I never tell. Even if they ask or suspect or were told I was.
I listen to a radio show on occasion called Love Lines (with Doctor Drew Pinsky).
Anyway... on this radio show men frequently call in with the following question. "I really love my wife (or girlfriend) and I want to spend the rest of my life with her but I cheated on her and it is killing me and I want to know, should I tell her?"
Doctor Drew explained how the desire of the man to tell his girlfriend or wife that he cheated on her is selfish and destructive. The man feels guilty and he wants to feel better. He thinks by telling his wife or girlfriend that he cheated on her that he will feel better. What will actually happen is that he will hurt his wife or girlfriend and sabotage the relationship. If he really cared about his wife or girlfriend and her feelings he would simply avoid making the same mistake again and bear the burden of his guilt. Confession to her only hurts her, he wants to hurt her or he is willing to hurt her, just so he can feel better. How selfish and non-loving is that?
Now I agree... if a man is a chronic cheater he should tell his partner. But if this is someone who made a mistake and if he intends to avoid making the same mistake in the future then he needs to deal with his guilt and not make it her burden just because he thinks telling her about it will make him feel better.
Sometimes women who transitioned think they need to tell a partner they transitioned. They believe that if they tell their partner that they transitioned that they will feel better. Personally having anyone in my life know I transitioned makes me feel dirty and poison's the relationship. I think I need to bear the burden of my guilt or get over it and accept myself. The way to accepting yourself is not through other people or making confessions.
To tell or not to tell or when to tell? That is totally up to you. Personally I don't tell. The man who confesses to his wife or girlfriend that he cheated on her becomes a 'cheater' by telling. The woman who transitioned who tells her partner that she transitioned (in my own personal experience) becomes a man. I didn't create that reality and I don't like it any more than anyone else. I hate it. But I found that in order to have the life that I need to have, I have to take responsibility.
If you feel like telling then fine. That is a good way to learn what you like and what you don't like. Maybe it will work for you. I just want to state that I advocate not telling. I mean as long as your transition is in order. I wouldn't be out to friends and neighbors but not out to him. I believe in loyalty over honesty. Honestly is not the virtue that people have pumped it as. Honesty is a way for people to obey the rules for the sake of the rules while walking allover someone they supposedly care about. Honesty is telling on someone, because you can. I believe in loyalty over honestly. Loyalty means not being out to everyone except the person you are supposed to care about most. Loyalty means being true to your nature, if you are female be female. Loyalty means not cheating on a partner. Loyalty means caring for another person, looking out for them, being their friend. But I have found that as a woman who transitioned in order to be able to be loyal to others I first have to be loyal to myself. That means not telling people something which they will translate as, "I am really a man who tricked you into thinking I was a woman."
Women never tell people that they are actually men. Women who transition and who are fortunate enough to have the option need to decide if they are going to betray themselves in order to be honest to someone else. I know it can work for some people and I know some people don't feel the same way as I do about it. I know that some people identify as trans or feel that being completely 'honest' feels good. It really doesn't matter. Experience will show you and there are plenty of fish out there.
There really are no answers. You decide.
