When's the right time to tell her? (relationship/trans issues)

Maybe on the third date? Whenever you feel the need to. If you absolutely feel uncomfortable being seen as a lesbian, you should tell her soon because it's just going to keep bugging you.

 

you dont have to answer but how does she identify? is she a lesbian, assuming she isnt.
if she isnt then urm, im pretty sure she wont mind but if i were you i would tell her a.s.a.p
otherwise she could accuse you of not being honest and she could be looking for a different relationship i.e. she might be wanting a girlfriend, but when youre not a girl....

long story short my ex was trans i would of appreciated if he was honest, i didnt like being lied to.

 

I would tell her as soon as a possible personally. I'd rather have someone know up front then string both of us along for a few dates just to discover that the other person doesn't want to be with my because I'm trans. Personally, I probably would have tried to tell them prior to a first date.

 

It is best to tell your partner that you are a trans before any kind of real relationship. That would help preventing any misunderstanding later on, and prevent the other to feel decieved by you, which can cause a lot of drama and complications. The stigma and stereotype being placed on transexual will make it worse if she start to believe in it because you didn't tell her before hand.

Still, I believe if you tell her honestly enough and show sincerity, she will still forgive you.

Good luck.