Mature Chastity Stories

35,203 results
Orientation
Length
Source
Infinite Scroll

Female Led Relationship

by CuckoldGuy on Sep 14, 2017
Reviews & Essays

Female led relationship, FLR is becoming the common, accepted life style. Girls are born with a natural instinct to be care givers and mothers which in a way makes them natural leaders. Boys on the other hand, come into the world as wild animals. They have to be domesticated. In their formidable years their mothers domesticate them by giving them spankings...

Made to Obey Ch. 03

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise. I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. Could I pass the tests? We reached the li...

Like Mother, Like Daughter

by catigm6 on Sep 26, 2017
BDSM

Just Married (Four days after the wedding) She was not the best looking girl that I had been with, but she was a catch. I liked her Greek/Mediterranean look, with her white pearly skin, her black her, dark brown eyes, thin eyebrows, and just the right amount of freckles to humanize her face. Her body was not bad at all either; she had a nice butt, a small...

Jerry becomes Jill Pt. 03: It Gets Serious

by gasissynora on Mar 2, 2020
Transgender & Crossdressers

This is the third part of my story about how I became Jill. My relation with Rikki takes a serious turn and I learn more about what life with her will be like. Each day Rikki gives me an article about a female led relationship. The article on Monday is about a couple in their thirties who are dating. The woman makes most of the decisions when they are in pu...

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...

A Touch of Lace

by DevisPixi on Aug 20, 2018
Mature

I don't know which is more vexing: how worked up I am over a slight flirtation or why my wife of twenty-five years would engage in adolescent petting with some random guy. We were at the convention, day four. That is usually about the time that the newness has worn off and the big sendoff with a banquet and ballyhoo is still a day away. I was beat and decid...

Finding Myself Pt. 01

by FreakyBiFantasyGuy on Oct 7, 2019
Fetish

The minute I turned eighteen, I was out of there. My birthday consisted of a shitty supermarket cake and a drunken rant from my liquored-up dad. Happy fucking birthday, Sam. But finally I'd done my time, and my birthday turned the page into a new chapter of my life. A chapter full of freedom, when I could break free from my fucked up family and reinvent my...

Femdom Future Ch. 01

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

If you haven't already done so, please read the prologue. * CHAPTER 1 John nervously sat in the reception area, back straight, head and eyes to the front, legs together, fists clenched and resting on his knees. He had recently been deemed mature enough to start his sexual slavery course. It had only been a couple of weeks since his eighteenth birthday....

Exposing Amy Ch. 06

by fannyrat on Jul 6, 2020
Fetish

It took quite a while for my wife and I to come to terms with the fact Amy had given herself to my life-long enemies. However we eventually, albeit slowly, settled down and concentrated on looking after our children. We spent many hours revisiting the last few years, reliving the activities we had indulged in and talking out the tremendous and traumatic affe...

Sub Lucy Takes Dominant Sex

by Intercontinental on Jul 30, 2019
Transgender & Crossdressers

It was not a simple wish. It was a need. A desire. Lucy had not been fucked for months, and she needed it. The preparation was an essential part of the ritual. A piping hot bath, the scrupulous washing and cleaning, the razored smooth armpits and legs, that tingling scented sensation on her naked body as she towelled down before returning to the bedroom to...