Your situation is not all that unique. A lot of couples get into this place, usually because of unclear communication, not having clear goals and a general unwillingness or 'fear' of actually talking about what is currently on their mind.
From all the clues you have seeded in this post you are the dominant person and he is the submissive person. You are older (ergo wiser - in theory), you are more affluent (thus a provider).
He is into bears - Most guys who want to be with a bear-type guy associate bear with masculine - masculine pretty much means dominant.
Most guys who want to be with a twink are looking for a passive fellow - once again the cover of the book is a huge clue as to what is inside - not always the truth, but a pretty clear clue that is often right.
Quote:We wanted to stay friends and not date but we got a little emotional and things swung in that direction.
And how did "We" arrive at this decision?
I wasn't there to observe this conversation but I have a sneaky suspicion that what really happened is you informed him and he played along and followed what you were saying and has played it back to you in order to please you.
You may not have done that intentionally, but you may have left way too many options on the table and appeared to not be that interested in an 'us' with him.
Passive/Submissive types do that - they allow their partner to make choices and decide things and they follow along. Yes the dominant party usually thinks that our conversation was of two equals - well no, that is rarely the case. Passives rely on trying to read their partner because more often than not a dominant fellow attempts to be as inclusive to the choice as possible, thus leave way too much room for questions that a passive person will not point blank ask for clarity on.
So what was said exactly? Who lead the conversation and lead 'We' to conclude that being friends is best? Did you formulate your question in a manner that left lots of room to doubt you wanted a relationship at the time? Did you hint more along the lines you wanted to be 'just friends' - if so he may actually be trying his damnedest to give you what you want because its in his nature to try to please you.
When did this conversation happen, was it before or after all these trips? If it was before then most likely he isn't there for the trip he is there patiently waiting for you to decide that there is an 'us' situation.
Yeah be might be emotionally manipulating you, but it may not be for your wallet, it may be for your heart.
I strongly suggest you take charge and set out the options clearly. And the options should not include 'Just friends'.
Tell him you want more than 'just friends' and his choice is to pursue a relationship with you or move along. And don't try to be 'just friends'. Take that option off the table.
You do not have to ask him if he is manipulating you for your money. That will confuse the matter and confuse his reply.
KISS - Keep It Simple Stupid.... Clear black and white choices work far better than many choices with a lot of grey areas.