Assuming a normally medium sized monk takes the Titan Strike feat to increase damage of unarmed strike as if +1 size category, and then uses the stonefist gloves to do a similar thing for a total of +2 size categories, how do I figure the damage?
What if that same monk is also a gestalt druid who wild shapes into a large creature thus gaining an effective +3 size categories to unarmed strike damage?
The chart shown for the monk is already set up according to size.
A medium monk starts at 1d6, then goes up to 1d8 at level 4, etc.
If you got Titan Strike as a medium creature at level 1, you'd be doing 1d8 with your unarmed strikes.
At level 4 it'd go up to 1d10. So on and so forth.
As far as I'm aware, you lose unarmed strikes in shaped forms to instead gain their natural attacks, and if you take a feat, you can use your monk (and any unarmed) abilities with those instead.
In that particular case, those natural attacks would be considered 2 sizes higher, because it shows the damage for that creature relative to it's size already.
My problem is that the chart doesn't go past a certain point for monks. What's after 2d10?
I want to say 4d8.
Refer to this chart
2d8 goes up to 4d6, I wouldn't say it's too far fetched that 2d10 goes up to 4d8.
Don't know what your damage die would be(it REALLY gets hairy after a bit) but as for the Natural Attack issue, just get Feral Combat Training. Any feat or effect that affects unarmed strikes affects natural attacks(as well as lets you flurry with them).
So you wanna be a flurrying Bear w/ Titan Strike hitting at +6d8? There you go.
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Assuming a normally medium sized monk takes the Titan Strike feat to increase damage of unarmed strike as if +1 size category, and then uses the stonefist gloves to do a similar thing for a total of +2 size categories, how do I figure the damage?
What if that same monk is also a gestalt druid who wild shapes into a large creature thus gaining an effective +3 size categories to unarmed strike damage?
Well, unfortunately, as far as size increases go - You can only have one to your damage die, and one to your actual size. So they wouldn't stack(though, I don't conform with Paizo on this one). This has been repeatedly expressed to me in the past by many people.. I'm sure the FAQ is out there and I will link it when I can.
You'd take whichever effect is greater, supposedly.
Now for your second question, I can answer that.
Since you're part Monk, your Unarmed Strike can be with any part of your body, including a headbutt or for more silly reasons, a pelvic thrust. It's also effected by Strong Jaw, btw. I'd recommend Strong Jaw + WildShape into a Huge creature. You'd be at Colossal sized damage. If you're damage maxes at 2d10, it'd suddenly be at 12d8 for colossal.