The quirky little part of my heart is screaming, "YES! WEAR A MONOCLE! (and take pictures with your headset!)" but aside from that, I can't be of much help. I wear glasses, and have never had problems with any headset, featherweight, or big muff.
No, wait, I just rememberd something. I started wearing a hat whenever I'm on hedset, because I was having the same problem with the big headsets, making my glasses push into my head and my head hurt. I got a leather driving cap sort of like this one:
The bottom edge is pretty far down on my head, close to my glasses. The edge of the hat takes most of the pressure off the glasses, creating a sort of gap between your ear, the hat and the headset and spreading the pressure out over a bigger area. Also, it's mad stylish and my crews are always amused about the generaly mild, female SM wearing a black leather hat to call the show.
I love my hat, but I imagine any hat that would fit under your headset and fit close to your glasses earpieces would have a similar effect! I've been doing it for so long, now, that I forgot the original reason; it's just part of my routine!