Sep 14, 2017
Fetish

This story contains adult fetish themes between consenting adults that may be upsetting for some readers. There are also scenes with vulgar language that some may find offensive. Please proceed with caution. ~ thank you for your patience ~ The sleek black towncar maneuvered through the downtown streets, the darkly tinted windows giving no hint to the passe...

The Sissy Diaries Ch. 1

by colettegrrl on Aug 18, 2017
Fetish

This is a story about my new life, my new way of being. I wanted to share my story so I started to record my events. I figured the best place to start was, well the beginning. Here's how it all started. * * * * * I come home to find you sitting at the dining room table, laughing and drinking with a tall, dark, well-built and handsome black man. You introdu...

Chrissy the Sissy

by Ide32 on Sep 14, 2017
Transsexuals & Crossdressers

Part 1 The Bank Job Chris or Chrissy as he calls himself has the job of his dreams, he works at a sperm bank for futas. His job is to dispose of samples that are non-viable, low sperm count etc. All day long he dreams about the creamy, yummy cum from futas waiting for him to dispose of it. While he is supposed to put it down the sink, he has a preferred met...

Discovering Mistress Sarah's World Pt. 02

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!" "I think someone is excited to see you," laughed Mistres...

From Her Ex-Boss to her Bitch Pt. 06

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. ***** It had...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...

Pizza Delivery

by Spango on Sep 24, 2019
Transgender & Crossdressers

I could not believe that I was actually going to do it. I had been fantasizing about it for months. I was not really sure where I got the idea, but I had been watching a lot of sissy hypnosis videos online over the past few months, hoping to help release my inner girly girl, and perhaps the idea came from a scene in one of those videos. Anyway, it does not m...

Mistress Commands Me in the Office Pt. 03

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

First a little clarification, if you've been reading parts one and two (I hadn't kept this quite straight up to this point). Here are the correct character names: Bob, or Robert, or Dick (or whatever my mistress decides to call me): Me Rick: My boss Brad: An office co-worker Rod: Office co-worker in an adjacent cubical, very buff, quite manly Wilson: Of...