Sissy Caption Stories Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

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...

My Friday Night: Switch

by honey28 on Sep 5, 2017
Fetish

Driving home on Sunday night, my phone rang when I was stopped at the light waiting to turn onto my street. Seeing Nick's name, I put him on speaker phone. Before I could say anything, he very loudly declared, "I want to lick your pussy." Hearing that deep, sexy voice usually makes me melt, but I had to giggle. Note to self: never answer his call on speakerp...

Pretty Chris-tine Ch. 02

by jealouscuck on Sep 26, 2017
Fetish

My wife, Sharon, and I were lifelong friends. We eventually began dating and then got married. The idea that eventually shaped part of our sex life was her grandmother remarking that I was too "pretty" to be a boy. She thought that my complexion and clean looking face was attractive. One time as a lark, Sharon asked me to let her put makeup on me. I initiall...

Montana Rhapsody Pt. 01

by Egmont0409 on Sep 16, 2017
Novels and Novellas

CHAPTER 1 Hard-faced commissioning editor Ruby Street looked at one of the publishing company's premier writers of soft romances that were laced with mild naughtiness. She smiled bleakly, thinking the success of this attempt to wrench Paris McCoy out of her comfortable rut to hit the bookshelves with a sexy sizzler were about as good as finding a hundred bu...

Loosening Up Bk. 01 Ch. 01-10

by SteveWallace on May 14, 2018
Group Sex

Book 1 -- Loosening Up: Initial Journey Chapter 1 -- A Crack In The Façade Alice sedately drove her seven-year old silver Honda Civic into the parking lot of the company she worked for -- Knightsbridge Manufacturing. She looked around, but only a few cars were present. Along the back side of the lot four cars were already parked in the spaces under the tre...

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...

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...

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:...