🌸 First Time Crossdressing: My Journey 🌸
If you’re nervous about crossdressing, or trying to understand someone who does, this post shares my first-time experience to show that 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, and for a long time I asked myself: How or why did I even contemplate this? After all, I’m not a girl.
To explain how it all began, let me take you back to my teenage years — through childhood, puberty, and the long journey toward feeling comfortable with myself.
🌸 Growing Up as a Crossdressing Boy 🌸
My sister and I grew up in a fairly strict household with older parents. They loved me and cared for us deeply, but they also held traditional values and had clear expectations — dressing up as a girl wasn’t one of them.
I wasn’t an only child; I had an older sister, eight years my senior. I admired her confidence, her style, and her independence. I would mimic her, adore her, and secretly wish I could be like her. Perhaps it was because I had such a strong bond with her, but I’ve also come to understand that I probably have autism.
At school, I struggled to understand times tables and was placed in special educational needs classes. That doesn’t mean I’m not intelligent — far from it. Later, I went on to further education, where I did really well.
Many people with autism also experience something called gender dysphoria — a natural feeling of wanting to be the opposite sex. It’s just how some people are built.
For me, even now, I notice what women are wearing on the train when I go to work. I’ll look up brands on my phone, imagining what it would be like to wear those outfits. Women just seem to have more fun with fashion, and I like imagining joining in. It’s a hard concept to explain, but it’s part of who I am.
I want to reassure you: this is nothing weird or strange. It’s like a cat wanting to be a dog when it’s the only cat in a house full of dogs — it’s just expressing a part of yourself that’s different from your surroundings.
🌸 Puberty and Curiosity 🌸
Puberty is a confusing time for anyone, and 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. My mum and dad had split up at the time, though they later got back together.
I found a delicate slip that his girlfriend had left behind and tried it on. I’ll never forget how the fabric made me feel. Standing there, I was overwhelmed by the sensation — it felt amazing. I remember thinking I shouldn’t be doing this, but I was irresistibly drawn to the fabric. It felt almost compulsive.
From that moment, I was hooked. I couldn’t stop wondering what it would be like to wear other women’s clothes.
🌸 Teenage Crossdressing 🌸
As a teenager, I developed a close friendship with a girl at school named Sarah. I confided in her, and to my amazement, she wasn’t shocked or disgusted.
Instead, she encouraged me. She helped me explore my feminine side and shared in the experience.
We spent hours experimenting with clothes and makeup. I would wear her skirts, dresses, jeans — anything I could fit into, which wasn’t hard, as I was always slender for a boy. We tried eyeshadow, lipstick, and every little detail that made me feel more like Aveline. It was exciting, electric, and unforgettable.
It’s important to note that I do not wish — and have never wished — to actually become female. I am completely heterosexual; I have always been attracted to women. This was never about sexual attraction, but about experiencing the female life and expressing a side of myself that felt amazing.
Sarah and I never hooked up. It wasn’t about that. It was about sharing something with love and respect, without crossing boundaries. We cared for and respected each other, and I always felt completely safe with her.
🌸 Living Alone as a Crossdresser 🌸
When I eventually moved into my own place as an adult, everything changed. I no longer had to hide.
I could explore freely and begin to truly understand myself. I didn’t have to hide clothes in bags anymore — I had drawers where I could neatly arrange my feminine clothing, and I could leave my products out in the bathroom. It felt amazing.
Sarah was always around. We would wear pajamas, watch TV, drink, dance, and think about what clothes to wear next.
I bought wigs, we swapped clothes, and it was so much fun.
Sometimes we’d go into town, get a little drunk, and just go wild.
🌸 Where I Am Now 🌸
Today, I live with an amazing woman named Alisha. She accepts me for who I am — both my male and female sides.
Navigating this hasn’t always been easy. Alisha didn’t just say, “Okay, great.” She had questions — many questions. One I didn’t anticipate was her assumption that I crossdressed because I didn’t find her attractive. That couldn’t have been further from the truth.
Crossdressing, for me, is simply about having fun. It’s about seeing something I like and wanting to emulate it — nothing more, nothing less. There is nothing wrong or shameful in that.
Think of it this way: what would you say to a woman wearing a man’s shirt? You wouldn’t stare or judge — you’d accept it.
Yet because men are often seen as “stronger,” people assume a man crossdressing is doing something deeply meaningful or “weak.” It’s not. I crossdress because I like what I see. That’s all.
If you want to know more or have questions. Please leave a comment after the beep …
Later
🌸 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
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