Lost mine at 14 to my boyfriend of six months (he was 13, I know, sounds disgusting now!) and we are still together five years later, even if it has been on and off. I don't have any recollection of it really hurting that much, or any blood. If I were you, I would use extra lube on a condom for the first time and make sure he gently eases into it and stops if it is too painful. Go slow and if it doesn't feel right down there, go gently or stop completely. Oh and also, it is obviously up to you, but I would really advise that you lose it to someone you love or are in a relationship with. It will be much less awkward that way, and from experience, feels a lot better. Hope everything goes well, good luck!