Lucky, that sounds great! It sounds like you both touched upon several different areas of the whole topic which needed to be addressed (again).
The one thing I don't think you said in your post was, did you make him understand that you would eventually be a WAW? You hinted at it, but did you really make it known? I am sorry to beat that drum again, but I just think it is important in everyone's sitch, precisely because I *should have* made it that clear to my ex-h ... so I know the price to be paid of not making it clear.
But as for your encounter, I just wanted to say (you may not have read this in another post of mine) that my guy has the usual, for his age, loss of erection at certain times, too. But we treat it as a non-issue and it really is a non-issue. However, yes, the condoms are something you really should find a replacement for because it is just so much easier for them (at this age) to maintain the erection without one. But my point here is that - basically, if we change positions, I know that I either have to do it really quickly, or we have to get him started up again. So just knowing and expecting it really helps us. Because that way, there is truly no disappointment on either of our sides. He has taught me well that he needs continual stimulation or we'll lose it, BUT...that it it is easier to get it going again with the right amount of sexy and effort.
If Mr. Lucky can come to a place of acceptance, like Bagheera is saying, it will help him so much! Because I know that it is because of my man's knowledge and understanding of his own body that keeps him grounded and feeling secure when there is erection loss. He knows his body very well and knows what it can and won't do, so he has taught me how to get him back in the groove when necessary. And he knows not to feel like a failure because he isn't one....temporary loss of erection doesn't mean the end of the sexual encounter. Usually the erection is only "half" lost and comes back within a few moments (and its sometimes nice for me to have a break, too). I know Mr. Lucky can get to this place too (but again, the condoms make it much more difficult).
I'm happy you had that talk, and happy he initiated, woo hoo!
You are on the right track, girl.
Oh and hey, I wanted to say, you didn't say it out right but implied that you do have O's from intercourse alone. If that is the case, you and Mr. Lucky need to understand how LUCKY you both really are! I'm totally jealous and I doubt I will ever have an O from intercourse alone. You really ARE a Lucky Girl!