When you add your first server, your card is immediately charged the $14. When you add your second, we don't bill you right then, but rather add it to your next month's bill. So let's say you just signed up with a server, and then a few hours later you added a second one. Your billing page would show that you've been charged $14, and your next bill (scheduled for a month later) will be $42. The bill after that would then be $28.