Chastity Sissy Cuckold Stories

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Discussing Terms and Labels

by XplrgMDCpl94 on Apr 14, 2020
Reviews & Essays

The author of "Fifty Shades of Gray" did an excellent job of playing on the words, her main character's name and the concept expressed by "fifty shades." There are so many variations expressed, most especially when it comes to sexuality, that fifty is probably too small of a number. That said, I was thinking about various terms in common use and how they cou...

Imprisoned in Chastity

by Longjohnsilver30 on Aug 31, 2017
Fetish

Lynchburg prison was a low security prison for non-dangerous criminals. Mostly white collar criminals with money ended up in this place. It was actually not too shabby a facility. It had single rooms with en suite bathrooms equipped with private showers, drawers for your limited clothing choices and a TV in each room. I was even able to take my Xbox into the...

How We Became An "Owned Couple" Ch. 12

by watchdwag on Sep 26, 2017
Loving Wives

The Conclusion It was strange coming home to Lee instead of my wife but over the next few days I became more accustomed to my new mistress. It took some time to adjust to the chastity device that had been installed but eventually I accepted the fact it was there to stay. I also no longer took issue to the panties Lee had me wear. I resigned myself to the fa...

The Sexy Cuckold Couple Pt. 13

by cuckcpl4play on Sep 19, 2017
Fetish

Part 13 Vegas Arrival We quickly departed the plane and as expected, Master had a limousine waiting for all of us. Getting into the limo, Master asked his slut / my wife loudly enough for all of us to hear, "Is that stretched out pussy already tender and sore?" My wife immediately responded that it was hoping that Master might express some niceties or co...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Sandra and Stevie Ch. 31

by Goodhusband on Sep 13, 2017
Loving Wives

Note: This story is the thirty-first installment in a series entitled "Sandra and Stevie". If you have not read the previous thirty episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongl...

The Dominatrix Order Pt. 02 Ch. 02 - Cuckold

by Jwwsmith on Jan 29, 2019
Transgender & Crossdressers

And so the days and nights passed at Johanna's home. With Sissy Slut gone, there were no slaves remaining who possessed any culinary skills. So Pomona took it upon herself to cook a fine breakfast every morning for Johanna, as a way to repay her for her hospitality. Pomona would wake early each day, fire up the wood stove, and cook a delectable meal of bacon...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

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...