I am on vacation with my wife and friends and the other day we were in Eureka Springs, AR. I was with my buddy and around the corner came a gurl in a blonde wig, blouse, skirt and make up, and owning it. She didn't fool anyone as later our wives mentioned seeing her while they were shopping so she was around for a while.
Our friends had the pretty normal reaction of thinking it was pretty weird, I down played it as she wasn't hurting anyone and who cares if a guy wants to dress up and go shopping. She did a good job dressing up but the traffic was pretty thin so we noticed fairly quick.
My wife has finally accepted my situation but our friends would probably flip if they knew. As we were packing for the trip my wife asked me if I wanted to bring a pair of heels and some naughty undies for "play" time with her. I did and have been relaxing in my heels most nights and we did get some "play" time in. I didn't have room for any clothing plus we did not want to risk it with friends along, too much to hide away. We did run across a lingerie shop and my wife said she looked around and wanted to buy us some "his and hers" panties. We went back a bit later and they were closed so we didn't, but liked it that the missus was thinking of it!