I agree with Mustang Alley that alcohol may be the way to get her to do it spontaneously. It worked for my wife. But she never got comfortable enough to do it every time we went out or leave the house without them. Until the time she really wanted this outfit badly. It was a little outside our budget and it wasn't something she would wear often. We discussed it and the sacrifices we both would have to make over the next few months. I told her I would be happy to make the sacrifice for her outfit if she promised to not wear underwear unless necessary when we went out. The decision was hers, she could walk away from the outfit or agree to go commando more often. She bought the outfit and when just her and I go out she has followed through with her end of the bargain. She won't do it if we go out with friends or if it would be uncomfortable (jeans) or if it is her time of the month but I am sure you agree those are understandable. It worked out well for both of us and she has admitted she does love the freedom and the naughtiness now that it has become more the norm for her.
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