Welcome to Sissy Play 101! We're doing a deep dive on this unique kink, what toys and techniques can enhance your sissification play, and ways to make sure everybody is having a great time.
Sissy play involves the feminization of a submissive-leaning partner for sexual use by others they consider their superiors. Often, this feminization is done for sexual arousal, and it features the hallmarks of sexualized femininity — high heels, short skirts, lingerie, make-up, and more.
Sissification play often involves highly sexualized outfits, subservient language, lingerie, a constant willingness to provide sexual services, an understanding that they are there to "serve" men and penis-owners, and an identification with the idea that the sissy's sole value is in the sexual services and visual satisfaction they can provide others.
Many people are only familiar with sissy play as a pornography trope, which makes sense because sissification play often mirrors familiar scenes from adult entertainment. For example, a sissy may be turned on by the idea that they need to hitchhike cross-country, and the driver expects them to pay for the service with their body.
Some people may use the word "sissy" to reference any type of feminized play. Sissy play (aka sissification), however, is not the same as feminization. Sissification intentionally takes feminine things and brings them to their extremes, often for the purpose of arousal. The emotions sought are commonly humiliation-based, but it could also be for relief, embarrassment, relaxation, vulnerability or serenity.
Think of it as the difference between drawing a portrait and drawing a caricature. You're intentionally expanding some of the primary, key attributes to really emphasize their presence.
In a non-sexual, non-sissification context, a person may wear a short skirt and heels and go about their day. They may feel sexy, and they may enjoy the attention they receive for looking attractive. In a sissification context, that skirt may be extra-short, the person may not be wearing underwear, and the person will often go out of their way to showcase their nudity and offer sexual service to anyone who requests it.
The sissy may identify with statements like "I want to look like a princess who's made to suck cocks like the whore she is" or "Serving men is a goal to aspire to. Sissies should feel more comfortable kneeling than standing."
It's important to note that sissy play is separate from someone's gender identity, though the lines can be blurred. Sissification play is a kink and often done for sexual arousal. Once an orgasm is achieved, many sissies will be uninterested in any further sissification play. That is not likely the case with someone who is experimenting with a more feminized gender identity.
Even with this definition, it's important to note that sissy play is unique to every specific person. It can be hard to define because it includes such a wide breadth of activities. It's like saying you enjoy "bondage." That could mean a whole host of things! I recommend a conversation to discuss what sissification means to any individual person instead of assuming a blanket interest in a wide variety of sissy play.
There are small subsets of kinks that make up the broader sissification kink, which means there are a lot of ways to play with feminization and sissification!
Feminized clothing, appearance, and behavior is a hallmark of the sissification kink. The sissy wants to appear, in both behavior and look, as an ultra-sexual, feminine woman when their transformation is complete.
A sissy's transformation can include body modifications, special clothes, or altered mannerisms such as:
People who are into sissification may take their crossdressing to an exaggerated level beyond what's considered modestly "feminine" in the modern age, especially if humiliation is one of the end goals of their sissy play. This may involve wearing frilly frocks, dresses, and skirts that would look entirely out-of-place in public. It may include a strict adherence to feminine etiquettes that aren't common in most modern spaces, like not speaking until spoken to or never making eye contact with a suitor.
Crossdressing may also include locking equipment or gear that "forces" the sissy to stay locked within their feminized outfit.
Another core facet of sissification is often sexual servitude, which often resembles the concept of femininity you see in porn. A sissy likely identifies with the idea that, during playtime, their sole value comes from their appearance, sexual skills, and willingness to sexually serve their superiors.
To achieve that goal, many people into sissy play engage in sissy training. This may include practicing oral sex skills on dildos, anal or vaginal stretching, endurance training, makeup practice, high heels training, and more.
The end goal of much of sissification training is to present a better finished "package" for their superiors to better enjoy. This may be a dominant partner, someone the sissy considers an "alpha", or simply anyone who's interested in sex with the sissy.
Oral servitude is a common feature in sissification scenes with anal sex being a close second.
In line with the core concept of sexual servitude, the sissy's pleasure may be entirely ignored during sissy play. Chastity cages (more about these below) are often part of the experience, with the sexualized framing that a sissy's value is in sexually serving others and any self-pleasure is unnecessary and distracting to that goal.
