A friend of mine in school had been sleeping nude for almost a year and had been oh so careful to keep anyone else in his family from knowing. Well one day he overslept and his mom found out he was sleeping nude. It turned out to be a non-event because his mom told him she didn't mind at all as long as he didn't come downstairs naked. So after that he stopped hiding it and eventually became comfortable going to and from the bathroom nude as well as just spending nude time in his room. Sometimes the mental barriers just need some help to get over.
