Sissy Cuckold Chastity Bdsmlr Post Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

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...

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...

Becoming a Sissy Cuckold Ch. 01

by Pantieslave on Mar 27, 2019
Fetish

Beth and Dan were married very young, just 20 years old each. As such both were virgins when they married. Beth wasn't an outstanding beauty but very attractive with a nice body and very nice breasts, 36D. Dan, on the other hand, was rather feminine looking and wore his hair long, in a ponytail. Being slightly built, on more than one occasion he was mistaken...

Cuckold Hypno Assignment

by DivinaTellsAll on Jan 1, 2019
BDSM

My name is Divina. I serve Goddess K. and Madam Vega. I am on a journey to become their perfect sissy girl, and a cuckold slave to Goddess K (who is my wife). The following is a true story of an assignment given to me by Madame Vega, and carried out with Goddess K. Assignment: Watch cuckold hypnosis video pornography, with my chastity cage locked and and...

Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

The Sexy Cuckold Couple Pt. 15

by cuckcpl4play on Sep 26, 2017
Fetish

PART 15 POOL 2 As we walked outside, I noticed that our private area was more populated than expected. There were a few more additional males but more than a handful of additional and very attractive females. Sir Jeremy approached my wife quickly and I watched as the other women gawked at her and then began laughing at her as several of them even engaged in...

The Sexy Cuckold Couple Pt. 10

by cuckcpl4play on Sep 19, 2017
Fetish

After the crazy collaring weekend, our home life shifted slightly back to some form of normalcy. Master would send us occasional texts, orders, etc., but overall there was nothing significant that was transpiring and in fact Miss Jenny seemed sad that more activity was not taking place. At work it was a bit of a different story...Master was his typical domin...

A Cuckold's Journey Pt. 03

by yukonnights on Nov 26, 2018
Fetish

The big day had finally arrived. In fact, for me it arrived so fast that I was on pins and needles all day until Sarah came home a little early from work. I had the house work done and was just sitting in the living room waiting when she walked in. "Hi babe," I said as I got up to give her a hug. "How was your day?" "It was good. We weren't too busy today s...

The Sexy Cuckold Couple Pt. 11

by cuckcpl4play on Sep 19, 2017
Fetish

This is part 11 of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneducated or despi...