Chastity Island Stories

24,344 results
Orientation
Length
Source
Infinite Scroll

Marabogo: Cuckold Island Ch. 01

by eeric on Sep 19, 2017
Interracial Love

Prologue The breeze that came in from the Atlantic ocean did not do much to quell the baking sun on the beach of Marabogo. The small island laid approximately one hundred miles of the coast of Namibia, Africa. John Morton and Henry Larsen sat on the beach in their sunbathing chairs looking at all the skimpily clad women and ripped black men. Both men were...

Survivor: Femdom

by pifan on Sep 13, 2017
Fetish

A dozen guys (including me) are picked up for a sex slave game. It pays a truckload of money so we sign a contract to be slaves for a year, disclaimers and all, and then are transported to a warm tropical paradise of an island. There are at least a dozen mistresses on the island probably more. Once we arrive, we are told about the rules for men. No clothes a...

Tease Island

by justincbenedict on Sep 14, 2017
Fetish

The Early Season "The new boat comes today" M. Fulbright Penopskott commented to Dawn as he squirmed on the bed. Dawn nodded, and continued her trail of flicks against M.Fulbright's suffering shaft. Dawn leaned closer, staring intently under her platinum blonde bangs, as her pink nails painted to match her tube top poked and stroked M. Fulbright's purplis...

Aphrodite's Curse Ch. 011

by Gaius8666 on Sep 15, 2017
BDSM

Standing on the bow of his ship, Demetrius was overwhelmed with feelings of sadness and loss. His status as an immortal was obviously a wonderful gift from the Goddess, a consolation prize to the curse of constant nudity and eternal frustration, but there was a catch of course. He had been away from his home now for over 53 years and did not appear to be any...

The Keyholder Ch. 15

by AndreaJordan on Mar 2, 2020
BDSM

Ben sat on the beach enjoying the view from their deserted Maldives retreat. With no one else in sight, he had stripped off his black board shorts and was stroking the small silver chastity cage that, as always, hung limply between his legs. He ran his fingers over his balls and enjoyed the tickling sensation and the resultant pressure build up his cage. H...

Marabogo: Cuckold Island Ch. 02

by eeric on Aug 29, 2017
Fetish

"Hold the elevator please." Megan and Joshua heard a woman's voice just as the elevator doors were about to close. Joshua quickly held out his arm to so the doors wouldn't close. Through the small crowd of newly arrived guests, they saw a very scantily clad and rather chubby young woman coming at them. She was slightly jogging, her huge chest and big belly...

Allison's New Life Ch. 22

by Goldeniangel on Sep 12, 2017
Novels and Novellas

When Allison found out that Todd was buying a new house she was thrilled, especially because he'd told her that he was buying from a couple who also had... unusual tastes... and there was a special room in it just for him and her. A full dungeon... and he was going to keep it well stocked with toys for when she was good, and other things for when she was bad...

Marabogo: Cuckold Island Ch. 03

by eeric on Jan 21, 2019
Interracial Love

A crowded lobby stood in front of Joshua as he began to drag the suitcases towards the elevators. Luckily two of the cases had small wheels on them, which made it a lot easier. Though the laughter he got from the women he passed made the whole matter a lot more humiliating. Joshua could hardly fathom how this had all happened. Just a few days ago he had go...

From Stephen to Stephanie Pt. 04

by nikkiwest101 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter one The morning after the party I answered the phone, it was Emma who had tormented me so much the previous day, she asked to speak to Karen who then told me that Emma wanted her scarf back and wanted me to deliver it to her. Karen insisted that I go and change into my maids outfit, she surely didn't intend for me to walk to Emma's house dressed li...

The Wedding Ch. 09

by betamale08 on Apr 1, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 9 – Coerced, Consumed and Consummated... After wrestling my Uncle John out of his suit and laying him out on his back, I knew his passed-out routine was all a farce as he looked to me winking with a smile before going back into his pretend-coma... Faking it in front of Patti and no doubt doing so in the want of stay...