Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

The Suitcase Ch. 01

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

Enjoy the story, more to come, as soon as I'm able. It all started when I was 25. After graduating with a 2:2 degree in English from Plymouth University, I'd moved to London and gotten a job as a journalist for the Evening Standard. The pay wasn't great, and I was making next to nothing after paying off my rent, travel and living costs. I certainly didn't...

Cockland Island Pt. 01

by Sissyhalo1 on Oct 8, 2019
Transgender & Crossdressers

It’s actually called Huntington Island. And it’s been around a long time and most of us in the area didn’t know much about it except they brought in guests and stuff by sea plane and set out for a lot of food and deliveries. I mean it was a mystery and not around town. Most people worked there from town ended up staying there because it was this private re...

The Suitcase Ch. 02

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

Part 2 is here! Hope you enjoy. More to follow ASAP. ***** I couldn't quite believe my situation. I was standing in my boss' office, wearing a camisole, a pair of pretty pink panties, suspender belt and stockings and he'd just cuffed my hands behind my back. I thought my clitty was going to explode, it was so hard! He ordered me to spin slowly and I compli...

Trip to LA Pt. 02

by gbr2004 on Mar 3, 2020
Fetish

This story is just a figment of my imagination and shouldn't be read if you aren't into forced fem, sexual service and discipline. Otherwise, I hope you enjoy the story and I love to hear comments about my writing. *** All I can think about is how out of control this all is. Here I am, in LA, god knows where, dressed up in pink and white and looking like...

Cockland Island Pt. 03

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I think my dreams that night were pleasant. I was kind of still just transforming back then. But when I woke up, I remember the feeling of my butt plug in my ass was pleasing and that my caged cock was perfectly sissy cute and I was good with that. It was kinda a trip to look in the mirror and see it all. And walking with the plug, sitting with the plug....

The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

A Visit to a Mistress

by fun4all6969 on Sep 19, 2017
Fetish

I have always craved humiliation ever since I was with a girl who humiliated me for my premature ejaculation and my small penis. I saw an ad online for a girl who loves submissive guys and we chatted back and forth for about 2 weeks before my business trip took me to where she lived. She told me it would be $250 for the domination session and that I had to p...

Nina Dresses me as a Girl

by Bakeboss on Sep 14, 2017
Transsexuals & Crossdressers

I cannot believe a whole year has passed but as I look at the calendar, I see Halloween is approaching and that is when it all started. The company my wife works for decided to have a costume party, well not the company, but my wife's boss decided. Nora was bugging me for costume ideas and I just told her I would wear any costume she decided on. You see that...

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...

The Booth in the Back

by mona215 on Sep 16, 2017
Transsexuals & Crossdressers

On my knees on the vinyl floor, the metal choke chain around my neck, one end of the chain under the pointed toe of her fuck-me heels, keeping me bent over so that my pantied ass is sticking up into the air. The sound of her crop slapping against my silky undies punctuating the mean things she says to me in a bored voice. "Real men don't wear girly panties...