Sissy Fired Stories

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Infinite Scroll

Sissy Serendipity

by minc_04 on Apr 22, 2025

The past few weeks have been the hardest you can recall in your life. The series of events were kicked off by losing your job. You were far from happy at work, but at least your paycheck came through each week. Without it, or any savings, your girlfriend agreed to let you stay with her. Rachel was surprisingly hesitant at first, however, claiming that you we...

Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...

Sissy: That Time of Year Again

by caprine on Sep 14, 2017
Erotic Couplings

[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. As such, the story may or may not totally conform to reality. All locations, events, and characters are entirely fictitious and any resemblance to actual persons, living or dead, is purely coincidental.] *****...

Sissy Construction Worker & Friend Ch. 02

by toontessa on Sep 2, 2017
Fetish

After the crazy fling with Todd, I began to live more and more like a woman. I was amazed at the way I would look at certain men and have an intense desire to suck them off, or my asshole would suddenly feel empty. And the way those clothes felt on me was incredible. How do women walk around dressed like that without having an orgasm every five minutes? I fe...

Surprised by Samantha

by Sissy_Desire on Mar 17, 2020
BDSM

A little kink can go a long way. This is something I tell myself while waiting on a special package. A couple of months ago, a site I've been browsing posted a huge sale for ready to ship versions of their custom products. Being able to hardly contain my excitement with little patience, I decided to do some yard work while awaiting the scheduled delivery....

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

A Sissy Shopping Trip Ch. 02

by cwsissy on Sep 16, 2017
Fetish

At the car, I headed for the driver's side as Cindy opened the passenger door. Before I could take more than the first step her almost shouted exclamation, "Excuse me!" stopped me in my tracks. I looking warily at her, wondering what was wrong. "Come on," she smiled tightly, "girls ride over here. I'll take care of the driving today." My macho pride rebelled...

The Diaper Sissy Project

by AlyssaDb on Apr 29, 2025

Jordan rolled over in bed and looked at his phone. It was 6 am; time for him to go to work at his fast food job. He hated this job and the way his life was going. He got out of bed, got ready and went to work. He made it on time and started his day. A few hours later, just before lunch, his boss called him into the office. "Hey Jordan, thank you for tal...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Ted and Lindy Ch. 01

by R410a on Oct 3, 2018
Interracial Love

This is not the standard boiler plate interracial story of black dominance or cuckolded sissy's. It is a romance between a white widower and a black girl from the ghetto. Thank you for all of the great comments I've received on other stories, I trust this will be to your liking as well. ***** As I stood in front of my dresser struggling to put in cufflink...