Sissy Chastity Stories

Sissy Chastity Stories
Are you ready to go “ Down The Sissification Rabbit Hole?” Then read this…
I t sometimes seems that sissies and chastity are mentioned in the same breath together more than any other two words. Whether that’s true or not isn’t really all that important. What is significant is that chastity and the sissy share a symbiotic relationship that just won’t be denied.
What is it about the two sharing the same bed that feels so goddamn right?
Chastity and sissies go together like paranoia and schizophrenia. They are pretty damn close to being inseparable. It’s not difficult to see why that’s true.
Sissies, by most all definitions, are submissive creatures. If you’re a sissy, then you were created to please. Although there are many ways to pleasure your partner, sex is one of the more obvious ways in which to express your willingness to submit.
This sexually submissive mentality can conjure up a multitude of sexual undertones. Both the sissy and her dominant partner—whether that happens to be a male or female—derive erotic pleasure from the extremely unequal power dynamic that is present.
It’s a huge turn-on for the dominant party to be sexually satisfied, sometimes to the point of blissful exhaustion, while their submissive sissy is kept completely denied and under wraps.
It wouldn’t be an exaggeration to say that this obvious discrepancy in sexual gratification is an even huger turn-on for the sissy. Therein lies the intoxicating power of chastity.
What better way for the dominant to flaunt his or her dominance than to physically ensure their chastised sissy is kept in a never-ending state of horniness and frustration.
On the flip-side, a denied sissy willingly foregoes her pleasure in order to funnel every last fragment of that pent-up sexual frustration in the direction of her lover. Could there be a more authentic way to demonstrate her submissiveness?
Many, if not most, sissies could probably benefit from some form of chastity. Orgasm denial is a sure-fire way of intensifying the entire sissification process . Also, younger sissies, with an abundance of testosterone flowing in their system, oftentimes need a little (or maybe a lot of) help to bolster their self-discipline—or as a replacement for their total lack of that remarkable trait.
A more mature sissy may be already acutely aware of her station in life and wouldn’t think of cumming—much less become erect—without the proper permission or command from her partner. In her case, a chastity cage could be a non-necessity.
For a sissy who enjoys venturing out in public often, sporting a flat feminine front is critical to her image. In that case, a chastity device would hinder her ability to have things tucked away in the proper fashion.
So, depending on the level of mind-control that the dominant party exerts over their sissy and the geographical proximity they are to each other, a chastity device might be—or might not be—entirely necessary.
Whether or not a sissy is chastised with or without a chastity device, the fact remains that sissies that have had their orgasm denied for a lengthy period of time are much more obedient than a sissy that is not kept chaste.
A locked sissy lives her life in a—more-or-less—constant state of low-level erotic arousal. Because of this, she makes for a more willing and enthusiastic partner in general; not to mention a stellar sex toy, fuck doll and all-around submissive slut. Since all of her pent-up sexual desire is internalized, it needs to manifest itself in some form.
It’s no secret that the Mistress or Master winds up being the beneficiary of those stifled sexual yearnings. A denied sissy is always super eager to please: in ways that are only limited by the cruelly creativity mind of her Dom. She mindlessly does as she’s instructed: from scrubbing the toilet to giving epic head to devotional ass worship .
From a purely aesthetic perspective, I find it to be much sexier to see a sissy locked away in a chastity device than to have her sporting anything that resembles a hard-on. After all, we’re talking about a sissy here.
A sissy, by definition , has relinquished her rights to manhood. She should be conjuring up ways—in her pretty little head—to keep her clitty tiny, limp and insignificant. She has accepted that she is now a sexual receptor, no longer in need (much less worthy) of wielding a real cock.
Wearing a cute chastity device is a constant reminder to herself, and the rest of her world, as to the submissive sexual creature that she truly is. And it looks absolutely perfect on her!
Like I’ve alluded to in the previous section, other than making herself look as sexually desirable as possible, a sissy’s goal should be to train her small, pathetic cock into something that resembles an eternally limp and shamefully impotent sissy clitty.
A chastity device can help to achieve that more-than-worthy objective and, there is a vast acreage of evidence to support that statement.
Searching online will reveal real stories of women who have been able to shrink their husband’s or boyfriend’s cocks down to a suitable sissy size by keeping them permanently locked away in chastity. The resulting size reduction can be shockingly significant.
Sissies that don’t have a current Domme or Dom to act as their chastity keyholder have been able to accomplish this on their own. Training your clitty to be permanently limp and useless by using a chastity device causes a psychological shift in your sexuality that needs to be experienced to be fully appreciated.
For a real-life example as to what’s possible, Devina Cox has spent (at the time I wrote this article) more than 1,700 days as a chastised sissy slut.
My very first chastity device was a crudely constructed, unsophisticated mess made from small leather straps sewn around thin metal rings. It was not only uncomfortable but highly ineffective. The current state of chastity has come a long way from way back then.
I eventually graduated to a CB-3000—used for several years—which was a huge improvement. I currently own a Prison Bird 316L stainless steel chastity cage. It’s quite heavy and obviously not airport friendly. But… it’s pretty damn comfortable.
Needless to say, there are soooooo many sissy chastity devices to choose from now-a-days; enough to make a sissy’s clitty twitch in her pretty panties. And because of there being such a large number of manufacturers competing for the privilege of helping to turn you into a chastised sissy, the prices have come waaaaaay down.
After being denied—or denying yourself—for a prolonged period of time, you begin to see yourself—and sex—from a more feminine perspective. My longest stretch so far has been 7 weeks (that wasn’t bragging… it was a cry for help).
Your masculinity slowly starts to succumb as your source of sexual pleasure subtly begins to shift southward from your increasingly limp and inadequate clitty.
You begin to explore a newfound interest in anal play. Of course you will need an appropriate toy, like a prostate massager . Your feminine fantasies will begin to inspire questions such as: “ What would it be like to cum like a real girl? ”
If you’re intrigued by the thought of having a sissygasm—one that is so goddamn intoxicating that you will lose all desire to cum like a real man ever again, then you might find my article: A Guide To The Elusive Sissygasm worth a read.
Are you ready to go “ Down The Sissification Rabbit Hole? ” Then you’ll want to read this…
Copyright © 2018-2022 • SissyThings.com

