Milf Chastity Stories

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Mind Games

by CaptainSwitch on Aug 6, 2019
BDSM

My husband and I have been married over 25 years. He loves to play dominant/submissive games, so for his birthday this year I decided to fuck with his head. I would never be unfaithful and I have no desire for other men but I could make him think otherwise as part of the game. To start I told him to strip, lock the chastity on, put on the wrist and ankle c...

Gilmore Girl: The Boys from the Band

by LL72 on Sep 12, 2017
Celebrities & Fan Fiction

When Lorelai Gilmore had mentioned to her Mom that she and Rory were planning to 'fuck round Europe over the summer' Emily had assumed that Lorelai had meant it metaphorically and had told her not to be so coarse. If she had known that her daughter and granddaughter had meant it literally her response would almost certainly been different-- not that, as both...

Two Moms, Two Sons

by kornslayer1 on Dec 20, 2020
MILF

POV: London "It is good to have you and your son over, Sandra," I mentioned, stirring the pot. "We're practically best friends now, and don't forget my hubby, who is currently locked in your bedroom with your husband," she whined, strolling towards me with her arms crossed. "If I didn't know any better, I'd say they were having sex.&...

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Neighbourhood Terror to Sissy Pt. 09

by Fibaro on May 27, 2019
Transgender & Crossdressers

While Mark was going through his night time ritual and sleeping Lisa was at CC's getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The th...

The Taste of Innocence

by AnonymousPerv on Apr 10, 2019
Fetish

This story is set in the world of Philthshire, where the bar for sexual engagement is very low. People fucking anytime, anywhere, is simply a part of life. Still, there are some protocols - even laws - and Anne Prichard, Attorney at Law, made it her mission in life to right wrongs, specializing in sex crime. This is one of her stories. ________ "Miss Prich...

Naughty MILF Caroline Pt. 01

by scooter111 on Dec 9, 2019
Humor & Satire

These stories are about Caroline, a stuck up, nasty, uppity MILF businesswoman who acts all prim and proper on the outside, but is a nasty cheating bitch underneath. She has a thing for young studs and gets a damp tingling pussy thinking of the lads working in the company next door to her Business where she works as a Company Director. She is not well liked,...

The Dinner Party

by JimGrinsted on Sep 13, 2017
Group Sex

Stan Greenburg -- retired billionaire -- peered over his glasses at the fat, snaggle-toothed grandma sitting across the table. She's not as old as she looks, he thought. Probably only in her forties. She reeked of stale tobacco smoke. "What's your name?" he asked. "Marsha McCoy." "And you want to be a housekeeper?" "Yup." "This is a pretty big hous...

Maimuna The Somali MILF Ch. 07

by Samuelx on Sep 14, 2017
Erotic Couplings

There is something to be said about Fate, seriously. That which you run from typically pursues you. Seems to be the way of the universe. My name is Stefano Saint-Mathieu, and I'm a young Haitian man living in the City of Ottawa, Ontario. I'm a student at one of the Canadian Capital's leading universities, and I also work as a security guard downtown. These d...

Drugged MILF

by SlutProblems on Aug 21, 2019
Mature

*Trigger Warning* The following piece of art may be offensive to some people because it contains rape fantasy, which is not real. Real rape is wrong. This is for people who enjoy rape as a fantasy or role-play and is not intended to be real or to be reproduced in any way. *** Tobi was the hottest mom out of all the moms. She had an hourglass figure with bi...

Samus and the Reality Altering Upgrades

by welldressedcrab on Nov 14, 2020
Science Fiction

Samus brought her ship into dock with the station, the docking bay walls closing behind her. In her adventures through the galaxy she had received a signal from a remote research station. The signal informed her that the station was inhabited by a scientist AI which was programmed to keep inventing and researching for eternity. If she came to investigate, sh...

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