How cross dressing progresses? 

 It is just the variety of clothes, hair styles, jewelleries which attracts male, he feels jealous that he is not getting chance to try. Some time gets a chance to try and then starts liking.
Most of cross dressers starts from bathroom by trying female under garments.When the opportunity arises he will try nighty/gown of some female members.
Many wears female under garments starting from occasionally to daily under his regular male clothes.
Some try cross dressing out of curiosity and mostly abandon after few try.
Some try full fledge by taking part in drama, dance and other entertainment program and mostly accepted by relatives, friends & public in general.
Majority of cross dressers for any of the known / unknown reason once started, progresses in the journey of becoming as perfect a cross dresser as possible, depending upon the limitations of physical features. A very small percentage of them could get away from cross dressing due to counseling and medical treatment in very early stage.
Almost all cross dressers maintain a very fine balance of living both the life together. No one can say he is a cross dresser because his behavior is absolutely manly and he equally satisfies his wife.
As once remarked by Sunitaji, cross dressing is progresses by amount of opportunity one gets, the encouragement cross dresser get for her looks, style of clothes and womanly behaviour builds up confidence and by practice becomes a perfect cross dresser. SOme of the cross dressers are even better than real woman. I have always admired Radhaa mohan for her grace, beauty and feminity.Less than 5% of cross dresser changes sex from male into female.