Mature Chastity Stories

35,203 results
Orientation
Length
Source
Infinite Scroll

Extreme Cuckold Fantasy Ch. 02

by Revan7 on Jul 29, 2019
Interracial Love

Prologue It's been two years since David and Jenny had started to fantasise about cuckolding. Two years after that jenny was pregnant with one of four black man's baby. They were on week away from a villa holiday in Spain with these four black men and were about to go out and get queen a of spades tattoos for Jenny. Jenny was pregnant with a black man's bab...

Letter from Radburn River

by justincbenedict on Oct 8, 2019
BDSM

Dear Taryn I met Melody, a 20 year old spitfire, when she and her sorority were having some sort of carwash fundraiser. You know, to benefit starving wooded owls or something. They were so hot, in their little wet tee shirts, cut offs... But when Melody approached me, her teased hair blowing in the wind, she wasn't even wearing a tee shirt, just a bikini...

Bisexual Men's Wives Ch. 02

by Samuelx on Jun 18, 2019
Interracial Love

Meet Tyrone Dumarais, a big and tall, handsome black man living in the City of Ottawa, Ontario. Born in the environs of Detroit, Michigan, Tyrone moved to the Canadian Capital for work opportunities. He works for Shared Services and makes decent money. Unfortunately, Tyrone is quite lonely and most women don't understand his unique needs. He has a sincere ad...

Letter from Los Angeles: Ms. Scunt

by justincbenedict on Sep 15, 2017
BDSM

Dear Shoeblossom, My name is Eliza Scunthorpe, a keyholder in Los Angeles I have read Leland T___'s whining letter to you and I want to clear things up! For instance there's Parrish! Parrish is a favorite client of mine. He is on a relatively lenient schedule--he is allowed to orgasm about once every other week. And he has privileges I don't usually gra...

An Indian Widow's Choice

by Devaro on Sep 12, 2017
Mature

Chapter 1: When Fortune Shapes Fate It's a hot summer day in India, but there is no happiness in Monee's family, the crop is failing due to a terrible drought that swept through southern India, and to make things worse, her husband who has been working in the city as a construction worker in order to support Monee's family died in an accident. Monee's fam...

Outside the Comfort Zone

by slutboynz on Sep 14, 2017
BDSM

One of the more intense periods of my life happened when I was searching for a new Mistress. I guess having been used as a slut for some time, and now being without a vicious Mistress I was missing the pain in parts of my body, especially my balls...but that was about to change. Meeting Mistress G for the first time, I was pleased to see all her description...

Irma's New Toy Pt. 02

by Sputnik57 on Sep 15, 2017
BDSM

Irma had Drake lap and probe obediently at the mixed perfumes of her cunt and arsehole, enjoying several rich orgasms as she indulged in the sheer pleasure of enforcing her dominance over him, revelling in her control and lusting to show her latest conquest to her friends; the first showing always gave her such a thrill, her pride bursting as she demonstrate...

A Wife's Process

by catigm6 on Sep 25, 2017
BDSM

Chapter 1 – The encounter "Life is pretty mainstream", or so I thought. I lived a pretty average life: 45 hour a week job, hanging out with friends on the weekends, meeting the family on Sundays, the daily workout routine, and the occasional fling or girlfriend. I have never been a Casanova, but never really had a hard way with girls either. Ever since my s...

Stocking Sperm Challenge Ch. 02

by wordyone on May 7, 2019
Fetish

The second part of the story of the Stocking Sperm Challenge will make better sense if the reader is familiar with the original story. * Naturally, Ruby was enjoying telling April every saucy detail about what she had just put me through at my first and failed attempt at the Stocking Sperm Challenge and the history of my unsanctioned meddling with her inti...

The Wedding Ch. 02

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake Part 3) Chapter 2 -- Party in Pink Purgatory... "Oh Wow Dale! You look fantastic! Very -- Very pretty... I can hardly tell that you're my boy anymore! Really sweetie I'm so impressed -- and Patti you look gorgeous too... I knew that dress would look stunning on you -- but Dale -- my pretty -- pretty -- son... That dress is perfect;...