I Found A Deeper Well

I absolutely love Kacey Musgraves and one of my favorite songs of hers is "Deeper Well".

I feel like as we get older we either go deeper or we stay shallow in terms of our approach to life and emotions. I found a deeper well in crossdressing and that's what I wanted to write about today.

Finding a deeper emotional well through expressing my feminine side as a crossdresser has

added so much to my life...I feel like I was walking around life with a box of 8 crayons and someone handed me a box of 32. My Maddie persona has allowed me to color my world with so many more experiences I never would have had the opportunity to enjoy. In this season of my life, I have the freedom to do what previously didn't even come to mind as I was busy living my "life". Don't get me wrong, I loved those seasons of my life. I brought 2 kids into this world and raised them which I consider to be my most important accomplishment. I have loved and have been loved and have no regrets. So this brings me to my present season of life where I have the time and ability to express my feminine side and I'm so grateful!

More Than Hair-Makeup-Clothes

For many crossdressers, exploring the feminine side is more than just about clothes and makeup—it's an emotional journey, a path toward deeper self-understanding. Crossdressing, for some, opens a gateway to emotions that might otherwise feel restricted or unattainable in the constraints of daily life. If you're like me, tapping into that feminine energy can be profoundly freeing, offering access to a deeper well of feelings that nurture a sense of authenticity, confidence, and emotional depth.

Embracing Vulnerability

Crossdressing often invites a natural exploration of vulnerability. Unfortunately many men are conditioned to suppress or avoid emotions like sadness, tenderness, or empathy—feelings stereotypically associated with femininity. When I allow myself to embrace my feminine side, I give myself permission to be vulnerable. The soft fabric of female clothes, the elegance of heels, or the delicate application of makeup is not just about physical transformation. It's about allowing my emotional walls to come down, letting tenderness and compassion rise to the surface. Vulnerability isn’t a weakness but a source of strength that allows me to connect more deeply with myself and others.

Expanding Emotional Expression

One of the most powerful aspects of crossdressing is how it encourages emotional expression. When I step into my feminine persona, I notice how my emotional range expands. In many ways, I feel less restrained, more comfortable expressing joy, sadness, affection, or even playfulness. It’s as though the act of crossdressing gives me permission to break free from societal expectations and connect with feelings that may otherwise be sidelined. Crossdressing can be a form of self-care, a way of nurturing emotions that aren’t always given space to thrive in a typically masculine role. In my feminine self, I often feel more open to expressing vulnerability and love—two emotions that can be both intimidating and deeply rewarding.

Authenticity and Balance

Crossdressing allows me to embrace both my masculine and feminine sides, helping me strike a balance between the two which is key because I do not have gender dysphoria and have no intentions of transitioning and love my male persona. My feminine aspect is not a mask but a part of my true self, one that enriches my emotional landscape. In this space, I feel more whole, more integrated, and ultimately more at peace with who I am.

In tapping into my feminine side, I’ve found a deeper well of emotions that has helped me grow emotionally, offering new perspectives on strength, vulnerability, and self-expression. It’s a journey of discovery that keeps expanding, offering a richer emotional life than I ever imagined.

Maddie