Crossdressing at Work: My First Day Wearing a Bra

Today was the day I finally did it — I wore a bra to work for the very first time.



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.

While my partner slept in the other room, I stood for a moment, admiring the feeling and the way my painted toenails looked against the carpet. Then I put on my work clothes 

trousers, socks, T-shirt, and jumper 

carefully making sure the bra straps stayed invisible. Before leaving the house, I added a touch of peach lip gloss.


Crossdressing at Work

Walking into work, my pulse quickened. I vaped outside first, tasting strawberry as I gathered the courage to go in. Once inside, I slipped into the bathroom for a quick check to make sure nothing showed through.

All day at my desk, I drifted between forgetting I was wearing a bra and savouring its comfort. It felt grounding. Calming. Right.

Later that evening, after staying late and finding myself alone in the office, I reapplied my lip gloss before walking home. The sweet shine on my lips carried me through the quiet streets in absolute bliss.


Will I Do This Again?

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

It even makes me wonder: if I ever go for another job, should I crossdress for the interview and start as I mean to go on? should I be crossdressing at work?

I only wish I could go further trouser suits, maybe even heels one day. That would completely blow my mind.

Now I find myself wondering…crossdressing at work would be amazing when I felt like it.


Blog Resources

Check out my post on what I’ll be wearing to Pride in 2026.


Crossdressing & Transgender Support Resources in the UK

Beaumont Society
The UK’s longest-established transgender support group, founded in 1966. They offer a confidential helpline, support groups, one-to-one guidance, and educational resources.
📞 01582 412220
📧 enquiries@beaumontsociety.org.uk
🌐 beaumontsociety.org.uk

Mermaids
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.
📞 0808 801 0400
🌐 mermaidsuk.org.uk

MindOut
A mental health service run by and for LGBTQ+ people. They offer support groups, online chat, and befriending services.
📞 01273 234 839
📧 info@mindout.org.uk
🌐 mindout.org.uk

Samaritans
A non-judgmental, confidential helpline for anyone struggling, available 24/7.
📞 116 123
🌐 samaritans.org

Pink Therapy
An online directory of therapists who specialise in minority sexual and gender identities.
🌐 pinktherapy.com

LGBT Foundation
Offering a range of services including free LGBTQ+ affirmative talking therapies online and by phone.
📧 info@lgbt.foundation
🌐 lgbt.foundation

CliniQ
A community interest service providing holistic sexual health, mental health, and wellbeing support for all trans people, partners, and friends.
📧 info@cliniq.org.uk
🌐 cliniq.org.uk


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

Location: United Kingdom

Comments

Post a Comment

Popular Posts

Here’s My Pride 2026 Look – Crossdresser Outfit Ideas

Image
I’m Going to Pride 2026! 🌈 This morning, I made a decision… I’m going to Pride 2026! Honestly, it’s never really been on my radar before, but here I am, excited and ready to dive in. I’ll be calling my friend Sarah today to see what she thinks—hopefully, she’s as excited as I am! I don’t know much about Pride yet, so it’s time to start learning. But honestly, that’s part of the fun. And then there’s the most important question: what am I going to wear? Hair, makeup, nails, dress? Do I go all out with a theme, or keep it simple? So many possibilities—and I can’t wait to play around with them. Next up: where to go. Brighton or London? Both are amazing options. Or maybe we throw in a wild card and try somewhere completely new, like Birmingham? The world feels full of Pride adventures waiting to happen. I’ve got roughly nine months to plan, dream, and create the perfect Pride experience. I can already feel the excitement building! Have you been to Pride before? What’s it like? Any ...
Read more

My Crossdressing Journey – How I Transformed in 2025

Image
My Crossdressing Journey – How I Transformed in 2025 Hi there I am Aveline Marlowe 💋 Hi lovely people 💖 My name is Aveline, and I want to welcome you to Aveline Marlowe . com my little corner of the internet where crossdressing, life, fashion, beauty, and self-expression come together with honesty and heart. ♥️ Discovering My Crossdressing Journey For as long as I can remember, I’ve been drawn to the feminine Crossdressing side of llife clothes, colours, style makeup, and that sense of freedom that comes with self-expression . Growing up, I often felt out of place, hiding the woman inside of me from the world. I thought I had to pretend in order to fit in. ♥️ Embracing Identity and Self-Expression  But as I grew older, I realised something powerful: embracing who you are is not just brave it’s beautiful. ♥️ Choosing My Female Name I started my journey privately with my friend Sarah experimenting with outfits, makeup, and my feminine identity behind closed doors. Later, I di...
Read more

How I Ended The Crossdressing Purge Cycle – A Personal Story

Image
What Does Purging Mean as a Crossdresser?  Purging as a cross dresser is when fear or shame takes over, and you throw all your feminine things away in an effort to stop Crossdressing .  Every crossdresser has been there at least once maybe multiple times.  Boxes or bin bags that started with a single outfit can suddenly grow into a mountain of clothing which is called bingeing  This is the flipside to purging .you hide your female clothes wigs and makeup wherever you can: the back of a cupboard the garage, under the bed.  When you’re at work or anywhere outside it's all you can think about. You worry about what will happen when you get home.  Will your clothes have been discovered?  Will the contents be dumped across the living room floor? Will someone demand answers "Are you gay? "  Is the most common question or  "Are you Transgender?"    "Do you want to be a woman?"  Like anyone has the right to demand answers in such a hum...
Read more

Aveline’s Crossdressing Journey 2025 – Seasons of Expression

Image
Aveline’s Crossdressing Journey 2025 – Seasons of Expression Chapter 1 - A New Feminine Identity is born   In the heart of bustling London , Aiden moved through crowded streets with a careful balance of hesitation and hope.  By day, he was just another commuter on the Tube, blending into a sea of grey suits.  But behind the closed door of his small flat, Aiden became Aveline Marlowe  bright, bold, and unapologetically herself challenging societies stereotypes.As Aveline he could embrace his emotional vulnerability. Crossdressing was never only about clothes. For Aveline, it was self-expression, the unveiling of parts she had hidden for too long.Aveline was now seeking validation as herself. Every outfit was a small revelation, each detail a declaration of identity discarding his assigned sex .  In this new city, no one knew her past, no one saw the cautious Aiden  she had once been.  She could carry her favorite lip gloss or her makeup, items she once...
Read more