Cuckold Sissy Stories

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My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021

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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Cuckold Hypno Assignment

by DivinaTellsAll on Jan 1, 2019

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...

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...

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...

Sissy Cuckold Husband

by bisissystephenie on Sep 16, 2017

If you don't like sissy, cuckold, bisexual men stories, then please don't read it only to complain. You look stupid! ***** Like many husbands, I've wanted to see my wife fuck other men. I like the idea of being a cuckold. I had thought my wife Pam had been fucking a man but I had never seen it. One afternoon a friend of ours came over while my wife was at...

Heiress MMM gets Her Cuckold

by mmms_ricki on Sep 19, 2017
Loving Wives

Mary had recently inherited a rather large family fortune and become a multi-millionaire. As a result She was feeling extremely Independent and Powerful. Now that she was independently wealthy she had the urge to release Her Female Supremacy and Female Dominance side. She especially looked forward to showing off the Power She had over Her sissy submissive hu...

Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...

Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020

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...

Story of a Sissy Cuckold

by HughJanus on Oct 24, 2019

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...

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Angel Learns My Secret

by Angelscuck on Sep 16, 2017
Loving Wives

My wrists strained at the ropes that bound me to the chair. The vibrator taped to my cock was driving me mad while I watched my leather clad bride mount her lover's huge black cock. Angel smiled at me teasingly, knowing the pleasure and pain I was experiencing.... Suddenly I heard her key in the door I quickly turn off the magic wand, put it in the desk dra...