Trans and Bra Challenged: Part Two
So amazingly clueless!!

I wrote a piece about my first foray into the bizarre world of bras. The article can be found here:
Bras for the uninitiated and in this case a late in life MTF transitioner like me, is like the Gordian Knot of women’s apparel. Trained male and supported by surging testosterone as a teenage guy I took great pride in the classic two-finger bra clip release technique as a triumph of my Neanderthal-inspired manhood.
Yeah, really embarrassing to share that now.
The sad reality even back then was that I was actually jealous of the girls I was dating, that they had breasts and always wore a cute bra. Not the best for an aspiring male libido. For a guy who was unwittingly ignorant of her true female gender, I was always uncomfortable dating. I just never knew why. Hard to admit I actually faked orgasms occasionally, but I did it to not embarrass the girl I was with. Condoms protected my secret. Wow so many clues and so much ignorance. It is embarrassing to admit that it took 60 years, a near suicide attempt and therapy to finally figure me out….
So amazingly clueless!!
OK, back to bras. It took a lot of do-it- yourself failures inspired by many YouTube and internet bra “help” sites to finally convince myself that I needed professional guidance. So, I started my search for the bra fitting professional that could work with a male body with 40D breasts.
It is a very unique specialty.
Starting once again on line with my new line of inquiry, I was informed that Victoria Secrets offered a bra fitting service. As anyone who has ever cruised by or actually entered their store, as a middle-aged male, I fit into the “creepy guy” category. Their style didn’t seem to fit my sense of age appropriateness, so why would I be skulking about the store looking incredibly shy and embarrassed?
I quickly struck them off the list. Strike one.
I next tried Journelle, a small lingerie boutique that had a shop I happened to walk pass one day. As I worked up the courage, I walked past it three more times. With a deep breath and long sigh, I walked in. I was the only customer and I was quickly approached by a saleswoman. I looked her in the eye and said: “Do you offer bra fitting for transgender women?”. She smiled sweetly and said: “Why of course we do.” I was ushered into a private dressing room. She asked me to take off my shirt…she was the first person to see my breasts. I blushed as she went about her professional measurements. With that she said: “I’ll be right back.” It gave me enough time to scream in my head “WTF was I doing?” for the 1000th time.
When she came back, she had three bras. One was lacier than the other. I tried one on for size. She realized that the she needed to look for bras of a different size. She left me alone again. The practical person that I was, I looked at the price tag. I was astonished. It was $169.00!!!
I may be inexperienced by that seemed a far cry from the 2 for $20 bras I bought at TJ Maxx. Also, given all the revealing lace, who was I dating at my age to need that kind of expense exposure. Quickly putting my shirt on and gathering my things, I thanked the saleswoman for her time and lamely told I had a business call I had to make.
Strike Two.
I took a few weeks off from my search. I finally asked one of the women who knew that I was transgender for advice…OK OK I know…about time right? Her advice was simple, go to Nordstrom. They have bra fitters on staff and they are known to be trans friendly. She also said that I may spend up to $80 for a bra to get the right one and one that I will wear forever because it fits perfectly.
I took her advice and went yesterday.
She was absolutely right. I am not trying to support Nordstrom but the saleswoman knew her stuff. When I admitted that I need to get fitted for a bra because I was coming out next year, her response was simply and enthusiastically: “How exciting!!!” I loved her immediately.
Bras fit the male frame differently regardless of breast size she explained. We just have a bigger rib cage. In the dressing room this time I tried on three bras. At that time I learned about the elasticity of a breast. You can move them around and reposition then inside the bra. So naïve! She found the perfect one for $69 but she wasn’t happy with the fit so she ordered a one with the right size that I will pick up next week, COVID permitting.
No more strike outs, a better knowledge of breast dynamics as well as bra architecture from a professional.
What a wonderful way to bring in the New Year!
Emma Holiday
Thank you for reading my work.
Please also read:
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.






