Hey there, Slipknot0129,
I, too, have a fat head. I mean really big, and I wear glasses. I ran into the same issues about which you're concerned.
The most comfortable pair of headphones for your head are going to be the Audio Technica ATH-AD700 (~$90). They are super-comfortable for people with big heads and excellent for gaming due to their open-back design. The most common complaint is that it feels like it's going to fall off, but that's for pinheads, not people like you or I! They are highly regarded in their price range by both headphone enthusiasts and amateurs alike, so buy with confidence. However, they do lack in the bass department, a downside of the open-back design.
If you want a super-comfy closed-back headphone and you've got a big head, the price jumps a bit for the Beyerdynamic DT770 (~$180). Super, super comfortable and bass-heavy without sacrificing quality, but not quite as good for first-personal shooters due to the closed-back design. Now, if both of these are outside your budget, you might consider the JVC HARX-700 (~$35), which I use on a daily basis. They're comfortable with quite a bit of bass punch.
Then you just need any number of clip-on or desktop mics and you're good to go. Go ahead and take a look through the Headphone FAQ at the top of these forums for additional suggestions, or visit this thread on Head-Fi for some additional suggestions.
Happy gaming,
Boz
*Edited to fix links*
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