Milf Chastity Stories

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Orientation
Length
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Infinite Scroll

I'll Drop My Panties for You Ch. 01

by mitchawa on Sep 13, 2017
Loving Wives

"I'll drop my panties for you," a voice whispers to me as large breasts push into my back. Without turning, I ask, "Do I know you?" "No, but we can change that." She molds her body to my backside. "Do you know who I am?" I ask remaining calm and finishing my glass of Dewar's. "You're a tall, handsome man whose presence has stirred my juices all evening....

Taking the Lad out of Alladin Ch. 10

by CaseyHeart on Dec 16, 2019
Transgender & Crossdressers

You know, video game peripheral designers might not have considered that someone would be using their stuff to learn to strip so that they didn't lose their penis. If they had, those floor pads for dance games would have been sturdier and wouldn't say you didn't tap the X button even though you totally did. Which was why I was currently flipping off the tele...

M.I.L.F. vs Stud Ch. 01

by mrsmillwood on Sep 19, 2017
BDSM

This is a continuation of "M.I.L.F. Takes Charge", available in my profile. * Much has transpired since I wrote about my encounter with the young buck who would make me his conquest, while I wished to make him my obedient submissive. Most of what happened, and certainly the most exciting, has transpired over this past summer. I will write a short prologue...

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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My Realistic Vision of Cuckoldry Ch. 01

by cuckoldme90 on Sep 17, 2017
Loving Wives

This is just a fantasy and did not happen. Feedback very welcome. ***** There comes a point in your life when you look back at your mistakes and look to the future and what you want to make you happy. After a failed marriage and many failed relationships. I was doing just that, looking seriously at how I could make my future happier. For a few years I had...

Nuns Vs. Knights

by MidbossMan on Apr 5, 2020
Fantasy

In front of a smaller than average congregation, unusually attended by a few of the kingdom's notably agnostic Knightly Order of Dyna, the head priestess of the Holy Church of Merridan addressed "her flock," as it were... even though the warriors in attendance actually outnumbered her faithful. "In conclusion, give generously, my brothers and...

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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...