Answering my own question....I generally raided my Mom's stuff when she was out (I had no sisters). I remember well the paranoia of trying not to disturb anything -- if I took something hanging in a closet, I took great care to note just where it was on the rack and replace it there. Bras, slips, and panties were more nerve-wracking...I had to carefully note how things were stacked and folded in order to recreate the "look" of a drawer's contents. (In reality, she might well have not paid close attention to how things were arranged, but why take chances?)

In my early 20's (this was the late 1970"s), I also had a risky (but thrilling) time when a young couple I knew asked me to check up on their dog for a few days while they were gone -- feed him, let him out, etc. The wife was a very pretty young gal with a lot of nice clothes, and owned a cute short blonde wig to boot! (Kind of a Goldie Hawn look, for those young enough to remember her "Laugh-In" days.) Yeah, I had a lot of fun while the pooch was out doing his business! :D The risk involved is that if I had been caught or left incontrovertible evidence that I had been playing in her things, her very macho (and very big) husband would almost certainly have beaten the snot out of me!