Latex Sissy Chastity Stories

20,354 results
Orientation
Length
Source
Infinite Scroll

Dear, We Have to Talk Ch. 06

by dr13bone on Sep 25, 2017
Interracial Love

I was in the house by myself for a month while my wife and Karen went abroad to get her augmentation done where the price was a lot lower, they made a vacation of it. When I picked her up from the airport it was a cold November day, but even through her coat I could tell her figure had changed radically. She had done a makeover, her hair short and blond now...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

A Cuck and Bull Story Pt. 02

by PBEnis on Jul 31, 2018
Fetish

Katie steps back into her titty top and pulls on her skirt. I grab her shoes and walk her back to my truck letting the hotel door close behind me, making sure the do not disturb sign will hang on until morning. I don't want the maids beating me back to this scene. Once I have her back in the truck I can see she's a little too far gone to get a play-by-play o...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...

The Nemesess Ch. 02

by ProfessorPlums on Sep 15, 2017
Fetish

Correspondence from older (50-70), dominant ladies most welcome. * The next few weeks passed slowly for Chris. He was initially terrified of his new Mistress, - after the ordeal of his 'breaking in'! However, his new Mistress (Theresa) didn't want a simpering bundle of nerves to play with. Dominance for her was a varied and protracted feast; full of spice...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Clitty Transformation - One Month In

by DivinaTellsAll on Jan 1, 2019
BDSM

Exactly one month ago, on a cold Saturday night in Dallas, Madame Vega and Goddess Kimberly evaluated what I had previously referred to (my entire life), as my cock. This evaluation revealed what I already knew at heart. It was far too tiny and small to be used as a cock, or even considered a cock. I begged them to allow me to embark on a quest that would...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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