Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

A Summer on the Road Pt. 01

by cerrotorre on Sep 18, 2017
Romance

Dear readers, this is the first chapter of a multi part story. I hope you enjoy this and come back for the rest of the story. ***** Jane looked down at her legs, shifting them from side to side, assessing her tan. They were still very pale, not unusual for early May, but she liked what she saw. Her long legs, highlighted by the black bikini bottom, were on...

Dressed To Kill Ch. 12

by GRGrayson on Sep 15, 2017
Novels and Novellas

This fills the story out, so stay with me as its will hot up next chapter. I promise! Thanks for reading. Gray. Tuesday was a day of calm in comparison to Monday. She had the three kids over for dinner and as they talked over their meal she found everything had calmed down with Damien. He was actually treating them well, even though Marcus, had put Damien...

Oops

by PTBzzzz on Sep 25, 2017
Loving Wives

There is no actual sex in this story, if that is what you want go elsewhere. I chose to put it in LW because there is no category for loss of trust. * The gunshots were loud; I could see him lying on the floor holding his groin. What was left of his equipment was sliding down the wall behind him. A few of the shotgun pellets had hit my wife; she did not r...

Scarlett's Big Project Ch. 03

by nextcenturyromeo on Sep 26, 2017
Celebrities & Fan Fiction

Romeo entered the sumptuously furnished hotel suite and threw his jacket on the couch. When the other girls started to take Romeo's clothes off, Scarlett joined in, hesitant at first but more confident when he didn't object. Scarlett held back when it came time to take off his underwear though and only watched as Kate pulled them down. Scarlett gave a sile...

Taking One for the Team Pt. 02

by Shadowforce1 on Apr 18, 2018
Interracial Love

So, the week had gone well for me so far. After tit-fucking my boss for the first time just yesterday at work, then finding a new apartment that was both larger in size and cheaper than my last apartment, I was on cloud nine. I had wanted to see my boss's huge tits since the day I was hired. Nothing I had ever thought of had even come close to the reality o...

Behind the Iron Curtain Ch. 03

by fredwriter on Aug 22, 2018
Erotic Couplings

The next morning Danica looked very smart in her skirt suit. The blazer and skirt were dark and the blouse was cream-coloured with soft big collars and buttoned down the front. The top two buttons were undone, showing a nice amount of décolletage. The skirt was tight round her ass and came to mid-thigh. She wore stockings with a seam down the back of her leg...

Nature Girl's Origin Story

by JayLikestoRead on Nov 26, 2017
Group Sex

In the course of my conversations with Rick and Marissa, I told them, as I've told the reader, about my thoughts concerning nature, spirituality, the universe and things like that. Rick found my ideas so interesting that he suggested I start a blog, and I did. It caught the attention of Gerald at the National Park Service. I forget his title, but his duties...

Marry The Knight Ch. 21

by Zev95 on Jul 17, 2018
Celebrities & Fan Fiction

Ivy nearly passed out the moment she laid her head down. Her brain was too tired of absorbing all that it had taken in. Plot and counterplot and revelation, all demanding to be made sense of. It was too much for her. Too much for anyone. And resolving to be Batman's—Bruce's—it was like a ten-ton load off her back. No more frenetic scheming and then preempti...

Room Service Anal Girl

by HeyAll on Dec 17, 2017
Anal

As floor manager for the executive suites, presenting the gift was an opportunity Sophia simply couldn't miss. All she knew was that the CEO's eldest son had recently been hired as a Director for the hotel franchise, and that a special gift was being prepared upon his arrival. It was almost 10 pm and he had just checked in. Normally the role of gift giving...

Boss Lady

by motoskoota on Sep 14, 2017
BDSM

It wasn't the first time I'd stood up to a woman and been knocked onto my ass. All I could think of at the time was that here was a pushy bitch riding roughshod on my plans; plans with much time and effort invested in them. She had come sashaying into my office while I was planning the day's schedule with my assistant, Bernice. "Tim, I won't beat around the...