Sissy Boss Stories

46,032 results
Orientation
Length
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Infinite Scroll

A New Thing

by venus1485 on Sep 14, 2017
Interracial Love

I just start a position which I've never done before. By trade I'm a nurse, a floor nurse not an office nurse there is a difference. And now I'm the new Marketing Director for a local medical facility. My boss is a kindly 62yr. old black man. I call him Mr. Sam. He calls me honey. I often wondered why he selected me for this position when I have no back gr...

The Goa Trip Ch. 01

by nick9056 on Sep 1, 2017
Group Sex

Hi! My name is Raj. I am a 20 yr old guy living in Mumbai .This is an incident which took place 2 yrs ago in my life .At that time, I was studying in B. Tech(first year).I had a girlfriend called Manjula. She was a tall, slim girl with hazel eyes and long hair. But what particularly attracted me towards her were her firm and round breasts. We loved each othe...

Katherine's Dream

by QueenieRegent on Sep 1, 2017
Group Sex

Lying in the golden sun, Katherine listened to the crashing waves with her eyes closed, blocking out the irritating chatter of fellow holiday makers; humans. She twirled her lapis lazuli necklace with an absent mind as her thoughts shifted from her present, if a little mundane, vacation. No drama. No dicks. No fun. Just serenity; the peace and quiet she had...

It Could Have Been You

by Prcious1 on Mar 12, 2019
Text With Audio

Original characters are used under permission from their creator Colin Pearce. ** Denotes Sound Effects My thanks towards Reddit user Kilbeggan32 for his editing skills. * * * * * Click Here to listen: .mp3 format or .ogg format. (11 min/mp3) * * * * * Audio starts with me giving myself a pep talk. "Ok Debbie you got this, you prepared for this day,...

Frustrated Phineas and his Fat Wife

by justincbenedict on Sep 23, 2019
BDSM

Phineas waited, trying not to tremble as his wife stomped in from her Weight Watchers meeting. She walked past Finny as he stood awkwardly holding the vacuum cleaner. She went into the bathroom and slammed the door. That can't be good, he thought dejectedly. Adair was a gorgeous woman. She had her flaming red hair in a crew cut, but she had nice full brea...

The Pink Orchid #03

by justincbenedict on Aug 21, 2019
BDSM

The bathroom door opened, and Wenceslas Octavian Meatowski emerged, a satiated man. Jeez, getting my dick sucked twice in about forty-five minutes. Hugh had taken Meat to see a priest that was really different from Father Bendetti. But he wasn't sure, still whether or not this was some kinda sin. He did know that the Roy Cohn guy was freaky for other reason...

A Snapshot of Jack's Life Ch. 03

by Yourstohave on Sep 14, 2017
Novels and Novellas

She'd been hired as a legal secretary at Johnson, Smith & Donald, LLP, eight years ago. She'd worked in the intellectual property division for four years but had moved up to litigation a few years ago. From the moment she transferred into litigation, she knew she'd found her place. She loved her position and her boss. Actually, she loved her "bosses", all th...

Confession of a Panty Thief

by Middleagepoet on Aug 19, 2017
Exhibitionist & Voyeur

It's not something I am proud of, I mean if it wasn't for this thing I'd be a really good person, I mean I am a good person now, except, except when I have to do it. I guess if it wasn't such a perverted little thing I might not be considered creepy or sick. Of course there are times I wonder if the women weren't a bit flattered that I stole their panties....

Black University Romance

by Samuelx on Dec 10, 2019
Interracial Love

Marion O'Neill is a newcomer to Brownstone University, a historically Black school located in South Lancaster, Massachusetts. Born in the environs of Galway, Ireland, and raised in Missouri, Marion has a lot to learn about the African American experience. As a teacher at a historically Black school, Marion has to get over her White privilege and try to conne...

Living with a firery wife

by ElwoodKain on Mar 6, 2010
Erotic Couplings

The air smells strong of cedar and oak, the dim light of the not yet sun rise brakes through to your still closed eyes and starts to warm your face. Your eyes start to slowly open as the warmth on your face brings you from the dream land to the world you live in. You slowly rise from your bed and look around the room you have lived it for three years now, ev...

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