A transsexual is not nor were they ever a feminine man or a man that had a feminine side that needed to be expressed as a contrast against his masculine side because they never had the male identity.
It is the life long sensation of knowing something is wrong and that you are living unnaturally.
I personally think there is a reason most crossdressers are sexually interested in women and it is this sexual attraction for women that is a component of their crossdressing. They identify with women through their sexuality but this is not gender identity.
They get into trouble when their sexuality builds their gender identity "as a woman" but you cannot build a gender identity out of sex even though many are trying to do just that.
A homosexual man could possibly turn himself into a female caricature to sexually attract straight men to him and even take it so far as to transition to complete the affect but this is not crossdressing to emulate a woman as an extension of a mans infatuation with women but his sexuality contrasted against men that he makes his gender identity while clearly staying a man to any woman that crosses his path.
A crossdresser identifies with woman because of sex but a transsexual identifies as a woman because of gender.
I have read the words of some who have or are transitioning because they want the freedom to express themselves without the fear of reprisal for breaking gender roles. To do this while not being in ownership of a female identity is to risk great unhappiness and adopt the delusion that one is indeed a woman while never showing any evidence of previous identity conflict.
Transitioning is not about gender roles (external/public) but identity (internal/private). If you stay honest with yourself about how you have always identified privately as to who you have identified with (who you are as a men versus a women) you will not fall into the delusion that you are a woman.
A man cannot replace himself with a woman by becoming one whether in dress or through surgery. It is simply impossible and there will be consequences.
Understand what is driving the movement toward women and explain it honestly to her.
There is no danger of making a mistake as long as the truth is held as ones highest value.
It is through self deception that people make themselves miserable.
