What Triggers Crossdressing? Unraveling the Motivations Behind It

It’s the weekend. You’re sitting at the edge of your bed, staring at that silky smooth stress you bought in secret.

You’ve been hiding it in the back of your closet and at the back of your mind for months.

But today, for some reason, you feel that pull, that irresistible urge to take it out, feel the fabric against your fingertips, and eventually drape it around your body.

Slowly, without making a sound, you reach for it not fully knowing what comes next.

Crossdressing—  it’s a part of you that you’ve struggled to make sense of.

After all, it’s not something they teach you at school. It’s not something your friends force you to do either.

But why do you feel the impulse to wear clothing that society tells you, over and over again, that isn’t made for you?

Are you this person? Maybe you have a close relationship with the person I described?

It doesn’t matter if you’re the former or the latter. This article will be helpful either way.

As long as you’re ready to forego any bias or prejudice, you’re ready to continue reading.

Together, let’s try to understand these urges better. You may just discover you’re not too different after all.

Gender and Crossdressing

Since we are going to discuss a nuanced and, dare I say it, controversial topic, let’s first try to simplify the modern landscape and compassing gender and crossdressing.

Traditional vs. Modern Views of Gender

Traditionally, gender is seen as a synonym of biological sex. You’re either male or female— all based on the physical body you occupy.

Today, after much back and forth, politically and socially, many recognize that gender is imposed by society and exists on a spectrum.

This spectrum explains that gender has a range of qualities, in various degrees, and with different conditions.

Gender covers how you see yourself and choose to express your inner identity for the outer world to acknowledge.

Some people who are lucky enough, have a matching internal sense of gender and sex assigned at birth.

Others were not so lucky.

Crossdressing and Gender Expression

The binary notion of gender has long existed and impacted us for who knows how long.

This fact is most obvious in our everyday choices of what to wear.

Crossdressing is wearing clothing that’s traditionally for the opposite or another gender.

It’s more than just clothing though. For some, it’s a way to display their inner gender identity.

Others use it as a way to meet a need, to fulfill a fantasy, bring entertainment, and many more.

Why Do Men Crossdress?

Crossdressers’, specifically Mtf crossdressers’, reasons to crossdress are as colorful as the rainbows in the LGBTQ+ flags.

Though not all crossdressers are members of the Pride Community, all support the group in one way or another.

To Entertain

Many men cross dress simply for work, entertainment, or as a theatrical hobby.

Try to remember how many actors you’ve seen in the past year who graced our screens with their crossdressing acts.

Crossdressing also applies to entertaining oneself.

Others simply do it for fashion purposes— to incorporate more feminine elements into their styles as men’s fashion is limited.

Crossdressers that fall under this category may do it for personal discovery or to protest against traditional gender stereotypes in their own way.

To Escape Reality

For most, as I’ve seen most of my crossdresser acquaintances have this reason, crossdressing is a form of escape or therapy.

Crossdressing, for these people, is a pass to take on an alter ego and leave the pressures of their everyday lives.

It’s completely normal for some crossdressers to use crossdressing as a way to explore their gender identity as well.

When reality boxes you to “male” or “female” and you find yourself not fully belonging to any, you’ll want to determine where you belong.

This determination often leads men to become crossdressers and discover unknown parts of themselves.

To Transition

A more serious tangent of the previous logic belongs to those who are preparing to transition.

Transgenders are a part of reality, but their current body doesn’t line up with what they know they should be in.

So, MtF transgenders may want to go through physical operations or live full-time as a woman.

For transitioners, crossdressing is an effective method to gradually become a custom to the change in their gender expression.

To Arouse

Some men find crossdressing sexually gratifying.

Crossdressing is originally considered taboo, making it an exciting component of an individual or a couple’s erotic adventures.

Though this is true in some way, note that most crossdressers don’t treat the activity for their sexual endeavors.

It’s always more about self-expression and freedom.

Types of Crossdressing

Let’s dig into the common types of crossdressers and why they’re participating in the activity.

Hobbyist Crossdresser

As a crossdressing enthusiast, the hobbyist crossdresser can range from amateur to experienced.

It will depend on his commitment to crossdressing and how much time he spends learning about the craft.

Hobbyists typically don’t think of crossdressing in relation to their gender identity.

The hobbyist treats crossdressing as a recreational activity. It’s a way to decompress and let his stress go.

It’s a way to embrace his femininity without consequences.

Because of this, he’s also one of the happiest crossdressers on the block.

He may even be a part of many crossdressing groups and may have performed in conventions crossdressed.

The hobbyist can also keep his hobby to himself, especially if it’s something he can’t disclose to the public because of his social status, work, or other reasons.

Femulating Crossdresser

The femulating crossdresser aims to be one with the women’s population.

His ultimate goal is to be seen as a woman and be treated as one.

He wants to pass as an ordinary woman; he does this by adopting feminine qualities, tendencies, and objects.

