Milf Boss Stories

45,019 results
Orientation
Length
Source
Infinite Scroll

Mind Control Ring

by plane84 on Apr 22, 2025

John Doe is a 19 year old. He lives with his stepmother and two stepsisters, who he hates and who also hate him. He works an internship at a company that he hates due to most of his coworkers treating him like crap. The only reason he even had the job was because his stepmother knew his boss. In fact, he was the only male at that worked at the company, so mo...

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Her Younger Man

by Bakeboss on Sep 17, 2017
Loving Wives

My wife and I are now in our sixties so I am sure you can understand that our sex life had slowed to a couple of times a month at most. It is not that we weren't capable of more sex just we didn't seem to have much interest in it. In reality, I was masturbating a lot more than having sex with my wife and, as I found out latter, my wife was doing the same thi...

Secret Dominatrixes

by Sfmm22 on Mar 22, 2018
BDSM

This story will provide a bunch of different scenarios of woman in the workplace who unbeknownst to everyone are secret dominating bitches. There will be points of view from both the secret dominants and their equally secretly submissive male co-workers or in some cases bosses. Basically the scenarios well primarily drive the type of fetish that will occur i...

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The Obedience Curse

by wicker on Apr 22, 2025

It may be a voodoo curse. It may be a witches curse. It may be an ancient curse. It may be a magical spell. It may be a powerful form of hypnosis, but somewhere somehow how a woman is cursed to have to obey any request or demand given her. There are three types of curse: 1) The woman is cursed and realizes she can't say no. 2) The woman is cursed, reali...

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My Very Own MILF

by Bakeboss on Sep 14, 2017
Mature

After being married to Irene for over forty years, I couldn't imagine her having any secrets from me but I sure found out I was wrong. Our boss wanted to get an early start on the long Labor Day weekend so he closed our office before noon. I came home to surprise my wife and to enjoy our long weekend together. I walked into our bedroom and immediately heard...

I can't stop being a slut

by NPC041188 on Apr 11, 2021
Fantasy

I admit it, I've been a slut ever since I hit puberty. I'm damn near a full blown nymphomaniac. There wasn't a cock I wouldn't suck, a cunt I wouldn't lick, threesomes, foursomes, orgies, bondage, pet play, humiliation, exhibitionism you name it I've most likely done it. You can imagine how quickly word spreads in a small town, which also stopped me from get...

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Hand-Therapy Foot Job Ch. 02

by milfleglover on Sep 25, 2017
Mature

I couldn't stop thinking about Shelley, my super-hot MILF hand therapist who I'd been going to for treatment of a thumb injury. Early one morning, before others arrived, this 50-something, thick-bodied beauty provided a most unique method of easing my suffering: She used her incredibly sexy old feet to make me cum, after getting out of me I couldn't masturba...

MILF Does it the Old Fashioned Way

by LushinLace on Oct 12, 2020
Audio

Milf Does the Job The Old Fashioned Way This is a tale about an older woman who gets a job as a secretary but struggles with the new technology needed in her role. To prove she can be useful, she shows her younger boss, some old fashioned skills that are rare to find in today's modern office. Script writer u/HoneybearGWA generously agreed to let me to sh...

Gretchen Carlson Sex Toy

by DickThePimp on Oct 15, 2018
Celebrities & Fan Fiction

This is a sleazy freaky fucktacular sex parody... It ain't real. I was standing on an elevator with my girl, Kathie Lee Gifford... and Gretchen Carlson. The former Miss America, turned news chick, turned female justice warrior, was standing in front of us. She was wearing a green turtleneck blouse and tight black mini skirt and black heels. She was wearing...

Fit MILF Adventures

by derekjones7399 on Apr 22, 2025

Sofia Perez: Age: 35 Height: 5'6 Weight: 150 lbs Breast Size: 32DD Sofia has two young boys that are 4 and 6 and went through a divorce recently. Now living in the inner city she struggles to keep up with payments and keeping her kids safe in a crime ridden neighborhood. Her job is long hours and she is running out of money quickly. The boss she currently ha...

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