The title to this thread is (admittedly) a loaded question. I just want to say that straight away.
Do you want acceptance?
Do you want no one to react to you, even if they recognise you as transgender?
Do you want to pass?
Is the most important thing to you that your SO accepts you?
Is the most important thing to you that society accepts you?
Do you want to feel able to wear what you want without anyone judging you?
Do you want to feel the excitement of doing something that isn't expected of you?
Do you want to be seen?
Do you you to be seen and recognised and accepted?
Do you want women to recognise you as a man dressed in women's clothes and their reaction to be intrigue?
Do you want women to compliment you on your attire?