I just read the edited update.
1000% called it. Fucking creep. I wonder who the hell all of these upvoters are saying it's normal to make unsolicited offers of free semi-nude photo sessions to strangers.
An open ended offer for TFP is one thing (though still weird for intimate shots), direct offers is something else entirely.
Boudoir isn't for beginner photographers, especially male ones who may or may not be more interested in the subject matter than the photography aspect of it.
These assholes that think buying a DSLR is the price tag to get up close and personal with a scantily clad woman makes it harder for everyone on both sides of the camera with a legitimate interest in making art.
I'll break with the top comments and say that any photographer soliciting explicit shots for free is sketch. That's not advertising services, that's trying to get a stranger semi nude in front of him.
If he wants to break into that space, he should be talking to models he already has established relationships with about it, not someone he's never worked with.
Being skilled and experienced doesn't preclude being a creep. I can't imagine a professional with a network of models just making unsolicited offers to randoms on IG offering a free boudoir shoot ... and the OP's update with the photographer's subsequent messages confirms my suspicion.
I'm not the most emotionally intelligent out there, but even I could see the bright red flags in that one. There is no legitimate reason to try and offer a young woman, model or not, a bottle of wine and a 'free' photo session in exchange for getting nearly naked in front of you and likely try to pressure her into more for his 'generosity.'
It's just so sickening to me.