Is There a Perfect Time to Start Crossdressing?

Is there a perfect time to start crossdressing? Or rather, is there a wrong time to start crossdressing?

 

There are all these expectations set by societies about what’s expected of people at different stages of their lives.

 

Do these milestones apply to us as crossdressers, too?

 

 

 

The answer is simple! There’s no perfect time to start crossdressing – it’s different for everyone.

 

Some people have known they wanted to crossdress since they were very young, while others only realized it later in life.

 

There’s no right or wrong answer, and you should do what feels right for you.

 

 

If you’re still unconvinced, I welcome you to read on.

 

I’ll explore some of the things you might want to consider before taking the plunge into crossdressing.

 

 

1. Too young to crossdress, really?

 

 

As a kid, I was always riveted by my mother’s clothes. I would try on her dresses and shoes whenever she wasn’t around.

 

I even put on makeup once but got caught in the act. My mother was not pleased.

 

She sat me down and said that only girls wear dresses and that I should be ashamed of myself for wanting to dress like one.

 

 

 

I didn’t understand why she was so mad. I just thought that her clothes were pretty and I wanted to look like her.

 

From then on, I stopped crossdressing altogether. However, many years later, I started to crossdress again.

 

 

 

Now, as an adult, I can finally crossdress without fear of judgment or reprisal.

 

I don’t have to worry about what other people think.

 

▶ So, when is the perfect time to start crossdressing?

 

The answer is frank: there is no perfect time. You can start crossdressing at any age, whether you’re a child, teenager, or adult.

 

If you’re comfortable with it, and you’re not doing it to harm anyone else, then go ahead.

 

 

 

So go ahead and express yourself however you see fit.

 

There’s no need to wait for the “perfect” moment.

 

Just put on your favorite dress and go out into the world as the beautiful woman you are!

 

2. I’m I too old to crossdress?

 

 

This is a common question. And the answer is… it depends!

 

 

 

There is no perfect time to start crossdressing, and there is no age limit.

 

Some people start crossdressing in their teens, while others don’t discover their love of dressing up until they’re middle-aged or even older.

 

 

 

What makes you happy? If you feel like crossdressing is something you want to do, then go for it! There’s no reason to wait.

 

 

 

However, there are a few things to keep in mind.

 

For instance, if you have young children at home, you might want to wait until they’re a bit older and can understand what you’re doing.

 

You also need to be mindful of your work situation – if you have a job that is public-facing, you might want to think about whether or not crossdressing could impact your employment.

 

 

 

But overall, there is no perfect time to start crossdressing. Just do it when it feels right for you!

 

3. At what age do I hang my boots?

 

 

The response to that query is that there is no perfect age. It’s never too late to start living your truth.

 

 

 

People often ask me when the right time is to start crossdressing.

 

My answer is always the same: there is no perfect time because there is no single “right” way to do it. Everyone’s journey is different.

 

 

 

Crossdressing can be a fun and freeing experience, but it’s also important to remember that it’s not all about fashion and appearance but rather about yourself.

 

 

 

So, whatever age you are, if you feel like crossdressing is something you want to do, then go for it! There’s no time like the present.

 

4. Can I crossdress throughout life?

 

 

The response to this query is unfortunately not as simple as a “yes” or “no.”

 

Many factors can influence when the best time to start crossdressing might be.

 

Some of these include things like your age, personal comfort levels, and societal expectations.

 

 

 

For some people, starting to crossdress at a young age can be incredibly freeing.

 

It can be a way to explore your own gender identity and expression without judgment from others.

 

If you’re comfortable with your body and have a good support system, crossdressing at a young age can be a great experience.

 

 

However, there are also potential downsides to starting to crossdress at a young age.

 

For example, you may not be fully aware of the societal implications of crossdressing.

 

This can lead to some uncomfortable situations, such as being ridiculed or discriminated against.

 

There’s also the potential for your family or friends not to be supportive of your decision to crossdress.

 

 

 

It would be best if you made the decision that feels best for you and your circumstances.

 

If you’re feeling uncertain about when the best time to start crossdressing might be, it’s ok to be patient with your progress.

 

There’s no rush – you can explore this aspect of your identity at whatever pace feels comfortable for you.

 

5. Factors that influence the best time to start crossdressing

 

 

● Your relationship status

 

Crossdressing can potentially have an impact on your romantic or sexual relationships.

 

If you’re in a committed relationship, it’s important to talk to your partner about your desire to crossdress before making any decisions.

 

 

● Your job:

 

Depending on your job, crossdressing at work may not be possible or desirable.

 

If you’re concerned about how crossdressing might affect your career, it’s worth considering whether now is the right time to start exploring this aspect of your identity.

 

 

● Your mental health:

 

Crossdressing can be a triggering experience for some people.

 

If you have a history of mental illness, it’s important to consider how crossdressing might impact your mental health before making any decisions.

