Why is it that wherever there are chastity cages there are sissies?
Whether or not you identify as a sissy, if you’ve spent any time in or around the male chastity community, you’ll have noticed dedicated boards, galleries, and product ranges for sissy chastity cages. But why do they exist when there are so many fetishes that complement chastity (pegging, bondage, cuckolding, sounding, etc.) Why is the femboy fetish so often singled out in the way that it is?
To answer this question, and better understand the harmony between the two fetishes, we need to look at:
- What it means to be a sissy.
- Why some people find it sexy.
- The dilemma of the sissy fetish.
Only then can we start to understand why these fetishes go together like cookies and chocolate chips.
(Psst! You can skip to the end if you already know you’re a sissy and want some beginner training tips from Mistress X.)
What Is a Sissy? 
‘Sissy’ is a derogatory term given to men who display weakness, show a lack of courage, or possess feminine qualities. It’s believed the term was first used in the 1800s. Back then men were all about pistols at dawn, honor, being the breadwinner, and other such stereotypically manly things. Unfortunately, many of these ideas trickled down to influence the torrent of toxic masculinity rife in society today.
It wasn’t until the 1970s and 80s that the term started being reclaimed by gentle, effeminate men in the gay and BDSM communities. That’s not to say the word has completely lost its negative connotations. But the acceptability of using this as a label to identify men who embrace female qualities has certainly broadened.
As with any fetish, how it’s enjoyed depends on the individual. For some femboys it involves wearing lingerie, applying makeup, and exploring personal character traits they may play down as a man. For others, being a sissy involves embracing a hypersexualized version of being a woman. Think meek and mild, submissive and willing, or having an unyielding desire to please their partner (or partners) sexually.
What a Sissy Is Not
A common misconception is that someone who identifies as a sissy wants to fully transition from male to female and completely give up their maleness. What’s more useful is to think of it in terms of gender fluidity. They want to be female some of the time so they can explore all that they are. But they’re perfectly happy identifying as male when not being sissified.
You can learn more about gender identity and chastity in our article, Do you wish you didn’t have a penis?
What’s Sexy About Becoming A Girl? 
The appeal of becoming a sissy depends on what the man wants from this fetish. For some, it’s not sexual at all. Rather, it’s having time to embrace womanly qualities, including wearing women’s clothes and putting on makeup. It’s a chance for them to feel comfortable in a way their male identity doesn’t allow.
But for others, becoming a sissy is about fetishizing feminine qualities to the extreme.
Forced Feminization and Sissification TrainingFor some, it’s not sexual at all. Rather, it’s about giving themselves the time to embrace womanly qualities. It’s a chance for them to feel comfortable in a way their male identity doesn’t allow.
Sissification falls under humiliation play and, when fetishized in the extreme, involves adopting a hyper-feminine, hyper-sexualized, ultra-submissive persona. Training a sissy involves consensual forced feminization led by a Dominant, and strips that person of their masculinity.
Getting the person to wear dainty pink outfits, changing their name, training them to speak softly, removing their body hair, and having them willingly assume the submissive role in all sexual play are just a few ways a Dom will remove someone’s maleness, and with it their power.
But it’s this emphasis on the hyper-sexualized quality of sissies—giving enthusiastically without limits and being sexually degraded by the Dominant—that can make it such an appealing, yet problematic, sexual persona.
The Moral Dilemma With the Fetish 
As already discussed, ‘sissy’ is a pejorative term. And not just to men. It’s also misogynistic. It frames female qualities as being lesser and something to be ashamed of, and proposes that acting like a woman is humiliating. Anyone with a feminist bone in their body will know this is not progressive thinking.
A mainstream, real-world example you may be familiar with is “You run/throw/kick like a girl.” That phrase is only ever used to degrade or humiliate. Within the sissy fetish, the hyper-sexualized interpretation of femaleness (being called a slut, being open and willing to take anything, and being sexually degraded) does nothing to aid female sexual empowerment and discussions around consent. It’s why some female Doms avoid referring to a man’s caged cock as his ‘little clitty’ during small penis humiliation. Because why should having a clitoris be considered humiliating?
There’s certainly an argument to be made that the sissy fetish isn’t progressive or empowering. But isn’t that the case with many fetishes? As with all fantasy BDSM play, the pleasure comes from stretching what we understand to be acceptable behavior in the vanilla world and, for a time, indulging in fantasy play that adheres to agreed limits.
