Guide to Crossdressing in Secret: Unveiling the Art of Self-Expression

Men and Crossdressing

To crossdress means to wear clothes society expects another gender to wear. Crossdressing is more prevalent in men than women.

I’m sure you’ve seen the rise of drag queens. But, this activity isn’t only for entertainment.

Crossdressing in secret is where most men start. 

Unlike common stereotypes, men don’t exclusively crossdress for sexual purposes.

Men’s reasons for participating in the activity are varied and nuanced.

Often, it has to do with society’s expectations that men should suppress their feelings.

So, before we continue this guide, you should know crossdressing can be done without malice.

Considering to wear another gender’s clothing doesn’t automatically put you in an immoral or perverted category.

Crossdressing and Self-Expression

Traditional notions of masculinity prohibit sensitivity and submissiveness.

Masculinity demands aggression, dominance, and selfishness.

On the flip side, traditional masculinity requires emotional control and toughness.

Men are not permitted to show “weakness.”

As these are the ideas men are born into, they lack channels to relieve themselves of negative feelings.

This negativity eventually festers and affects men’s health — both physical and mental.

Crossdressing breaks every barrier society implanted in men regarding how they can reveal themselves to the world.

Men who crossdress use female clothing to convince themselves it’s okay to be vulnerable and weak.

It’s okay to explore “weak” feelings.

It’s also okay to explore taboos society deemed unacceptable — all within a nonjudgmental environment and with other consenting adults.

Crossdressing in Secret: How To Start

Men who are still unsure of how crossdressing can help them should start with crossdressing in secret.

Since it’s an intimate act to discover your identity beyond what’s expected of you til now,

it’s best to focus on how crossdressing makes you feel. At this time, your crossdressing’s focus is you.

At its core, crossdressing is letting yourself acknowledge both your masculine and feminine side,

which is your most potent strength to confidence empowerment.

Behavior is the most powerful form of communication.

By starting to crossdress, you start to mitigate your learned masculine behavior and draw out behaviors that are more considered feminine.

This doesn’t mean you become “less of a man.” It just means you’re now more aware of what you are as a whole.

You get to have a more balanced take of your emotions, for example.

It’ll be easy to accept it’s okay to be sensitive at times because doing so is healthy.

The best way to communicate this to yourself is to see yourself in a female getup.

Choosing the Right Attire

Identifying your body type is the first step to choosing what attire suits you the most.

Check this article on Body Shape and Outfit Recommendation to get an overview of what I’m talking about.

What body type does your body resemble the most? Don’t worry if you’re unsure.

You can take a guess for now, but it’s best to eventually know your exact proportions.

Next, delve into the women’s section for nice clothes. If anyone asks, say it’s a gift for your twin.

There are also various crossdressing shops online.

Alternatively, just pick whatever attire you feel the most connection to.

At this stage, you’re crossdressing for yourself. So choose whatever clothes you want to wear.

When you’re standing in front of the mirror, you’ll see if the clothing fits you the way you want it to.

If it doesn’t, don’t be offended or feel negatively. It just means the clothing doesn’t fit you well enough.

You can then move on to another piece of clothing. Self-expression is a journey — you don’t have to get it right in your first try.

Later, you can dive into what crossdresser fashion mistakes to avoid.

Enhancing Your Curves

To truly imitate, the female figure, you have to use props to enhance your curves.

Yes, men have curves, too! Although generally, men have a more linear or column-like shape,

it’s now easier to replicate womanly curves through foam or silicone products like hip and butt pads.

What product material you’ll get will all be up to you. As an experienced crossdresser,

I highly recommend choosing HQ silicone products as they offer the best immersive experience.

Just a quick note: Be certain about the sizing so these enhancers don’t sag when worn.

Creating Cleavage with Breastforms

Another excellent product every crossdressing man should get is breast forms.

Every crossdresser should have at least one pair of reliable breast forms.

Breast forms, just like what the name suggests, are fake boobs MTF crossdressers wear.

There are different materials to create breast forms.

But like in the previous section, fake breasts made from high-quality silicone are the best.

They can be attached through medical adhesives or be wearable type where you can just put them on like a top.

