• Mistress Ava via Chattr

A deep dive into cross dressing

Cross dressing is the act of dressing in clothes that are intended for wear by the opposite gender, according to the binary gender model. I personally disagree with the binary model of gender.

While being a man and being a woman are two valid identities, there is a large spectrum of genders people can identify with that are not within the binary (did you know that on Facebook there are over 70 gender options to choose from now?) and many cultures actually recognise a multitude of other gender identities.

People of any gender and any sexuality can engage in dressing up as another gender for any number of reasons, and can gain a multitude of different results from doing so. The clothing used in cross dressing can really be anything a person desires, however choices are often made up of strong gender signifiers.

A signifier is a sound or image (or a texture or taste) strongly related to a concept (signified). A gender signifier in this sense would be how we associate blue with boys and pink with girls. In modern Western fashion, often male clothing is considered fairly gender neutral, so the most visible gender signifiers are often the feminine (skirts, dresses, lace, low-cut tops etc.) which makes crossdressers who dress in feminine clothing much more visible in the public eye much more prominent in pop-culture.

In my work as a professional dominatrix , which involves catering to cross-dressing fantasies, it’s the masculine-to-feminine cross dressing that I am regularly exposed to. For these reasons much of this article will focus on masculine-to-feminine cross dressing, although feminine-to-masculine cross dressing has historically been quite prevalent as well.

So, what are some of the reasons that people want to dress as another gender?

Gender curiosity and discovery

Some people might want to cross dress simply out of curiosity, or perhaps because there is a curiosity around their gender identity or sexual preferences. Cross dressing may be used as a discovery tool to help a person learn about themselves, how they identify and what they desire.

I know many people who at first identified as cross dressers, but the act of crossdressing helped them realise they were actually transgender. Despite this, it’s important to distinguish that transgender people are not the same as cross dressers, despite the fact that some may have identified as cross dressers prior to beginning their transition.

While we make the distinction that transgender people are not cross dressers we must also understand that cross dressing is not simply a stepping stone to transitioning into another gender. Both identities are different and both deserve respect and care.

Performance and entertainment (i.e Drag)

A drag queen is a person, usually a man, dressing up in hyper-feminine clothing and exaggerated makeup for the purposes of a performance. Drag was actually a term coined by Shakespeare to describe cross dressing.

In the early days of theatre, drag was often used as a device to mock women, but in the present day many drag queens use this tool to embrace and lift up femininity, with many queens saying they were inspired to do drag by the women in their lives.

There are also drag kings who are typically women who dress up in hyper-masculine wear and exaggerated make up (such as fake facial hair and muscles) for performance. Drag queens also played an important role in the LGBTQ+ rebellion, continuing to cross dress and perform despite it being illegal and the risk of persecution and systemic abuse. They have also played a big role in various protests and riots worldwide, fighting for the rights of all LGBTQ+ people.


Some people just feel comfortable in a certain type of clothing. Perhaps it’s the feel of the fabric on their skin or the way it fits their body. I’ve had several clients who wished to cross dress in feminine clothing during our sessions, not for any sexual gratification, but just because that’s what they felt comfortable in, which helped them to relax into the session.

Aesthetics and social interactions

Sometimes people feel sexy in clothing typically associated with another gender – it’s simply putting something on and thinking “damn! I feel good in this and I look good in this”, and it doesn’t have to go beyond that.

Everyone enjoys different interactions and reactions. Some crossdressers might just love people looking at them (regardless of what they’re thinking). Some crave more humiliating interactions, while others crave positive feedback on how they look.

Sexual fetishes

Well, this is really the reason I’m writing this article and probably the reason you’re all reading it – what is it about cross dressing that has such a strong sexual pull for some people?

I’ve written before on how humiliation can be erotic and is not inherently negative. Sometimes that feeling of being humiliated can get us really hot and turned on. For some people, being dressed up in typically feminine clothing can feel really humiliating. There are different reasons one might feel humiliated in women’s clothing.

Here are just a few examples:

  • The globally perpetuated idea that women are inferior to men most definitely has a role to play in why some men who want to be humiliated wish to incorporate cross dressing. Various insults such as “sissy” or telling someone they “throw like a girl” reinforce this.

  • Some people would not see being womanly as a humiliation, but would still feel humiliated in an exaggerated feminine get-up – where they don’t look like they’d really fit in anywhere.

  • Others delight in objectification and – as women tend to be more objectified than men – they feel that cross dressing is a great way to feel like a piece of meat.

Let’s not underestimate the importance of feeling comfortable and sexy when engaging in sexual activities. For this reason, the cross dressing may not be sexual in itself, nevertheless it opens the door to a more heightened sexual experience.

Also, sometimes people get off on feeling like they’re being forced to do something against their will. Of course, consent is a big part of any kind of sexual activity, but consensual non-consent, and other coercive or forced style activities, can be a great way to push boundaries we have built up and explore things we otherwise might not be comfortable with.

Role playing is another reason people might engage in crossdressing. Sometimes it’s fun to pretend to be someone we’re not – playing a different character can help us to remove our inhibitions and explore different things sexually. When I perform medical play sessions, I get much more into it if I’m dressed more like a doctor or nurse. Similarly, cross dressing can be an effective way to more easily engage in certain types of play.

This is obviously not an exhaustive list. There are so many reasons why people might enjoy cross dressing. A prominent Australian cross dresser on Twitter, @rhiannon_t07, told me they crossdress and become a character, ‘Rhiannon’, as more of a hobby than anything else. Cross dressing is fun and exciting.

Rhiannon also told me, “it also happens that ‘Rhi’ is a vehicle for my kinks and fetishes. I only partake in kink/BDSM activities as ‘Rhi’”, and while they enjoy a range of BDSM activities inclusive of humiliation and “role playing – French/sissy maid etc.”, they say that it is not the dressing up that is humiliating – they simply like to “take the role similar to that of a submissive female”.

So how do I get into cross dressing?

There are so many ways to get into cross dressing. As long as you do so in a way that is not disrespectful or degrading towards the gender you are wishing to portray, then there is no wrong way to do it. There are loads of great resources on how to start with the basics, as well as various forums, organisations and other sites where you can do some research and find like-minded cross dressing kinksters on various social media sites such as Twitter.

Just remember to stay true to yourself – everyone has a different journey with cross dressing and yours is just as valid as anyone else’s.

Most importantly, listen to people and their own unique reasons for why they cross dress. Support them – cross dressing is not negative and it doesn’t need to be a problem. Just keep an open mind, let them lead the way and be grateful they chose to share this potentially vulnerable part of their identity with you.

This is an edited version of an article that first appeared on Chattr.com.au. View original here.

293 views0 comments

Recent Posts

See All