Chastity Island Stories

24,344 results
Orientation
Length
Source
Infinite Scroll

Letter from Tanglevale

by justincbenedict on Dec 25, 2019
BDSM

Dear Shoeblossom Truffles loves giving me a scented bubble bath on the night of my ninety day release-after three months in the cruel tube, my dick is finally out for business, and it's a thrill having her pretty hands rubbing and washing it, as well as all over... She knows how to make me quite excited, washing under my arms, etc. When the bath is over,...

The Advice Columnist

by colonellunchmeat on Sep 16, 2017
Fetish

Dear Debbie: What is your opinion on your submissive's RIGHT to occasionally kiss your boobs? My husband is totally hot for my full, pink 36D melons, but since he became my slave,I gradually weaned him off of them. Part of the problem is, I'm not as attracted to Joel as I used to be, he's kind of chubby now, and having his hands groping me when he brushes...

Black Sissy For Black Dominatrix

by Samuelx on Sep 1, 2017
Group Sex

As a Black mistress, I totally love it when my Black male Sluts dress up for me. Gleefully I slid my strap-on dildo into Reginald/Slut Gina's ass while spanking him and cussing him out like the bitch he is. The big Black dude is now wearing a frilly pink dress, red panties, stockings, and a wig, and his ugly mug is well-made up. Transforming macho Black truc...

Creamy Island Ch. 16

by AsheramL on Feb 12, 2018
Novels and Novellas

Chapter 16 : Exploration A drained Aiya and sleepy Tasha deplaned and waited for their baggage with everyone else. It was soon apparent that the entire plane had been filled with females in their same age group. Not all of them had been from their campus either. After they grabbed their bags, they were shuttled off to their hotel to try to rid themselves of...

Pleasing Master Hans

by justincbenedict on Sep 17, 2017
BDSM

Congressman Roger Malvern exited the Ethics Committee meeting and walked to where his office was. It had now been three days since Simone had put that damned thing on Roger's cock! Sheila had taken it pretty well when he'd shown it to her at home. Curious, really. "You like having this thing on your dick, honey?" Sheila had asked as she'd lifted the...

Into the Fire Ch. 06

by Swig on Sep 18, 2017
Interracial Love

Note: Several of you wanted longer posts, so I combined the 6th and 7th chapters. Doing so means it'll probably be a couple weeks before the next installment. Hopefully it'll be worth the wait. Thanks for reading! Chapter 6 I didn't see much of Shane over the next two weeks. He explained that early summer was a very busy time for the station -- barbeque...

The Blind Domme

by justincbenedict on Sep 17, 2017
BDSM

My fingers moved quickly across the last of the raised dots. "Allison" my fingers read "I've been looking all over town for you! You have company at home. A young man all the way from New York. His name is David Noyes. 'Thank you' cried Allison and waved her hand. She hurried, and when she reached Beech Street, she ran all the way up the block to her hous...

The Secret of the Island Pt. 01

by neoview on Sep 25, 2017
Transsexuals & Crossdressers

Hello, this is my first story I upload (not the first story I made). I am sure I didn't do a good job expressing my thoughts so please excuse me. You will notice the walls of dialogue and not so much "explaining". That's just my style but I hope to improve for the future. Anyway I expect some constructive criticism but please use simple words, I'm not stupid...

Creamy Island Ch. 21

by AsheramL on Mar 12, 2018
Novels and Novellas

Chapter 21: Aftermath A chime from overhead, "Processing complete." The doctor looked at her two subjects as a few techs began removing the many different connections. It was morning, and she had played with Sara for a few hours before heading off to bed herself. She made sure that she was there when the allotted time was up. There was a pool of different...

One Glass of Wine

by sublocked on Sep 11, 2017
BDSM

David heard the TV faintly in the background of his breathing and his heartbeat. He sat awkwardly on the leather sofa, arms restrained in leather arm splints, frustrating devices of restraint that allowed the use of his hands for long distance manipulation, but allowed no close-in usage for scratching, eating or drinking. All his nutritional sustenance was c...