Being Bra Challenged
Whether you agree I am a woman or not

Ok whether you agree I am a woman or not as a trans woman, after over two years on HRT, I have breasts. In fact, according to all available bra sources on the internet, I am 40D. After countlessly measuring my chest, technically I am 44 ½ inches on the top and 40 inches underneath. Trust me, I know how to measure. I did it lying down, standing up and bent over to be sure. Those are the numbers.
My breasts are very important to me. It is the only observable indication that I am physically transitioning. I find myself juvenilely proud of their size and not in a creepy guy way! They give me a sense of validation and they constantly prove to me I am certainly not cisgender. Going for a consultation for my gender altering surgery certainly was absolute proof that I am transgender.
I can no longer deny it, even to myself.
OK back to bras. I was raised wearing male clothes. There is a certain logic to them, even a jock strap is relatively easy to put on but bras absolutely defy any clothing logic I understand. Fortunately, I don’t need a bra right away. I have to stay stealth male for a year for professional and personal reasons. Bra straps would be a sure give away that I was a creepy fetishist or at the very least, a cross-dresser. Both totally off the mark for me. Being transgender would not be anyone’s first guess.
I currently have three bras, a sports bra, a multi-strap nylon bra and a padded bra. I also purchased, in a panic when my breast became noticeable last summer, a breast compression shirt. Strangely it wasn’t necessary because no one, male or female, looked at my chest. Simply wearing a t-shirt was ample camouflage.
After all, who looks at a guy’s chest?
My problem is all the straps and hooks and the cups don’t seem to fit and all them seem to have a life on their own. The internet also recommends trying them on in a store…yeah right… picture me in the Victoria’s Secret dressing room strangling myself with straps. I would definitely set a new speed record for a police response.
There isn’t even a consensus rule of thumb on how to select a bra on the internet. I really need a big sister to take me shopping. Having a male body and being 6 foot tall just makes the mission even more impossible.
And who prices these things? It’s a bargain to get two bras for $80? How does that compute? I can get six jock straps and cups for that much. Even if I double up the jocks to account for one for each breast I am still ahead and that includes the jock cup as body armor for each breast if I decide to play any contact sports.
OK, OK I know I am exaggerating but the mechanics of any bra other than the sports bra still defy me. I then go on to the purpose of the bra. That is a whole new arena of controversy.
Do you really need one?
I now go braless. I do notice that they bounce and occasionally hurt when I get up from lying down but beyond that I don’t feel unsupported. I agree that my breasts are really only two years old and that the effect of aging and gravity could be years off, so other than gender validation for myself and the outside observer, what is the point?
I truly accept that I can’t wait to wear one. I have been told by women and other trans women that I will feel tired of wearing one soon enough and that it will become another part the daily drudgery of getting dressed as a woman…but I can’t wait to feel that drudgery. It means that I have achieved the status of a normal woman and not just some over excited crossdresser.
And I can’t wait to just be a normal woman or if you prefer, a trans woman. Not a wannabe. I love the lace straps. I love the t-back sports bras. I want to see my cleavage on a low button blouse. I am not looking to dress like a slut, I just want to look like I have a natural style…with maybe a bit of little class.
I have lived a life of tidy-whitey cotton briefs and cotton t-shirts. I am so desperate to wear underwear that has style and not just function.
Give me a little lace please.
Forgive me if I overdo it but I am finally getting permission to shop in the right side of the store.
I have been stuck in the Men’s Department way too long!
Emma Holiday
Thank you for reading my work.
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Writers note: If you have read any of my writings on Medium you will have noticed a definite theme: the incredible pain of gender dysphoria and all the difficult aspects of just being transgender.
My writing has three specific goals:
1. Writing is my therapy. I have a very limited outlet for my thoughts so I write to find a way to process the most profound experience in my life. I need to understand and I need to accept myself to move forward.
2. Being transgender, for me, is a very lonely existence and if I can share some of the things that I feel and think as I go through the process of transitioning with others who are transgender and, in some way, lessen their pain and sense of loneliness, then all of this public exposure of my personal thoughts is not a waste.
3. I write to help cisgender people understand that all trans people want is to be simply understood, accepted and treated as a normal person. We are.





