Sissy Chastity Cuck Stories

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How I Became a Chastized Cuckold Ch. 09

by gizzard on Jun 18, 2018
Fetish

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * The next week and a half seemed to skirt by as if Father Time himsel...

Adult Trip Pt. 02

by cuckcpl4play on Jul 3, 2018
Interracial Love

The trip back to the room was embarrassing given I was coated with the cum of my new Master. I rushed back and within seconds of arriving, my phone went off. The text read, Dearest white slut, please provide an inventory of the sex toys that were brought with you. It is now 4:00 and I expect you and your small dicked cuckold husband to join us on the beach...

Mama Mia Pt. 02

by grizzley123 on Jul 27, 2020
Fetish

This story contains many themes including cuckolding, gay sex, bsdm, incest and submission. If these are not your things, please skip. This is the second installment and it obviously helps to read the first part. The starting point here: I have just finished sucking off my temporary neighbor's cock. I have been set-up by my wife and her lover to be a submis...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

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...

Cuckold Sissy Husband Goes Further

by keptsissy on Sep 18, 2017
Loving Wives

PART EIGHT: "Baby, I've been thinking about you. Been thinking you need something more to look forward to. I think that you would enjoy cumming more, enjoy your little thing played with more if it was more a special occasion." She's seated at the kitchen table. She has a small package on the table. "Come here." She watches as I walk to her. "Mistress, I n...

Sissy Comes Clean

by Cuckyboy3 on Oct 6, 2020
Fetish

Reflections after Mystic: On the scenic drive back home from a fall getaway vacation with my lovely wife, I pondered quietly how the excursion would be remembered as a first of a kind. I had begun the trip with the expectation of a quick and routine spanking followed the next day by an epic sex experience. Three days later, however, I emerged having not onl...

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...

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...

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...