This is definitely the right place to have so many questions! I'm glad you came here to talk with us.
Masturbation and pleasure are so
individualized. What feels good to one person may do nothing for the next. Getting to know our bodies can be a really daunting task at first -- but it gets easier with time, and it's *so*
worth it in the end.
Many, many people can't climax with penetration alone. It's very common. So the question may not be whether being penetrated can make you orgasm, but rather, whether you enjoy it as its own experience. Have you read our article Going Solo: The Basics of Masturbation
? It may help to read up on a whole bunch of things to try re: masturbation and see if it sparks some ideas.
Let me know what you think of all of that! You can also ask any of the other questions you mentioned if you're comfortable doing so.