It’s not likely we wake up one day and just… decide to wear “girl clothes”. It’s more likely we have been wanting to do so for a long time… but we “can’t” because we are a boy, at least according to the doctors when we were born and that is based entirely on our genitalia. No matter how we try to push it out of our minds and hearts, we can’t help but let our imagination drift back to a beautiful world of pink and lace and leather and pencil skirts and nightgowns and everything our heart desires.
For many of us, clothes can represent a way for us to present in a way that aligns with our identity. For others, not so much, we just love dresses and lingerie.
The tricky thing is knowing what is right for us.
So, how do we know? It’s different from person to person and all of our journeys are different, but it tends to be a slow and gradual process when it comes to figuring it out. And it probably starts with clothes.
I am not meaning to trivialize or simplify anyone’s identity, but rather talk mostly about my own experiences and possibly others who may feel something similar. When it comes to the colliding worlds of “girl clothes” and transitioning, we might think that the only way we CAN wear “girl clothes” is IF we transition.
Of course, that’s not true, but it might be right for yourself.
So, how does one start? How do we know what is the right path for us? In my experience, it started with testing the waters of presentation aided by the very items that I couldn’t stop thinking about.
We slip into a pair of panties, we daydream about a gorgeous dress, and fantasize about what it’s like to strut around in a pair of five inch stilettos. We tentatively test the waters and fall in love with clothes that compliment and confirm our gender identity. Presentation finally matches what is in our hearts. And it’s wonderful.
Most of us do not go decades of only wearing “boy clothes” to completely presenting en femme in one singular moment. We tend to start with “borrowing” a skirt from a family member or buying a pair of panties.
Annnnnnd more than likely we fall in love. An innumerable amount of emotions reveal themselves to us including happiness, peace, excitement, and potential.
I mean, there are also feelings of fear, specifically the fear of being caught, but let’s focus on the positives here.
An innumerable amount of emotions reveal themselves to us including happiness, peace, excitement, and potential.
When we like something, we tend to want MORE. One piece of chocolate is amazing… AND we want another one. We finally own a pair of panties AND it doesn’t take long for us to explore pairing it with a matching bra.
Annnnnd then? A garter belt? Stockings? And we are OBVIOUSLY going to need heels…
All of a sudden one simple pair of panties has led us to a drawer full of beautiful lingerie. And then possibly a second drawer of beautiful lingerie (or in my case, a second dresser). Before you know it, a dress is hanging in the back of our closet, mixed in with our boring white button up dress shirts.
Of course, we need to be wary of The Pink Fog and not let ourselves run away with all of this and make decisions that haven’t been fully thought through, but again, let’s focus on the positives.
It’s natural to wonder where all of *this* is going. After all, we seem to be constantly and consistently going in a straight line and we have seen a step by step progression. One pair of panties turned into dozens and then each pair had a matching bra and that one dress that was hiding in has multiplied and taken over the entire closet.
Somewhere along the way we have likely accepted (and obviously embraced) this side of us. All of this, despite a myriad of other emotions, feels RIGHT. It’s not unusual for us to wonder if we will, well, keep going.
And where does this journey end? I mean, one can only buy so many clothes, right? I mean, in theory, I know I am nowhere finished with adding to my drawers and closet. It’s not a surprise if we (or our loved ones if we are out to them) begin to speculate if we are going to transition.
It’s possible that with every new pair of panties, or every single new type of clothes, we wondered and possibly agonized over what was inevitably next. What does all of this mean? Does this mean we are meant to transition? Why do we like “girl clothes”? Why does this feel right? Does that feeling of peace mean that we SHOULD transition? Presenting en femme makes us happy, but should we be presenting en femme all the time?
I feel the happiness whenever I am en femme, but I do not feel the unhappiness when I am a boy.
These feelings can cause consternation. We possibly fear transitioning and the potential effects that it could bring. All of a sudden wanting to wear panties has led us to speculating whether or not hormones and therapy and legal decisions are all in our future. What have we done, lol?
Transitioning is probably the biggest decision one can make in their life and it should not be taken lightly. In my opinion, there are two significant emotions that I think I would need to feel in order to know that transitioning was indeed the right path for me. Those emotions are happiness and unhappiness.
The unhappiness would need to come from identifying and presenting as male. When I am in male mode, I do not feel unhappy. I mean, in most cases it would be more fun to wear a dress, but I do not feel depressed or “wrong” when I am wearing boy clothes. Being male does not stress me out and it does not make me feel I am being inauthentic.
The happiness comes from being en femme, using she/her pronouns, buying a new dress, getting a makeover, and allllll the other things I do that align with (one of my) gender identity.
I feel the happiness whenever I am en femme, but I do not feel the unhappiness when I am a boy.
Perhaps that is an oversimplification when it comes to such a major life decision, but that’s how I know that transitioning is not for me.
Crossdressing when I was younger, in a way, saved me from making a decision that I now know would be wrong for me. I don’t think I would have regretted transitioning if I did, but knowing that I didn’t have to in order to wear girl clothes or to present as feminine was enlightening.
Of course, crossdressing confirmed that I did indeed love wearing the clothes I daydreamed about. Although I loved the idea of wearing panties, I wasn’t sure if it was just a daydream or not. Sometimes fulfilling a dream makes one realize that the dream was more fun than the reality.
Transitioning and gender identity is more than just clothes of course, but I feel that wearing what you want is the first step in knowing if it is indeed the right path in your journey.
Love, Hannah
Well-written and spot-on!
Thanks for haring your awesome awesome insights Hannah.
Perfectly addressed and composed from experience!
Hello Hannah,
I really enjoyed this nicely written thoughtful article. It caused me to reflect on my own feelings and motivations on why I crossdress. Ever since I was little I wanted to be a girl. I would blow up balloons and wear them under my shirt to emulate my mom. Of course my parents would let me know this wasn’t proper behavior for a boy so I suppressed these feelings growing up.
At puberty I had gynecomastia. My breasts grew and nipples got very puffy. I was terrified that all my wishes to be a girl were coming true. After a few weeks my male hormones won the battle of the breasts and instead of a sense of relief I felt loss and disappointment.
As a single young man I kept some lingerie and I would sleep in a sexy nighty with my blow up boobies. When I married and raised a family the nighties remained hidden hidden and I would dress as opportunities arose.
After the kids left home we divorced and. Although I’ve stayed in the closet, I was finally free to dress as I pleased when I pleased. I was very lucky to have met a woman that loves the male version of me and enjoys the Vickie side of me too.
I thought of transitioning at an earlier age. But that wasn’t in the cards for me. I still have longings to live as a woman. Crossdressing is a release for me. I’m most comfortable in panties, bralette, men’s shirts, short skirts. Man I feel like a woman!
This has really helped me to sort out my feelings and understand a bit more about myself. Check it out – https://www.avitale.com/
There is so much to say and yet I am reassured that I (we) am not a ‘freak’. I started transitioning very late in my journey, ( now almost 70 years young), and started the HRT. Thank you for the comments and encouragement from all of you. Val
Hi Hanna,
Your story is much like mine. In my late 20’s and early to mid 30’s the pink fog descended hard and fast. I was going out with gurlfriends at least twice a week, the neighbors were very confused, as was my wife. I thought about transitioning, but knew if I did my wife although she loves me very much would have left. Much like you though, I found that I didn’t hate being a boy. I just loved being a girl. Thats been 30 years ago now. I still underdress daily, wear pretty nightgowns to sleep and run around in dresses, skirts and blouses at least a couple of days a week. My wife has become much more understanding of my needs and even occasionally will buy me a little present for Jessica. Well thought out article.