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Showing posts from October, 2025

Crossdressing at Work: My First Day Wearing a Bra

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Today was the day I finally wore a bra to work for the first time as a crossdresser since coming out to my partner. Not long ago,  we went shopping together and bought some women’s cotton briefs and matching bras. Right now, as I write this at 3:15 a.m., I’m on the couch in an oversized pink T-shirt, slouched over my shoulder, wearing a pair of peach and white striped cotton briefs. They feel so good against my skin.  I had worried women’s underwear might not fit me properly, but it turns out I had nothing to fear they fit beautifully. I can’t believe I didn’t try this sooner. Crossdresser dressing for work This morning, I opened my drawer and chose my underwear for the day  peach and white cotton briefs with a peach lacy 34C bra.  My partner and I are nearly the same size, so we bought bras we could both share.  I slipped into my briefs, clasped the bra behind my back, and admired myself in the mirror.  I felt more feminine in the way I stood. While my ...