Becoming The Perfect Sissy Slave

Posted by Andrew Schroeder on Updated on September 22nd 2023

Sissy slave wearing lipstick
Love the idea of trying the sissy fetish, but not sure where to start? You’re in the right place! We’ve gathered some of our finest minds together and built some simple and easy things you can do to get you started on your journey.

What Is a Sissy Male Chastity Slave?

If you already know what a sissy is, or you already know that you are one, then feel free to skip ahead to the tips. But, if you’re not sure, or ended up here by accident, then let’s quickly go over what exactly this fetish is and what it has to offer.
For those that are beginners to chastity, a sissy is simply a feminine slave. Some just enjoy doing things that usually women do, some want to actually be a woman. Some enjoy the humiliation and stripping away of their masculinity, some just like dresses!
Whatever the reason, sissification (the process of turning a man into a sissy) is a popular facet of chastity. At the most extreme end, slaves can completely renounce their manhood and take on a full time femboy persona. Less enthusiastic slaves may only enjoy delving into sissy play occasionally, then returning to their usual chastity play the rest of the time.

Why Do Male Chastity Sluts Enjoy It? - Humiliation And Feminization

Beyond the simple definitions, we can explore the reasons a man might enjoy this kind of play.
Full-time, extreme sissification is something that becomes more accepted with each passing day, with relevant discussions being common place on reddit and quora and youtube. With society’s growing understanding of terms such as gender dysphoria, there are more and more cases of people not feeling like a man or a woman. This kind of fetish play allows someone to cast off their birth assigned gender, and adopt one they feel more in tune with. Doing it within an existing chastity relationship provides a safe framework for the play to happen within.
On the more casual end, being a sissy can be freeing. Just as handing over responsibility for his penis to a chastity keyholder can be a freeing and exciting experience for a man, adopting a new persona can be just as interesting. While caged he can explore these different facets of life, and do so in an environment that’s “separate” from his everyday life. What happens in the cage, stays in the cage…
Both kinds of sissy play lend themselves well to other aspects of male chastity. As the slave adopts a more and more feminine persona, he might be subjected to much more intense ridicule and chastity humiliation by his Mistress as “he’s no longer a real man”. Similarly, she might treat him in a way that women are typically viewed by hyper-sexualizing him, commenting on his outfits or body at any opportunity. While this kind of play might not be for everyone, it can add a fascinating new element to your relationship if you’re brave enough to try it.
Obviously we’re only just scraping the surface of this massive fetish/lifestyle, but you get the idea. If you’re interested in learning more, then we’d encourage to read some of our other chastity blog posts, and do some of your own research into the topic.

Finding the Perfect Sissy Chastity Cage

When we talk about feminization here at Lock the Cock, we’re more specifically looking at it through the lens of male chastity (we are a chastity site after all). So naturally, the first step in your slutty transformation is to find the perfect sissy cage.
  • Cages focused on the sissy aesthetic.
  • Cages focused on shrinking or hiding the penis.
Pink Cock Cage
Getting the “femboy look” is the simpler of the two, and doesn’t differ much from choosing any other cages. Most of the time though, you’ll be looking for a pink chastity cage. You can choose vibrant hot pink, or a more muted and gentle pink cock cage, but either way you’re going to have a cute little package once the cage is on. Usually sissies will opt for softer, silicone cages, which are more gentle and feminine in nature. Other than that though, the world is your oyster!
If your idea of feminization involves not having a penis though, you’ll need to look for something much more specific. Cages that cause chastity shrinkage will naturally be small in nature, with the most popular being the Nubs. These are a micro chastity cage size variant of many popular small cock cages, so you’ll still have a lot of options.
Hiding the penis completely is a bit more difficult, and will require either a flat chastity cage, an inverted cock cage, or a chastity fufu clip.
Flat/inverted chastity cages are basically what they sound like. Rather than the standard tube design, they simply have a cock ring, and a metal or resin plate. This plate pushes your penis back into the pelvic area, completely hiding it from view. Some even have designs on the surface of the plate like the Golden Clitty Chastity Cage, which has sculpted lips to give you the look of a vagina.
Fufu chastity clips approach hiding the penis a little differently. Rather than pushing it back inside your body, they make use of both the penis and scrotum and arrange everything in a way that it looks like you have your own, 100% natural, vagina. They are a little bit harder to use, and a bit less secure than a cage, but clips are probably the closest a man can get to the female genitals he desires.

