Hi Natalie,
I just finished working with a mom who had similar issues. Baby had a labial frenulum, a posterior frenulum, and micrognathia (underbite). She had intense pain, which she rated as a 7/10 for most of the feedings. She got the posterior frenulum clipped, and had a little improvement in the nursing pain. We went to a speech pathologist (I went with her since the speech pathologist did not have much experience working with breastfeeding mothers, but was very willing to do what she could) and she recommended that the mother reach into her baby's mouth and massage or rub the ligament at the back of the jaw where they meet, just for a couple of seconds on both sides (the idea being that it would loosen that lower jaw to come forward in a way that might allow him to do what he needed to with his lower jaw rather than the chewing he was doing at that point). She found this also to be helpful, and had to do it every time for a couple of weeks before being able to nurse without doing it. And finally,she got the upper frenulum clipped by an ENT (the same one who had done the posterior frenulum) and this is when things really got right for her. She is still having very slight pain sometimes, when she describes him as being particularly chewy with a feeding, but otherwise, is pretty comfortable. She tried to go without clipping the upper frenulum, but just couldn't find a comfortable way to nurse. She did a really good job of educating herself (and me!) about this condition. Take a look at this blog for a nursing positioning. 

http://thefunnyshapedwoman.blogspot.com/2011/03/introducing-maxillary-labial-frenulum.html

Also

Dr. Kotlow: http://kiddsteeth.com/
http://kiddsteeth.com/articles.html first article has great picutures. 

But I think that clipping that labial frenulum may be the only way to truly get beyond the nursing dysfunction in this couplet.

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