Milf Chastity Stories

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Mistress Sharon’s Control Challenge

by CaptainSwitch on Jul 6, 2020
BDSM

My wife challenged me to a contest. She would give me a hand job and I would try to keep from cumming for five minutes. If I could maintain control for five minutes, l would get to fuck her anytime I wanted during the upcoming weekend. If I got too close to orgasm, I had to let her know and "give up" before cumming. If I "gave up" for losing control and gett...

Innocence Lost Ch. 17

by bradley_stoke on Sep 16, 2017
Novels and Novellas

In Which Gryphon purchases affection and gains a little satisfaction; the provision of Chastity to those willing to pay; and Gryphon's discovery of the hidden virtues of Innocence. Despite the rewards of her affair with Chastity, Gryphon still didn't feel that her sex-life was wholly satisfactory. She acutely felt the insecurity of having a relationship wit...

Pulling a Train

by grgy56 on Sep 13, 2017
Exhibitionist & Voyeur

It was a warm, lazy Wednesday afternoon. I noticed the train was mostly empty as we entered but rather than taking a seat, I leaned against one of the closed sliding door as I normally would. My 19 year old girlfriend Amber had her arm around the small of my back as she snuggled her head against my shoulder. As the train pulled out from Union Station, Ambe...

Innocence Lost Ch. 02

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Blanche learns the Truth about Innocence and Chastity, whilst Chastity furthers the experiences of Innocence. Innocence's sister, Chastity, had many friends, some of whom came from other shires and parishes. One such was Blanche, who came from Brook, a county, Innocence was fascinated to discover, where naturism was pretty nearly the rule and where...

Becoming Friends Ch. 02

by mrbillcollecta on Sep 17, 2017
Loving Wives

"What time are we expecting Chastity over for drinks baby?" Stefan quizzed. "About 7 or so and she is bring the Margarita mix with her!" Kenya yelled from the bedroom. He replayed the events that unfolded before him in his own bedroom a few short hours ago. Seeing Chastity tugging and sucking on Kenya's huge 42DD tits was definitely the highlight of his da...

Chastity's Lessons Ch. 05

by Goldeniangel on Sep 19, 2017
Interracial Love

The next day Chastity was unable to make it out to see Jeremy, which made her sad, but she was a little afraid of him putting his big black cock into her poor little asshole, so she wasn't that sad. In fact, she wondered if she would be able to find the courage to go out to his next lesson even when her father DID go out and leave her home alone. She was s...

Somali MILF Goddess in Edmonton

by Samuelx on Sep 12, 2017
Erotic Couplings

So, um, I was at the University of Alberta library in downtown Edmonton, quietly doing research for my Law term paper due in three days when I actually saw something...amazing. I was taking a much needed study break after hours of writing, and since all the coffee I'd been drinking shot straight through me, a brother had to pee quite badly. When nature calls...

Carl & Chastity: 3rd Date

by Ninjafish on Sep 14, 2017
Erotic Couplings

Carl and Chastity spoke for over an hour once they were both home, the cinema, dinner and alleyway activities clearly had not been enough for either of them. Carl had made the phone call, but secretly Chastity was already planning on doing the same thing but had just been beaten to the punch. There was a spark between them that caused butterflies to dance e...

Becoming Friends Ch. 01

by mrbillcollecta on Sep 17, 2017
Loving Wives

"Chastity Wright!" He smiles and greets her with a warm hug. He hadn't laid eyes on here since she left where they worked together last spring...and couldn't believe his luck running into her. She was a knockout and was also the subject of several of his masturbation sessions over the past 2 years. He also notices that she hasn't lost her ability to look sex...

Taken and Changed

by dpcarpenter on Sep 15, 2017
Sci-Fi & Fantasy

My name is Robert. I was, at one time, addicted to the online world called Second Life. I guess I cannot say I am not addicted to it any more but that is what this story is all about. I first heard of second life on a TV show called CSI New York. I was a little intrigued by it but did not do anything about it for over a year. I then decided to try it. My fi...