Chastity Island Stories

24,344 results
Orientation
Length
Source
Infinite Scroll

Letter from High Coombe

by justincbenedict on Sep 24, 2019
Exhibitionist & Voyeur

Dear Shoeblossom... I don’t know if my involvement with Satanic Silki is my fault, because of my neurosis? You judge... First, my parents were weird, warped people. The oldest of us kids, Breanne, became an adulterous bitch, and my brother Brian’s effect was, he was a cruel asshole. And he ran off with my first wife. I’m Brogan, the youngest, the “sensiti...

The Captive of San Ramiro

by PaxNurgle on Sep 14, 2017
BDSM

WARNING/DISCLAIMER: This story features scenes of extreme female domination and BDSM, including pee/toilet play and forced bisexuality. If such content is offensive to you, please do not continue. Note: that this is a re-write of an earlier piece that was originally published and subsequently removed. San Ramiro Island is a desolate place. Like most of the...

Andy and Stephanie Pt. 02

by justincasetiger on Sep 14, 2020
Fetish

This is part 2 of the story of Andy and Stephanie. Please read part 1 first, or this won't make much sense! Andy I guess I get why she wants to wait...it isn't like I'd be having a lot of sex if we weren't together. It'll be worth it. She's so sexy. I'll respect her wishes for now and when we're married I'll get to fuck her and she'll suck my cock and it'l...

Playing For Keeps Ch. 06

by TanithLow on Sep 26, 2017
BDSM

For Quentin... Diego collapsed in the overstuffed chair that sat not far from the examination table where Aurora lay unconscious. She was beauty and sex personified. Especially with her legs sprawled open wide by the stirrups. He had a nice view of her shaved cunt that was swollen and wet. The scent of her pussy juice was driving him wild but he needed to...

Jason's Secrets Exposed Ch. 12

by jlenil on Jan 8, 2018
BDSM

The reader is strongly encouraged to read the first 11 installments before reading this chapter. ***** Lillie's trip had been extremely fruitful, both in pleasure and in new ideas. Ariana, being extremely rich and extremely evil, had decided to embark on a new adventure. She would be expanding her slave endeavor to America. This would entail a lot of prepa...

Daniel and Jamie's Romantic Night Ch. 02

by lockedinsteel on Apr 17, 2019
Group Sex

Daniel woke up and realized that someone warm was pressed into his back, their arm draped over his side, their face nuzzled into his neck. As he opened his eyes he saw the clock and realized that it was later than usual, almost 10am. The events of the previous night came flooding back as his mind shook off the tendrils of sleep. He remembered submitting to...

A Special Day In The Life Ch. 09

by hotbox on Sep 14, 2017
BDSM

Why'd They fix my makeup and hair now and why like this? I'm having a good time dancing. I keep hoping another of the Dommes that occasionally walk by will like me and want me. I make sure to slide my hands down my body, fondle my tits, roll my hips around when a cute Mistress stops to watch me. The ones that look cruel and strict in their tight leathers ge...

Slave Spalding

by justincbenedict on Sep 19, 2017
BDSM

One Spalding Tyll walked home disconsolately, his knapsack hanging off his arm. It had now been 103 days since Mother had allowed him to masturbate, and it was hanging heavy on his young balls. Spalding had asked his Mom to dominate him when he finished his first year of college, at age nineteen... Yes and she'd put him in chastity...although he'd had a p...

Black Cuckold Trend is Rising

by Samuelx on Sep 16, 2017
Interracial Love

Jay Fulton had always known he was attracted to both women and men, although he didn't explore his bisexuality until he completed his studies in civil engineering at Clark-Atlanta University in the City of Atlanta, Georgia, in the early 2010s. He met lots of lovely, big-booty young Black women who were exploring their sexuality and would bring them back to h...

One Glass of Wine, Revisited

by sublocked on Sep 14, 2017
BDSM

Note to reader: My last entry, "One Glass of Wine?" was not very good. That was partly because it was hastily prepared in fantasy mode. This version, "One Glass of Wine, Revisited" (without a question mark) is, I think, better and here is why. The first was fiction, with things added that I would like to see done to me. But that is not up to me, so in this s...