Cross Dressing and Sexual Pleasure; The Allure of Transvestic Fetishism

Crossdressing. Whether our knowledge is limited or extensive, this is a term the majority of us have heard of, maybe even talked about with friends. In fact, for some of us, it was a big part of our prime time entertainment throughout the 90s — I’m looking at you Eddie Izzard (I was always in awe of your style). 

The thing is, there’s a lot more to crossdressing than putting on some makeup and different clothes. There’s actually a whole community of people who crossdress on a regular, sometimes even daily, basis. In fact, sometimes these individuals will spend large portions of their time “dressed up”, simply because they see it as an intrinsic part of their identity, a means of expressing a different side of themselves. Working alongside this, there’s also another community who crossdress purely for sexual pleasure, e.g. they do it to turn themselves on and enjoy sex. 

Sometimes the two interconnect, much like with any other fetish, but they’re not necessarily one and the same. 

Furthermore, it’s important to point out that being non-binary, gender fluid, and/or trans is not the same as crossdressing, although it’s fair to say that they share some similarities, most specifically in the fact that they wear clothes not typically associated with their perceived gender. In addition to this, there’s also the similarity between all these examples — crossdressing, drag, transgender, and gender fluidity — in that they’re about freedom of self expression and who we are as an individual. 

Consequently, there’s always going to be a connection between these different elements, with one sometimes feeding into the other, such as an individual crossdressing and then discovering there’s more to this practice than a wish to change aesthetic, that their need for self expression runs much deeper. Nevertheless, while they’re similar, and often mistaken for one another, it’s important to recognise their differences and why they should be respected and seen as different ways of identifying with oneself. 

What is Cross Dressing?
We’ve got the basic “trait” of wearing the opposite sexes clothes, but what else, if anything, qualifies the label of cross dresser? In truth, the clothing aspect plays a bigger role than you may think, with the perception of the garments and their role in society being highly significant. 

Therefore, different societies may understand and consider crossdressing examples that differ from our own. For example, in the UK we may identify someone as a crossdresser if they enjoy wearing women’s underwear, yet in another culture, this might not garner the same response. As a result, you’ll find that Eastern and Western cultures have different opinions on what crossdressing consists of. 

In addition to the clothing worn, it’s worth noting that nothing about crossdressing is based on sexuality, with it being a practice that heterosexuals, homosexuals, bisexuals, pansexuals, and so on can engage in. It isn’t a limited forum of expression due to your genitalia and/or who you sleep with, it’s purely about the clothing and how it makes you feel. 

Of course, the reason we tend to think of this act as a male orientated one, is merely because of how much easier it is to identify male crossdressers, in that they wear gender coded clothing, e.g. the colour pink, a dress, make up, etc. Although it can be argued that all of these signifiers are open to all genders, we can’t ignore that societal influence has conditioned us to see certain items as created for one sex and not the other. This is changing, but it’s a slow process, and one that’s hindered by the diversity of viewpoints we as a species share. 

Does A Categorisation of Crossdressing Exist?
Before writing this article, I firmly believed that crossdressing was a simple, one category only experience — you either did it or you didn’t, that was all the definition needed. However, as my introduction demonstrated, there’s different types of crossdressing practiced across the globe. 

To ensure that we fully recognise the broad spectrum that this practice is, we need to explore each type to recognise what makes them different from one another. If for nothing other than to remain respectful at all times.  

One of the most commonly recognised forms of crossdressing is drag, with a lot of the public, even those not familiar with LGBTQ, enjoying the performance of drag artistry. There’s even people out there that will gladly visit Funny Girls (a drag/burlesque nightclub in Blackpool) to enjoy a night out, but will also spew hate speech about queer people despite wishing to consume the entertainment they create. 

