For me, it was not really clothing, but makeup, especially lipstick. As a little boy about 5, I got my moms lipstick, which in the late 1950's was red. Of course my aim was terrible, and she saw me, and cursed me out for messing up the tip of the lipstick.
Then, when I was 7, an aunt and a cousin named Sue picked me up to stay over at their house for a couple of days. My aunt worked days as a nurse, but I remember Sue letting me wear a white lacy slip of hers into bed as a nightie at night. The next day she went up into their attic, and found her old girls dress (Sue was 6 years older then me), and Mary Jane shoes. Sue dressed me up in them, then started to put a little bit of makeup on me. I got scared when she wanted to brush mascara on, as I thought she would poke my eyes out (silly now, isn't it?), and her lipstick which was a shade or orange, which was popular with bleached blondes then. I obviously enjoyed it, as she took me for a walk to a local drug store that had an ice cream parlor in front. Funny, I don't remember what she did for hair, as then as a boy I had to wear a crew cut.
I kept any feelings of clothes or makeup inside of me until I was about 13, then sneaked around my house and wore what clothes my mom had when she wasn't around. Too bad I had no sister to share with.
The best time was when I was in the Navy, and got a complete makeover under the pretense of an initiation party at a Merle Norman Studio. I thought I had died and went to heaven!
Leilah
The start of Leilah
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Beauty
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Hi Leliah,
Thank you so much for sharing your beginnings story with us.
I was 5 when I started too, but I never had a gal friend or relative who asked me to dress up.
I'm still happy you did though! 
I'm so glad you were able to open up and share your first dressing experience with us.
Your childhood experience seems like it was incredibly thrilling and a total dream come true. 
Thanks again for posting your beginnings story it was great.

Beauty
Thank you so much for sharing your beginnings story with us.
I'm so glad you were able to open up and share your first dressing experience with us.
Thanks again for posting your beginnings story it was great.
Beauty
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Leilah W.
- New Member
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- Joined: Sat Jul 09, 2005 9:54 am
more about Leilah
After I got out of the Navy, I moved to a midwestern town as there was no work where I originally from. After I had built up a little bit of finances, I would go and order dresses from Lane Bryants, and buy makeup from those 'clubs' that send you the package once every 2 months.
Living where I was, I had a very natural time during the hours I wasn't working just wearing nighties around the apartment, enjoying the fact that I could wear various cosmetics, and feeling normal.
But, after a year or so, I had decided to move back to where my family was 1,000 miles back east due to family problems, and had to supress my feelings. Then came the Internet, eBay for items on the cheap, etc.
Living where I was, I had a very natural time during the hours I wasn't working just wearing nighties around the apartment, enjoying the fact that I could wear various cosmetics, and feeling normal.
But, after a year or so, I had decided to move back to where my family was 1,000 miles back east due to family problems, and had to supress my feelings. Then came the Internet, eBay for items on the cheap, etc.