I honestly don't know when it started or if anything in particular triggered it. I've always joked about size, but I'd say just within the past year or so have I really started thinking about it all the time.

I do usually orgasm (99.9% of the time). It does make me feel good that I can make her do it, but then that doubting voice in my head tells me things like "she's just really sensitive and anybody could make her do it". I don't know why I worry about it, but I do.