I have a friend who won't wear heels because "they're not comfortable." Have you heard this one? Keep in mind that this friend once wore a rather unfortunate ensemble (at home) that involved a significant camel toe. My argument here is that in no way is a camel toe ever comfortable (or attractive, but that's a whole other eggplant), so clearly comfort cannot be the only consideration here. So, why exclude beautiful shoes from your wardrobe if you're going to allow the above travesty?
Now, I will admit that my running shoes are more appropriate for walking than four-inch platforms, but that doesn't mean I'm going to wear them with a pencil skirt. And I have to say that many of my heels are no less comfortable than my flats (and so much cuter!). I only have one pair of heels that are actually uncomfortable. My four-inch leopard platforms are four hour shoes (meaning that I regret wearing them after four hours). Usually if heels are getting unpleasant, sitting down will relieve the discomfort; however, this particular pair of shoes is not improved by sitting. It has to be something to do with the design, since I have other shoes in similar styles, the same height (or higher) that are not uncomfortable. Regardless, don't knock it until you've tried it and slip on some heels!
And, now about that other issue... if your girly parts are visible, your pants don't fit. It's not comfortable for the rest of us (and I don't know how it could be for you).