Thank you for reaching out and taking it upon yourself to talk with someone, sometimes the only thing someone really needs is an outlet to talk themselves through their own questions.
Gender identity can be a complicated concept to wrap your head around, and there are no clear cut answers that anyone can give you. That being said, I’ve come across some interesting questions you might consider thinking about that might shed some much-needed light on the subject.
You mention you sometimes wish you were born female. Knowing everything you know and feel now, what about that might make your life easier or better? What might make your life different or harder?
On that same token, another type of question you might ask yourself is picture that same scenario, you can start your life over knowing everything you know and feel now, but you can choose and change only one of two things. One, you can change the sex that you were born (much like the above question). Or two, you can change your feelings so that you never have an issue with your sex. Basically as male-to-female transexual, you can choose to have been born a girl, or been born a boy without your gender identity issues or questions? How would either outcome affect your life, for better and for worse?
Another interesting question that was brought up was if you have trouble dealing with the idea of transsexualism, “a woman trapped in a man’s body” or something of that nature. Could these be less of a definition and more of a pop-culture category that has come about? Some people may have those deep inner feelings while others may not fit so nicely into strict categories or constructs. Perhaps speaking with other people who have gone through what you’re going through might be a good way to further understand how feel about your gender identity.
Here is a link to where I found those questions, as well as many others. Maybe reading some over and thinking about your answers might help:
Also, the GLBT Helpline might be a good resource to get in touch with people who have dealt with gender identity issues. Their website is here:
I hope these questions and resources are of some help, and that they can put some of your questions and doubts to ease.