The Different Phases of Cross dressing

What is a cross dressing phase?

Remember the first time you wore your mom’s panties and thought it was just a phase?

And here you are, probably sitting in lingerie right now, reading this blog.

You weren’t wrong; it was a phase, but only a single phase of a long crossdressing journey.

Most crossdressers undergo a similar mental and emotional journey.

I have many cross dressing friends, and our stories share parallels.

We may come from different backgrounds, ethnicities, nationalities, and upbringings.

Still, deep down, we share many of the same feelings and face similar dilemmas and traumas in life.

All of these become part of our crossdressing journey.

In this blog, I will discuss the various phases of crossdressing that you will likely relate to and provide guidance on navigating through them.

After reading this, I hope your cross dressing journey becomes smoother.

Let’s get started.

7 Different Phases of Cross dressing

The Initial Realisation

I would say that the initial realization phase is the most innocent one, where you simply want to be a girl.

No questions asked; you just aspire to be girly.

I vividly remember being just 5 or 6 years old and secretly wearing my mom’s necklace and heels.

I didn’t even realize I was crossdressing, though I knew it wasn’t something acceptable.

Do you recall your initial phase, filled with fear and cluelessness, just wanting to wear skirts and dresses, hoping to be like a girl?

Even a pink t-shirt would spike my adrenaline at that stage.

For most crossdressers, this initial realization occurs at a young age; for many, it surfaces during puberty when sexual hormones take over.

For others, it happens in their 20s, often triggered by a single crossdressing event, like during Halloween, due to a dare, etc., which provides the first taste of how comfortable and stylish women’s clothing feels.

Secretly Borrowing Clothes

This phase is the closeted one for a crossdresser, which comes right after the initial realization.

In this stage, as a child, you’re always looking for opportunities to crossdress, seeking windows when no one is watching so you can try on your mom’s or sister’s clothes.

Most crossdressers at this point wear their mom’s or sister’s clothes because they lack the funds and understanding to buy their own.

Yet, in those early days, even the smallest things felt so special. Simply wearing a camisole top or a skirt is significant, regardless of whether they match or not.

The mind and imagination often fill in the gaps, making the overall look seem incredibly pretty.

For instance, when I was young, my mom’s bra was too big for me, but I still felt incredibly feminine wearing it.

This stage can be confusing, as many of us are unaware of what crossdressing is, and we’ve likely never seen anyone else doing it.

I would constantly look for opportunities to crossdress, only to immediately regret it afterward.

Yet, it felt so right that I couldn’t resist.

If you find yourself in this situation, I want to tell you that there’s nothing to be concerned about, and you shouldn’t feel ashamed.

What you’re doing is entirely normal, and there are many others like you.

Crossdressing doesn’t make you weaker or any less than other boys in your class.

If you feel like dressing up, go with the flow and embrace it.

Exploring Styles and Fashion

This is the phase where you upgrade your personality and style as the hormones kick in, and you don’t just wanna dress but also look feminine and sexy.

At this this, you don’t like your mum’s mature styles and want to try something chic.

I remember when I was around 15, I stopped wearing my mom’s clothes and started dabbling in my sister’s wardrobe, and that was like heaven for me.

OMG. She used to have everything: bikinis, all types of bras, shorts, everything a 15-year-old crossdresser needs.

But fitting always used to be an issue, and the fear of what they realized I wore those clothes, so I tried managing my own secret feminine wardrobe.

I started purchasing smaller things like lingerie, makeup kits, wigs, breast forms, and other essentials that I can hide easily and also get a decent feminine look while cross dressing.

This is a very fun phase where you almost crossdress every day and constantly hustle to wear a dress and then remove it so as not to get caught.

In this face, most of us also discover our sexuality and relationship with crossdressing.

This phase probably lasts a very long as it takes a lot of mental preparation to come out.

Some crossdressers like to stay closeted and enjoy being a closeted crossdresser.

The Denial Phase

This is a very common stage that typically arises in the late teen years, around 16-18, when you try to convince yourself that you aren’t a crossdresser and that crossdressing was just a phase in your life that has passed.

I went through the same thing.

The denial phase can occur for various reasons, such as the rise of testosterone(male hormone), academic pressures, or feelings of self-shame.

During this stage, many crossdressers attempt to resist the urge to crossdress and suppress their feelings.

In fact, some even try to overcompensate by acting extra macho.

Listen, honey, the denial phase is very common, so don’t stress too much about it.

Crossdressers often struggle with uncertainty and shame during this time, but this resistance doesn’t help.

