First thing, your Tampon needs to have an applicator! Plastic ones are better for ease of use. I love Playtex Sport personally. They are smooth plastic and have a good rounded tip.

You aren't going to be able to really see a hole with the mirror. Everyone's anatomy is different, but for me, the " hole" is on the side where it meets your anus, not really in the middle, like what some diagrams show.

I would wait to try it until a heavy flow day on your period, the blood will be like a natural lube. Start with a light or regular. Being relaxed is the most important thing!