That photography is essentially me, except I'm not trying to jump into the girl's pants, only there is a slight anxiety to "getting the first girl" in one's portfolio officially.
If he wants to butter you up to make you feel more confident about your modelling, feel free to revel in it, but if he's making unprofessional/sexual advances he's a creep like Uncle Terry and its wise to drop him.
Yeah, bring a friend so it's not too awkward/help you change/hold stuff/talk to.
Make sire you have the kind of contract that allows you to make use of the photos as you wish (sell/copy/modify/distribute), short of defamation. He should have the same kind of contract with regards to having you as a subject.