✨ 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. I...