Anima/Animus will provide insights on this from both genders. Jung was freakin' brilliant in this stuff.
but the following is good too....
"Each boy has traits that society considers feminine. When a boy displays these traits, they meet with disapproval. The boy represses these feminine traits, which become the anima.
The boy develops a normal male persona (mask), and enters the world. He goes to school and follows a career. The urge to actualize his repressed female potentials manifests itself in dreams and fantasy.
At midlife, he experiences unhappiness due to the unrealistic and limiting nature of his masculine persona. At this time he may feel a strong, even overpowering interest in wearing women's clothes, or of being a woman in fantasy. This urge is natural and healthy: it is because his completeness as a person requires expressing the potentials he has repressed.
Lacking societal cues that validate or guide his impulses, he experiences confusion. The world says crossdressing is wrong, but his 'heart' says it is right. Guilt, shame, moral concerns, and his own overly idealized view of masculinity constrain his crossdressing. He also asks questions like "Am I gay" and "Should I change my sex?"
The stage of confusion can last years and decades. The crossdresser may dress often, delve into the culture of crossdressing, or even take female hormones. Or he may remain highly closeted. But the hallmark of this phase is that he remains confused and highly ambivalent, uncertain how to proceed.
This seems a terminal point for many. However, the theories of Jung and others imply that this is not the proper end point, but merely arrested development.
If the crossdressing urge is really adaptive--a response by the organism to remove barriers that have effectively repressed half of the man's potentials--we can speculate that further developmental stages are possible:
The crossdresser recognizes the positive, healing meaning of crossdressing. At this point, crossdressing becomes supported, rather than rejected, by the ego; he may then pursue crossdressing as a constructive activity, now freed from previous moral constraints. But, by the same token, recognition of the positive meaning of the urges also brings an appreciation of sensible limits.
The crossdresser gradually experiences his "inner female." As he does, he finds parts that are of fundamental importance, and realizes that these transcend labels of 'male' or 'female'. He also learns to distinguish the positive, profound parts of the anima (spirituality, love, beauty, etc.) from the trivial (promiscuity, vanity, etc.).
For a while the crossdresser experiences his male and female personalities as distinct. Eventually he allows parts of the female into his ordinary male personality. This stage gradually merges with the next.
The inclusion of the female effects a change in the male personality, producing a new personality that is better than either alone. The female empowers and transforms the male. This stage is ongoing. The new self continues to grow--presumably in the direction of greater spirituality and service to others.
It is consistent with the anima theory that the urge to crossdress may diminish during these later stages. The crossdresser now understands that it was not the clothing or being a woman that he sought--these merely symbolized the deeper aspects of his personality he sought to express. Once he experiences and expresses these aspects directly, female clothing itself has less meaning and importance."
The source is a Russian unknown.
Note also that "cross dressing" does not actually have to be literal as in women wearing men's clothes (which for many is really common to do) and men wearing women's clothes (which is far less common as it is so much more societally unaccepted) but it is more about taking on the spiritual and acceptance and nurturing qualities so often more more attributed to the feminine than the masculine aspects of the physche.
Ps: Do click on the link I provided at the outset of this post. I think many of you can benefit by it.
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