Odd though it is, the performance aspect of drag, and how we as the audience enjoy it, is part of the reason why drag and crossdressing aren’t typically seen the same. They have the same quality of dressing up, but with drag it’s evidently about putting on an exaggerated performance and being seen, while crossdressing is normally a very personal and private experience. What is more, drag is usually an extreme of the gender being depicted: large lips, big hair, over the top make-up, huge phallic objects, while crossdressing tends to adopt a more realistic approach. The objective here is to blend in rather than standout, though again, there’s always exceptions to this. 

Another category of crossdressing we need to discuss is that of “passing”, a term a lot of us are familiar with in the context of transgender, specifically whether they can pass as cis gendered or not. The phrase has come under a lot of scrutiny of late because of how problematic the idea of passing is in the first place. Nonetheless, in the context of this article and crossdressing, it’s about being able to be treated like the opposite sex, therefore being able to do/act in a way not normally accepted (think of Mulan or She’s the Man). 

Then, finally, we come to the last type of crossdressing, one that’s culturally specific and therefore not shared universally. The prime example of this occurs in Indian, where they have three recognised genders as opposed to two; the Hija don’t necessarily dress as women, but what they do is transcend gender norms, thus allowing them a fluidity that crossdressing does in the Western world. Alongside this, you also have some Native American rituals/performances which involve men dressing as women. This is similar to what we see in the art of pantomime, in which crossdressing isn’t just expected, it’s a time honoured tradition that we love to see.

Transvestic Fetishism
When it comes to specifically referring to individuals who derive pleasure from dressing as the opposite sex, it’s called transvestic fetishism, and (unfortunately) it’s regarded as a mental disorder by healthcare professionals. 

Crossdressing in itself isn’t, with the common belief being that a disorder only exists when sexual pleasure is triggered from the act of donning this other persona. It’s important to make the distinction between the two here, simply because throughout adolescence, crossdressing is regarded as a normal part of teenage experimentation. Much like when we grow curious about our bodies and sexuality, crossdressing is a way of exploring our identity, what gender means (if at all anything), and how we feel in ourselves. 

So why does this acceptable experimentation suddenly become regarded as a disorder in later years?

Quite simply, it’s about how long you have the need to crossdress for, as well as how consumed by the fantasy of crossdressing you are, e.g. does it impact your daily life. Personally speaking, the idea of having such fantasies doesn’t register as a disorder to me, as we all have fantasies (recurring ones) that we think about on a daily basis, and so I find the idea of this being a disorder offensive. Yet, it doesn’t surprise me that it’s referred to as one — it was a mental disorder to be a homosexual up until the early 70s. 

Nevertheless, there are some people who become upset/distressed by their feelings and urges, and so sensitivity and understanding about this topic is needed when discussing it, especially if you know a loved one who may fall into this bracket of crossdressing. 

Freedom of Expression and Exploration
Disorder or not, savouring the way crossdressing makes you feel is a part of what has so many individuals donning different clothes, creating personas, and engaging in sexual activities that they might not normally. 

For those among us who are slipping into a sexy dress and/or wearing a suit and boxers, the allure is about the feeling it brings, that sense of “other” and freedom. It isn’t about eventually living as the sex you dress up as, at least not for the majority. 

One of the main reasons a lot of crossdressers have given for their love of this fetish, is that it allows them to explore a side of themselves they don’t usually, normally because they’re unable to. For example, a high number of cis gendered, heterosexual men crossdress, with the practice enabling them to embrace femininity in a way that society can (and often) tries to limit men in doing. 

If we take a look at accepted gender roles and beliefs in the last 50 years or so, there’s been a very rigid notion that men should have a stiff upper lip and not show their emotions. This has then fed into showing sensitivity as being feminine and gay. Although this belief system is shifting constantly, and we as a society are becoming more outspoken about the need for men to be able to express themselves as openly as women, there’s still many who feel suffocated by the norms that have been imposed on them. As such, crossdressing removes those norms and allows for men, in particular, to enjoy the act of putting makeup on or doing their hair, free of shaming and/or abuse. 