Cleavages are undeniably a female feature.

You can easily copy it by pressing your breast forms together to create a cleavage.

For a more detailed guide, read Sizing Breast Forms for a Perfect Fit and

How to Create an Eye-Catching Cleavage: Step-By-Step Crossdressers Guide.

Makeup and Hair Styling

Hair and makeup is the epitome of femininity.

Throughout the history of humankind, it’s only women who are afforded the option to pamper themselves to look aesthetically pleasing.

Although vanity is considered a feminine trait, there’s nothing wrong with wanting to look presentable and pretty.

As an MTF crossdresser, you have to at least learn the basics of makeup and hair styling.

When I say hairstyling, I am referring to your natural hair and the crossdresser wigs you’ll purchase in the future.

The most basic makeup product you’ll need is a foundation that matches your skin color and lipstick for your lips, doubling as blush and eyeshadow.

You can also add eyeliner and mascara to make your eyes pop.

Here are some great articles on makeup and hair styling for crossdressers:

Male to Female Makeover Checklist: 10 Elements for Flawless Feminine Image

3 tips of hair styles can make you look more feminine

Face Masks for Crossdressers: The Best Alternative to Makeup

Accessorizing Like a Pro

Accessories complete your whole feminine look. Though men do accessorize too, women have more options.

As a crossdresser, you’ll slowly learn how to properly accessorize to enhance your feminine charm.

As there’s a wide selection of accessories, it generally falls into categories.

These categories often include jewelry, footwear, belts, handbags, and hair accessories.

The goal of accessorizing is to create balance.

So, be wary of the patterns, colors, and shapes of your outfit and accessories — they shouldn’t clash.

At the same time, your accessories should not take away from your main attraction which in this case is you.

As a new crossdresser, the most basic accessorizing tips are as follows:

Pick a main accessory. This accessory will be the center of your whole outfit.

You can base your other fashion picks on it. Other accessories should support this statement piece.

Don’t over-accessorize. In fashion, sometimes less is more. But you have to know when less is perfect.

For instance, wearing large boho pendants over a vibrant, psychedelic printed dress is overwhelming to look at.

Accessories should save you money. When you decide to crossdress in public, you don’t have to buy a whole fit to match a certain event.

Say, with a simple black dress and a dainty set of jewelry, you can go to a nice, casual meetup with friends.

Take that same dress, wear a garter belt, and stilettos and you’re ready for a hot date.

Only buy accessories you can use on many occasions.

Confidence and Self-Acceptance

Even if you have the best dress, the best silicone products to enhance your curves,

and the best makeup team in the world to help you transform,

if you don’t have the confidence, how will you be able to accept yourself?

This is why, at the very beginning of this article, I already told you to start crossdressing without prejudice.

Keeping your mind open to the advantages crossdressing poses is crucial.

At this stage, as I said before, focus on you. Don’t think of how others may perceive you or what society tells you to be.

Not yet. Give yourself room to explore first.

Remember, you’re crossdressing to hopefully start embracing your true self and be confident in your appearance,

both as a man and as a female. Yes, there will be societal stigma and judgment once you decide to come out.

But your most powerful shield against all of this is self-love and confidence.

Reminders for a Secret Crossdresser

Since you’re still crossdressing in secret, here are some tips to avoid others finding out:

Be discreet. You don’t have to go all out immediately. Start with the subtle changes and discreet crossdressing products.

Plan ahead. Think of the what-ifs first before purchasing crossdressing products.

Where can you hide them? Is the shipping policies confidential?

Note your goals. You’re crossdressing for a reason, jot them down.

Your experiences will help you unveil if you’re ready to get to your next crossdressing level.

Wrap up

Crossdressing in secret removes the burden of letting others know.

At this phase, the MTF crossdresser can only be restricted by his inhibitions and concerns.

Crossdressing helps men tap into their feminine traits and shed toxic masculinity.

It teaches many important lessons about self-expression. But the most important is learning to be yourself outside of others’ expectations.

When you realize you’re not as chained as you think you are, your possibilities become endless.

This endless possibility is at the tips of your fingers, and all you have to do is to grab it. There is no right or wrong way to crossdress — it’s all about expressing your true self.