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When Mistress K and Slave D aren't packing your orders or answering your emails we like to take some time out to write chastity stories for you all to enjoy reading. There's nothing quite like the feeling knowing that many of our customers and readers have spent time squirming in your locked cock cages while reading these. We love a little tease and denial and hope that these stories go some way to making your swollen balls a little less comfortable.
Some of these stories are completely fictional and figments of our collective filthy imaginations. Others are direct accounts of our private play sessions. We'll leave it up to you to figure out which ones are fantasy and which ones really happened.
Each time we write and post a new story on our blog we'll add a link to it on here.
We also love to hear your feedback and suggestions, so please do leave a comment at the end of the story you read and let us know what you thought of it.
Chastity Stories: Male Chastity and Anal Play #1 - Part 1
This was the first chastity story that I ever wrote and it gave me the confidence to write more, which has led to the other stories you can read below.
Mistress K messages slave D and orders him to put on his chastity cage and await further instructions. Once she returns home for some light impact play before fucking her submissive with a strap-on.
Male Chastity and Femdom #1 - Part 1 / Part 2
A short trip away for slave D and Mistress K turns into a severe play session that includes humiliation, a harsh caning and anal play before a stunning new dominatrix is introduced to join in with the fun.
Male Chastity and Femdom #2 - Part 1 / Part 2
With a new Beast stainless steel chastity cage locked onto her slaves cock, Mistress K decides it's about time slave D found out what it's like to be a sissy. If you're a fan of sissy chastity stories you'll love this.
Chastity and Femdom story featuring Mistress Adreena Angela - Part 1 / Part 2 / Part 3
This is a 3 part story that involves 1 male submissive, 1 female submissive and 2 female dominants. Mistress K returns home with a few friends to play with slave D in our new play space. Lots of kinky fun is had.
We commissioned Sushiyo to create custom artwork for each part of this story, which can be found at the top of each part.
Chastity Stories: Double Domme Femdom and Forced Bi - Part 1 / Part 2
There's a first time for everything. The chastity slave in this story attends a private play party for his Mistress and gets a very big surprise; his first experience of forced bi play.
Chastity and Femdom story featuring Mistress Terra - Part 1 / Part 2 / Part 3
Written for Mistress Terra to be read out for her OnlyFans account as more of a script. The dialogue sections are marked in bold.
This story is written at the time when social distancing restrictions were put in place during the Covid-19 pandemic are finally lifted and the chastity slave finally gets to meet with Mistress Terra for a private play session, or so he thought. He takes a good beating before being used for the latex clad goddesses pleasure.
Chastity Stories: Play Session #1 at the Secret Dungeon - Part 1
A few years ago Mistress K and I had an overnight stay at the Secret Dungeon in High Wycombe. We had two full play sessions during our stay and this is the story about the first of them.
After a day of servitude to Mistress K in central London with my cock caged we then got the train to the Secret Dungeon and my devious latex clad dominant toyed with me before ruining my orgasm and making me clean up all of the mess.
Chastity Stories: Forced Bi with Another Kinky FemDom Couple - Part 1 / Part 2
After weeks of tease and denial from Mistress K I was expecting another weekend of servitude to her without the possibility of an orgasm. A text message from a mystery sender changed everything.
I love to fantasise and if you've every wondered what it would be like to serve two beaufiful dominant women while one pegs your ass and the other forces you to such a cock then you're in luck!
I thoroughly enjoyed writing this one and hope you all enjoy it.
Chastity Story - Considering a Hearty Yield - Part 1
What happens when your lover expects you to cum big, thick, hearty loads every time you orgasm, but you just love masterbating? It's time to get a chastity device and lock that cock she thinks.
Short Story: Pegged after 3 Weeks in Chastity For My New Keyholder - Part 1
With the aim of becoming a collared slave for Mistress H, slave D receives a visit from his new keyholder. She decides it's time to have a little fun with him and pegs him to orgasm before locking him back into a new cage.
Lesbian Chastity Story: Chastity and Cultivating Desire - Part 1
A sensual story sharing a lesbian woman’s hesitant introduction to chastity. Overcoming sexual dysfunction and exploring the cultivation of desire through denial and submission.
Chastity and FemdDom Tasks List Story - Part 1
During a rare free weekend Mistress K sets slave D a list of tasks to complete within 2 days. As long as he follows the rules and completes all of the tasks he will earn a reward of her choosing. Will he succeed?

