Yeah Baggy...what LG said....there isn't any need to figure out "when" is a good time if you are truly listening to your primal urges, right? Whenever you have the primal urge, you go for it, just like the silverback will do. Then if she beats your ears for it, you know its not the right time. But not fearing rejection at all is the key here, and I do understand that given your history of rejection, you can't just shake that off overnight.
I guess I can at least tell you all though, that if you can set aside your fears of rejection or of "doing it perfectly" or whatever else may be in your fears, and if you can just authentically "go after" your woman when the urge hits you, SHE WILL respond to you in a way that is new to you. She will be turned on by it. It is in her nature to be so turned on by it that her body will take over and she will be physically aroused by the time you get there. That's how this stuff works! But give her the whif of any insecurity, and her body knows the difference. She won't be responsive to your insecurity, why would she be? Not to say that she doesn't share in the responsibility for that insecurity in your case, Baggy, because of your history together. But at the same time, she needs to let go of her insecurities too, and you need to let go of yours.
What the worst thing that can happen? She will say "no"? Pffft, if that's all, then you are used to that one! LOL!
All I know is that if my man's body is coming after mine with the intent of taking me, I have no choice but to respond sexually to him!