I'm in love with a man who doesn't see past the fact that I have a penis. We got drunk a couple days ago at a party, and he said that even though he supports transgender people, he would only have sex with a woman who had a vagina or who was "originally" a woman. Therefore he would only date a woman who was "originally" a woman at birth. This just upsets me so much because he's a good friend of mine too. It breaks my heart that I'm not good enough just because I was born with the wrong genitals.
I’m sorry to tell you this, but if he can’t see how amazing you are for your self and personality then maybe it’s time to move on. The only way i could see this not emotionally hurting you would be if he changed his mind, otherwise he’s transphobic and will only cause pain in the long or even short run as it is causing upset.
Do remember that others transphobia does not define your worth, “I’m not good enough” is incorrect, they don’t deserve you, if he makes you feel awful then he does not deserve you. You deserve someone who isn’t transphobic because you reserve the right to be judged by action not genitals or gender.