I had dabbled a bit in my younger days, mom's clothing when I was very young, and in my teens I had some undies but I stopped because life got in the way.
My wife bought me a pair of high heels, as a joke. She told me that if I liked them so much that I should wear them. I did, and liked it. Of course I needed pantyhose, then undies and down the slippery slope I slid.
She about freaked out and told me it no girlie stuff or she was gone, so I gave in. After some time she sat me down and we had a long talk and she was ok with me buying some shoes and clothing as long as I keep her informed. We since have "enjoyed" dressing in naughty bits together.
The other day I repaired our toilet and some other chores wearing black, leather over the knee boots with stiletto heels while she was messing up the kitchen.
