My Bra-tober Challenge

By Paula Gaikowski

As a Femulator, I have always celebrated the special occasions when I could embrace my feminine side. It was a chance to be myself for a few hours, reveling in the experience. However, I often wondered what it would be like to wear a bra every day, as a part of my daily routine rather than just on special occasions. 

This October, I embarked on my Bra-tober Challenge to find out. The aim was to experience, on a daily basis, what it’s like to wear a bra, something that had always been a special occasion occurrence for me. The experiment was not only a chance to explore this aspect of femininity, but also to gain insights into its role in shaping my identity.

In the midst of my Bra-tober Challenge, I continued to navigate my daily life. My wife, who typically had reservations about my feminine expression, initially doubted my commitment. She believed that I wouldn’t enjoy wearing a bra every day. However, as I discreetly went about my daily routine, her skepticism waned and she became less enthused. There were days when she knew about my experiment, but for the most part, it went unspoken.

One day, in the kitchen, she noticed that I was wearing my favorite Vanity Fair bra. She playfully took hold of the backstrap and gave it a good snap. We both shared a good laugh about that, a moment of light-heartedness amidst the challenge.

Typically, I wore my male clothing most of the time. However, there were occasions when I incorporated some elements of my feminine expression into my daily wardrobe. While working in my home office, I would opt for leggings and a knit top or occasionally don ladies’ jeans and a knit top. These choices allowed me to balance my authentic self with the expectations of my daily life.

I am an avid hiker and here in the picturesque landscapes of Maine, I make it a point to hit the trails at least once a week. It’s a pursuit that brings immense joy and serenity. The trails are often graced by the presence of fellow hikers, many of them women, who don traditional hiking outfits. This ensemble typically consists of comfortable leggings, sturdy hiking boots and a cozy sweater or perhaps, the iconic L.L. Bean vest or jacket. It’s a timeless combination, ideal for braving the ever-changing weather of Maine.

What I’ve found intriguing is the ease with which I’ve embraced this attire, not only during my Bra-tober Challenge but also on numerous occasions beyond it. These hiking trails offer a haven of acceptance, where no one raises an eyebrow or gives a second glance to my choice of clothing.

Living and working as a man and putting on a bra every day was a profound change. It became an integral part of my morning routine as I selected the type of bra to coordinate with my outfit. Fastening hooks, adjusting straps and pulling on the bra, once reserved for special occasions, now became a part of who I was on a daily basis. The various styles of bras I wore throughout the month presented unique challenges and feelings.

The Rago firm control longline bra stood out as a favorite in this challenge. This specialized undergarment provided not only support, but also a sense of firm control, sculpting and enhancing my silhouette. Wearing it in the morning gave me a sense of empowerment and confidence and taking it off in the evening was a moment of relaxation and unwinding. I was filled with joy all the while wearing this bra, relishing the confidence it brought me.

Sports bras were a category that made me very aware of their presence. They offered robust support of my breasts while working and doing physical activities, which I greatly appreciated. However, they were also hot, uncomfortable and would chaff and poke me during physical labor. Despite the discomfort, the thought of taking them off seemed somehow disloyal. They remained among my favorites.

T-shirt bras were easy to put on, but not necessarily my favorites. Despite being comfortable, they never seemed to fit right, often requiring constant readjustments. While they offered ease of wear, the fit left something to be desired. I wasn’t as that happy with these bras, as they often caused inconvenience due to their fit.

Underwire bras offered a different experience. The underwires provided enhanced support and shape, maintaining a well-defined silhouette. These bras often felt the most feminine and cute and I couldn’t resist pairing them with pretty lingerie. The poking underwire became less bothersome when paired with matching undergarments. 

Throughout the month, I was consistently aware of having a bra on. It tugged at me during different times of the day, serving as a reminder that this was a unique garment typically reserved for women. This heightened awareness brought joy and fulfillment. 

There was one memorable instance that epitomized this awareness: I was in a supermarket, dressed in jeans, a sweatshirt, sneakers and of course, my bra. A glance around the store revealed that all the women present were dressed similarly. It was a moment of revelation. I realized how deeply connected I felt with them, as if I had been granted membership into a shared experience of femininity.

Wearing different types of bras brought a range of sensations. Some days, the bra would pinch or poke, leading to discomfort. On other days, those same sensations brought a sense of comfort, as if they were a ticket to a shared experience. It served as a reminder that embracing femininity comes with its own set of challenges and occasional discomfort as part of the journey. I felt privileged to experience the joy of feeling both the comfort and discomfort that comes with wearing a bra.

After a month of wearing a bra every day, it became an integral part of my daily routine. There were mornings when I eagerly put it on, finding empowerment and confidence in the process. There were also evenings when I found relief in taking it off, a moment of unwinding and relaxation. This Bra-tober Challenge had not only been an exploration of femininity, but also a very small part of understanding of what women go through daily.

Wearing Bebe

Unknown Femulator