Last week went shopping with the wife for women's exercise shorts and tops for both of us. We both got tops but I could not find any running shorts. we like to shop the stores like Goodwill for clothing. Good clothes for very little money. Anyway I found a above the knee light weight skirt that I could use on the treadmill but wife said that was crossing the line.

Yesterday went shopping with the wife wearing women's tennis shoes, trouser socks, Lee's skinny jeans (love how they stretch), and panties. Again did not find any running shorts but the skirt was still there. Wife said if I really wanted it, go ahead and get it. And I did.

I guess this sounds a little lame, but it exciting to me to get my first skirt and it was a good day for me. Some days she is does not like it at all, but most she seems OK with it. Panityhose is next, but I'll wait awhile before asking for them. As others here have said better to take it slow and let her adjust.