Sissy Stories Caption Stories

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Length
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Infinite Scroll

How I Became a Chastized Cuckold Ch. 08

by gizzard on Sep 26, 2017
Loving Wives

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * Thin rays of golden sunlight glimmered through the bedroom window bl...

Types of Cuckolds

by cuckwhofucks on Sep 14, 2017
Reviews & Essays

What does it mean to be a cuckold? It actually means many different things to different cuckolds. But let's start at the beginning: The truth vs. the Truth. The Truth, or an absolute Truth, is actually unnamable, or rather it exists, but when you try to interpret it and put words to it, it becomes one of very many truths, as many truths as there are peopl...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Hotel Mix-up

by Woulditkillyou on Sep 13, 2017
Loving Wives

This story deals with Cuckolding, sissy, and impregnation. Please do not continue if any of these subjects offend you. This is a work of fiction, meant to be enjoyed. Please click back if this does not suit your style. In a fantasy, there are no STD's, and pregnancies become nothing once you stop reading. Sorry it is so long. I get carried away with the deta...

Exploring My Fetish

by fetishguy81 on Jan 7, 2018
Anal

Note: This story plays off of my previous 2, taking place after both of them. You won't miss too much but you can get more of the backstory by reading my other 2 stories first. ***** I developed to rather uncommon fetish's in pretty uncommon ways through out my life. My first was a fetish around salon capes and haircuts in general. When I was younger I dre...

Discussing Terms and Labels

by XplrgMDCpl94 on Apr 14, 2020
Reviews & Essays

The author of "Fifty Shades of Gray" did an excellent job of playing on the words, her main character's name and the concept expressed by "fifty shades." There are so many variations expressed, most especially when it comes to sexuality, that fifty is probably too small of a number. That said, I was thinking about various terms in common use and how they cou...

CFnm Adventure - 2nd Visit

by lovelicker99 on Sep 13, 2017
Fetish

Note: This is the second story involving encounters between me as a submissive male and a Dominant BBW who responded to an ad I ran online. These stories are fantasies, but some of the specific acts are things I have done and enjoy doing. If you are a woman or a couple that enjoys doing any of these things I would like to hear from you regardless of where yo...

The Botanist

by Carnal_Flower on Sep 19, 2017
Erotic Horror

Q: Why do you write erotica? A: Because if I didn't put sex in my stories, no one would read them. --Anonymous Part One. The Master hated these trips into London, but they simply could not be avoided. The Thief, so peculiar in his demands, would not meet with anyone else. This was perhaps understandable in the beginning, when he was completely unknown,...

Mistress Tanya Ch. 01

by Palancar on Sep 18, 2017
Fetish

This is the first chapter and is a little tedious without any actual sexual situations. Please bear with it. I needed this to set the stage for following chapters. I promise it will get much better. Also please remember it is only a work of fiction. I welcome critiques both good and bad but if the storyline isn't your cup of tea then don't read it. I see s...