For those like me, who began on family member's clothes...

[Raychel]

When I was young and stupid, still living at home It was only my mothers underwear. Now that I am old and stupid, I only wear mine. My wifes are to small and she would get really p!$$ed, ife she caught me in hers.

[erickka]

For me , It started with mom's hose (which were in the trash when I got them) and those great 1960's ultra pointed toe pumps with a heel no thicker than a pencil! Needless to say, bought my own stuff once I got a job @ 15. Can't say I ever rummaged through her closet or dresser (at least not that I can recall)

[Janailene]

Started with girdle and bra, but quickly started to try EVERYTHING! If Mom had things or used them, I did also. By 9 dressed completely and by 12 was going out to walk our dog using rollers and a hair net as I didn't have a wig.

[trannie T]

I was very particular about which of my mother's clothes I wore. I only wore the things that fit.

[SabrinaDubh]

I wore it all and watched my sister get in trouble for it. (We're not close, the female relative and I)

Edit: I never touched my moms things... I was (and still are) too afraid of my mother to mess with her things. I never even went into her bedroom unless I had permission.

[immike]

For me , It started with mom's hose (which were in the trash when I got them) and those great 1960's ultra pointed toe pumps with a heel no thicker than a pencil! Needless to say, bought my own stuff once I got a job @ 15. Can't say I ever rummaged through her closet or dresser (at least not that I can recall)

To this day,I love to enter mothers closet&dress in her wardrobe,especially
her good short skirtsuits&one of her silk blouses,with pantyhose&heels

[immike]

For me I could never try on my mothers clothes, I had no desire to, I was totally turned off by it.

I had a blast wearing mothers clothes,especially her dresses,dress slacks,
tops,blouses,mini skirts,hose&heels

[Cheryl T]

I would never have worn anything of Mom's that was cotton... so drab...lol.

Being a baby boomer I was fortunate enough to have a mom that wore corsets and hose, heels and skirts, silky slips and panties. All of this was so extremely feminine that the thought of something so plain as cotton was abhorent. At the time I began dressing the most feminine of women were those on the pages of Playboy. Sensuous lingerie, filmy nighties, sheer hose and heels were the ultimate expression of womanhood.
While I still enjoy those things on occasion now I prefer to mix into the masses, not stand before them waving the flag. Of course I'm a little older now ....

[laura.lapinski]

For me I could never try on my mothers clothes, I had no desire to, I was totally turned off by it.

I agree with Jill. I never tried on any of my sisters clothes either for the same reason. I think my cross dressing was mostly fantasies in the young years, however, I do remember trying on my cousins bathing suit when I was 13. I felt so sexy and good.