He copies women’s hair, fashion, makeup, and more.

Because he doesn’t want to stand out, the femulating crossdresser often chooses things that are currently adored by the ladies.

This is a sharp contrast to crossdressers who attract attention through their creative fashion choices.

Many femulators identify as trans or non-binary.

There are also those who are perfectly content with being male but enjoy temporarily adopting a feminine gender expression.

Crossdressers femulate as it allows a more “authentic” persona.

They get an inside scoop of what it feels like to be a woman when they blend into the female group.

Drag

Drag queens usually choose a caricature or a highly stylized female persona.

Compared to femulators, drag queens need to stand out and attract attention.

They achieve this through over-dramatic makeup or obnoxious stage performances.

This is expected— drag is the exaggerated, almost theatrical form of gender expression.

Drag performers are one of the most talented types of crossdressers.

They’re not simply wearing clothes.

They also need to know how to dance, sing or lip-synch, and even do stand-up comedy.

Drag queens don’t typically identify as their opposite gender in the binary.

But they’re often members of the LGBTQ+ group.

Non-Binary/Genderfluid Crossdresser

Crossdressers who put more emphasis on their gender identity than crossdressing’s aesthetics are acknowledged under the gender they identify with.

Non-binaries, aka non-bis or NBs, and genderfluid people don’t strictly associate themselves with one gender.

They are either “both male or female,” “not male or female,” or “moving between genders.”

In short, their gender identity fluctuates.

It’s not easy for others to see what the non-bi or genderfluid person identifies with in a certain time or day.

So, crossdressing comes in handy. For instance, a non-bi man can lean more to his feminine side one day.

He can’t just announce it to everyone he meets that day, so he can instead wear female clothing as a clear declaration.

Sissy

“Sissies” is a reclaimed slur now used by sexually-liberal individuals.

It points to men who enjoy being the submissives in their sexual exploits. Sissies crossdress to feel “less than” their doms.

Their doms will often emasculate them, so making them wear embarrassing but still sexy clothes is expected.

In BDSM, sissies can be considered masochists as they enjoy elements of humiliation or subservience.

They wear overly girly costumes, like frills or laces, to fuel their kinks.

Sissies may be of any sexual orientation or gender identity.

Misconceptions and Stereotypes

I wonder why it’s so hard for those who aren’t familiar with crossdressing to assume they know everything about the subject.

Not all men crossdress for their fetish or kink

Contrary to prejudiced beliefs, MtF crossdressers do not do so just because of sexuality or perversion.

Crossdressing can be sexually arousing to some, just some.

A majority of the crossdressing population is driven by the need to express themselves better.

While some crossdressers engage in kinks and fetishes, that isn’t the main motivation or goal for most.

Not all MtF crossdressers are gay

Sexual orientation and gender identity are two separate topics. Don’t confuse the two.

In fact, many MtF crossdressers are heterosexual men who are attracted to women.

They simply enjoy the newfound, albeit non-traditional, way of expressing themselves through feminine clothing and styles.

Their interests and attraction are still focused on women.

Not all MtF crossdressers want to “become” women

Not all crossdressers wish to permanently change their sex or gender.

They like the temporary change, but the idea of permanence can be terrifying to them.

It’s just the experience, the offer of a wider selection of styles used to dress up and present themselves.

Even with this, remember that some men do crossdress as preparation for transition.

But don’t take all crossdressers in one basket.

Not all MtF crossdressers are living the high life

Many assume crossdressers can afford the activity because they’re living grandiose lives.

Lives they want to flaunt to others. In truth, many lead ordinary lives. Crossdressers come from all walks of life.

They walk ordinary jobs, have families, and outwardly seem like ordinary men.

Crossdressing is something they do privately in their spare time, as a way to unwind.

They don’t seek fame or make their lives a public spectacle.

Crossdressing is more of a personal thing than a public one.

Like other misunderstood minorities, crossdressers face unfair stereotypes and judgments born out of ignorance.

But crossdressing is a natural human variation, a creative form of art that may or may not be linked to one’s gender.

Conclusion

In the end, there’s no one reason that triggers crossdressing.

For some, it’s about expressing a hidden feminine side.

For others, it can be sexual or purely a fun way to experiment with gender roles and expectations.

No matter the motivation, men should embrace their crossdressing in a healthy way— preferably without shame or secrecy.

Though I know, all too well, that this will depend on your personal circumstances.

Try to live by the creed of wearing what makes you feel the happiest and the most confident. But still do so in a safe and respectful way.

At its core, crossdressing is about celebrating the diversity of being human.

As humans, we crave independence, freedom, and exploration.

We all contain multitudes within us— masculine, feminine, and everything in between.

It’s a great motivation to express ourselves— our complete selves— regardless of the clothes in our closets.

So keep exploring this side of yourself and see where it takes you.

Labels don’t define you— only you get to do that.