Sissy Fired Stories

33,497 results
Orientation
Length
Source
Infinite Scroll

Phone call interrupted Pt. 01

by ambise on Mar 2, 2020
Toys & Masturbation

Steve had enjoyed a rather extended evening pub crawl after work, and was relieved that Jill was not home when he staggered in. Rather than wait-up and watch some late night talking-heads debate on TV, he thought it more prudent, if not diplomatic, to retire to the spare bedroom. After undressing, he retrieved his laptop from the study and lay down, or rat...

A Model for CC's

by Fibaro on Oct 5, 2020
Transgender & Crossdressers

(This story was requested by one of my readers. This is a stand alone story, but reading "Neighbourhood Terror to Sissy" first is advised as this story takes place in the same universe.) Intro Victor was just a regular guy down on his luck. A month ago he still had it all, a beautiful girlfriend, a nice apartment and a decent paying job working for an acco...

Casey's Submissive Journey Pt. 12

by corduroysissy on Jul 31, 2018
Transsexuals & Crossdressers

Mistress Maxi -- Part 1 Maxine Montgomery was sixty-four years old, five-foot seven-inches tall, and one hundred and forty pounds. She was an attractively handsome woman whose looks and demeanor were very similar to the character Katherine Chancellor on the soap opera The Young and the Restless. "Distinguished" was a very good adjective for Maxine, "arrogan...

Sissy Awakening Ch. 02

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- A Sissies Choices - It was sometime in the middle of the night I woke cold, just laying on top of the covers I realized I was hungry as hell too. Still wearing the clothes they had put me in when I left the spa, I wrapped a blanket around my shoulders and headed for the kitchen. Standing there hungry but not wanting to really make anything I saw the jar...

Cuckold Chronicles: Todd

by deltonaman2man on Sep 15, 2017
BDSM

Lord, how I hate Monday mornings! A wise man once said," Monday morning is a shitty way to spend one seventh of your life". I believe it. Of course I feel that way about the other 4 days of the work week as well. It's not like I have to get dressed and go to work, mind you. It's just that after getting to sleep in for 2 days, I don't want to leave that warm...

Eve Quest

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Master's Degree in Crossdressing Ch. 01

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

This series is the follow up to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making confessions to the public for the first time, my wife has generally been aware o...

Sailor Moon Ch. 02

by embarrassednakedmale on Feb 3, 2020
Transgender & Crossdressers

The alarm had been buzzing for a solid two minutes when a bleary-eyed Scott finally rolled over and slammed his hand down on the offending device. The harsh noise ceased immediately, and Scott groaned as he rolled back again and cautiously stared at the ceiling. It was still dark in his bedroom, although a single beam of light cut through a tiny gap in his...