OK Dazza, first of all, the answer is, "it feels better than anything you have ever experienced"
I had my first at 16(which i still am) and I think its the most common age for guys to "jump in"
14 mite be early, but hey, if I was 14, and my gf wanted to, i'd go 4 it. As for condoms, c'mon people, in US, u don even have to buy those, they give 'em for free, just so not to mess wit unwanted pregnancy. U got a gf,rite??? yes? she wants to?? uuuum, its up 2U. luck matie.