This will offend him if you flaunt it, or if it is evident due simply to the social magnitude of the task you've assumed (for example, if you take his hand and lead him through a crowd).
That offense will reflect negatively on you and the relationship.
In other words, ask yourself "Am I attracted in spite of or because of his shyness? A very close friend of mine is extremely shy, and I know plenty of other guys that are shy. Shy guys, almost by definition, do not have the balls to initiate and pursue women.
" If you answer these questions sincerely and still want to date him, you then face the problem of making it happen - or rather, making him make it happen. They fall outside of the predator-prey model for sexual interactions that is assumed in the "don't initiate contact" rule.
A post I made about why women shouldn't take the initiative in relationships evoked some questions about how to deal with shy men - after all, shy men don't chase women, and are unlikely to initiate anything.