Mature Chastity Stories

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My Chastity Story Pt. 01

by Digger66 on Oct 3, 2018
Fetish

[Massive re-write of this story. Good feedback. I flushed out the character's motivations.] * It all started because I jerk off too much. Every night, I would retreat to the basement after my wife, Kate, would go to bed early. Both of us are in our mid-forties. I often asked for sex, but my wife complained that I was never any good at it. She always said t...

My Chastity Story Pt. 03

by Digger66 on Dec 11, 2018
BDSM

**For those that like femdom, humiliation, chastity, cock cages, FLR, and cuckolding, WELCOME. For those that hate that stuff, STOP and don't waste your time** *** Three months! My wife was going to keep me in a cock cage for three months! Actually, it was three months from today, so three months plus one week. Kate circled the date on the calendar. Over...

Jennifer in Chastity

by Wifetheif on Sep 14, 2017
Fetish

Some of Jennifer's friends had told their secret to affording college. They had found sugar daddies, older men who paid for their college tuition and expenses in exchange for sex. Amy, Jennifer's best friend was bedding a local banker and was doing very well indeed. Freed from the financial burden of massive debt from college loans, and with her sugar daddy'...

Chastity Debauched: Penitent

by MorganHawke on Sep 15, 2017
BDSM

In Which Chastity has an appointment with the Unholy Father... For Bear Part One: The Club “I can’t believe my Dad had me to come to his company pool party at the Club.” Chastity grumbled to herself while standing before the tall mirror completely nude. She stared into the mirror’s reflection of her deep violet eyes as she tied her waist-length, strawberr...

Come Sail Away With Me

by robertreams on Sep 13, 2017
Romance

Chastity, in a long, elegant evening dress of deep green satin, whirled around the dance floor with one man after another, thoroughly enjoying the swishing sound the dress made, the way it contrasted with her flaming hair. She was the official hostess of this dinner party. Since her mother had died four years earlier, when Chastity was only fifteen, Chastity...

Tormented by a Mature Dominatrix

by Harryj34 on Jun 4, 2019
BDSM

A text appeared on my phone: "You have some nerve messaging me again boy". I had contacted mistress online some time ago but lacked the courage to go through with the meeting, she was very unimpressed... She was a mature mistress of around 40 and was in search of an "inexperienced and innocent plaything" and I had decided I would be a suitable candidate. S...

From Charity to Chastity

by carrteun on Mar 10, 2020
First Time

This is my submission to the 2020 Valentine's Day contest. Please take a second to vote if you enjoy reading it. I've already enjoyed reading some of the submissions and look forward to reading more entries. Good luck to all the authors. * I almost felt like I didn't belong the first few weeks. Many of the faces were only a handful of years younger than me...

Short Taboo Mature and Bondage Stories

by Odalisque75 on Jun 1, 2020
Mature

1 A FATED MEETING The Jaguar pulled up in a jeep. It's too much. Convenience Store Flirt. She bought some rolling papers. Outside, she was smoking with some people talking about scratch tickets. He offers a light and smokes himself. He ask for a drag from the joint. She laughs. They get to talking as often happens. They exchange compliments about their bod...

The Tree House

by drlust on Sep 13, 2017
Exhibitionist & Voyeur

The Tree House My thanks to Chastity420 who suggested that I turn this real life adventure into a story. Every year on May 1, my wife and I put the kids to bed, pour ourselves a strong drink, or two, and then recite our favorite poem: Hooray! Hooray! It’s the first of May. Outdoor fucking begins today! I learned this poem many years ago from a book by th...

Turning Mother Out Ch. 01

by brucinator on Sep 17, 2017
BDSM

A Brief Introduction To My Story I'm Chastity Stake, an only child daughter whose divorced Dad lusts after teenager flesh. He tries without luck to lure me into incestuous affairs. I'd be happy to oblige except I'm a bent arrow, a lesbian - you know, gay. Still, my Dad and I can share at least one thing, an immoral young woman ready to do the nasty with any...