I can't use tampons for a few reasons. One, I'm rather small and tight, because I never stick anything in there, so it's quite an effort to get anything in (for medical reasons, of course). Also, whenever anything does go in there, I feel quite strange. Not scared, not disgusted, not nauseous. Just weird. Something just feels wrong about it. Wrong like when you see a dog taking a crap on the side of the road but you think he was a little gray man hunched over. Wrong like when you see a man who's missing an arm or a leg. Wrong like when you have a large splinter lodged into your leg, it doesn't hurt, but you can feel the object embedded into your skin. Just wrong.
I've never had a pap smear. But I'll have to before I start T, I imagine. Or rather, after I start T. I'm not sure which, but because I have a female body, it's going to have to happen eventually. I've had a yeast infection rather recently and I had to stick a plastic device up in there so I could inject medication. That for me was very difficult to do. It really just felt wrong to me to have something lodged into a hole in my body that isn't even supposed to be there.
I don't have to close my legs during my period. You should ask your doctor about that... if it smells or is a flow that heavy, I mean. I don't think any of the boys here like their periods.
My pain is during my period, because blood is coming out of a hole I shouldn't even have. It's like an open injurty. I feel like a wounded soldier who got stabbed in the nuts, except I just keep bleeding and bleeding and bleeding.
As for a purse, I prefer a briefcase. I'm looking for something like this:

It's actually a doctor's briefcase. They're quite hard to find in this particular style (this one's vintage).
But really, there's no reason to need all that "stuff" when you're out and about. I carry around my MP3 player, my harmonica, my phone (which is on my belt) and my wallet. Most guys don't even carry that much. You won't need a purse/backpack if you carry only what you need. As for school, you can use a messenger bag if you want. That's not a purse.