Mature Woman Stories

226,474 results
Orientation
Length
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Infinite Scroll

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Watching Porn with Mature Friend Pt. 01

by ikemay on Feb 6, 2018
Mature

While growing up my family was friends with another family with kids about the same age. For a few years both families lived in the same neighborhood in Southern California. We lost touch with them after we moved to Arizona. Years later, after I had left high school and spent a couple of years in the Navy, and was back living in California, I got a call fro...

Cougar Training 101

by wife2hotblk on Sep 16, 2017
Text With Audio

* * * * * Click Here to listen. (7 min/mp3) * * * * * Demi Moore did it...with style. Madonna is doing it. Hell, even one of the popular new television shows of the year is all about it. Cougars. Older women with younger men. This once almost unheard of and scandalous phenomenon has now become a popular trend. But why? Is it just a fad or the next step in...

Car Pooling Pt. 09

by TonyMA70 on Apr 11, 2018
Exhibitionist & Voyeur

The couple was up early, because of the noise the SCAG mower next door made as the young man cut the lawn. Hal looked out the window to the next door neighbor's yard; the same young man was on the machine, as a week and a half ago. It was about a half hour later the doorbell rang. Martha knew it was the young man at the door to inquire if they wanted their l...

Older Woman Holiday

by lilguy on Sep 26, 2017
Mature

This is a story that takes place on a Holiday. You pick which Holiday It also a tale of 3 mature women that hang together. They are 3 women with an appetite for young men and women (especially virgins). They are 3 women who loved to get into trouble and have adventure The characters Beth- Beth was black with short black hair and big hazel eyes. She was 55 an...

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The Cuckold is Black This Time

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

After months of hesitation and much soul-searching, a momentous decision finally got made. The big Black dude burst into Mistress Chocolate's den in downtown Ottawa, Ontario, and told her of his rather unusual request. The six-foot-tall, gorgeous Black Canadian female dominant listened to him, and then agreed to make his most forbidden fantasy come true. It...

Mature Bliss Ch. 03

by MarcusWoolf on Sep 14, 2017
Fetish

My family had planned to be at the beach all day, but on my way to lunch I saw them in the lobby. My mother and my stepfather were clearly arguing, talking through clenched teeth in order not to scare the children or make a public scene, but my small stepsisters looked pretty sad and miserable all the same, and I think my mother had been crying, for her eyes...

In Praise Of The Mature Woman

by English Bob on Sep 11, 2017
Mature

I've always had a real thing about older women, and moreover, older married women. Its definitely not a case of "the older the better", but when certain women reach a certain age they almost seem to reinvent themselves. Lethargic spouses that often take them for granted and seem happier with golf or drinking can lead to a whole new outlook for some women. Vi...

Quality Time with Annie Ch. 02

by rcwilliams on Jun 19, 2018
Interracial Love

Author Notes: Sorry for the lengthy delay but with my recent promotion to department manager, I've been a little busy so I apologize to my loyal readers out there. So without anymore delay, here's chapter two. Enjoy, rate, and review. :) Disclaimer: This story is pure fiction. No plagiarism is intended as this is an original story. All involved are of the a...

Surviving in the Old West Ch. 04

by fannyrat on Nov 8, 2017
Erotic Couplings

Before reading this story it is important that you read 'Surviving in the Old West' parts 1 and 2 to fully understand the characters. For the more observant amongst you, you will notice a small name change between the stories. I always meant for the character to be called Clara a name more in keeping with the times in which the story is set. I have no idea h...