Mature Boss Stories

64,820 results
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Length
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Infinite Scroll

Banality: No Guilty

by Tiberius_Daniel on Jul 14, 2020
Loving Wives

Claude Look, I'm not at fault, I'm sure if it wasn't me it was another ...I mean, that woman is a tease, so it was to be ... Guilty is her husband who didn't choose better. I didn't break their marriage, it was a sham from the start. What was between us? Only sex. Why is it good to have mistresses at my age? Because a mistress allows me to take Viagra....

The Sales Boss

by T3Bloke on Sep 14, 2017
Mature

I was a salesman at the time and was doing very well for myself. I was part of a six-man team and we'd always have a competition to see who had the best figures for the month. Usually we'd chip in and buy a bottle of Vodka or something as our grumpy old sales manager at the time couldn't give a toss if we were happy or not. That was until the old git crocke...

My Hot Boss Ch. 03

by hornycoupl on Sep 14, 2017
Erotic Couplings

Shirley and I have worked together for years and never even considered having an affair. A few months ago we went for drinks and after several rounds she confided in me that she and her long time boyfriend were not getting along. She told me that he had quit paying any attention to her, especially physically. This revelation just blew me away since Shirley...

Tag-A-Long Ch. 02

by behindtheseeyes on Sep 16, 2017
Group Sex

I started undressing and put my trunks on, feeling a slight bit nervous as I did. "What if they were there?" I kept thinking to myself. "How would I start talking to them?" I grabbed my towel and continued my thinking as I walked down to the pool area. Peeking in the window, I noticed no one was there. "Well, I guess that's kind of a good thing," I whisper...

Tina the Supervisor

by Romeomaj on Sep 15, 2017
Mature

For as long as I can remember, I have always had a fetish for the older more mature woman. But I never thought that I would ever get to fulfill my fantasy. How wrong I was. Her name was Tina, and she was a colleague of mine at the local supermarket. She was a big woman, with large breasts and a big bum, she was 36 and I was only 22. She had a geek pair of g...

Hole in the Wall Ch. 02

by plushpeach on Jul 16, 2019
Mature

NOTE: Sorry for the long gap, but here's the much-requested sequel to the first of Jillian's escapades! She can't help but up the ante this time, so I hope you enjoy it as much as she does. If you have any feedback, comments, or requests/suggestions, please let me know below. Enjoy! -- As she looked across the bustling store, Jillian couldn't help but feel...

Who's Your Daddy Bitch

by DickThePimp on Sep 24, 2019
Celebrities & Fan Fiction

Belching and farting as I wake up, sitting on the side of the damn bed. Another bitch laying beside me. A neighbor's 18 year old daughter. She wants to be a damn stripper at my club, so I fucked her. No reason to... I just wanted to fuck the slut. I grab a beer off the nightstand and down it... Belch again. My damn head is killing me. Too much coke and beer...

Doin' the Boss Ch. 05

by RobynG on Sep 12, 2017
Mature

(A continuation of my experiences with a former boss, as requested by Bill, Jeremy and Jackie). It was one of those whirlwind days, the kind of day where the phone doesn't stop ringing, my boss won't stop nitpicking and my co-workers disappear and leave me to be wonder woman. Just a normal day. Jack O'Connor was a barrel-chested Irishman who had a hearty...

Bea - My First Mature Woman

by lancelot49 on Sep 17, 2017
Mature

Beatrice – my first experience of "dogging" When Ed and I were twenty-two, we were working in a local garden centre to get some money for a vacation after finishing college. The rest of the work force was mainly female from girls to older married women earning some pin money. We tended to get all the dirtier heavier jobs but also more overtime and a bit of...

Woman-In-Charge

by eroticorgasm on Sep 12, 2017
Mature

Susan looked back over the numbers as she sipped her coffee. In the background, chatty morning talk radio spoke of sports and sex positions and someone laughed. There is always laughter on morning talk radio. Something is always funny. But Susan couldn't enjoy it, because there was no time to laugh. She was crunching her businesses' numbers. Yesterday, seve...