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Man in a Bra

How a masculine man wears Women’s Clothes

By Justin MikkelsenPublished 3 years ago 6 min read
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Photo by Fahad Waseem on Unsplash

You might think I’ve jumped ship on being a man. Well, that was my wife’s immediate concern when I told her that I wanted to start wearing women’s underwear. After all, she wants to be married to a man, and not a woman, so if the transgendered conversation was getting started she wanted to know about it.

Let’s be real for a second. I am totally supportive of the LGBTQ community. I’m just not one of them.

What I am is a man that has discovered a liking for women’s clothes, including underwear, and not your average run-of-the-mill plain colored briefs. I like the pink, frilly, lacy fabrics that look cute when I take them out of my drawer in the morning. They are soft, they feel good, and the crazy part about it is I’m not alone. Don’t believe me? Do a search on the internet for men in women’s underwear. Panties are a thing for guys, and the number of men that enjoy them are not small in number.

Photo by Juli Kosolapova on Unsplash

After panties came into my life, and a glorious moment it was when they did, I started to wonder about other things, like skirts, dresses, blouses, and even nightgowns. I’ll confess. I am not a small person, and I’ve actually struggled with being overweight and obese for most of my life. In other words, shopping for women's clothes is not easy.

When I started looking, I mentioned to my wife that finding my size is tricky. She chuckled, and welcomed me to the wonderful world of women’s clothes. As it turns out, shopping in the women’s clothing world is not particularly simple, especially as a man. Sizes among brands differ. Petite vs. Ladies vs. Womens, all representing vastly different things. I can’t simply look for a 3XL, I have to find it in the right flavor of women’s clothes, and even then it depends on any number of other factors.

The most obvious difference between shopping for men and women is variety. An age-old cliche among men, that women take forever to go shopping, turns out not to be a cliche at all. It is a stone-cold fact of life that is completely and totally justified. Ever since my eyes opened to women’s attire, I spend most of my free moments browsing Amazon, Lane Bryant, and department stores for cute outfits, wondering what they would look like on me and how they might feel. Cute skirts, revolting shirts, and every manner of lingerie under the sun are no longer passing curiosities, they are active questions about what might fit in the growing wardrobe inside my boudoir. Want to know the funny part about all of this? It’s a crazy amount of fun!

Some of the fun comes with nerves. With my large size, man boobs have been a struggle of mine for most of my life. When I was in high school, the thought, at some point or another, came to mind that I should try a bra to give myself some support. Soreness in my upper back, maintaining good posture, and just feeling uncomfortable with the size of my man boobs all pointed to a bra. I could never bring myself to do it, though. What would that say about me? Would it mean that I was gay, or a girl in boys skin? Would it mean that my whole identity was going to shift? How would it make me feel. All of these questions were big fears that I refused to overcome, and as a result I have maintained my level of discomfort and lack of confidence in myself for many years.

That all changed when I bought my first bra.

By Artem Beliaikin on Unsplash

Well, to be honest, we bought four bras, and it was not a comfortable search. First, we went to a Hanes store in a local outlet mall. Having taken my measurements, we had a pretty good idea of what I should be, and based on the measurements it was going to be a difficult task to find. We found two suitable bras, or so we thought.

The task of walking around a store filled with bras, or looking on the aisle dedicated to them in the department store, was a nerve wracking experience for me. Growing up, I used to go shopping with my mom frequently. She would go clothes shopping, I would look at video games, books, toys, or something not feminine. It made me uncomfortable, as I’m sure it makes most young boys feel odd shopping in the women’s intimates aisle. I’ll give my wife enormous amounts of gratitude in this new adventure, she was right there with me, walking me through the store and helping me make my search. What in the world would I do without her?

After buying them and bringing them home, because trying them on anywhere but home would be a hard ‘no’ at the moment, I learned that a woman's bust size differs from a man in one critical area. You see, where a woman carries her breast tissue is mostly in the front, where man boobs are more of a collection of fat. As a result, man boobs don’t shape the same as a woman, they hang with some fat in front, and distribute more fat around the sides and onto the back. Between the increased girth of a man in comparison to most female measurements, the cup size measured way bigger than it actually is.

In other words, the 50D cup size I measured didn’t fit.

Fortunately, a trip to the local Wal-Mart revealed a wide collection of sports bras that would be worthy of trying, and they are serving as a good interim until my normal bras come in from Cacique. I’m super glad I’m ending up getting them from a more specialized store. The colors I found in the local stores on-ground were pretty limited to white or a nude color. My new bras coming in have pretty flowers and nice colors to them. Score!

Want to know the best part?

I feel freaking amazing. My clothes fit differently. The shoulders of my shirts don’t feel as tight any more, and my overall stature feels more balanced. I feel more confident in myself, my posture impacting my sense of well being and awesomeness. In other words, wearing a bra is transforming my life and my attitude in ways I didn’t possibly think it could.

So, are you weirded out yet? If you are, good. If you aren’t, good. Both ways, I’m really happy that you are here to share my story. I’ll have more stories to share soon, including my experience putting on a skirt for the first time and wearing it to a public location. I’m still at the beginning of my journey into having a wardrobe filled with new and exciting things. It’s exhilarating. I will say this for sure, it’s a moment of self discovery and transformation in my life, something I never expected, but it’s here and I couldn’t be happier. See you in the next article!

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