The Pros and Cons of Crossdressing at a Mature Age

wWhen we think about crossdressers, it’s easy to remember the new generations. As society becomes more open-minded, and prejudices start to vanish, the youth makes use of this newfound freedom. That’s why nowadays it’s easier to see crossdressers, femboys, and transgender people than it was a few decades ago. But crossdressers always existed, even though they used to be repressed and love closeted. This way, when discussing things related to crossdressing, we must consider our mature sisters. That’s because crossdressing isn’t limited to young people.

This way, we must understand both the advantages and disadvantages of crossdressing at older ages. Mature crossdressers may have more freedom and money, but may find it more difficult to accept themselves. If you were closeted for to long, you’ll have to make it up for all the time you lost. But seasoned crossdressers tend to enjoy their mature crossdressing adventures.

With that in mind, my plan is to show you through this article all the pros and cons. It’s meant to increase the self esteem of mature crossdressers and give them more confidence.  With that in mind, I hope it helps them to overcome most challenges that come with aging.

1. Mature crossdressers have more freedom

Freedom is a key word for mature crossdressing, and it comes to us in many different ways. The first and most noticeable is, of course, financial freedom. I mean, if you’re over your 50’s, you’re way more likely to have a stable job than teenage crossdressers. This way you can buy your own stuff with your own money. The best part about it is that you won’t have to do any kind of accountability. I mean, the money is yours, and you can spend it however you want to. I had to wait till I was 18 years old to even start crossdressing, since I didn’t have a job before that. Besides that, I didn’t come out until I was 20, and asking my parents for women’s clothing was out of the question.

Another way that crossdressing at a mature age can improve your freedom, is by the fact that you may have your own place to live. Younger crossdressers that live with their parents sometimes struggle with privacy. Thus, they are unable to practice or dress up too often. Sometimes, the opposite is true, and crossdressers with childs have a hard time trying to hide it from them. But once your kids move to their own place, you can expand your closet and dress up more frequently. What I mean is that living with other people tends to make things harder for young or middle-aged crossdressers.  It restricts their crossdressing habits, but if you live by yourself you won’t have such a problem. And once you are in a mature age, you have higher chances of living like that, with much more privacy.

Last but not least, it’s worth mentioning that mature crossdressers tend to have more resources. At least, enough to try out crossdressing services and clubs. It’s a good way to experiment upon new trends and techniques that are popular among crossdressers. This way you can keep in touch with younger generations and make new friends in the crossdressing community. Try to interact with other crossdressing sisters this way. It reduces your loneliness and helps you to build more confidence.

2. It’s a bit harder to pass as a woman

Teenagers and young adults have higher chances of passing as the opposite gender. That’s because they have not undergone the process we call “second puberty” yet. During this process, our hormones make the differences between male and female bodies much more visible, so passing is way harder than it used to be. This way, crossdressers that didn’t do any kind of hormone replacement therapy tend to look less convincing. That’s the case for the majority of mature crossdressers, since HRT has become more common and accessible only in recent years.

With that in mind, mature crossdressers must be reminded that crossdressing isn’t limited to passing. It’s about expressing yourself as who you really are, about having fun, and sometimes a matter of art. Whenever you feel down about not passing, think about how free you are now to express yourself. Embrace your feminine side and dress up in clothes that you like. That’s the true spirit of crossdressing!

For trans people that worry about second puberty, I strongly recommend them to start HRT with a professional. The purpose is to regulate the changes in their bodies, ensuring they reach a mature age as passable as possible. It’s good for their self esteem, but medical and psychological assistance is needed in order to do so safely.

3. As time passes, we become more experienced

We get better with time. In terms of crossdressing, practice leads us towards perfection, as we learn from our mistakes. If you want to confirm what I’m saying, compare a picture from the first time you ever crossdressed, and another one from now. We get better and more experienced, we get used to many different techniques, and our makeup gets more effective. We also adapt to shape wear, enduring corsets and different compression gadgets that make us look more feminine.

And after all the time we spend perfecting our skills, everything seems easier and the results are more rewarding. The new generations of crossdressers have much to learn with the mature generation. They are the more experienced members of our ever growing community. I’d like to use this section of the article to promote the dialogue between the older and newer generations of crossdressers. Such dialogue may improve the overall experience in our community, and make every member feel like part of something big.

4. Sometimes we have to make it up for the time we lost

The mature crossdresser of today, was born decades ago, when crossdressing was a taboo. It was even a crime to crossdress in most countries, as it is today in some conservative locations. This way, they might have lacked proper freedom and resources to crossdress when they were young. As a result, they started to crossdress more recently, after years of building confidence and courage. Sometimes, this kind of situation ends up in a feeling of lost time. When a crossdresser feels that way, they think a big part of their lives was in vain, for not being able to crossdress and express themselves.

The more serious cases can turn into depression and suicide attempts. With that in mind, it’s recommended for mature crossdressers to seek professional support from a therapist. My advice here is to be grateful to the fact that you can now crossdress, and try to enjoy it as much as possible.

5. We can experience the good things in life and enjoy it

As a mature person, you might feel that you did everything you had to do in your life. After all your accomplishments, it’s time for you to enjoy the simple things life has to offer. And what can be simpler than being yourself? Now you can experience the world as a whole new person. You are free to dress up the way you want, even if it means crossdressing. You deserve this happiness, and everything else about this experience.

6. How to dress up as a classy, mature crossdresser

Once we reach a mature age, we start to feel that our days of beauty are in the past. Most of the charm we had while young has now left our mature bodies. But just because it’s harder to look sexy when we are older, it doesn’t mean that we can’t look good. The best thing to do is to aim for a classy good-looking outfit, better suited for the ages of 50 and beyond.

My tip is for you to try and dress up in the same way other women your age do. If you do that, you’re more likely to blend in and pass as a woman. You can leave most shapewear behind, and wear a less revealing outfit. Black is a color that suits any body type, and the elegant tends to replace the sexy. But at the end of the day, what matters is to have a good time and be yourself. With that in mind, the clothing you should use is the one that makes you happy. For example, some crossdressers prefer long dresses, while others are fond of short skirts. It’s up to you to decide upon whatever makes you happy, and dress up accordingly.

In the end, a mature crossdresser is still a crossdresser. As such, they have undergone many difficult situations, generally even more than the young generations. It’s never too late to be true to yourself, and crossdressing isn’t limited by age. Of course, as time passes, it brings a lot of both advantages and disadvantages. When we get older, we must learn how to deal with each one of these situations, to make sure crossdressing keeps being a fun and healthy activity. If you’re a mature crossdresser, make sure you share your thoughts and experiences below in the comments! The dialogue between generations is important to keep our community strong and whole.