At what age approximately did you have your first dressing encounter?

Hi Fiona-Ann.

My earliest memories are from sometime around the age of 5. There was a neighbor boy who was my age and lived down the street who (I suspect) also grew up to be a crossdresser. He had an older sister and we would often go into her room when she wasn't there and play with her things, trying on her clothes and makeup. This was before I even knew what sex and gender was, so that confirms for me that being a crossdresser is something that is ingrained in many of us, it's not a choice or a "lifestyle".

Hugs,

Holly

My first time dressing was when I was 11 or 12 and wore one of my mother's bras I found in the clothes hamper. I would regularly wear her bras I found there. She caught me one time but didn't make a big deal out of it. I was hugely embarrassed at the time, but didn't stop. I suspect she knew that and was okay with it.

I was 5 or six. I used to live at my grandparents house with my mom and other aunts. The only men in the house were my granddad and an uncle. So, you can imagine! I remember so well I used to open my aunts' drawers, particularly for the bras and panties. I loved the texture,the cuteness, I don't know. One of those occasions I decided to take one pair of panties and wear it. I loved to see how I looked with them on. Unfortunately, one of those early times my mom wanted to tuck my shirt into my pants and she saw I was wearing my aunt's panties. She got so angry! And even more when I told her I did it cause I didn't have clean underwear. She went to my drawers and showed me my own whities. It was bad.

I didn't care, though. I kept taking my aunts' clothes progressively. Bra, stockings, dresses, skirts...

Wow, Fionna!

What are the odds of finding a crossdressing sister at an early age! That's wonderful.

4 or 5 approximately, asking my mom to borrow her underwear and stockings for playing nice lady going to a party, and I was allowed. I was lying about the playing, I just really liked the feel of the clothes and the fabric and especially the stockings.

Sometime in my early to mid teans. I used to babysit for a young couple on my paper route. The child was a toddler and was usually always sleeping while I was there. The first or second time I was sitting for them I saw a pair of pink silk or satin bikini panties on the top of the laundry hamper that was in the washroom. I remember having this inexplicable urge to try them on and have been hooked ever since.

It's all a bit fuzzy for me. I don't remember a lot of specific events and ages. I do remember playing dress-up and wearing a wig and a dress for fun when I was quite young (probably 6-8) but I don't think I really started x-dressing with any intention until I was somewhere between 9 and 11. Definitely with my moms', and later my sisters', underthings. I remember my mom had some pale blue satin bloomers from the 50's that I loved and then I got into the makeup and everything else. Around the same age my sister had this gold one-piece swim suit that I used to take showers in and imagine.

-- Abbie 🥰

At four I was dressed up as a 'lady' by mum for a fancy dress competition. At five I was wearing my sisters dresses for'fun' and in secret. And so it went on......

I believe I was about 11-12, but around 14 the interest and effort intensified.

Probably about 10 or 12. I found  old one piece bathing suit of my Mum's in the laundry and I used to put that on with tennis balls for boobs. Not much later I would be left on my own for weekends and that's when I "went for broke". Bra, girdle, funny old fancy dress white wig, slips and dresses.

Eventually got cuaght by some relatives who called in one night to check on me. Got the "talking to" from my father. Typical 60's Australian Dad. "Dont do that again son, cos when you grow up, "The Boys on The Pub" will call you a queen!!

Horror of Horrors!!!. What fate could be worse in 1960's Australia than to get on the wrong side of "TBITP"

Caty

It is a very long time ago, but I did get into my mother's make up at approximately age three or four.  My actual main event was at five years old, when I served as a flower girl at a wedding.  I recall the frilly dress, hair ribbons, black patent-leather shoes,  nail polish, etc.  It took a while to get ready, then there were photos.

From reading many CDH profiles and participating in many support meetings, it would seem most of us started very young?

From reading some of the replies I am the odd person out. I started to wear my SO's panties with her permission when I was just over 70; 84 now. Since then I have embraced CDing and have bras, wigs, makeup, etc. Only been out in public twice; with my SO to a mall. My SO is 100% accepting saying it is just clothes and I still am a man no matter how hard I try to be otherwise. Sitting here typing in bra, panties, cami and earrings while SO potters around. Best, Marlene.

I think I was around 10 or 11.

You're not alone. I started a few years ago, in my early 60's.