Coming back to drag and drag queens for a moment, we can see that the need for crossdressing to have a meaning for the wider public is very much why drag is accepted and crossdress isn’t. The act needs to be entertaining and/or funny. The moment it starts to move beyond that, many people who support traditional roles find themselves uncomfortable and thus act out, often abusively. As with anything that steps outside so-called convention, like lesbianism, if it can be packaged and repurposed for entertaining the masses, it’s perfectly acceptable, but anything else just isn’t okay. 

This freedom goes hand-in-hand with exceeding boundaries and acting without rules, which is another reason a lot of crossdressers have given. As a society, while we can claim conservatism, we have an obvious romance with transgressive behaviour, that love of doing the “wrong thing” because it feels so damn good. Thinking about this in the context of a relationship, if someone cheats, they might enjoy that transgression of acceptable boundaries, even if it means hurting the person they love. 

Another transgression a lot of us are familiar with, and partake in, is BDSM; this type of fetish is deemed as overstepping what sex and pleasure should be about, which is often why so many of us love doing it. Age play, spanking, bondage, breath play — they all feel less acceptable than the expected missionary sex that we all joke about being boring. None of these BDSM practices are morally wrong, but the idea of it being taboo is what gets many of us nonetheless, a bit like that rush of having sex in a public place even though you may get caught. 

Sex and Our Sexuality
Very much in-keeping with both of the above examples, another reason for crossdressing is it acting as a conduit for the exploration of our own sexuality. Regardless of how you identify, for a lot of us, we fantasise about bending our perceived sexuality and seeing what lies beyond it. After all, think of how common experimentation is during your younger years, with the age old notion that your college years are for experimenting. Then look again at how many straight women watch lesbian porn and just how many queer women enjoy gay male porn; it’s all about being able to go against the grain. 

Of course, sometimes it’s a way of discovering that actually we’re not as straight or gay as we first thought, but for others, it’s nothing more than being able to genderbend and try on a different identity for a while. This is why, even more so nowadays, sexuality is recognised as a spectrum rather than being the limiting either/or of straight or homosexual. 

Exploring sexuality once again seems to resonate more deeply with male crossdressing than female, simply because experimentation between men isn’t as openly talked about as with women. When a group of girls admit they all kissed one another, no one bats an eyelid, but if a group of guys do the same, they’re immediately branded as gay. What’s okay for one isn’t for the other. Therefore, crossdressing allows a straight man to experiment and to see what his sexuality brings without fear of rejection and ridicule. This isn’t to say that this immediately stops the public from being intolerant when they learn of crossdressing, but rather that the men who crossdress feel more able to explore their sexuality because of the act. 

Problematic Language, Beliefs, and Behaviour
Although crossdressing in itself isn’t problematic, at least not to most open-minded people, there are parts of this subculture that feed into the problematic behaviour of society. For one, there’s the fact that it can and sometimes does reinforce a shame element about doing it, which is why many crossdressers keep their “other identity” to themselves. 

When reading through an article from Medium, it seems fair to say that quite a few crossdressers are open and honest with their partners about their activities. In fact, several of the men interviewed were in stable relationships. Nonetheless, there were some throughout the article who are afraid of being completely themselves. They experience shame and fear at enjoying this part of their identity, with some of them hiding it from their partners altogether. 

Alongside this need for secret keeping, those that didn’t share with their partners also seemed to worry about their sexuality more, which fed into some old fashioned mindsets. One crossdresser spoke about how dressing as a woman and then being “forced” to serve other men was a “degrading” experience. Yet, this same person then spoke of the sexual high he received from that kind of domination. Then, slightly later in the post, a different crossdresser remarks on how he’s worried that if he keeps having sex with men he’ll become gay, which again feeds into a range of views no longer shared by younger generations.

