Mature Boss Stories

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Reconnecting with Rene

by dpingjessie on Sep 25, 2017
Mature

More than a year ago, I posted a story that shared a fantasy of mine that I had otherwise kept to myself for the past few years, namely, fucking my older female boss over her own desk at work. While I found the woman, Rene, anything but sexually attractive when she first hired me (if for no other reason because she was in her early 50s and I in my mid 20s),...

Veronica and Mr. G. Ch. 01

by kyle2 on Sep 11, 2017
Fetish

I've co-authored this story in partnership with sexyslut of Pandora's Secret (not Literotica's sexyslut). Major thanks to Literotica's DiamondStar for her fantastic editing services! This is the first part of what we hope will become a multi-chapter series (that, of course, will be determined by reader response). Happy reading! -----------------------------...

Pizza Delivery to the Stars

by DickThePimp on Aug 20, 2018
Celebrities & Fan Fiction

This is a parody... It is not real Part 1: Andrea Mitchell Andrea Mitchell was waiting for the pizza that she ordered to be delivered. She was very hungry from work and her extracurricular sexual activities. She was wearing her hot work clothes, a skin tight black satin blouse and jacket and very short and very tight black satin mini skirt. She had on blac...

Mature Woman Has Her Way Ch. 05

by Panty_Licker on Sep 19, 2017
Mature

I know it's been a while since my last story but I had stuff to do... so without further ado on with the show. The morning sun twinkled through a gap in the curtains of my bedroom. Bleary eyed I turned onto my side and saw the panties on the pillow beside me. Just the very sight of them made my cock twitch. I moved my head closer and inhaled deeply through...

Mature Woman Has Her Way Ch. 02

by Panty_Licker on Sep 12, 2017
Mature

The following morning I arrived for work exactly on time just as she had said I should. I had dispensed with the suit in favour of a smart but casual look. Mrs... what was her name? It dawned on me that although I had eaten her pussy the previous day that I didn't even know her name. "Good morning Jo..." she began to greet me as she lifted her head up from...

Banging My Boss

by bignfirm on Sep 26, 2017
Mature

The day began innocent enough. It was the day of my coworker's wedding and a number of us from the office were invited. We made plans to get dressed and get ready at the office after work and head over to the event together in one car. As the day came to a close my three coworkers and I piled into one of the guy's cars as he did not plan on drinking at the w...

Who's The Boss?

by Seidah on Sep 16, 2017
Interracial Love

Zehna enjoyed it when the office was empty. No noise, calls, and no staff! She did it every Tuesday and Thursday to clear the mountain of stuff as area manager. She had worked damn hard to be getting above £100,000 a year. Not easy as a Hijabi Pakistani female in today's racially divisive times. Her 5'9" curvaceous frame, 140lbs, young face and good health...

I Love Older Women

by bbw4youngercocks1 on Sep 12, 2017
Mature

I will make a confession right here and now: I love older women. Ever since I was eighteen and lost my virginity to my next door neighbor who had really given me an education in sex that one could have learned neither at home nor at school, I couldn't think about either going out with or fucking any woman under forty. I admit I have had sex with a few chic...

Me and Georgina

by rockycoveboy on May 22, 2019
Mature

An ex-NewForester story that I have tidied up a bit and re-issued under the new name Rockycoveboy. ************** Georgina Lent was my first boss. I was 19 and it was my first job, in a little accounts office, and Georgina Lent seemed ancient. Gradually, however, I had become infatuated with her, and very often thought about her at night. She did filthy th...

I Love Older Women Ch. 02

by bbw4youngercocks1 on Sep 12, 2017
Mature

It had only been about an hour and a half since I had fucked my boss, Kerry, in her office at the car dealership where I worked for a year. After that, she had given me one of the two positions that were open for sales managers before she pushed me up against the wall, asking if I wanted to discuss my new job over dinner. Of course, I took her up on it, a...