Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

My Wife, My Boss, & I Ch. 03

by James Quiller on Sep 17, 2017
Loving Wives

The layoffs were announced on Friday morning and by the afternoon, three of the men I had started work with a year ago were gone forever. I think they were all quite surprised that I was still on the payroll. It certainly didn't make sense. I mean, what had I done to distinguish myself from them? But then, my wife had the given me an inside rail on the compe...

The Double D Ranch Ch. 02

by JDBones on Sep 15, 2017
Transsexuals & Crossdressers

Jeff Malville awoke slowly, moaning softly. He almost forgot where he was in that moment where sleep and being awake clashed. However, after that split second, it all came rushing back and he moaned in delight. He was a captive on the Double D Ranch, and even though he was considered an employee, the only thing that he'd come to be good for was a sex slave...

The Gynecomastia Kid Ch. 02

by Johnboy9 on Sep 16, 2017
Transsexuals & Crossdressers

It's been two weeks since I got out of the hospital and I was feeling better and better as each day passed. Having no income and no real money of my own, to speak of, I was forced to continue wearing the clothes that Crystal left me since I couldn't afford to go out and buy clothes of my own. I must say though I'm getting to like the soft, airy feeling of t...

He Wears The Panties

by Quietoldie on Sep 19, 2017
Fetish

I like to put my wife in charge of things when I get home. I have a very demanding and difficult job which takes up a lot of my energy and it is nice to relax as I walk through the door of our house. The kids all have their own careers now and live quite a distance from us so we have entered into a new phase of our relationship and enjoy our new lives. Mary...

Fetish & Fantasy Pt. 01

by GavinIsaNuisance on Jul 13, 2020
Transgender & Crossdressers

This work is completely fictitious, any similarities to any persons living or dead is purely coincidental and entirely unintentional. All persons depicted in naked/sexual acts are 18 and up. Down and out aspiring model Taran Kilkenny becomes the hottest commodity in an escort service for trannies! But first he's gotta get trained by his new and domineering b...

Sissified by My Sister Ch. 02

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

Well about a week past, and my sister continued to come into my room to bury that hard strap-on into my ass. It started to become routine. Actually I was just thinking it was starting to hurt less when Olivia came up to me in private, and said "Ohh, my pretty little Dee-bear, my boyfriend is coming up for the end of winter break, just letting you know~" And...

Magic Panties Ch. 06

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! Here's the last recap for you loyal readers out there (I apologize for the delay, life got hard, un...

Cassy's Game Ch. 4

by wormwood on Sep 19, 2017
BDSM

Another day late for work, with the new sensation of my cock cage lumbering under my panties, my hair still plastered down to my head from my session with my Mistress and the feeling of my hairless legs and ass under the silky material of my panties. The strong smell of my wife's feminine moisturizer, making a silent announcement of my new found femininity,...

Discovering Mistress Sarah's World Pt. 08

by oneguy4fun on Sep 14, 2017
Transsexuals & Crossdressers

Part 8 -- Complete Surrender Chapter 21 Leaving Behind Joe's Life Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelphia suburbs. "I'm sending May with you Josie," announced Mistr...