Milf Boss Stories

44,764 results
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Infinite Scroll

Inga Swenson Ch. 03

by JoMaddox on Sep 24, 2019
Interracial Love

Inga suddenly had second thoughts about what she had just done. But a part of her wanted the street thug and drug dealer to at least come over to her house. Since that day at the party, the Swedish milf had thought about what it would have been like if she had somehow ended up with Tone and his friends instead of with Marcus Jefferson. She could still rememb...

Naughty MILF Caroline Pt. 01

by scooter111 on Dec 9, 2019
Humor & Satire

These stories are about Caroline, a stuck up, nasty, uppity MILF businesswoman who acts all prim and proper on the outside, but is a nasty cheating bitch underneath. She has a thing for young studs and gets a damp tingling pussy thinking of the lads working in the company next door to her Business where she works as a Company Director. She is not well liked,...

Celebrity Summer School Ch. 07

by DarkSwordsmanReturns on Jun 1, 2020
Celebrities & Fan Fiction

Tuesday, August 4th, 2020 Parent-teacher nights at Sofia Vergara's Summer School for Girls were always a sight to behold. Such evenings at more traditional schools generally made for a rather drab affair, and while crowning moments of such events might include a balding, divorcee English teacher questioning a dumpy housewife about their daughter's choice of...

MILF: Mothers I'd Like to Frame

by majus on Jun 12, 2020
MILF

Mikey Franchetti felt like had just won the lottery, dodged a bullet, and been struck by lightning all in the same day. He was sitting in the back of a brand new Cadillac Coupe, series 62, riding through the Los Angeles night towards the Sunset Strip. The suit he was wearing felt just like a second skin, which shouldn't be surprising - it was brand new and t...

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I Wanted to Meet a MILF For Sex

by Eroticalust on Jul 27, 2020
Mature

The first week at my new job had come to a close on Friday at six pm. I was grateful to Mr Brown for employing me at his factory after I was fired from my previous job four months ago for taking a day off on my ex-girlfriend's birthday without permission. I was apprehensive about taking the day off, but she said that I didn't love her if I didn't do it. The...

Naughty MILF Caroline Pt. 02

by scooter111 on Dec 9, 2019
Humor & Satire

So, the basis of these stories is that Caroline is a stuck up, nasty boss that everyone fuckin' hates, with a passion. She's mean, but pretty, although sarcastic, with a plummy English Home Counties accent. She thinks she is better than everyone else. Caroline is a Senior Partner on a Business Park/Industrial Estate and works with her Husband, Peter. He is...

Sarah's Sexcapades 01

by TommyTells on Sep 15, 2017
Illustrated

Sarah the Sexy Secretary The Sexual Awakening of a 40 Something MILF Sex with my wife, Sarah has always fun...but was pretty vanilla for many, many years. Then in her early 40's Sarah started to loosen up, big time. Not sure exactly why? Perhaps a combination of factors: a change in hormones, a more relaxed attitude in general (and willingness to have a co...

Futa Free Use World

by Callum95 on Aug 6, 2020
Miscellaneous

You get to choose your character and your adventure within the new futa world. Your character can come from any standard of life and it is your choices that dictate how you will fare in this new world. Some background: Futas are now the gender that rule the world with an sexual iron fist. They control the lives of every female and male, prefering to call the...

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From Nigeria with Love

by Samuelx on Sep 2, 2017
Erotic Couplings

"Stephen, have you been pissing me off because it secretly turns you on when I'm angry?" Gladys Osinbajo asked, looking at the big and tall, twenty-something and burly young African-American man who stood before her. Well-dressed and handsome, Stephen Volta decidedly cut an impressing figure. A newcomer to the City of Lagos, Nigeria, by way of Boston, Massac...

A Good Day at the Office

by MickNeighbor on Sep 12, 2017
Erotic Couplings

Being your own boss is great, no-one tells you what to do, everyone is deferential towards you and you basically get whatever you want, even to the point of hiring and firing people. On this occasion as I looked across the room at the beautiful, well stacked body of Georgina, I was remembering with particular pleasure the day I had decided to hire her as a s...