I've been binding 3 1/2 years now, much to my chagrin, with Underworks binders. Thus far, I don't have any rib damage that I'm aware of, but incurred bursitis in my right shoulder numerous times due to the strain the binders put on it.
As per binding 36C, I know plenty of guys who've managed with even bigger bitch tits. Sorry for the term, but it's the one I prefer. I was about 38 between B & C when I started binding, and didn't have any trouble flattening them. At this point, after 60 lbs weight loss and all the binding, they're pretty flat regardless of whether or not I'm wearing a binder.
SD