The Bond Between the Femboy Kink and Chastity
Once you’ve explored what being a sissy is, it’s easy to see why these two submissive fetishes are enjoyed in tandem. Wearing a male chastity cage removes access to what physically defines someone as being male. From a psychological aspect, caging the penis removes the power of the penis. Revoking that level of manliness can, for some, mean taking it a step further and exploring its binary opposite – ‘femininity.’
Wearing a cage isn’t an essential part of being a sissy. It’s just that some prefer the added restriction, the nullification of their penis, as part of their sissy fetish experience.
On a side note, wearing a cage isn’t an essential part of being a sissy. It’s just that some prefer the added restriction, the nullification of their penis, as part of their sissy fetish experience. But does this explain why sissy cock cages gets its own section in stores and on community boards?
The reason it’s separated may simply come down to the stylized look of the fetish. Someone who isn’t into sissy is less likely to want a pink or feminine-looking cage. Giving discussions for the fetish their own space also makes it easier for this subset of the chastity community to find each other. And we all know that finding people with similar pleasures to our own is part of the fun.
Becoming a Sissy Slave With Forced Feminization Training 
So now you know what a sissy is, why it’s sexy, the controversies around the fetish, and why it goes lock and key with chastity. If all of this sounds comfortable to you (and you’re getting aroused at the thought of it) then you may like to start playing with forced feminization.
Becoming a sissy involves both physical and mindset changes. Pro Doms will refer to this as ‘sissy training’.
Some of the changes involved in becoming a femboy include:
- Wearing clothes traditionally associated with women.
- Changing your voice, and adopting a softly spoken tone.
- Adopting feminine body language (e.g. crossing your legs).
- Taking on a passive demeanor.
- Sitting down to use the toilet.
- Wearing makeup and a wig.
- Using a female name.
- Removing your body hair.
Sissies will also strive to avoid erections and have a soft or limp cock – even when they should be aroused. To do this, they may tuck their penis in so it’s not visible or (you guessed it) wear a LTC cage.
But there’s more to sissy training than donning a dress and wearing a wig. Here are Mistress X’s 5 tips for those starting on the road to sissyhood.
Tip 1: Temporary Makeover or Permanent Persona?
The first step is deciding whether your forced feminized state is only for scene time, only at home, or as a more full-time role. If playing with a Dominant, let them know whether you’re comfortable taking any parts of your sissy play out in public. You may not always want to wear your full adorable little pink maid outfit. But you may be happy to go out wearing frilly panties.
Tip 2: Decide on Your Femboy Style 
Collect several outfits you’ll wear during your time as a sissy. These might be highly feminized fetish outfits such as a maid outfit or cutesy little dresses. Or you may simply choose to wear mini-skirts and tank tops, which you can easily buy at a thrift store (unless you want to splash some cash on the high-street).
Besides clothing, you may also choose other traits you’re comfortable with adopting from our earlier list. So you may want to shave your legs, paint your nails, and give yourself a female name. You could choose the female equivalent of your male name (if there is one). For example, Daniel becomes Danielle, Sam becomes Samantha, and so on. (If your name doesn’t work for that, tweet me and I’ll give you a sissy slave name you can have all to yourself.)
Tip 3: Set Feminine Tasks
Being a sissy is about exploring the stereotypically feminine. If you’re the Dom doing the training, start with lessons in shopping, dressing, and applying makeup before progressing to domestic tasks and chores. (You want your sissy to look pretty and be well groomed before letting them near the washing you need folding, shoes you need cleaning, and floors that need to be swept, right?)
If you’d like more inspiration when it comes to sissy training tasks, there are sissy training courses and YouTube channels by professional Dominants. Have a play around to find challenges that suit your sissy.
Tip 4: Balance Your Dominance Over Submissives
We know sissification is a form of humiliation play. Punishments and name calling may be part of the role. But I suggest balancing it with cuddles, reassurance, and encouragement. Sissies can be delicate. Remember, you’re dealing with someone who is hyper-feminine. They’ll have a sensitive side too.
Tip 5: Sex Should Be on the Agenda
Sissy play is unlike other forms of BDSM in that sex is much more likely. One of the delights of toying with a femboy is getting to play with their accentuated sexual desires. Their pleasure comes from being objectified and used as a fuck toy. Explore and (consensually) exploit this characteristic by trying pegging (or other strap-on sex) and ruined orgasms.