1. I don't see why that question pertains to LGBT
2. Yes. It is weird. You can't make a cd for someone you haven't met yet. What if the person you fall for hates all the songs in that cd?
I would have to question whether or not he has had any sexual contact. Being a virgin doesn't mean he hasn't had oral sex. You can catch STDs from oral sex.
Start by having him got to his normal physician and if he can't figure it out he'll recommend someone else.