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My mother made me do it LOL. Actually, my mother forgot to do the wash and I realized I was out of clean underwear. Rather than go commando for the day, she gave me a pair of panties to wear for the day. They were comfortable and different and from there I started trying on more and more of her clothing. I must admit I did have a fetish for the latex(?) girdles of the early 60s. I must have been about 5 or 6 at the time.
Almost 60 years later I'm still at it.
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For me it was, as a few others have said, originally out of a mild curiosity which then led me try on a lovely floral-patterned dress. When I got into the dress, it just felt absolutely wonderful. From that point on, I took every opportunity I could to dress. It quickly grew from there. Skirts quickly became my personal favourites as, I recall, at that time, seeing lots of women wearing long skirts, so thats how it all more or less started.
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What’s that thing that killed the cat...? Oh yea curiosity :)
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When I was 8 or 9 for some reason I tried on my mothers OBG, panties and nylons. Shortly after that it was bra slip and heels and I have been dressing ever since.
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First, I seen pic of me with a dress as toddler. I was always fascinated with bras, girdles with garter belt.
I envied the ladies when visiting our house and wish I could dress like that.
First time shopping it was a bra and garter belt with stocking. It was a joy that will never forget to this day.
Its has never stop to this day.
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My mother did sewing and alterations for extra income. I was around 12-13 and got drafted as a dress form for clothes in my size range.
Many times to makes the dress hang right, I would wear all the appropriate under things - panty girdle, bra, nylons, slip and heels. It didn't take long for me to get hooked. Unfortunately my enthusiasm didn't go unnoticed and I got replaced by a dress form from a second hand shop.
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I am not really sure what made me crossdress the first time it was so long ago, I would have to say the clothes just called to me.
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In my youth our family lived in a rather small house, small enough that my mother had to hang all her dresses in the bedroom closet of my shared room. By around age 7 I found myself drawn to reaching into the closet and touching those dresses on occasion. I felt perhaps a combination of loving the tactile feel as well as the comfort that they were my mother's. And the adventure began...