Oy. I was never caught wearing women's clothing and makeup. But there were two incidents of note. My mom discovered my very poorly hidden stash of various items. I believe this was 1984 or something. I came home from school, and she didn't talk to me. I had no idea why. Then dad came home. He took me aside and talked to me. I don't remember what he said, only that mom had called him about it. He didn't seem hugely concerned, now that I reflect on it, but clearly he wasn't thrilled either. Over time, mom moved on, of course. It represents the most embarrassing event in my life. Even to this day I would love to erase it from the historical record!
Then a few years later, I was almost caught by my dad. Everyone was out of the house, and that meant I had a few hours to dress up in mom's yellow dress. I went all out with makeup, shoes, hosiery, and even messed with my hair. I was in my bedroom admiring myself when I heard keys in the main door, and the door opening. What the hell!? Dad had come home early. I somehow had to run across the short distance between my bedroom and the bathroom to get cleaned up. I was one flight of stairs above the living room, so theoretically anyone in the living room could look up and see me. I kept looking to make sure the coast was clear. It was. I made a dash for it and, of course, dad walks through the living room. He didn't see me though. I cleaned up and afterwards pretended I had been taking a crap. What a nightmare it would have been had he seen me. We would have both been scarred to life. After that, I didn't dress until college many years later...