❤️ I finally did it — I wore a bra to work for the very first time. ❤️
Wearing a bra to work for the first time can feel both amazing and nerve-wracking. As a “Boss Girl,” the key is choosing a comfortable fitting bra, a style that boosts your confidence, and gradually getting used to the new sensation throughout your day.
Ever since coming out to my partner recently, I’ve been exploring this side of myself more openly. We went shopping together and picked out some women’s cotton briefs and a bra that fits me well and felt right for me.
I’d always worried that women’s underwear wouldn’t fit me, but I had nothing to fear. Everything fit beautifully. I can’t believe I waited this long to try it.
❤️ Getting Dressed for Work as a Crossdresser
This morning, I opened my drawer and chose my underwear for the day. My partner and I are almost the same size, so we pick clothes we could both enjoy.
I slipped into my clothes, clasped the bra behind my back, and caught a glimpse of myself in the mirror. Something about the way I stood… I felt more feminine, more me.
❤️ Crossdressing at Work
Walking into work, my pulse quickened. All day at my desk, I drifted between forgetting I was wearing a bra and savouring its comfort. It felt grounding. Calming and Right.
“If you’re trying a bra at work for the first time, start with a soft, wire-free style. Make sure the straps aren’t too tight and pick a top that keeps everything hidden perhaps a hoody or a baggy jumper. Small adjustments throughout the day can make a big difference.”
❤️ Will I Do This Again?
Absolutely. As long as my clothes keep everything underneath hidden, I want to keep enjoying these wonderful moments.
Crossdressing at work isn’t just about the clothes you wear it’s about relationships.
Unlike a brief outing where no one sees you for long, work is Every day.
You interact with the same colleague’s and customers, and your role there is crucial: it’s how you earn a living and support yourself.
This means that crossdressing at work comes down to trust. Do you trust your colleagues to respect your privacy and your choices?
Are you comfortable with the idea that your female identity might mix with your work life?
For me, it was a balance between wanting to express myself authentically and feeling secure in my workplace relationships.
The experience isn’t just physical;
it’s emotional. Feeling safe, respected, and confident makes the difference between a stressful day and a fantastic one.
If you found this post by accident and want to read more, you can read my blog here.
I’d love to know what you think — feel free to leave a comment below!