OnceInALifeTime - To me the fact that he makes you feel painfully insecure is a warning sign. That's often a red flag. A person who can "suck away" your confidence like that is very likely the type of person who wants to dominate you.
Manipulative people do just this: First they - often by their mere presence - take away your confidence, then they offer to give it back at a price. Be warned. There can't be a normal relationship with such a person, it's a constant state of them holding your confidence hostage and only momentarily giving it back.
Maybe part of your attraction to him is simply the fascination of the new experience of being attracted to an older man or a person in a position of authority? If I understood right.
Being attracted to a type of person we haven't been before (f.e. much older/younger), is a "micro first love".
(A necessary reminder; just my point of view, and I obviously could be wrong.)
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