👠 I realised I was actually a Boss Girl - Aveline Shares Her First-Time Story [ 2026 ] 👗

Identity

By Aveline Marlowe
Updated on 26/08/25 at 06:59 PM

Hi there… My name is Aveline

If you are nervous about crossdressing, in this post I cover my first-time story to help you realise there is nothing wrong or shameful about dressing up.

Crossdressing has been part of my life for as long as I can remember. It wasn’t something I ever expected to enjoy. I often asked myself: how or why did I even contemplate this? After all, I’m not a girl.

To explain how it all started, I have to take you back to my teenage years, through childhood, puberty, and the long path toward self-acceptance.

🌸 Growing Up as a Crossdressing Boy 🌸

I grew up in a fairly strict household with older parents. They loved me and cared for me, but they also had traditional values and clear expectations.

I wasn’t an only child. I had an older sister, eight years my senior. I admired her confidence, style, and independence.

🌸 Puberty and Curiosity 🌸

The symbol of my blog

Puberty is confusing for everyone. For me, it raised even more questions. I became curious about clothing — especially the clothes my sister and other women wore.

The first time I tried something on was at my father’s flat. I found a delicate slip and tried it on. I’ll never forget how the fabric made me feel.

🌸 Teenage Crossdressing 🌸

As a teenager, I developed a close friendship with Sarah. She encouraged me, helped feminise me, and shared in those moments of exploration.

We spent hours experimenting with clothes, makeup, eyeshadow, and lipstick. It was exciting, electric, and unforgettable.

🌸 Living Alone as a Crossdresser 🌸

Every girl should have lip balm

When I eventually moved into my own place, everything changed. I no longer had to hide. I could explore freely and begin to understand myself.

🌸 Where I Am Now 🌸

Today, I’ve found a balance. I give myself time and space to explore who I am, without guilt or shame.

🌸 Support Resources (UK) 🌸

Beaumont Society
📞 01582 412220
🌐 beaumontsociety.org.uk

Mermaids
📞 0808 801 0400
🌐 mermaidsuk.org.uk

MindOut
📞 01273 234 839
🌐 mindout.org.uk

Samaritans
📞 116 123
🌐 samaritans.org

Pink Therapy
🌐 pinktherapy.com

CliniQ
🌐 cliniq.org.uk

❣️ If you enjoyed this post, please leave a comment below 👇

🌸 This post was checked and polished on January 3, 2026