Sissy Chastity Cuck Stories

13,492 results
Orientation
Length
Source
Infinite Scroll

The Two-Month Break Clause Pt. 02

by TheBiGuy on Mar 25, 2019
Fetish

After my first post, I received several comments. Some of the comments were positive and others negative. Any comments that were constructive, I will take the criticism and learn to incorporate those suggestions into the subsequent chapters and other stories I write. One of the comments was about numbering the story as Part 1 or some variation like that. Tha...

Taking Laurie for My Own

by n00bwriter on Nov 26, 2017
BDSM

I am extremely thankful for the simply wonderful job MamaK did in editing this story for me, going above and beyond any assistance I could have hoped for. Her instructions on creative writing have been nothing short of phenomenal and have certainly helped me to become a better writer. MamaK - Thank you! ***** I met Laurie working at my previous job. What...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

How I Became a Cuckold

by Rjt72088 on Feb 6, 2018
Fetish

This is the 100% true story of how I became a cuckold. It took about 10years to get to this point so if It is your fantasy to be a cuck be patient. Sometimes it just takes waiting for the right situation. A little back story. I'm 31 my wife is 32 and we have been together since JR year of high school (2003) she is very attractive and has always been able to...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

Don't Stereotype Cuckolds

by eviltwin52 on Apr 27, 2020
Loving Wives

Let me start by saying that I am a cuckold and a happy one. It was my choice and I found a Woman that would lead me down the path to unbridled satisfaction. Unfortunately too many Lit readers either disregard our lifestyle altogether or deride those of us who are strong enough to give our Women what they want and thereby meeting our own needs. But what are...

Somewhere In Between

by MistyMorgan on Sep 17, 2017
Loving Wives

My name is James and I have been married to my wife, Cali for twelve years. All of those years we were very happy and we enjoyed being with one another. We liked the same types of movies and had lots of friends with whom we socialized. We didn't enjoy the same sports, but that was all right too. She loved baseball; I was into football. We had parties with o...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

Step-Mother has a Secret

by call_me_dana on Feb 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** "Rachel ... Wait! I can explain." The curtain had already closed and she was gone. I looked in the changing room mirror and my untucked bulge was quite evident. I hurriedly re-tucked, stepped into my leather skirt and into my heels. Looking at the pretty young woman who had been...

Cuck Husband

by SatinSlip on Oct 15, 2017
BDSM

We didn't choose this lifestyle. It was forced upon us. Well, perhaps that's not quite true. Maybe best to say that my wife and I were forced to confront who we truly are. My wife is way out of my league. I'm a nerdy, small accountant. About my only good feature is my nice ass. Though even that's a bit too feminine. My wife, Cherry, on the other hand is...