I was out in a Walmart today getting some stuff for a friends birthday and while I was there I somehow got the confidence to pick up a pair of black tights, and a nice waist cincher that I had been looking at online for a while. After I got back into my car I decided "what the hell" and put them on for the drive home. I have never tried underdressing before, but I felt like I could do anything I wanted at that point. Seeing as it was 9:30 at night I wasn't actually able to go many places but I did end up stopping at another big box store, and a thrift store on the way back to browse the women's sections (but still haven't managed to find my first pair of shoes yet).

It was very strange seeing as I have never had the confidence to do that before. I was wondering if anyone else has had similar experiences?