Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...

Cucky Trained by CD DOM Pt. 05

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

It was 9:00 am, Sunday morning. I let you sleep since you had a busy day yesterday. Today would be nothing like yesterday. Today was the day you were going to be presented to your owner, you used to call her your wife, and her bull. I was standing in your door when you woke up. Cup of coffee in my hand. I had been up for hours and was fully dressed and read...

Steve's First Adventure Pt. 02

by gbr2004 on Mar 26, 2019
Fetish

Total fantasy. Do not read if not into gay sex, domination and forced fem. ***** After that first experience, things didn't get too crazy like I was afraid they might. I did meet with Daddy several more times in the next couple months. There were more spankings as he taught me it was better to do as told, that if I resisted things would just get worse. He...

Steve to Stevie to ?? Ch. 07

by gbr2004 on Sep 13, 2017
Fetish

I had returned to work after my first nite with Ms Storm. The night she turned me from a young man to her slave. Ms Storm had came to my work place and had talked to my boss for a long time but I don't know what she told her but my boss, Ms Hunter, had talked to me like never before. Then I had been ordered to return to Ms Storm's house that night. Upon arri...

The Making of Davina Ch. 01

by Timewarp10 on Oct 31, 2018
Transgender & Crossdressers

It was 1966, England had won the World Cup! The swinging sixties were in full swing. David had started working in the sale's office of Telford Safety Engineering Ltd. He held the grand title of Assistant to the Sales Manager, which meant in reality he was the office boy; he ran errands and made the tea. At eighteen, it wasn't his first job. Since leaving sch...

Shades of Black

by lululuvsblack on Sep 16, 2017
Transsexuals & Crossdressers

My name is Luke, but you can call me Lulu, and my favorite color is black. Most people don't have a favorite color, not really, but I'm not most people, so believe me when I say I have a very strong attachment to black. Just let me take you through a typical day and you'll see what I mean. I wake up early, while the night sky is still black outside and get...

Black Cuckolding Journey Trois

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

Salutations, my friends and devoted readers. Wanda Philogene here. Your favorite Haitian dominatrix, taking the beautiful City of Brockton, Massachusetts, by storm. Ladies and gentlemen, I have some good news. I've dumped Sean Prescott, my favorite white dude, on account of him becoming possessive of me. Sean and I were cool, and we had some fantastic sex, b...

Abducted and Turned Out Ch. 04

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

I let the landlord in and he immediately pushed me over the arm of my sofa and yanked my skirt up and pulled my panties down. I moaned and purred while he plunged his cock in and out of my pussy, fucking me furiously for about 5 minutes until he filled me with a nice hot creamy load. Then, without a word, he zipped up and left. I stayed there for a couple o...

From Her Ex-Boss to her Bitch Pt. 04

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel his ex-employee, encouraged along the way, with a little titillation, a lot of flirting and confessions of her bisexuality. She'd used her submissive Claire to help...

Mistress Commands Me in the Office Pt. 04

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Continuing Cast of characters: Bob, or Robert, or Dick (or whatever Mistress decides to call me): Me Rick: My boss Brad: An office co-worker, loves to get on my case Sharon: A pretty co-worker Jim: another co-worker, very cocky and arrogant David: another co-worker, pretty suave, the women all like him Rod: Office co-worker in an adjacent cubical, ver...