Sissy Cuckolds Stories

7,178 results
Orientation
Length
Source
Infinite Scroll

The Night of the Comet

by dragonmann72 on Dec 31, 2017
Loving Wives

I dedicate this story to all those Alpha males with big cocks, all of the size queens and cuckolds out there. To all of you grammar and literary experts, I don't care if you find a mistake, this was done for my and your pleasure not to win a Pulitzer Prize in writing. Try to enjoy any way. Ps: No Alpha male were really injured is this story. ***** Thank...

Mistress Aminata Kanu's Dungeon

by Samuelx on Feb 7, 2018
Transsexuals & Crossdressers

As Salaam Alaikum, to any kinky fellow Muslim reading this. Salutations and greetings, ladies and gentlemen. I am Aminata Kanu, also known as Mistress Ka, an expert on BDSM and Black sexuality. I'm a young Black Muslim woman living in the City of Santa Barbara, California. Before we go any further, I must warn you that I'm into some truly extreme shit, and I...

Filipina Cuckolds Her Sissy Husband

by nancyvasquez on Sep 14, 2017
Transsexuals & Crossdressers

If there's anything more sexy and exciting for a closeted sissy than dreaming about being a woman on your knees getting ready to serve a big black muscleman, it's actually having the balls to go out there and make it a reality. It happened to me! I was married, to a hot sexy girly-girl Filipina. When we got married I was still trying to be in denial about my...

Wendy The Haitian Cuckoldress

by Samuelx on Sep 16, 2017
Interracial Love

My name is Wendy Stephania Polydor and I'm a 29-year-old Black woman of Haitian descent living in the City of Boston, Massachusetts. I work as a Nurse at a certain hospital and I am the proud mother of a son, Jefferson, and a daughter, Lilandra. Life as a single mother isn't easy, and the fact that my ex-husband Alan Stephenson, a Boston-area cop, is a miser...

The Alchemy of My Remaking

by pansgarden on Sep 16, 2017
BDSM

THE ALCHEMY OF MY REMAKING: YELLOW INTRO: The Code: Yellow is the color of trust Orange for royalty Red for lust Brown for the richness of the earth, coffee, cocoa, and crude oil There were sophisticated ladies and there was Lady M. Everything about her was out of a fifties Hollywood movie. She used a long filter to smoke cigarettes. She wore long glo...

White Mistress & Black Sub

by Samuelx on Sep 17, 2017
BDSM

The year is 2008. The place is New England. And my bitch is black, folks. And he likes it rough. Am I a lucky woman or what? My name is Marie Louise Nelson. Friends call me M.L. and find it funny. At six feet two inches tall and two hundred and sixty pounds, I'm nothing to laugh at. I'm a big and tall, thick-bodied and big-bottomed, blonde-haired and green-e...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

He Looks Like His Father

by RainStevens on Sep 13, 2017
Interracial Love

WARNING! This fictional story isn't for everyone. It involves cuckolds, male feminization, submission, interracial sex and breeding. If you're not interested, go find another story. * I am a white fifty something year old married cuckold and a proud member of the W.B.A. My wife is twenty years younger than I and we have four children (with one on the way),...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

My Girlfriend's Sissy Roommate Ch. 04

by SEVERUSMAX on Nov 21, 2017
First Time

"So, you softened up faster than I expected on the issues of fellatio and vaginal sex, babe. Not that I mind, as it's between you and Rain, and I think that it's rather sexy, anyway, but what prompted that? Just the knowledge that Rain has meekly accepted his lot and will be a loyal husband to you? I wouldn't go so far as to call him a cuckold in the typical...