Chastity Island Stories

24,344 results
Orientation
Length
Source
Infinite Scroll

Black MILF Femdom For Black Guys

by Samuelx on Aug 18, 2017
Fetish

Salutations, my name is Ginette Ambrose, and I'm a fifty-two-year-old African-American woman living in the City of Brockton, Massachusetts. One of the most diverse towns in all of New England, I swear. I'm five-foot-nine, chubby but still lovely in a wholesome kind of way, with dark brown skin and long Black hair. Thick Black mama with big tits and a big rou...

Aphrodite's Curse Ch. 001

by Gaius8666 on Sep 25, 2017
BDSM

Demetrius was sweating heavily now. Having just turned 18, he and the other young men in his village were subject to the annual lottery. This lottery, held once a year, determined which young man in the village would be the sacrifice to the Goddess Aphrodite that year. All young men aged 18 were subjected to the lottery and there were no exceptions. Diana, h...

Letter from Grand Island

by justincbenedict on Sep 24, 2019
Sci-Fi & Fantasy

Dear Shoeblossom, As an artist of sorts, I remember reading that the writer William Burroughs spent his final years, after his debacles in New York and Tangier, in very quiet Lawrence, Kansas. It wasn't as exciting as Mexico, where he'd shot Mrs. Burroughs' head off while playing "William Tell" with a martini glass so precariously placed...but it was time...

The Secret of the Island Pt. 03

by neoview on Oct 12, 2017
Transsexuals & Crossdressers

Sorry about the long delay. I was supposed to finish this like 2 months ago. But I got lazy and I couldn't really decide how to chain things together. It's a long story so it may probably need at least another 6-7 chapters before I finish it. I have other projects I'm working on, so I didn't really took priority. Anyway enjoy this shorter part. ------------...

A Sissy's Uniform Pt. 01

by Deeznuts4pm on Sep 14, 2020
Transgender & Crossdressers

I suppose the best place to start here is what my life currently looks like. I'm a 25 year old chastity sissy maid that lives with my dom. I would tell you my name before I was a sissy, but there's little point, so the name we are going by here is Jessica. I've always had a skinny build, and this is well complemented by my dark brown hair, which after servin...

Letter from Providence

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- I love your letters, but noticed you had nothing from our humble Rhode Island. During corner time after a painful discipline session, I turned my phone's recorder on. I love my stepdaughter, and wouldn't embarrass her, but she is so wild she doesn't care, and of course she is of age. This is for your "Taped Confessions" Eugene Scobrinks...

Letter from Des Moines

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom My first husband was an asphalt salesman; he sold cork flooring, too. I locked him in a plastic belt soon after we met; that much time on the road can make a man quite frisky. And of course you know the type. Ralph "Rip" Muztagh was a flirt from the word go. And he had what you'd call a long "cunt collar" amongst his friends. One of his...

Return of the Contract Killer Pt. 01

by 100 Angry Bananas on Sep 13, 2017
Erotic Couplings

Considering I hadn't killed anyone for months, life was good. People say, "Do what you know." I know killing people. This is not a skill accepted in great degrees by our society. If you're good at killing people, you go into the military, or if you're really good, you get into politics. Neither option appealed to me, so I had used my skills in an illegal f...

The Island Ch. 04

by zwer256 on Apr 23, 2019
Fetish

Author's Note: the fourth story from "The Island" series where we go to the office of ISL&L and find out how it works. The appearance and the behavior pattern of Chloe were taken from the game series "GDS Games Chloe18." The author expresses his deep gratitude to GDS for permission. The author expresses his great appreciation to Sloopb for editing this sto...

Stocking Sperm Challenge

by wordyone on Jan 1, 2019
Fetish

My sister Dorene was on the phone asking me if I could accommodate her friend Ruby during the Summer holidays. "She's a really delightful woman, generous and easy going, I wouldn't ask you otherwise," said Dorene. Ruby was studying theatre and dance and had to attend a six-week contemporary dance course at the local university. I was certain that my girlf...