Choosing Your Feminized Name

Whether you’re looking for full time sissification, or just a fun fetish to explore in the bedroom, a sissy name can go a long way in making the play more authentic. Just as Mistress might make you call her Goddess, Princess, or any other name, adopting a name that you use during play can help you get in character and enjoy yourself much more freely.
This is quite simply a form of detachment. Often men will worry that different kinds of sex or kink play makes them gay, or is a comment on their masculinity (or lack of). But by adopting a femboy name, you are very clearly setting the boundary that while we do this play, this isn’t “me”. Instead it’s a character that you’re playing the role of, just like an actor in a movie or play.
If you’re using chastity to explore issues of gender dysphoria, then you might even take on this name more permanently. While you use your sissy name you’re exploring the “true you”, and setting aside the gender that came at birth.
But what should you choose? Well, we can’t really help you there. Your new name will be personal to you, and to your situation. If you’re just exploring it as a fetish, then you might choose something more obvious and exaggerated like Princess or Kitty. If you’re exploring a more permanent form of gender swap, then you’ll probably want to pick a normal girl’s name.
Think carefully about what name you choose. Swapping regularly can diminish the play, as you never truly stick to a single character to explore and enjoy.

Building Your Femboy Wardrobe

Another popular aspect of femboy play is costumes. Again this can take on various different forms depending on your reasons for exploring your feminine side, and what kind of sissy you want to be.
The most obvious (and sometimes overdone) style you can try is pink. Completely overdone, throw-up in your mouth, trying too hard to be feminine, pink.
These kinds of outfits lean heavily into the emasculation and humiliation elements of male chastity, and can be a fascinating dynamic to experiment with. Forcing a slave to go on a shopping trip in a cute pink tutu is a sure fire way to strip away some of his dignity, and works great as a punishment for misbehavior.
Similarly, some men like to be turned into maids for their Mistresses, so a simple black and white French maids outfit is the ideal choice. That way they can truly feel like they’re in the role of someone serving a more worthy owner.
Woman in red dress
On the less extreme end, simply exploring chastity underwear can open up a whole world of options. There are plenty of slaves who will squirm uncomfortably at the thought of having to wear frilly knickers or even a thong.
For more serious sissification, then simply any women’s clothing will do. Imagine what your style would be like if you actually were born as a woman, and start exploring it. Dresses, skirts, bras, fancy hair dos, painted nails, go nuts!

Sissy Play During Sex; Prostate Pegging, Femdom, Bondage

Taking on a new female persona isn’t just something that can be fun in everyday life, it’s also something that can add a ton of extra fun in the bedroom. For some men, this will be the only place that they take on a sissy role, but it’s still just as exciting as dressing up or using a sissy cage.
One of the simplest ways of doing this is reversing who has the power, which also fits neatly into a chastity dynamic. Typically the male will have control over the situation (often called being the “top”), while a woman will be more subservient (often called being the “bottom”). By simply flipping these expected gender roles and giving the woman control over the sexual situation, you’re already exploring and opening opportunities for a different sexual experience than what you’re used to.
Taking things a step further, we can look at pegging. This involves a woman wearing a strap on, and penetrating a man anally, basically flipping around the dynamic of standard sex. As you’d expect, being pegged is a completely different sensation for the man, and probably as close as he can get to being a woman in the bedroom. Naturally for gay men this doesn’t involve a strap on, but for a man who usually tops being the taker for a change can be very different.
Beyond the simple, there’s a whole sissy world to explore. It really depends which aspects of it you enjoy the most. If you enjoy humiliation, then you can explore more hardcore chastity BDSM scenes that will humiliate you. If it’s the emasculation, then wearing a penis sleeve during sex is a good way to physically show that you penis isn’t good enough for your partner. For those who experience gender dysphoria, then keeping their penis caged and using a strap on instead can get them closer to their desired experience. The only limit is your imagination.

Don’t Be Afraid to Embrace Your Sissy Side

While full fledged sissification might not be everyone’s idea of a good time, there’s plenty of interesting dynamics within the fetish that you can explore to spice up your sex life or your chastity pledge. Don’t be afraid to step outside the lines and see what sissy play can do for you!
Chastity Lifestyle Written By Andrew Schroeder

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About The Author


Our guy who’s walking the walk, Andrew is a long-term cage wearer who found LTC when shopping for devices early in his journey. So he’s gone from customer to consultant. 

He taps out articles that discuss the lifestyle. From debunking myths to offering commentary on the most-debated chastity topics, Andrew S is inspired to write because of his ardour for the caged life.

“Pardon the pun, but there’s a lot of cock and bull information about male chastity and the people who partake in this lifestyle. My want, and why I write for LTC, is because I believe we need more straight-talking, experienced voices to speak up about their journeys with chastity. People who are familiar with the lifestyle and community. People who want to help those who are new and interested."

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