Sissy femdom play often includes sexual denial, and it can be an especially good fit for the femdom partner. Keeping the sissified partner aroused ensures that the play can continue until the femdom is fully satisfied and ready for play to end.
The length of sexual denial can vary. Some sissy play may only deny the sissy throughout the scene itself. Others may require sexual denial for the weeks leading up to an expected playdate. Some dominants prevent sissys from orgasming at all times unless they've been granted permission. While the denial itself is often a facet of play, the length and intensity of that denial can vary by kinkster.
A subset of sexual denial included in a lot of sissification play is chastity play and the use of chastity devices. Often called their "clitty" in sissification contexts, penis-owning subs may wear a chastity device to prohibit erections as another way to visually emasculate a sissy.
An entire subset of chastity devices are crafted specifically for this purpose. These devices may feature vulvas on the front or may endeavor to hide the shaft entirely, tucking it back into the body.
For people who are dedicated to this kink, chastity devices that make the flaccid shaft virtually non-existent may be an end goal. Sissies can wear progressively smaller and smaller chastity devices, essentially adjusting to the constant compression required by small chastity devices until they arrive at their desired (lack of) size.
If sissy femdom play is involved, the femdom likely holds the key to the chastity device and determines when the chaste bottom is unlocked. If that happens, the femdom may be known as their keyholder.
For prostate-owning sissies, prostate play may be a main focus of their sissification scenes. This may become a sexualized trope where the sissy is expected to orgasm only from p-spot stimulation. With chastity cages and orgasm denial involved, this may become much-more-achievable for sissy play kinksters because of the sexual build-up that comes with the inability to touch the penis.
Sissies may pride themselves on their ability to have p-spot orgasms, and they may consider this a "bonus" for anyone having anal sex with them.
When enjoying sissification kinks solo, prostate massagers and p-spot dildos are often used as stand-ins to enjoy prostate play or prepare themselves for future service of a play partner.
Typical porn tropes showcase an ultra-feminized, "perfect" version of womanhood. While some porn viewers are attracted and turned on by the idea of getting with someone like this, those into sissification may be turned on by the idea of "becoming" someone like this.
While every kinkster has their own reason for being turned on by sissy play, some common reasons you'll hear include:
If you're interested in engaging in sissy play with a femdom, it's important to have a conversation about whether they enjoy sissification play. Sissification play can often feel frustrating to people raised female. The kink plays on caricatures and tropes of femininity that have had negative consequences for women their entire lives. Being in charge of bringing more of it into the world can be triggering for many femdoms. This is part of the reason that many femdoms consider sissy play a hard limit.
Have a conversation with your femdom about what they can get out of sissy play and if they find this kind of play particularly triggering. If they do, get a clear understanding of what aspects are triggering so you can avoid them in your sissy play or decide to skip sissification altogether.
Once you have all this information, lean into the things that make your femdom enjoy the kink.
While sissy femdom play is interesting to dominant women for a variety of reasons, some common reasons are:
Leaning into some of these motivations behind sissy play, in addition to the acts themselves, can ensure everybody is having a great time without any resentment.
While sissification play can be extremely rewarding, it can also be difficult to start. There are a lot of preconceived ideas wrapped up in gender, and the idea of exploring some of those ideas can be terrifying.
Rest assured, wearing a pair of panties won't change your sexuality. And if you don't like something, you can always stop doing it! Unless you've shared it with others, no one will even know you've tried it. With online shopping, it can be easy to ship a pair of panties to your doorstep to try while no one else is around.
For any sissies out there who are waiting for a sissy femdom to explore, don't wait! Try things yourself now. If you need to, think of it as a service you're providing to your future femdom. Not only will you be able to tell her what activities you do and don't enjoy, but you'll already come to her as a polished sissy who knows a bit about what you're doing. That's much more attractive to a potential femdom than someone who's never put any effort into their own kinks.
Just like every other kink out there, sissy play is all about having a great time. Find what turns you on and sounds like fun, and then just do that! As long as everyone is having fun, you're doing it right. That's what kink and BDSM is all about.
