It hurts like any piercing, a quick and sharp pinch.
Good thing you are doing it during the winter, the cold weather is like a mobile ice pack. Real ice helps with the swelling. Keep the new piercing clean! Listen to your piercer when they talk about this.
A hallow piercing needle is best, the piercing gun method at Claire's is ok. The piercing gun makes you more prone to keloids, because a piercing needle is hallow and removes the piece of ear to make a hole rather than the piercing gun which shoves the earing into the ear displacing the original ear tissue.
I hope this helps, and feel free to message me for any questions.
-emily
The Giver is a great book, are you planning on reading the other two books in the series? They're called Gathering Blue, and The Messenger. I really enjoyed all three books.
I'm currently reading Eragon by Christopher Paolini.