I have used the Telex 5X5 for my years in the military on the DC10 and for Delta on the MD-88. Your dentist can make the ear molds. No, I'm not joking. Ironically, it is their area of expertise (don't ask, just believe).

If you use the headband to support your boom mic, your ears should not get sore. However, if you use the earmolds to support your boom mic, the torque applied to your ear canal / ear might give you some grief.

I hope this helps ...

-Fatty