Sissy Boss Stories

46,032 results
Orientation
Length
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Infinite Scroll

For Love of E Ch. 06

by Dragonteacher53 on Oct 6, 2020
Group Sex

Monday morning...Eliza was humming to herself in the elevator as she rose to her office level, still buoyant after her weekend getaway with Kit. She pursed her lips and remembered just how thrilling the ride back had been, as her well-serviced pussy had been subjected to the throbbing vibration of the old V-Twin engine...she had come several times on the tri...

My Hot Boss Ch. 02

by hornycoupl on Sep 14, 2017
Erotic Couplings

My very hot Boss Shirley is a total knockout 5'5" Blond. Her hair is really Black but she colors it blond. Her boobs are perfect natural 36-C with large nipples. Her legs are nice but her ass is wonderful. She has left her pubic area more natural until recently, now it's nicely trimmed - making it more suitable for me to lick her clit. Shirley and I have wo...

Black Man One Ch. 14

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

I was devastated by the sudden presence of the young black stud at our front door. After I finished relieving myself, I walked out of the bathroom with the front of pants partially wet. I looked over to my wife, Julie, who was still passed out cold on the bed. Numerous black ink spade stamps were strategically placed all over her body and face, and they we...

Nothing but a Jersey Ch. 02

by KinkVariety on Sep 13, 2017
Exhibitionist & Voyeur

As I walk into the conference room I notice my boss Jan in there, along with a couple of people that I now remember as new additions to one of the teams at the company. I sit next to Jan. "Nice jersey, Meg. Aren't you hot in it," she asks. If she only knew. "Not at all, I wish I could wear this every day!" She doesn't say anything about my lack of shoe...

The Precocious Pool Girl

by Ibis1074k on Sep 19, 2017
Romance

It was a hot afternoon, and although rare for the high plains, very muggy as well. Jay stopped his boss' Chevy pickup at the crest of the hill and left the windows down. Huge old cottonwood trees, their hard shiny leaves rustling in the light breeze, ringed the park below them. Cottonwood seeds drifted around them in the air like snowflakes and lay thick al...

Cam Life Pt. 02

by AllisonsRange on Oct 9, 2018
Erotic Couplings

After talking to Kayla and Jessie for a while that night I had made up my mind. They told me what kind of money I could make and how fast I could make it. No more shitty customers to deal with at a diner where the tips were barely even worth going to work. No more cranky boss. No more worried about getting fired because I was going to be my own damn boss. No...

The Sleaziest Agent Ch. 01

by DickThePimp on Dec 11, 2018
Celebrities & Fan Fiction

This is a porn parody... It's a fantasy only... It ain't real This is a two part story based in 2012 and stars Chyna aka Joanie Laurier... R. I. P. "Yeah... that's right Steve. You get me 4 tickets to Madonna's LA show and I'll hook you up with Christy Canyon. You scratch my back... I'll send you some big titty whores." Christy smacked me as I fucked her...

Everything Has A Price

by tamol on Sep 14, 2017
Erotic Couplings

Firstly let me introduce myself, my name is Simon, I am in my early fifties, medium height, deep blue eyes and my only downfall is my stomach which I am afraid to say has fallen foul of the dreaded mid-life paunch disease or as some would say the good life. I have a very good job as a manager of a leisure centre earning around £50k a year with bonuses. I ha...

Just a Game Ch. 01

by Dark_Rose90 on Sep 16, 2017
Transsexuals & Crossdressers

Stan Johnson is just you're average twenty year old guy. At least he used to be. But before we get into that, let's look at his background. Stan grew up like any other guy. He played a few sports. Mostly baseball. He developed one bad habit during this time though. He would bet on things all the time and play games with interesting twists. Tonight, he woul...

Used & Abused Ch. 13

by Jessiebnh on Sep 19, 2017
Loving Wives

Glen began to tenderly lift me off of Mr. Pruit as Clem continued to stare at me. Mr. Pruit looked dazed and embarrassed as he shook himself and raised himself on his forearms. "Before you go downstairs and clean-up, I need your help with Clem. You know how he is!" barked the vice-principal in a no-nonsense voice. I was confused. What help would she need f...