Sissy Story Caption Stories

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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...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

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:...

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...

Being Jenny's Summer Boyfriend Ch. 02

by Lucas96 on Mar 5, 2018
Fetish

Disclaimer: This story contains cuckolding, humiliation, homosexuality, and incest. All characters in this story are above the age of 18. ***** Here I was, on my knees between Jenny's legs as she sat back on the couch. Slowly, reluctantly, I stuck my tongue out and moved it toward her naked body, dripping with my dad and brother's cum. I was so grossed out...

Lucas's Older Brother

by Lucas96 on Dec 2, 2019
Fetish

Disclaimer: this story involves cuckolding, humiliation, etc. *** Lucas and Emily, both 21 years old, had been dating for about a month. While Lucas had had previous girlfriends, he'd never felt the way he felt about Emily. They'd met in class at their small liberal arts college, hit it off immediately, and gone on several dates. After a week or two, Emil...

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...

Boredom and Therapy

by oldhippie1949 on Aug 31, 2017
Group Sex

The following is a true story. Naturally, all the names have been changed but all the events described took place just as I have written. If a bi-sexual threesome is not to your tastes then move on. If you are too young to be reading this, then move on. ***** I was so bored. Even my dog couldn't shake me out of it and. believe me, he tried. I didn't care t...

The Conditioning

by wifeownseverything on Sep 17, 2017
BDSM

This story contains female domination, verbal degradation and humiliation, and perceived exploitation. Both characters are consensual adults. Please skip if these subjects offend you. ***** This is the fourth story I've written about my wife and myself. It is the only story that isn't mostly true. While fantasy in the sense that it hasn't happened, I thin...