Hello A., I am the mother of two boys with headache conditions, one migraine and one cluster headaches. I'm also a cluster headache sufferer and the Vice President of OUCH. The Organisation for the Understanding of Cluster Headaches as well as being OUCH's ambassador to the World Headache Alliance. Thankfully, your sons' headaches do not sound like C H!
I would strongly urge you to both keep a headache diary and press to see a headache specialist neurologist. I can help with a list of those in your area if you need. Neurology is a large field and you don't need to see a neuro who's primary interest isn't the subject you need. There are over 600 headache types so diagnosing is a finely tuned thing.
Within the headache diary please note time of day, duration, build up, any other physical signs, (droopy eye, raised temp, aversion to light) It would also help to note sleep patterns and foods so you can use a process of elimination for all of the common factors. I can give you examples of headache diary formats if that helps.
No reoccurring head pain, particularly in children should go undiagnosed and in all probability an MRI should be ordered too. If you would like any more advice or links to useful sites please contact me, I'll help in any way I can