 

 

● Your physical health:

 

Crossdressing can also have physical implications, such as breast binding or wearing shoes that don’t fit properly.

 

It’s important to consider how your physical health might be affected before starting to crossdress.

 

 

● Your financial situation:

 

Some aspects of crossdressing, such as buying new clothes or cosmetics, can be expensive.

 

If you’re on a tight budget, it’s worth considering whether now is the right time to start exploring this aspect of your identity.

 

6. Inspirational crossdressers who’ve gone all the way to their old age

 

It’s never too late to start crossdressing!

 

There are plenty of inspiring stories of people who only started exploring their gender identity later in life – and they’re living proof that it’s never too late to start embracing your true self.

 

 

 

Here are five inspirational crossdressers who’ve gone all the way to their old age: 

 

 

1. Richard O’Brien:

 

Richard O’Brien is a 77-year-old actor, writer, and musician best known for creating The Rocky Horror Show.

 

He didn’t start crossdressing until he was in his 50s but has since become one of the most prominent older crossdressers in the world.

 

He often appears in public wearing flamboyant and glamorous outfits and is an outspoken advocate for crossdressing and gender fluidity.

 

 

2. Roberta Close:

 

Roberta Close is a Brazilian model who was one of the first openly transgender women in the world.

 

She began crossdressing in her teens but didn’t begin hormone therapy or transition until she was in her 30s.

 

She’s now in her 60s and is still a successful model and outspoken advocate for transgender rights.

 

 

3. Renée Richards:

 

Renée Richards is a retired tennis player and ophthalmologist.

 

She began crossdressing in her 40s and underwent sex reassignment surgery in her 50s.

 

She caused a stir in the world of professional tennis when she tried to compete as a woman in the 1976 US Open but was ultimately allowed to play.

 

She’s now in her 80s and is considered one of the most famous older crossdressers in the world.

 

 

4. Caroline Cossey:

 

Caroline Cossey is a British model and actress who was one of the first openly transgender women in the world.

 

She began crossdressing in her teens and underwent sex reassignment surgery in her 20s.

 

She featured in the James Bond film For Your Eyes Only in 1981, becoming the first openly transgender woman to appear in a major Hollywood movie.

 

She’s now in her 60s and is still an active advocate for transgender rights.

 

 

5. Caitlyn Jenner:

 

Caitlyn Jenner is a reality TV star, former Olympian, and transgender activist.

 

She didn’t start publicly crossdressing until she was in her 60s but has since become one of the most famous older crossdressers in the world.

 

She has used her platform to speak out about the challenges faced by transgender people and is an outspoken advocate for transgender rights.

 

 

6. Lady Blue Stocking:

 

Born in 1892, Lady Blue Stocking was one of the first public figures to crossdress openly.

 

She was a fashionable socialite and an accomplished writer, and she continued to crossdress until she died in 1979.

 

 

7. Marlene Dietrich:

 

The iconic German actress and singer began crossdressing in the 1930s when it was still very taboo.

 

She famously wore men’s clothing both on and off-screen and even served as a muse for Yves Saint Laurent.

 

 

8. Billie Jean King:

 

Billie Jean King began crossdressing in the 1970s to gain an edge over her male competitors.

 

She has since been a candid supporter of LGBT rights.

 

 

9. George Jorgensen Jr.:

 

In 1952, George Jorgensen Jr. made headlines when he became the first person to undergo sex reassignment surgery.

 

He changed his name to Christine Jorgensen and went on to have a successful career as a nightclub singer and actress.

 

 

10. Candy Darling:

 

Candy Darling was one of the first openly transgender celebrities.

 

She featured in several movies by Andy Warhol and was close friends with Lou Reed and Truman Capote.

 

 

11. Jayne County:

 

A pioneer of the punk rock scene, Jayne County was one of the first musicians to identify as transgender openly.

 

She has continued to perform and record music over the past four decades and is still going strong today.

 

 

12. Laverne Cox:

 

An Emmy-nominated actress and producer, Laverne Cox is best known for her role in the Netflix series Orange Is the New Black.

 

She has been a voiced supporter of transgender rights and visibility.

 

 

 

The final verdict is that there is no perfect time to start crossdressing.

 

Everyone’s journey is different, and there is no single “right” way to do things. Trust yourself and Follow Your Bliss! 🙂

 

 

 

If you’re thinking about crossdressing, there are a few things you can do to prepare.

 

First, it’s important to understand why you want to crossdress.

 

What is it about crossdressing that appeals to you?

 

Do you enjoy the way it makes you feel or the way it allows you to express yourself?

 

Once you have a better understanding of your motivations, you can start to figure out how you want to approach crossdressing.

 

 

 

If you’re not sure where to start, there are plenty of resources available online and in bookstores.

 

There are also many community groups dedicated to supporting people who crossdress.

 

These can be a great way to meet other crossdressers and learn more about the lifestyle.

 

 

 

Learn More:

 

When Is It Too Late to Crossdress?