Crossdressing at Work: My First Day Wearing a Bra

Peach top

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 partner slept in the other room, I posed a little, enjoying the soft fabric and how my painted toenails looked against the carpet. 

Then I put on my work clothes trousers, socks, T-shirt, and jumper checking carefully if the bra straps or silhouette showed through. I added a little peach lip gloss before heading out the door.

Crossdressing at work

When I arrived at work, my pulse quickened. I vaped outside, tasting strawberry as I gathered my courage. Inside, 

I slipped into the bathroom to check again in the mirror, making sure the underwire and straps were invisible under my clothes.

All day at my desk, I alternated between forgetting I was wearing it and savoring its firm, comforting embrace. 

After working late and finding myself alone in the office, I reapplied my lip gloss before walking home, the sweet, slick feeling on my lips carrying me in bliss.

Will I Do This Again?

Absolutely. As long as my clothes conceal what’s underneath, I’ll keep enjoying this wonderful, affirming part of myself.

I only wish I could wear trouser suits and heels that would blow my mind. If I go for another job should I crossdress for the interview and start as I mean to go on? 

Blog Resources

Check my post on what I will be wearing to pride in 2026 Pride 2026 Outfit

Crossdressing & Transgender Support Resources in the UK


Beaumont Society

Founded in 1966, the Beaumont Society is the UK's longest-established transgender support group. It offers a confidential helpline, support groups, one-on-one counselling, and educational resources.

Contact:

📞 01582 412220

📧 enquiries@beaumontsociety.org.uk

🌐 beaumontsociety.org.uk


Mermaids 

is a charity supporting transgender and gender-diverse children, young people, and their families. They provide a helpline, online chat, and resources for parents and professionals.

Contact:

📞 0808 801 0400

🌐 mermaidsuk.org.uk


MindOut 

is a mental health service run by and for LGBTQ+ people. They offer support groups, online chat, and befriending services to improve the mental health and wellbeing of LGBTQ+ communities.


Contact:

📞 01273 234 839
📧 info@mindout.org.uk
🌐 mindout.org.uk


Samaritans

provides a non-judgmental, confidential helpline for anyone going through a tough time, regardless of their background. They are available 24/7 to listen and support.
Contact:
📞 116 123 (free, 24/7 in the UK)
🌐 samaritans.org


Pink Therapy

 is an online directory of qualified therapists who identify as or are understanding of minority sexual and gender identities. They offer a range of therapeutic services tailored to the LGBTQ+ community.
Contact:
🌐 pinktherapy.com


LGBT Foundation 

offers a range of services, including free talking therapies online and via telephone, providing access to LGBTQ+ affirmative therapy and counselling with specialist therapists.
Contact:
📧 info@lgbt.foundation
🌐 lgbt.foundation


CliniQ

 is a community interest company offering holistic sexual health, mental health, and wellbeing services for all trans people, partners, and friends. They provide support in a safe and inclusive environment.
Contact:
📧 info@cliniq.org.uk
🌐 cliniq.org.uk



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Location: United Kingdom

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