Mature Boss Stories

64,820 results
Orientation
Length
Source
Infinite Scroll

2 x 4 Club

by 1946EW1 on Oct 8, 2019
Mature

©2011 1946EW Gregg Owens was smiling broadly as he reached under the table and brought out the 2 X 4. As he held the polished 3 ft. hickory slab, most of the other party goers of his firm also begin smiling, most with shit-eating grins. Eyes flitted from Maude Roukema, the sexagenarian bookkeeper, to Rodney Skelton, the 19-year old office boy. Rod was not s...

Granny's Calf and Ass Twink

by milfleglover on Sep 16, 2017
Mature

I'd just gotten home from errands when the bell rang. I answered and there stood little Jimmy, a shy 18-year-old from the neighborhood. He smiled. "Hi, Mrs. V!" he said brightly. "Just wondering if you needed, uh, help with anything?" I laughed. I'm 68, a good-looking single, retired blonde school teacher with willowy, lean body, and this little buck was h...

Maximillian Mazan's Marvellous Machine

by chriscole on Mar 17, 2015
Miscellaneous

Author's Note: Feel free to create your own fantasies with whomever you wish. Please do not continue someone else's specific stories. However, you may start a story with the same character(s) someone else already has a story for. The POV (you) can be male or female. The default POV in the intro is male, but the machine can change that. You don't have to foll...

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Mature Woman New Job for Family Ch. 01

by Marriedandneedingmore on Sep 19, 2017
Loving Wives

This is my second story series. Bear with me while I improve! It revolves around a mature married woman who has to become the family breadwinner after her husband has an accident. She becomes a Secretary for her Husband's Boss. If you are expecting lots of sex you better go elsewhere, this is about setting the scene for future chapters, As usual comments...

Vengeance Ch. 01

by Evolution20XX on Sep 15, 2017
Mature

Sunlight... How long had it been since he'd seen the sun? Not the bleak sunlight that beat down on the prison yard every day; that was light, but not true sunlight. Real sunlight carried freedom; he knew this now. Even as he stood buffeted by the icy November winds, he stood in the sun as if there was no place he would rather be. It had been almost seven...

Mature Woman Has Her Way

by Panty_Licker on Sep 19, 2017
Mature

Due to the great and unexpected comments I have had with my first little story I felt encouraged enough to write another. I hope that you have as much fun reading this as I had writing it. * * * * * Finding life on unemployment street very boring, not to mention the fact of always been broke, I decided to go job hunting. In the job office were all the typ...

Michele Tafoya vs. Erin Andrews

by DickThePimp on Oct 3, 2018
Celebrities & Fan Fiction

This is a sleazy ass freaky fuck parody... It ain't real "I'm really looking forward to working with you James. I've heard a lot about you. I just want you to know, I will work very hard and be someone you can count on at all times." "Thank you Michele. The feeling is mutual. I've been a fan of yours for a long time. I know you and I share some similar opi...

Doin' the Boss Ch. 06

by RobynG on Sep 12, 2017
Mature

(For Rich, Davis and Marty, who always encourage me to tell all). If K. Linford Little was anything, it was a creature of habit. He liked eating ham and eggs weekends at diners, listening to soft rock and cheering his beloved hockey team. He loved his family, his work and his weekly golf game at the club. Oh, and he liked me. Yes, he loved his family,...

Boss Ch. 01

by Debutante on Sep 17, 2017
Mature

Anne was the first person to give me a job and take me seriously as an ad writer when I was just a fresh faced college kid. The local office was filled with dusty old women, and let me tell you, Anne was among the dustiest. At about 5 foot 3, with glasses (spectacles seemed more appropriate), Anne was like most aging career PR people - cynical, quiet, pensiv...

His Sweet Girl Ch. 01

by naughtysexmouse on Sep 19, 2017
Mature

After graduating, I took a job as a secretary to a very successful businessman in a large office. I considered myself over-qualified for the job but at twenty years old I wanted a steady income without too much responsibility, and I had heard from a friend that the position was available. The novelty of professional life had not worn off yet, and I still enj...