In June 2008, the New York Times carried a fascinating story about women in Albania who live their lives as men, largely because their families had lost viable males in honour killings, war, etc. This practice is, apparently dying out. Today the NYT has a story about girls in Afghanistan who are dressed as boys. Many of these girls are loathe to return to female roles/clothes because of the constraint this places on their lives. Be sure to read the comments (click on the 'Highlights' tabs of the comments section): some people are shocked, amazed, puzzled, intrigued, etc. The particularities of situations like this vary, but there have certainly been examples of women dressing as men (in life and fiction), men dressing as women, in all cultures through many ages.