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Question From a Reader:

Hello Mistress, I've got a chastity cage and I've been increasingly curious about and intrigued by the sissy lifestyle. Why should I give sissy chastity a shot? How would I get started?

Mistress Natalia Answers:

As a Prodomme, one of the most common questions I am asked by both clients and online is “do I have to be a sissy to try chastity?” - the answer is no, you don’t. But there are many reasons why it makes the chastity experience so much better.

Chastity is inherently a submissive fetish. Any way you cut it, locking your penis behind bars either voluntarily or at the command of your Dom is not a masculine thing to do. Not everyone who wears a cock cage is a chastity sissy, but almost everyone who loves it has a curiosity to discover their submissive, feminine side. If you stick with it, you will find over time that you naturally exhibit less and less typical male traits, and start to act and feel more in line with female traits.

Learning to love and embrace the sissy side of yourself opens you up a whole new world of possibilities, female lifestyles, and pleasure.

Pleasure? In chastity? Yes. A chastity sissy knows that caging their penis is a pathway to even more pleasure than they could ever find without it. By denying access to your penis, you force yourself to pay more attention to the rest of your body. Most men go their whole lives without ever learning that their whole body can be used as an erogenous zone. Nipples, neck, ears, thighs, and of course, the sissy favorite, anal, can bring about intense pleasure and literally make you orgasm. When you’ve been caged for a week and start to feel desperately horny, you start to learn how tantalizingly sensitive your whole body is and how easy non-penis orgasms are to achieve.

So eager are chastity sissies to orgasm without touching their penis that they coined a new word - Sissygasm. Achieving orgasm without stimulating your penis.

Chastity and sissy play fit together perfectly if you want to explore other, more feminine avenues of pleasure, and chastity cages force you to do this by removing your penis from the equation. Hypersexuality is a defining sissy trait, and exploring how to make yourself cum while caged from anal, or simply by nipple stimulation becomes easier when you abandon any pretense of masculinity. Accepting that you are in fact, a little sissy, is the first step you must take before surrendering control of your body to a Dominant and being used like a toy. 

Aside from pleasure, sissy play focuses around acting and being treated like a woman. You take a gentle, easy-going, submissive and subservient role in the bedroom, and eventually in life if you choose. Far more than just sexual activity, sissies learn to enjoy every part of the lifestyle that comes with being a woman, and this can be broadly summarized by saying you enjoy wearing sexy female clothing, talking like a girl, using feminine care products, all the way up to getting fucked like a girl. Keeping your penis caged out of sight and out of mind in chastity makes all of this easier. 

So if half the population enjoys all of that, why can’t a man? Aside from ever-vanishing social stigma, there’s no reason not to. But, many sissies also enjoy that very stigma. The last reason to try sissy play is a deep-rooted desire for sexual humiliation and degradation. This is usually the last area a chastity sissy learns to find pleasure in. Once you’ve discovered just how much you like acting like a woman and being used like one, you’ll find that you like to be humiliated for it. This can start with simple insults like “slut” and “whore” during sex, and enjoying being used with no regard for your own pleasure, and can also extend to small penis humiliation, which ties in perfectly with wearing a pathetically tiny pink sissy chastity cage. Some take this to an extreme with cuckolding - you watch as your partner is fucked by a real man, a bull. A good chastity sissy would relish the opportunity to see how a real woman takes it and if they were lucky, give the bull pleasure as well.

Natalia Author Profile Picture


A secretary turned Mistress who had never even heard of male chastity, but got sucked into the community and now makes a living writing blogs and guides to help both slaves and Mistresses alike. She first discovered chastity at the age of 25, and has been a full time dominant for the last 3 years.

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