Sissy Cuckold Story 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

A Cuckold's Story

by yumacd on Sep 25, 2017
Fetish

Part 1 I sometimes have submissive tendencies when it comes to sex. These are never full-time thoughts, just fantasy interests I like to explore occasionally. A while back I started gravitating to this one particular dominant woman on the interent. Her name is Lexi Lapetina. She has a cool website, but that's not where I found her. I first discovered her...

Cuckold Story

by Grey Eagle 286 on Sep 19, 2017
Loving Wives

I watched my wife of ten years as she entered the den where I was working on a report for work. She was looking very good. Grace wore a light brown leather skirt with a pale yellow shell and Cardigan sweater set over brown boots with high stiletto heels. Her body is amazing, and is centerfold quality for playboy. I am very proud of her. I smiled at her, "Yo...

Jackie and Artie Ch. 04

by Goodhusband on Sep 18, 2017
Loving Wives

This is the fourth episode in a series entitled "Jackie and Artie". If you have not read the previous three episodes of this series, I encourage you do so before beginning this chapter. "Jackie and Artie" is a romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an a...

Story of a Sissy Cuckold

by HughJanus on Oct 24, 2019
Fetish

Hi there, my names Michael but everyone just calls me Mike, i'm a 46 year old guy, i was an average guy living an average life, married to the love of my life, her name is Samantha. Shes my high school sweetheart, we dated all through high school then when we graduated we got married. She still has a smoking hot body, even all these years later, she works ou...

My Cuckold Story

by ohsubmale on Jul 15, 2020
Fetish

The story below is how I became a cuckold for the first time and probably for life. My wife and I had been married about 10 years and have been through as many Christmases. We have no kids, live in a nice home, both work, and in general have a great life. We slept together non-stop and were open and kinky; willing to try just about everything there was to...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

Cuckold Story - Christina's Revenge

by cuckcreampielover on Sep 12, 2017
Loving Wives

Cuckold Story 3 – Christina's Revenge Disclaimer: This story may contain bisexual activity, cuckoldry and humiliation. If this offends you please move on to another story. Otherwise, enjoy. Recently, after a night of creampie cuckold humiliation, I somehow got lucky enough to blow my load in my wife's best friend Christina (see my previous story for deta...

The Sexy Cuckold Couple Pt. 12

by cuckcpl4play on Sep 19, 2017
Fetish

AGAIN, cuckold story with humiliation and if this offends you, please don't read! While fiction, we have experienced ample aspects of this story and this lifestyle. ***** Part 12 Vegas The men hustled out of the limo and rushed up the stairs to get a seat in close proximity to my wife. Master ordered me to keep sucking the used condom and rather than allo...

Cuckold: Mia and Greg's Story

by glmike523 on Sep 17, 2017
Fetish

For the last 5 years Greg has been a cuckold husband. It all started one evening when he and his wife Mia decided to relive the spark they once had by going to a darkened parking lot and to have sex in their car. Mia is a very attractive woman and Greg is a handsome man. Greg looks a lot younger than his 42 years but if there is any downside to Greg it is h...

Infertility

by CuckoldGuy on Sep 14, 2017
Loving Wives

A true cuckold story. My name is Karen and I want to share with you my short love story. When I was dating, I had three steady boyfriends, Nelson,Tony and Jimmy. It was two years after I graduated high school that I started dating Tony. He is a tall, muscular, handsome guy and all of my girlfriends would have died to go out with him. On our first date he...