Wednesday, November 8, 2023

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.

Source: Bebe
Wearing Bebe

Unknown Femulator
Unknown Femulator


  1. Our favorite state legislator is moving up in Virginia (and the world)

  2. I ALWAYS wear a bra when I'm out in public as my cup size is DD. And I seldom wear trousers (pants) and wear dresses, even for hiking, shopping, doctor appointments, and to church. Putting on a bra for me is like putting on a pair of shoes. My go to brand is also Vanity Fair, and all my bras are of the underwire type.


  3. I've proudly worn a bra nearly every day for many years.

    At first I was worried that someone might notice and feared that someone could harm me.

    As an abundantly filled body type, I started buying small "a" cup breast forms to wear in my bra. After a while, I'd forget to switch my "c" cup forms before leaving for work and then it just became normal for me to wear the larger forms every day.

    On days when I'd not be going to work, i'd wear my biggest forms to the store and not even care.

    One year ago, it all changed. We were asked to dress nice for our holiday picture at work. A coworker suggested we "dress pretty" for the photo. I did. I haven't dressed in male clothes for work in a year.

    Wear a bra, Brah.


  4. Wearing a bra, panties or pads and tampons is an essential part of feeling feminine, a wonderful ritual for us sissies.

  5. Priscilla CollinsNovember 08, 2023

    Paula, I loved your story of Bra-tober. I'm sure many of us love the feeling of wearing a bra, surely the most feminine garment in our wardrobe. Do you wear breast forms of any sort inside the bras, or do you have enough shape to fill them? I'm impressed at the range of bras you own, and of the knowledge of the use of each. How have you learned this, from online, your wife's advice, or from lingerie shopping? Have you had a bra-fitting session to ensure that you are wearing the right size for you? Do you just buy online, or visit lingerie stores to make your choice?
    My own experience is to have occasionally worn a bra all day either under male clothing or while dressed. I have even slept in a bra. Whiled dressed I use breast forms, but usually while in male clothes it is unpadded unless the clothes are full enough to disguise the chest swellings. I can fully relate to your feelings while wearing a bra; much of the day, I forget I'm wearing it, but fortunately there are occasions when it reminds me that it is there, intensifying the pleasure.
    Now that you have had the month's joys of wearing one, do you plan to continue and find more occasions to wear a bra? You are so fortunate that your wife is tolerant, and it seems that she almost encourages you, possibly sharing the pleasure you are experiencing.
    I hope you don't mind me asking so many questions, but your posting so interested me.

  6. If I'm not being too nosy, Paula, are you one of the lucky ladies who are naturally endowed? Or are you "padding up" for the challenge?


  7. Stana: this is off topic, but your femulater of the year Troye who put out the great “one of your girls” music video a few weeks ago just dropped a behind the scenes video. Thought you might like to see it.

    1. Just watch this, oh my God, best femulation I’ve ever seen

      Paula G

  8. Paula, a wonderful story! Thanks so much for sharing. I will look forward to taking the same goal as soon as I can! I am curious, have you thought about going forward in November ?

  9. I’m a naturally endowed 38C. Hormone imbalance the last 10 years. Doc says I’m 20 lbs overweight went straight to my bottom and breasts. I wear a bra everyday. Sports bras for summer. Underwire in the winter months. I have gotten use to them and are comfortable. My wife is the one that suggested wearing bras after I was having troubles with compression garments.

  10. Yes . Paula Gaikowski , Passes ….

  11. My wife and I sleep in separate bedrooms for medical reasons; bad backs and snoring. It's much more restful not being awoken by tossing and turning and moaning. Anyway, I have taken up wearing a bra and panty set under a nightgown every night. My wife is a late riser so it's a bra from about 1:30 PM to 9:30 AM. Before our daughter moved back to our small city from the mid-west my wife would visit her for seven to ten days. As a retiree I was able to express myself and wear female clothing (dresses only) which included a bra 24/7. I do not own commercial forms so it's home made pseudo breasts. I sleep in an old Nerf ball which has been cut in half. The advantage for that type of form is it mashes down my rolling around. When awake I used water filled balloons which do give the proper weight to the pseudo breasts and a nice fluid bounce. They also give a proper tug on the bra straps. I will say the feeling of wearing a bra does not disappear, but it is not bothersome. However, I can understand why my wife sheds her bra when the temperature rises.

  12. Hi Paula, thank you for sharing such a wonderful article with us! I adore those days that I get to wear a bra long enough that I can experience the pleasure at the end of the day of finally taking this thing off haha. I find that it is in these moments that I am one small (high-heeled) step closer to understanding the daily life of women.

  13. I started wearing bra , almost everyday ,during COVID times and have been continue wearing since. I wear a bra even at work now, whenever I go in the office. I work in the Server room mostly if I go to office so hardly anyone comes in contact.Now it has become a routine and it feels strange if I dont wear a bra and feels like I have been ogeled on my chest. I know exactly how women feels now.