Thanks for your input. I haven't asked them to, but I would like for someone to just ride along with me to check my positioning out. To answer your questions:
Do you sit a lot - especially for your job? Yes, I have a desk job

And I cross my legs...REALLY hard habit to break.
Do you do any stretching? Not really...now and then, not enough!
How do you warm up for a ride? Start riding, lol
Does the pain happen right away or does it develop over time as you are on a ride? I've developed a sore spot, so I immediately feel it (unless positioned as I was this past weekend).
Do you have the same pain if you wore regular non-cycling shorts? In my shorts quest I purchased a couple of tri-shorts, which seemed to help, but actually just moved the sore spot in question from my left side to my right (wtf?).