Different strokes for different folks.

Try riding a short-to-moderate distance (20-30 miles?) in unpadded shorts and see how you feel. If you feel good, try increasing the distance - and see if that works. We are each a grand experiment of one.

Typical entry-level shorts (probably PI?) tend to have a relatively thick, stiff chamois. You might want to look at slightly more expensive shorts, European brands, or even tri shorts. Personally, I'm a big fan of Castelli shorts - from the bottom of the line to the top, the chamois tends to be thin and flexible and exceptionally comfortable.

If you aren't using it, you might want to try some chamois butter as well.