Why and When Do I Crossdress?

As part of this new section in this blog, in which we tell you all about our personal experience with crossdress, today I am writing about why and when I love to dress up.

I am going to tell you the reasons why I enjoy wearing feminine clothing when I get the chance to do so.

Hopefully, you will find some insight here, and it will help you open up to this lifestyle a little more!

Every crossdresser is subject to living in a society that is not always accepting of alternative lifestyles.

That’s why we believe that sharing our thoughts and experiences will help you connect more with the feelings and habits of other members of this community.

You will see that you are not alone, and there are many ways you can crossdress without any peril to yourself.

If you are interested in reading why this lifestyle is so wonderful and gathers this many people from around the world, then join me in this little tale of why and when I get to explore my femininity!

Why Do I Crossdressing?

I believe that I speak for everyone here when I say that crossdressing was almost always present in my life.

It’s not something that you come across in your life all of a sudden. For me, feminine clothes were always beautiful.

I never understood why society is so hard set on the thought that men can’t wear skirts or any other kind of attire aimed at women.

The colors, textures, and variety of feminine clothes that are on the market are, most of the time, much more compelling than their masculine counterparts.

I always felt more comfortable wearing something outside of the male standards.

Crossdress makes me feel not only free but also lets me express another side of my personality that, for some reason can’t express otherwise.

One who is not always trying to make a stand and is anxious about getting things done.

On the contrary, while en-femme, I feel relaxed and more connected with my feelings and those of others.

I find peace in relaxing in my cami while drinking a nice cup of wine on a quiet night at the end of a hard day’s work, for instance.

I also think that in time one gets surer about oneself and expands this form of expression to new horizons.

What I mean by this is that there comes a time in every crossdresser’s life that it is not only about the clothes.

Skincare routines, feminine perfumes, long hair, and makeup are only some examples of how this lifestyle grows naturally as time goes by.

In reality, few things can be reduced to a black-and-white scenario, and masculinity and femininity are present in every individual.

I think that once you initiate walking down this path, despite some insecurities at times, the urge to feel feminine comes back eventually, only to make you realize that you shouldn’t fight against something that makes you feel good about yourself.

Crossdress opens some doors inside your mind that allow you to see the world with a different perspective than most people.

As I grew up and sexuality became an important part of my life, I also realized that my feminine side wanted to express itself.

There’s no point in comparing the sexiness between “women’s” and “men’s” clothes.

Among the reasons mentioned above, the texture of feminine clothes is the first thing I notice while wearing them.

Opposite to masculine clothes that are mostly rough and rigid, I feel more contained and even caressed by feminine clothes.

The soft and delicate feeling of panties, dresses, blouses, and leggings, among others, makes me wonder why the fashion industry took this turn and differentiated them so extremely.

This seems to be changing a little nowadays but it seems it is struggling with the public’s acceptance.

As I was saying before, there came a time when I not only felt more comfortable wearing feminine clothes, but I felt sexy.

The way I looked and felt was truly an eye-opening experience.

Another reason why I love crossdressing is that it motivates me to get more connected with activities that I normally wouldn’t.

Dancing for instance, is one of the things that I do more freely and unembarrassed.

And, of course, wearing a skirt or a dress for me becomes the absolute experience of crossdress.

When Do I Crossdress?

To be absolutely honest, I crossdress, fully or partially, any time I can without making a scene.

It is obvious that I fully dress in feminine clothes whenever I get home, and I am not expecting visits.

I get rid of all the clothes that I was wearing as soon as I cross the door and doll up in whatever lounging outfit I want. I have a pair of fennel outfits that I got at a Victoria’s Secret sale that I absolutely love.

I have mentioned before that I love to relax after office hours in my favorite cami while drinking a cup of wine.

And, as you can imagine, I love going to sleep afterward while still in it.

Wearing feminine pajamas makes me not only rest profoundly all through the night but also makes me fall asleep easier as I feel really comfy.

I often add a splash of nice perfume to make the experience more comforting.

I do this most nights unless I have a very particular reason not to.

I have mentioned that I love dancing while crossdressing, and not only at home but sometimes I hit the nightclub with some friends for a non-stop girls’ night out fun.

It is easily one of the moments when I enjoy myself the most while en-femme.

Going out with my girlfriends, dressed to kill, and feeling one of them is such a wonderful feeling that I am very glad I got to share.

But the experience of going out on a GNO wouldn’t be complete without the required preparations.

Getting ready together, selecting and modeling our outfits, and doing our makeup is so much fun!

It allows the time to bond in a very particular way that many don’t know they are missing.

Before the pandemic started, I had a job that required me to meet many customers and had to maintain a professional look.

As you can imagine, I couldn’t do it while crossdressing, unfortunately.

Even so, I still wore panties and leggings from time to time, tucked my shirt in my pants, and wore long socks to avoid any uncomfortable situation at the workplace.

Luckily, with the change of habits came a change of job, and I got one that allowed me to work from my home.

I couldn’t be happier, not only because my paycheck became better but also because I could dress however I wanted!

Of course, I was taking full advantage of this opportunity and bought myself many outfits to wear as if I were still working in an office, but this time as a girl!

I love looking like a sexy female office worker while working nowadays!

I go all out and even paint my nails and do some basic makeup with lipstick and mascara.

I have never enjoyed working so much as I do now that I can do it dressed in such sexy clothes.

If you love crossdressing as much as I do and have the opportunity to get a job that allows you at least some home office days, I suggest you do.

Believe me you won’t regret it not one bit.

Lastly, I have told the story in an older post of how I confessed to my girlfriend of my crossdressing some years ago.

It is true that at first, even though she wasn’t surprised, she wasn’t very thrilled either.

But in time, we got to share it more and more. Nowadays, we sometimes go out on dates, and I get to be the lady in the relationship!

The fact of my coming out has brought us closer, and we got to share more things than we used to.

We even do some sexy role-playing and make bets to determine who is wearing what outfit!

I’m very glad that I dared to come out to her and that we get to share this amazing lifestyle.

I hope that you have enjoyed reading the reasons why I crossdress and why I enjoy it so much.

Perhaps having read this little story inspires you to become more open to this lifestyle and start caring less about what others think.

Maybe you even have found some ideas to indulge you and your crossdressing in situations that you were reluctant to.

And you? Why and when do you crossdress? What activity do you enjoy the most while en-femme?

I would love to read your story in the comments below!

Feel free to share your thoughts and become an active part of this lovely community!