Sissy Chastity Cuck Stories

13,492 results
Orientation
Length
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Infinite Scroll

Roxanne and Willie Ch. 21

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the twenty-first episode in a series entitled "Roxanne and Willie". If you have not read the previous twenty episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongly r...

How I Make You My Toy Ch. 01

by SadistGoddess on Sep 14, 2017
BDSM

Chris exhales and winces as the spikes on the inside of the choke chain pinch his neck. It's not the first time he's been on a leash for his fiancee Natasha, but it's the first time it's not just metaphorical. "You sure that's safe?" Sebastian asks from the bed. His smirk doesn't do much in the way of concern. "Not too safe," Natasha says flatly. As if fo...

Cuckold Fantasies

by LogNTR on May 29, 2020
Cheating Spouses

Hello Readers, Just wanted to say that this 'introduction' chapter will be used as a guideline for random cuckold stories. You, as the reader, can always give me suggestions for ideas, new paths, and I'll try to implement them. My wild hotwife: Claire catches John masturbating cuckold porn, what happens next remains to be seen, or rather, to be read. Short s...

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Birthday Party Pt. 01

by JamieMcKafee on Jan 22, 2020
Transgender & Crossdressers

**First public story submission, so apologies if things are a bit jankey. Contains lots of nastiness, including but not limited to: futadom, futa on female, cuckold, SPH, bondage, etc. All character are over the age of 18. Hope you enjoy :) ** ***** "Harder!...Ughh! Harder, fuck my dripping pussy harder, Skye! I love you, keep fucking me, baby! Oh god,...

Whore of the Dragon

by Conan The Librarian on Feb 19, 2020
Fantasy

There, amongst the remnants of the dead race, where their greatest queen reigned, two dragons lie dormant. One of pure evil, one of pure good, both yearning for a vessel, both lusting for a mate... She may be adequate for that purpose, our forlorn child... We shall see. "Silence, fools. We are close to the inner sanctum." The two mercenaries exch...

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An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

The Ultimate Cuck Experience

by Joggles44 on Mar 12, 2021
Cheating Spouses

(UPDATE: Custom names for all main characters have been successfully added! Enjoy!) (Note from the author: Hello! Hope you enjoy my story. Before you start reading let me clarify that this story is set to "private", meaning no one can edit it or add chapters but me. I'd like to keep the writing to myself while the project is developing. HOWEVER, I...

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A Cuckold is Seduced Ch. 03

by wants2bsub on Sep 25, 2017
Loving Wives

This is the third part of the story that I had started some time ago. I had written it, but then I thought it was a bit surreal for me, so I just let it sit for a long time. Then, after reading Karenkay's brilliant "White Slaves of Eban" stories that she is currently publishing, I have changed my mind. I'm so taken with them, that I decided more content in t...