Sissy Caption Porn 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...

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...

The Trophy Wife Next Door Ch. 01

by LaPatitMort on Sep 13, 2017
Erotic Couplings

Even though I had officially lived in my new home in the exclusive Cooper Trail Estates for six months, I did not know any of my neighbors. In fact, over the long winter months, I had been traveling for fun but now it was spring and I was working to get my prized possession in good working order. I had only put ten thousand miles on my custom California Chop...

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:...

Inception Cuckold Pt. 01

by Alizered on Sep 10, 2018
Fetish

John and Danielle. Typical white couple living in America. Good jobs, nice house and John is secretly addicted to cuckold porn. Sound familiar? It should considering more and more people seem to adopt this fetish, but when couples actually cross that line and engage in cuckolding, the husband might stop and wonder how it all happened. Every cuckold couple ha...

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...

Courting Cheryl

by RonWCB on Sep 14, 2017
Humor & Satire

Steering up the long winding driveway I had a feeling of apprehension. Leaving everything I've known my entire life and traveling half way across the country was more than just a little out of character for me, it was borderline insane. Up until a few weeks ago I was working in a managerial position for what I thought had been a stable successful manufactu...

I Put on A Cock

by ndeavour on Jan 6, 2020
Erotic Couplings

Hi, my name's Liz. I'm not about to tell you how old I am -- but I have a 25 year old son, so that should give you a sense. I've only just stopped coloring my hair and begun letting a whole lot of silver to emerge. I no longer have the slim figure I did before having my son; I gained nicely in the boob department, but picked up some extra padding all over. I...

Art Heist

by Gato Medio on Sep 16, 2017
Novels and Novellas

It is quite possible that Mirella's sense of reality has become somewhat warped as a result of watching too many James Bond movies - or watching them too many times. She owned tapes of every movie ever made and watched them constantly. Needless to say, those were her favorite films. There was, however, one aspect which got up her nose. The female agents who...