Sugar relationships should be pretty easy and straightforward and this already sounds awfully complicated. I think he is a time waster who likes free attention and I hope you are not already role playing with him.

Ddlg is a fairly common kink and I seriously doubt that he cannot find a lady in his area (especially if he is generous).

He sounds like the type of guy who get off at the idea of having an SB/little rather than actually doing it (or maybe he cannot afford his fantasies). Those kind of time wasters love to carrot dangle.

I'd suggest you make an Amazon wish list (make sure to keep your info private) with some cute outfits and items which would be perfect for "play time".

Send him the link. Don't tell him you are testing him, just be super cute about it. If he doesn't get anything for you and comes up with another excuse, block him.

Added Keep in mind that he could always order your items, take a screenshot then cancel it so don't entertain him further until you actually receive it.