A Glimpse Into Sissy Training With Chastity Cages

As society becomes more and more accepting of gender fluidity, people all over the world are beginning to take the time to explore different aspects of their sexuality.

Sometimes these changes can be small and simple, but others are willing to take it to the extreme. One such group is male sissies, who completely eschew their masculinity in favor of their sissy side.

What is a Sissy?

Sissy is often a word used to describe a weak, cowardly man, or one who is interested in things that would typically be associated with women such as fashion. While the term has been around for a long time, its use has become less common as it can be very offensive.

In some relationships though, this kind of ridicule is desirable.

A typical sissy relationship will involve elements of dominance and submission play, as well as plenty of humiliation. The man is viewed as pathetic, and unable to fulfill the masculine role in the relationship. Instead, he takes on a feminine role, often being looked down on by the more dominant partner.

Many men explore this dynamic in different ways including:

  • Cross Dressing
  • Male Chastity
  • Doing housework and chores is traditionally viewed as a “woman’s job”
  • Wearing makeup
  • Speaking in a higher pitch
  • Adopting a female name

Forced Feminization

Sometimes a man doesn’t become a sissy of his own accord but is forced to by his partner. This is a more extreme form of domination often called forced feminization.

While it seems involuntary on the surface, this kind of BDSM play should always be carried out in a safe, sane, and consensual way. Both partners should discuss what they are and aren’t willing to do beforehand and stick to their agreements during the relationship.

When done properly though, forced feminization places the man in a completely powerless position. His partner will make all of his decisions for him, sometimes even going as far as deciding what he wears, what he does, and who he makes friends with.

But what does the man get out of all this? For some, it’s simply a form of fantasy play they enjoy indulging in from time to time. Others see it as a stepping stone on the journey to becoming more openly transgendered. And like most other BDSM kinks, there are plenty of men who enjoy the humiliation and shame aspects of the play.

Sissy Training Techniques

When a man starts to explore a sissy kink, there are many different techniques he can use to train himself to embody the new role effectively. These include:

  • Learning to walk in heels
  • Learning to put on makeup or style hair in a specific way
  • Voice training sessions
  • Roleplaying in public and trying to convince others that he’s not a man
  • Anal training to prepare for penetration
  • Learning to give good blowjobs
  • Watching sissy hypno videos

There are plenty of other ways to train a sissy, and which ones are used will depend on the individual and their goals for the kink.

What is Sissy Chastity?

Sissy chastity is simply the addition of a male chastity element to a man’s sissy fetish. These two kinks fit together perfectly, both involving dominance, submission, humiliation, and the removal of a man’s masculinity.

Most chastity pledges involve a man and his Mistress, with her taking the dominant role in this female led relationship. As part of his submission to her, he locks his penis in a chastity device which she holds the keys to. Only when he gets permission is he allowed to unlock the cage and enjoy himself.

Sissy chastity combines elements of sissification with the traditional chastity dynamic. Sissy slaves wear a cage to hide their penis away, often because “they don’t deserve it”, “their penis isn’t good enough”, or “taking away the reminder of their manhood”. Whatever the reasons to try it, chastity can form an integral part of sissy play.

How To Enhance Sissification With Chastity

There are many aspects of chastity that can enhance your sissification. The chastity device that the sissy wears can transform the penis rather than just hiding it. Some are designed to look like vaginas, some push the penis back into the body to remove it completely, and some devices use the skin of the testicles to create a vagina with your own body!

To get you started though, there are plenty of pretty pink cages that will fit in great with your existing sissy outfits. Models like The Silicone Sissy take a traditional chastity device, and simply add a sissy touch to it. This cage is a great place to start if you want to explore the role of chastity in your sissy lifestyle as it isn’t too extreme and very comfortable to wear.

The way a Mistress treats her slave can also greatly enhance the sissy dynamic. Often Mistresses will use derogatory language, which can naturally emasculate the slave. Many Mistresses enjoy pegging and prostate play as opposed to penile stimulation, which is something more extreme sissies will already be looking to explore.

5 Chastity Products For Your Sissy Man

When you start to explore the vast range of chastity devices that can enhance your sissification, there’s plenty of options. Here are some great products you can try to experience the different kinds of restrictions they offer.

Fufu Chastity Clips


Fufu clips are the most interesting toys on this list, as they do away with the traditional lock and key aspect of a chastity device. Instead, these simple clips take the skin of the scrotum and arrange it in such a way that your penis is pushed back inside your body, and in its place, you have a vagina made with your skin. This is possibly the most realistic way to have a vagina without actually having surgery, so is a favorite for many sissies.

Seamless Sissy Chastity Cage

sissy seamless

Most cock cages have one big problem – they’re very obvious. Even though the penis is covered up, every time you see the cage it’s a giant reminder that your penis is inside. This can break all the immersion of your sissy play, and make it harder to stay in character.

The Seamless Sissy is a cage that attempts to rectify this by coloring the cage as closely as possible to real skin. While it’s not quite as good as the chastity clips mentioned above, it’s a good way to disguise your cage a little more without sacrificing too much comfort.

Inverted Flat Cock Cage

inverted flat

Unlike the other cages on this list, the Inverted Flat Cock Cage aims to completely remove your manhood. Instead of surrounding the penis, it pushes it back into your body. This means when you look down you’ll find nothing dangling between your legs, just like a real woman!

The low profile also works great with some of the tighter clothing that sissies love to wear. Unlike regular chastity devices that will leave a noticeable bulge under tight dresses or leggings, the flat cage will be smooth and discreet.

Pink Plastic Sissy Male Cock Cage

pink sissy

Another approach to sissy chastity is to simply use a cage that looks like a vagina! These sit somewhere between the Fufu clips and the flat cages, often sitting on the smaller end of the cock cage scale.

Most of the penis will be pushed inside your body, a little will be held inside the small body of the cage, and at the front is a sculpted pair of vaginal lips. The tip of the foreskin can poke through the gap at the tip of the cage, giving Mistress something to tease while she humiliates her sissy.

The Holy Trainer V4

holy trainer

In the world of chastity, the Holy Trainer is one of the most popular forms of cages ever. Designed to be comfortable, easy to use, and long-lasting, most long-term slaves will have at least one in their collection. Luckily for sissies, there are Holy Trainers that are perfect for you.

The V4 nub comes in a gorgeous pink and is small enough to make your penis almost unrecognizable. If you’re getting started and you really can’t decide which cage to go for, then you can never go wrong with a Holy Trainer!

Closing Thoughts

Sissification can be a fun and gratifying way for men to explore different aspects of their personality. The transformation into a woman can be as subtle or extreme as you desire and can be an occasional fun way to play, or a permanent lifestyle change.

Whichever kind of sissification you enjoy, chastity can offer a great way to enhance it. We hope this simple look at these cages will inspire you to start exploring your sissy chastity pledge!