Just go with the flow and follow your instincts. Don’t suppress your emotions.

If you feel isolated, consider talking to someone like a trusted friend.

You can also express yourself on online forums.

If the stress becomes overwhelming, consider therapy.

The key is to communicate and not bottle up your thoughts.

All I want to say is that you shouldn’t deny your feelings about crossdressing; it won’t be beneficial.

The Self-Acceptance Phase

The denial phase often becomes the most pivotal phase in a crossdresser’s life because it offers significant clarity.

During this time, many understand their relationship with crossdressing and their expression of femininity.

Most crossdressers discover their unique style and vibe, embracing it wholeheartedly. In this self-acceptance phase, crossdressing no longer serves as a source of stress.

Instead, it becomes a means of relief.

Many individuals determine how they want to carry on their cross dressing journey and define their identity within the cross dressing community.

For instance, some are drawn to the femboy aesthetic; others find themselves on stage as drag queens, while some prefer to remain closeted, relishing their moments in dresses and makeup.

If you’re in the self-acceptance phase, first and foremost, congratulations on reaching this mature stage as a crossdresser.

In this phase, I would advise making as many friends as possible.

If you’ve come out, consider establishing a presence on social media to educate and guide other cross dressers in finding their unique identities.

Going/Coming Out in Public and 

Coming out or going out in public is the scariest phase of cross dressing, yet they are also incredibly exciting.

I still remember the first time I went out in a dress; my heart was racing.

The fear of being discovered or humiliated coexisted with the thrill of being feminine in public.

It was a complex but exhilarating sensation.

Coming out as a crossdresser elicits a similar experience; it feels as if a heavy rock has been lifted from your shoulders.

While there’s relief, you also have to face the repercussions of revealing the feminine side of yourself.

From this phase onward, you’ll only continue to grow and mature as a crossdresser.

You’ll gain insights into how to present yourself confidently and authentically.

Interacting with diverse individuals will also enrich your understanding of the world from a feminine vantage point.

If you’re in this phase, I’d encourage you to muster the bravery to live openly.

However, always prioritize your safety when out in public.

Becoming a Pro Crossdresser

This is the stage where cross dressing becomes routine for you.

Most crossdressers at this stage either live independently or have already come out, so there’s no lingering fear of being discovered by parents or peers.

Many crossdressers in this phase truly relish their experiences, casually cross dressing, shopping en femme in public, dating, going on outings, and having intimate relationships.

I believe this is the pinnacle of the cross dressing journey because you spend much of your time in a feminine avatar.

People recognize and accept your feminine persona without judgment.

Everything feels fresh and thrilling.

The earlier you reach this stage of crossdressing, the more opportunities you have to enjoy it fully.

Nowadays, it’s simpler to become a pro at cross dressing, given the wealth of information and resources available for the cross dressing community.

I encourage you to tap into the online cross dressing community to upgrade your skills and embrace your identity at a younger age.

Retiring or Full-Time Crossd ressing

Crossdressing is a fun journey, but after a certain point, it no longer provides the same excitement and can become monotonous.

Sometimes, life’s other priorities overshadow crossdressing, leading many to set it aside because it no longer holds the same excitement.

This is why some crossdressers choose to “retire” from the cross dressing.

If you find yourself in this situation, you can take a break and return to crossdressing when you feel the sexiness and excitement of bras and panties once again.

Many crossdressers do this; they pause for a while and then re-engage with the cross dressing after a point of time.

After the pro cross dressing phase, some opt for full-time crossdressing.

Indeed, certain individuals decide to live en femme completely, as they recognize that crossdressing isn’t merely a hobby or fetish; it’s an integral part of their identity.

Some choose to identify as gender non-binary, while others embark on a journey of transition, undergoing hormone replacement therapy, feminization surgery, or SRS to fully embrace a female identity rather than just being a crossdresser.

Conclusion

Now you know that cross dressing unfolds in phases and isn’t just a single phase that will pass.

There are multiple stages in crossdressing, and each one is crucial for crossdressers because it offers insights into your personality and helps you to navigate the crossdressing journey.

It’s important to live each stage and embrace the emotions and thoughts that come with it.

Accepting yourself will make you stronger while suppressing your feelings can make the journey more challenging.

I view cross dressing as a blessing because it enables me to experience both femininity and masculinity in a single lifetime.

Experiencing the sexiness of feminine dresses, makeup, and styling as a man is an amazing feeling.

So, embrace each phase of cross dressing.

Let us know where you are in your cross dressing journey.

Until next time, be feminine and be yourself.