✨ First Time Wearing a Bra to Work: A Boss Girl Story (2026) 👑💼✨

Crossdressing story

By Aveline Marlowe
Updated on 10/02/25 at 03:30 AM

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 empowering and nerve-wracking. As a “Boss Girl,” the key is choosing a comfortable fit, a professional style that boosts 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 even 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.

And right now, at 3:15 a.m., I’m sitting on the couch in an oversized pink T-shirt that keeps slipping off one shoulder. It feels incredible against my skin.

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. Right.

Will I Do This Again?

Absolutely. As long as my clothes keep everything underneath hidden, I want to keep enjoying these wonderful moments.

I’d love to know what you think — feel free to leave a comment below!