I will never forget the day I bought my first bra. For a transgender woman, it was more than just a shopping trip – it was a rite of passage, a moment of validation. My breasts had just started to bud and the itchiness and tenderness were undeniable.
At the time, I was still living a dual life: a man at work and a woman after hours. I was already on hormones, but the growth was painfully slow despite my high expectations. Both my mother and sister are beautifully endowed and there is a theory among trans girls that a transgender daughter is typically a bra cup size smaller than her mother. I would have been more than happy with that, but my body didn’t seem to know it yet.
On the other hand, the slow growth had one advantage: I could still keep my job while presenting as a man. I desperately needed the money and coming out was simply not an option as my employer did not support the LGBT+ community. Because of that, wearing a bra never even crossed my mind. Besides, I still felt completely flat, as if there was nothing to support anyway, which, in reality, wasn’t true.
But one day, my sister – always perceptive and supportive – took one look at me and declared, “Monika, we need to get you a proper bra!” Of course, this wasn’t my first experience with bras. Before that day, I had secretly borrowed from my mother’s and sister’s drawers, slipping them on in front of the mirror and dreaming of the day they would fit. But those stolen moments always ended in disappointment with the cups sagging against my flat chest, the straps slipping off my shoulders. This time was different. This was real. This was my own bra, one I would wear regularly, one that would truly belong to me.
My sister, ever extravagant in her taste, insisted that we go to a posh boutique, one that carried luxurious lingerie from a famous brand whose name started with a T. The moment we stepped inside, I was overwhelmed. Racks upon racks of delicate lace, satin and silk surrounded me, each piece more intricate and feminine than the last. It felt like a secret world, one I had longed to be a part of, but never dared to enter.
The shop assistant noticed us immediately. Her sharp gaze flickered over me, assessing, scrutinizing. I could almost feel her eyes dissecting my barely-there buds beneath my top. My heart pounded. I was sure she had clocked me instantly. If my sister hadn't been there, I would have bolted out of the store without looking back. But she must have sensed my fear because she took my hand and squeezed it reassuringly.
“Is this for you?” the shop assistant asked my sister, her tone polite but inquisitive.
“For her, for my sister,” my sister answered without hesitation. “And we need something special. It’s her first bra.”
My stomach plummeted. She had given me away! I wanted to protest, to deny it, to run, but there was no time. The shop assistant had already shifted into professional mode. Though I could see the flicker of realization in her eyes – my being trans now confirmed – she remained composed, asking about my band and cup size as if this were just another ordinary fitting.
I was still frozen, unable to find my voice, so my sister took charge, answering on my behalf. She had always been my protector and now she was guiding me through this daunting yet beautiful moment.
The shop assistant nodded and led us toward a section filled with soft, lightly padded bras. “For a first bra, comfort is key,” she said. “Something gentle yet supportive.” As she spoke, she guided us through the options, explaining the different types.
“When it comes to construction, bras can be padded, non-padded, wired or non-wired,” she continued. “Coverage-wise, there are demi-cup bras and those that offer full coverage. And in terms of neckline shapes, we have sweetheart, plunge or balconette styles.”
She spoke with such ease, as if this were the most natural thing in the world. I felt overwhelmed trying to absorb the details while standing there feeling completely out of place. But she wasn’t done yet.
“Once you know your size, experiment with different styles – demi, push-up, contour – to find what suits your shape. Size matters, but shape matters more, so focus on what feels comfortable and supportive rather than squeezing into a specific trend. When trying on bras, use your hands to adjust your breasts into the cups. The edges should lay flat and your bust should sit midway between your shoulders and elbows. If the cups gape, the bra is too big; if they create a “double bubble” effect, you need a larger cup size.”
I nodded, as if I understood completely, but my mind was spinning.
“Straps shouldn’t be doing all the work; 90% of the support should come from the band. It should fit snugly, but not dig in. Always start on the loosest hook, since elastic stretches over time, allowing you to tighten as needed.”
It was a lot of information to take in all at once and I was still trying to process it when my sister, decisive as ever, plucked a delicate, lace-trimmed bra in a soft blush pink from the rack. She held it up with a grin.
“This one,” she said. “It’s perfect for you.”
As I held the bra in my hands, I felt a strange mix of emotions, excitement, nervousness and an undeniable sense of euphoria. This was happening. This was real. For the first time I wasn’t pretending. I wasn’t “borrowing” someone else’s femininity. I was embracing my own.
Trying on that first bra was a moment I will cherish forever. It wasn’t just about fabric and fit. It was about stepping into my identity with confidence. And as I walked out of the boutique with my first-ever bra in a beautifully wrapped bag, I felt one step closer to the woman I was always meant to be.
Monika has been interviewing trans people in her blog, The Heroines of My Life, for over 12 years. Click here to see who she has interviewed lately.
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| Wearing Ann Klein |
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| Volker Spengler femulating in the West German film In a Year of 13 Moons. |
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