I started out with my mom's panties, which was very exciting, if you catch my drift. The I discovered her girdles. I loved how tight they were on me. Then, or course bras, stuffed with socks. My mom didn't have any pantihose, only stockings. I watched a movie on TV where one of the actresses pulled on and hitched up stockings to her girdle. That's how I figured out how to use the garters on the girdles.
Next, I got into my mom's lipstick and jewelry. She didn't have her ears pierced, so I could try on her earrings.
My mom alwas had a very neat and organized pantie drawer. I was always very careful to put everything back where it came from. One time, I opened her pantie drawer and it was all messed up. I thought it was a trap to catch me, so I didn't touch anything in her room. I went down to the basement where she kept her "extra" clothes. I found a couple of bathing suits, and all kinds of other clothes that I didn't have to worry do much about putting them back "correctly". She also had some jewelry down there, including a ring that almost got stuck on my finger.
But, best of all, the had a beautiful, blue, heavily-beaded evening gown. I thing it would have fit me at that time, but I was afraid to pull the zipper all the way up, in case I got stuck in it.
Fast forward to today. Name a piece of women's clothing (except socks) and I probably have more of them than my wife does. SInce I'm in a DADT marriage, my wife tolerates, but doesn't want to see me dressed, never mind shop with me. As a result, I've always shopped myself, or with TG friends, and I've developed my own style, totally different than my wife. I've gone out and about a lot, been to Keystone 8 times, and I've probably gotten 30 makeovers.