holly i had attachement issues this time due to engorgmentm i too had to express off a little to make it easier but the damage was done, took a few days of getting the attachment perfects and my nipples healed just fine., key is to make sure your nipple is lines up with his nose, big mouth and chin on boob first, this make sure his head to tilted back slightly, hope i havent confused you, :hug; hang in there though