Both of these separate remarks on sexuality and perception reinforce homophobia, some of which comes from society and themselves. Granted, not all of the men interviewed felt this way, however, the fact that some do goes to show that there are problematic elements to crossdressing. Not necessarily because of the act itself, but how it can be used to strengthen damaging beliefs and opinions. 

Don’t get me wrong, enjoying being called a slut during sex doesn’t make you one, however, if you believe you are one in a negative content, e.g. you’re bad and dirty because you like sex with lots of people, then being called it during sex can help to further reinforce that belief. If these men worry about their sexuality and feel guilt for enjoying sex with men, even if they’re dressed up and thus apparently removed from their masculine self, then it’s possible that self loathing will eventually kick in. 

Loving Yourself and Openness
This may sound like a very cliche and cheesy thing to say, but loving yourself is something that will help you to learn more about your crossdressing and sexual pleasure. It isn’t easy, for anyone, regardless of your preferences. Nor is it something you’ll be able to do overnight and without hurdles along the way. Nonetheless, learning to love yourself is one of the best ways to fully allow yourself to exist in the spaces you choose to create, free of embarrassment and disappointment. 

Should you be interested in exploring the possibilities of crossdressing further, or perhaps you’ve done it for some time now and are wanting to be more open about it, then the next step is talking about it. This doesn’t mean you have to go and tell every member of your family, including your weird aunt that nobody ever sees. It’s about being honest and open with the people closest to you, the ones you feel safe with. 

Revealing anything about your personal self is never easy — even if it’s just saying we prefer anal to p-in-v sex, we can feel nervous about admitting it. However, once we take that big step, a shift in how we see ourselves, and how we interact with our partners, can begin. This is why the crossdressers who are open with their spouses appear to have a more fulfilling and accepting relationship with their fetishism. Even if their partner doesn’t participate and/or understand crossdressing themselves, the fact that they’re accepting of what their partner needs helps allow further self expression and love. 

It’s understandable to worry what others think, and it’s a lie to claim that you won’t experience bigotry because of who you are, because unfortunately you will. Everyone does at some point in their lives. That being said, there’s plenty of people out there who will support you and even enjoy your crossdressing in a similar capacity as you do. One of the most fitting articles to demonstrate this is from a 2019 Metro article, in which a Canadian couple share their crossdressing experience. 

Nastia Cloutier talks about how she enjoys her boyfriend crossdressing, and how they go on dates together while he’s dressed up. Yes, the article discusses some of the backlash they receive, but by and large, it’s a positive read about how they work together so well because of the openness and honesty they share. In fact, when Benjamin Altmejd (Nastia’s boyfriend) revealed his fetish, she in turn created her own persona to accompany his. Her persona is female, however, in its creation it seems to allow Nastia to further embrace the feiths in a way that’s wholly unique to her. True, she doesn’t crossdress, but she performs and explores her identity alongside her partner. 

Beyond the Sexual
Throughout this post, a lot of emphasis has been put on the fact that this particular fetish is sexual; that’s its definition, how it’s recognised. Nevertheless, while many crossdressers will never explore beyond that definition, there are some who will, with their crossdressing becoming less about sexual pleasure and about something more. 

This more doesn’t necessarily mean they wish to transition, but it may mean that the activity becomes less of a choice and more of a need, as mirrored by Robin Pickering, when he was interviewed by The Guardian about his crossdressing. Despite the article being from two years ago, what Robin discusses is still incredibly relevant today, with him touching on how society still regards crossdressing with close mindedness, and how his crossdressing enables feminine expression. 

For those of you reading this, crossdressing may only ever be a role playing fantasy, a means of trying on something for size and then discarding it later on. It may turn into another identity that works alongside your own. And it may even end up being a vivid and important part of who you are and how you identify. 

Transvestic Fetishism doesn’t have a nice ring to it. It sounds clinical and deviant, but in truth, the world of crossdressing is anything but; it’s a colourful tapestry that more of us are willing and wanting to explore. I look forward to celebrating more people genderbending the norms and getting their kink on.

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