Cuckolding Sissy Stories

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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...

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BWC for Black Male Sissy

by Samuelx on Sep 12, 2018
Transsexuals & Crossdressers

Meet Bass, which is short for Bashir Malong, a six-foot-seven, dark-skinned and ruggedly handsome man originally from the nation of South Sudan. Bashir is definitely more than he seems, and that's just the tip of the iceberg. A lot of people, upon meeting the tall, handsome brother with the deep voice, wonder if he's some sort of professional athlete, and Ba...

Black Sissy For Black Dominatrix

by Samuelx on Sep 1, 2017
Group Sex

As a Black mistress, I totally love it when my Black male Sluts dress up for me. Gleefully I slid my strap-on dildo into Reginald/Slut Gina's ass while spanking him and cussing him out like the bitch he is. The big Black dude is now wearing a frilly pink dress, red panties, stockings, and a wig, and his ugly mug is well-made up. Transforming macho Black truc...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Cuckolding Ricki

by mmms_ricki on Sep 17, 2017
Loving Wives

MMM's HotTub Party & Cuckolding ricki MMM had not been back to Oregon for over 8 months and was anxious to spend some time with her best girlfriend Jill and her significant other Roger. Mary was sure that Roger had a crush on her and was anxious to take things a little farther if Jill approved and Mary made the opportunity occur. MMM had been training her...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

Such a Deal Ch. 06

by Angelscuck on Aug 31, 2017
Fetish

Here I was, in full sissy regalia, desperately sucking Alex's semen out of my fiancée's pussy trying to prevent her from becoming pregnant and avoiding becoming the nanny to a little half-black baby. This wasn't quite what I had in mind when I answered the dominatrix ad in the newspaper. I thought maybe a spanking, some groveling, a little pussy worshipping...

Mistress Kia Versus Samuel X!

by Samuelx on Sep 17, 2017
BDSM

For over two years now, the bisexual Haitian-American male known as Samuel Xavier had been pleading with his tall, curvy and sexy African-American dominatrix, Kia Holbrook, also known as Mistress Kia or simply Lady K, to turn him into a submissive Sissy slut like he was born to. For the dominant Black woman, doing something this drastic to a Black man wasn't...

Black Cuckolding In Montreal

by Samuelx on Sep 11, 2017
Interracial Love

Never say never, I guess that's what the moral of the story is. When my husband Benjamin "Benny" LaCroix told me that he wanted me to cuckold him, I think my jaw hit the floor. Benny is six-foot-one, lean and muscular, with dark brown skin, curly Black hair and lime-green eyes. My darling husband is biracial, born in the City of Montreal to a French Canadian...