His "known" boundary (his business card) has his email address on it so it would be unreasonable of him to declare its use "off-limits" and a boundary violation. Don't think a T would be that unreasonable :-)

Another way I like to look at it is that I'm a "wimp" and he knows it so is probably going to be "happy" if I take any action at all and know that, since I'm scared, I'm not going to do that action very often since it's so hard for me?