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Sometimes things happen - things you'd never expect. So let me tell you a story about one such a thing.
I (my name is Christopher, but everybody calls me Chris) moved to Texas from Europe about 10 years ago, just a few years after I finished my University. A month after I migrated I met Jane - she was wonderful, a thin but very feminine and "rounded" woman....

My very worst fear and quite possibly biggest fantasy have finally come true. Sir and I have been discussing his long-term goals for me, and he wanted to know my preferences so he could perhaps take them into consideration in his decision if he so chose to. The topic we were to discuss? Denial. Orgasm denial. Permanent orgasm denial. He wants to know if I li...

Disclaimer: this is my story, hence it is my intellectual property, do not post elsewhere without my permission. This story is for adults, and should be treated as such, at the moment it should only be available at the ooc section of the following dot-coms: lockedinlace, fictionmania, bdsmlibrary, literotica and mistressdyvia. An alternate version will most...

CONTRACT of SLAVERY and
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Whereas I, submissive p, hereafter called "The SLAVE", agrees to voluntarily give up all rights, personal and legal, and become the personal property of Mistress M, hereafter called "The OWNER"; and, whereas The OWNER has accepted The SLAVE as her legally titled property, the purpose of this Slave Contract is to co...

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I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it.
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Carl was shaking when he walked back into his own house, the memories of the night before vivid in his mind. The image of his own face after the make over and his wife's face filled with both pain and pleasure, her tired cries froze into his mind, replaying over and over. The worse part was the memories made him erect which only hurt due to the chastity devi...

It was in the year 2012. After along six year war that started in China spread to the Middle East, then to Africa and then to Europe and ultimately to North America.
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