My Crossdressing story

Hello to the CDH community,

I am 64 years old and decided to write about how and why I am a Crossdresser.

It's a long post, hope others will find it of interest and I would welcome any comments:

A Journey into Crossdressing: Self-Discovery, Comfort, and the Struggle for Acceptance

For many, self-discovery happens gradually, shaped by experiences that leave a lasting imprint. My journey into crossdressing began unexpectedly, rooted in an early encounter with women’s clothing that, over time, evolved into something much deeper—an essential part of my life. Though I am a heterosexual male, crossdressing brings me a unique sense of calm, confidence, and erotic excitement.

Adding to this complexity is the fact that my urge to crossdress has increased dramatically with age, for reasons I don’t fully understand. What was once an occasional indulgence has grown into a deep, persistent need—something I can no longer ignore or suppress. At the same time, I have realized that crossdressing has become one of my most powerful sources of relaxation and anxiety relief, especially when I can fully immerse myself in the experience—complete with makeup, shoes, jewelry, and a carefully coordinated outfit.

The Joy of Dressing and Outfit Coordination

Crossdressing is more than just wearing women’s clothing—it is an art, a form of creativity that brings me immense joy. One of the aspects I enjoy most is putting together outfits based on color, creating a coordinated and elegant look that makes me feel complete.

There is something incredibly satisfying about selecting a red dress and pairing it with matching red panties, bra, slip, and heels. The harmony of colors, the way everything feels perfectly put together, adds to the immersive experience of dressing. Whether it’s a classic black ensemble, a soft pastel combination, or a bold and striking monochrome look, the process of choosing and wearing a fully coordinated outfit enhances the pleasure and satisfaction of crossdressing.

When I take the time to dress fully—with makeup, accessories, and perfectly matched lingerie—the transformation allows me to step away from daily stresses and into a world where I can feel elegant, beautiful, and at peace.

The Thrill of Completing the Transformation

One of the most exhilarating moments in my crossdressing routine is standing in front of the mirror and completing the transformation by stepping into high heels, adding jewelry, and applying lipstick. These final touches are not just about appearance; they are deeply validating and satisfying, marking the culmination of my metamorphosis.

Stepping into high heels instantly changes my posture and the way I carry myself, adding a sense of elegance and confidence. Adding jewelry—such as earrings, necklaces, and bracelets—brings a touch of sparkle and sophistication, enhancing the overall look. Finally, applying lipstick adds color and definition to my lips, making them appear fuller and more luscious. These finishing touches are more than mere accessories; they provide a profound sense of completion.

Challenges and Triumphs in Shopping for Women’s Clothing

Exploring women’s clothing and lingerie departments has always been a thrilling experience for me. The array of fabrics, styles, and colors offers endless possibilities. However, purchasing items that fit correctly has often been a source of embarrassment and difficulty. Concerns about judgment from others and the challenge of finding sizes that accommodate a male physique have made in-person shopping a daunting task.

The advent of online shopping has profoundly enhanced my ability to buy women’s clothes. It offers privacy, allowing me to browse and select items without fear of judgment. Additionally, many retailers now provide detailed sizing guides and cater to a diverse clientele, making it easier to find clothing that fits well and suits my style. This shift has made the process of acquiring women’s clothing more accessible and enjoyable.

Fluctuating Urges: The Impact of Environment on Crossdressing

One interesting aspect of my crossdressing journey is how the urge fluctuates depending on my environment. When I am at home, the desire to dress is nearly constant, and I find myself continually thinking about what outfit I want to wear next. However, when I am away on vacation, the urge significantly decreases. Perhaps it is the change in routine, the distraction of new surroundings, or simply the absence of my wardrobe that makes crossdressing feel less pressing. While I always return home eager to dress again, I find it fascinating that my need isn’t as strong when I’m physically removed from my familiar environment.

Early Family Dynamics

Looking back, I realize that my early family relationships may have played a role in shaping my crossdressing journey. I had a difficult relationship with my father and brother, which often left me feeling disconnected and distant from them. In contrast, I felt a strong desire to be closer with my mother and sister. Their warmth, understanding, and presence provided a sense of comfort that I didn’t experience with the male figures in my life.

As a child, I desperately wanted my mother to buy dresses for me—beautiful, flowing garments that I could wear and feel a part of their world. I never voiced this desire, but it was always there, a quiet longing that stayed with me. Perhaps, in some way, crossdressing became my way of fulfilling that childhood wish.

During my teenage years, I grew my hair long—partly to embrace the counterculture of the hippie movement, but also because I loved how it made me appear different. It was one of the first ways I could subtly express my desire without drawing too much attention.

The Fascination with Women’s Clothing and Materials

One aspect of my crossdressing experience that often surprises me is my near-encyclopedic knowledge of panties, pantyhose, and half slip styles, brands, and materials. Some of my favorite panty brands are Olga, Wacoal, Jaclyn Smith, and Vanity Fair. I tend to prefer briefs with pretty lace for full coverage and always choose the softest possible nylon.

I also always wear a slip, either half or full, even though slips have mostly gone out of style. I prefer slips between 18 inches and 24 inches in length, and they must always feature pretty lace and often have a slit on the side or back. Some of my favorite slip brands are Christian Dior, Farr West, and Vanity Fair.

I have always had a love of wearing pantyhose, and they are an essential part of my crossdressing experience. I enjoy matching the shade to my outfit, often choosing tan, nude, blue, or black. While I once wore inexpensive brands like L’eggs, I now prefer high-end options like Wolford and Hanes. Tight control-top pantyhose with shapewear help me achieve a smooth, flat appearance.

Wearing high heels has always presented several challenges. Obviously, they are an essential part of the transformation process, but finding the right size and fit is a major challenge. Men’s feet and women’s feet are definitely different! While I would love to wear truly high heels, I have come to accept that comfort is just as important as style. These days, I am happy with comfortable flats, which still allow me to feel put together without the discomfort of an ill-fitting shoe. When I wear and walk in them, it just feels right.

Conclusion

My journey into crossdressing was sparked by a childhood moment but has since evolved into something much greater. It is both an erotic thrill and a source of deep emotional comfort. Though I am a heterosexual male, dressing as a woman allows me to connect with a part of myself that would otherwise remain hidden.

As I said above, I am a married heterosexual man. I don’t believe that I am “trans,” although in some ways, I feel as though I have a greater understanding of their struggles. However, I have never had any desire to change any aspect of my male body. In fact, part of the thrill of crossdressing is knowing that I am still a man, even when I am fully dressed in women’s clothes.

Yet, despite my personal acceptance of this, sharing it with my wife has been one of the most challenging aspects of my journey. The anxiety, guilt, and secrecy that still linger make it difficult to fully embrace this in the way I truly desire. However, I love my wife, and I know that she accepts me for who I am. She is respectful and tolerant of my crossdressing, and that is of great comfort and support.

For now, I find peace in my home—fully dressed with makeup, shoes, and jewelry—where I can truly relax, reduce my anxiety, and enjoy the creative pleasure of putting together the perfect outfit, down to the very last detail