Milf Boss Stories

44,764 results
Orientation
Length
Source
Infinite Scroll

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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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...

Nice Neighbors Ch. 05

by Lauries Husband on Sep 16, 2017
Novels and Novellas

(Please read Chapters 1, 2, 3, and 4 if you haven't already. This multi-chapter story could be listed in several different groups. It contains group sex, bisexual and gay contact, incest, BDSM and other fetishes. If this offends you, please stop now. If it doesn't, I hope you enjoy. And a special thanks to Julie, my kinky muse, for her wonderful inspiration...

Morgan's Lunch Break

by Ben Rosewood on Dec 5, 2018
MILF

The alarm assaults my ears so my hand returns the favor by smacking it. Time to get going. In the shower, I decide to have a quick play with myself and my vibrator. A little bit of me time before I have to get my son ready for school and go to work. Between spending time with my son Max and my job as a lawyer, I didn't have much time for dating, so I take wh...

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Vice The Trickster

by Samuelx on Sep 21, 2020
Interracial Love

Gutierrez Janitorial Services, whose office lies in a seedy neighborhood not far from the Saint Laurent Mall, is one of the largest cleaning companies in the City of Ottawa, Ontario. They compete with Aramark and GDI and the other big shots for access to schools, labs, shopping centers and Canadian government buildings. The owner, Marisol Gutierrez has a com...