I did realize that the virginity was lost BEFORE, and precisely because of that said that once the house is on fire, it does not matter much if the shed catches fire.

Saying that you would transfer him the money is not the same as sending him a prepaid envelope with your address without any verbal commentary. Two very different things.

Getting another guy to accompany you was a good idea, and it would have been ok to postpone the visit until after the errand.

No damage done and you saw what kind of a person he was, insisting and playing mind games.

A better idea yet would have been to meet all three of you - this guy, you, and your guy friend - at a public place such as a coffee house and there this guy would have turned the book over to you.

Again, no damage done but these are tips for the future.