Try starting out with "junior" or regular strength tampons. They're thinner and easier to insert. After you become comfortable with them you can switch to whatever strength fits your flow. Also, I recommend beginning with the smooth applicator-type tampons, like Kotex Pearl. Smooth plastic is much easier to insert than the cardboard ones, and a LOT easier than O.B. Those don't have an applicator, and when I tried them they always ended up going in sideways. Hope that helps