Age Is No Barrier: It’s Never Too Late to Crossdress

Don’t let middle or old age be a reason to stop you from dressing up; fulfilling your inner desire can always be done.

Getting older can be rough. It creeps up on you slowly, and before you know it, grey hairs begin to appear, and you’ll notice a few lines on your face.

I first began to notice my aging when my beard began to take on a more salt & pepper coloring than it had before.

Shedding weight with just light exercise became harder as well.

These struggles combined with the more and more adult responsibilities that can pile up, and while you might want to dress up en femme, it’s quite easy to be discouraged by your slowly aging appearance and tired out by normal daily life.

Depending on your life situation, a desire to crossdress can be difficult to integrate into family life, married life, or whatever.

But I don’t think that gracefully aging or the stress of adult responsibility is a reason to stop dressing up or to prevent you from trying for the first time.

No matter if you are a first-timer, curious about femininity, or getting worried that your transformation won’t be what you desire, don’t let age be a barrier.

Embrace the aging process, and you can still be a beautiful, elegant woman when you want.

We’ll discuss some advice for the first-time mature crossdresser: who to involve, what to wear, and when to dress.

1. Should I come out to my family?

Perhaps you’ve been curious about crossdressing for a while and just never got around to trying.

Perhaps you had an experience that piqued your interest in becoming more feminine.

Whatever it is, it’s quite common to be unsure and insecure about exploring what can feel like a very taboo hobby or activity.

To start, I think the first decision you’ll have to make is whether or not to tell a partner or friend about your curiosity.

It’s understandable to be apprehensive about this because you don’t know what the reaction will be.

As a general principle, keeping secrets from a life partner isn’t a good idea; moreover, they are hard to keep.

Therefore, I’d encourage openness, however difficult that may sound.

Every “coming out” story is a bit different, but from the ones I’ve heard, there seem to be a few common threads.

Finding a good moment is important.

Perhaps slowly building up to the conversation by commenting on women’s fashion you see in shops, or fashion TV shows.

Dropping a few hints beforehand can soften the blow for a life partner or friend who might not have any idea what’s coming.

Also, having some external support is immensely helpful.

Finding a supportive online community or, if you’re feeling daring, introducing yourself to a local meet-up group will give you a sounding board or even a peer to help guide you through the process.

I assure you that in almost any reasonably sized city, it’s possible to find a CD community.

They even exist in more culturally conservative places.

If you’ve decided to keep this desire to yourself, your journey is going to be more difficult but not impossible.

YouTube has loads of videos for beginner crossdressers of any age.

Crossdressing Lifestyle is a great channel for general advice and support.

It’s administered by an older crossdresser who often shares her experiences as a mature CD female.

2. How do I dress?

As I get older, this is something that I confront anytime I decide to go into girl mode.

I don’t have time to keep myself in the physical shape I’d like to, and as a result, I’ve got a slight belly and quite a male physique. A

Also, as I get older, I notice lines and thinner skin on my face.

The clothing that I could look good in as my younger self wouldn’t be suitable for someone of my age anymore.

Perhaps a tight little black dress is fine for me at home alone for a quick thrill, but it’s a look that would get me clocked if I went out or raised eyebrows if I dressed up with friends.

One of the things I noticed as I got older and as my female friends got older, is that our fashion choices changed.

Try to observe what women your age are wearing when out and about.

If you’re in your 40s or 50s, a more classic look will let you blend in a bit easier.

Choosing styles that are snug around your hips but looser and longer around your legs will be more appropriate than a tight pencil skirt.

You’ll also need to be a bit more informed about the tops that you’re choosing.

Bare midriffs and spaghetti straps are going to be a big no-no.

Try to choose outfits that draw attention upwards rather than downwards to your curves.

Once you begin noticing the fashion choices of slightly older women, you’ll see.

Bold cleavage isn’t a thing that women often do in their 40s and 50s, but perhaps a top with a high neck and keyhole opening can give a hint of the sexy look we all want to achieve.

Shoes, again, should be less daring.

Tall stiletto heels won’t be comfortable and won’t coordinate well with the more classic, toned-down look you’re likely to be going for.

If it were me, I would choose shoes that offer me comfort and stability over a specific look;

Some people might say shoes like these could be considered clunky, but I’m afraid I have to disagree.

A lower, wider heel shouldn’t detract from anything and will look fine with slightly longer dresses, skirts, or slacks.

Don’t dismiss flats either; when paired with the right slacks, they can be just as classy as a heeled shoe.

Finally, achieving a feminine shape is going to be more difficult than when we were younger.

Foundation garments are going to take on some added importance.

One advantage of a more mature look is that we can rely on our clothes to give more coverage of our shapewear.

I’m sure you’d be surprised if you knew how many women were wearing some shapewear on a daily basis to keep themselves looking good.

I think the most important consideration as we get older is our waistlines.

Fear not, there are a load of options for you to try. Spanx has a lot of different options to help you obtain a nice figure.

There is even an option in their shapewear section to shop by level of strength: smooth, shape, or sculpt.

Roanyer’s Femini Girdles are also a good choice for slimming your waistline, as well as adding some extra feminine touches.

I think the middle-length options would work best, as they have the highest waists; they’ll also compress your thighs a bit to help get that desirable thigh gap.

Combining these with some padding around your hips can quickly change your shape to be more feminine.

On your upper body, I think that you must use some breast forms and a good supportive bra to hold them.

In my younger days, I could count on a padded bra to give an appearance of some bust in a tighter dress.

Still, now, as I need to wear slightly looser clothing, I’ve noticed that I have a desire to be bustier and curvier, so I can still rock feminine curves in looser clothing.

3. When to dress？

This might be the most difficult challenge to overcome, especially if you don’t live alone and have lots of personal obligations.

Timing your dressing is another reason I think it’s important to be open with a life partner about it.

I currently live alone, so finding time to dress at a time and place isn’t a massive struggle;

But I still worry about an unannounced knock on the door or package delivery.

If you’re worried about finding a secure place or time to dress, I have one or two suggestions.

If you’re lucky enough to be able to travel for work, there are going to be a number of opportunities to dress in hotels and possibly even venture out en femme in cities where you’re sure not to be recognized.

I would be very mindful about the type of items you travel with, though.

I recently traveled internationally with all of my female clothing and had a very close call at a customs desk when a customs officer asked me what the two ovals in my bags were.

Apparently, silicone breast forms stand out on the X-ray machine display.

I was able to escape with a short conversation, but the idea of my D-cup breast forms being inspected for the whole terminal to see was terrifying.

Keeping foam breast forms made of memory foam would avoid this problem and save weight in your luggage.

I hope you’ve found this discussion helpful and reassuring. It really is never too late to start a crossdressing journey.

Generally, having spoken with other crossdressers, they don’t regret continuing to dress into older age and might only regret not starting sooner.

Everyone is unanimous that they are glad they’ve found themselves eventually.

For some older CDs, taking these first steps in self-discovery can just be the beginning of a much bigger wave of self-awareness, and learning to be secure with their dressing leads to deeper questions about the root of their desire.

Whatever is the case for you, if you don’t try, you’ll never know.

No one learns to swim without first dipping a toe in the water.

I wish you all the best on your feminine journey!