Naive Milf Stories

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Orientation
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Marcy, the MILF Masseuse

by localjesse on Oct 26, 2020
Mature

Do you remember when you saw for the first time, the most beautiful woman you ever would see? The one that made both time and you stop, and the one that you would forever compare all other women to? I do. I was 18. Naturally. At the height of raging hormones and horniness. I had spent the day with my Dad, going about his new town as we searched for cheap fu...

Easy Women on Easyjet

by johnthepostman on Sep 2, 2017
Erotic Couplings

I'm not a big fan of air travel but last week I experienced something a bit different and thought I would share it with you. Flying Easyjet is sort of OK. You get what you pay for. Delays are the norm and the scramble to get on the plane brings out the worst in everyone. I arrived at my departure gate with a little time to spare and noticed the Easyjet staf...

Guidance

by fantasticfic on Sep 18, 2017
Interracial Love

Fiona Hendrickson glanced at her next appointment. Marcus Chapman. Well, this should be the highlight of the day, she thought. He was her last appointment of the morning before her lunch break and the students had been a pretty depressing bunch so far. In an unexceptional school, Marcus stood out. His grades were uniformly excellent and his extra-curricular...

HotWife Iris Does Young Bros Again

by Aynsley on Sep 13, 2017
Loving Wives

As I gazed across the hotel room that we had just checked into, I caught an air of flirtation from my voluptuous MILF wife, Iris. If you caught our first story, you know that I had surprised Iris, by having her new young lover, Jack (28yo), bring his younger, virgin brother Jason (22yo), to our last 'date'. That night went really well, and Iris had asked me...

Fuck the MILF Slut

by RiaBella69 on Sep 13, 2017
Group Sex

Maria is a slut, she knows this, and she never hid that fact. For thirteen years she has been shackled in a loveless relationship. Perhaps loveless is not the word. Perhaps the correct description is lust-less. Her ex-husband at first did care for her, at first, he would buy her chocolates on holidays, and talk to her sweetly, call her things like “baby” or...

MILF Summer

by NobodyImportant on Aug 4, 2018
MILF

It's summer but there is definitely something in store for you from spring break. Even though you have a college degree in [use fantasy], it's become pretty pointless since your wives are taking in large amounts of money from their divorce settlement, investing it wisely, and making it so you never have to work a day in your life. All of you have come to liv...

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Dinner Date With a MILF

by NobodyImportant on Jun 20, 2015
MILF

Background: After winning a bet with an entity in a dream, you are able to mind control whomever you please. Characters: Mrs. Busty: A 5'4" orange haired milf with H-cup titties, a luscious ass, and the best blowjob lips you've ever seen. After thoroughly dominating her, she becomes your 24 hour fucktoy. Mrs. Done: A 5'3''asian MILF, in her thirties, ha...

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Off Broadway Public Theater Pt. 01

by TonyMA70 on Mar 11, 2019
Mature

The Jasmine Drama Group has been struggling to keep the Yonkers Theater open; due to the down turn in the economy many people are not going to off Broadway productions, produced by amateur theater groups such as the Jasmine Drama Group. The director of the group Jack Frost has been trying to keep the Yonkers Theater open. He has contacted many of his friends...

Club Glitter

by TheOrcKing on May 15, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Synopsis: Club Glitter is the 'it' place to be on Friday nights. Every hot party slut and Futagram bimbo can be found there tearing up the dance...

MILF and Chocolate Blue Eyez

by Silfy69 on Sep 13, 2017
Interracial Love

Jilly was a woman who seemed to have lost everything. Her Husband; Her expensive lifestyle and - just last month - her job. And yet, as she lay sunbathing in her garden, she felt younger and freer than she'd felt for a long time. She could say it now, but her husband had been an idiot. He'd left her for the reasons so many middle aged men leave their wiv...