Hey Charismakween,
Welcome to the boards
Your post was not too long at all! That's what we're here for.
There are a bunch of things you brought up that I want to respond to
First, one of the main ways that people with vulvas/vaginas masturbate is by stimulating their clitoris. Most people with vulvas need direct clitoral stimulation to orgasm, only 10% or 20% (I've seen different statistics) of people can orgasm solely from vaginal insertion. This is partially because the clitoris has FAR more nerve endings than the vagina, even more than any other part of the body! So hopefully that helps explain why you weren't always experiencing much, if any, pleasure when inserting things inside your vagina. (Also, for vaginal insertion to feel good, it's important that one is very aroused and relaxed, which is not always the case when we are first experimenting with our bodies in masturbation.)
You said that you get "no stimulation" from your clitoris, but actually when you are squeezing your legs tightly much of what is giving you pleasure is your clitoris! What we think of when we think of the clitoris (what we can see on our bodies) is actually just the glans of the clitoris. It is a much larger structure that also is within the outer labia and surrounds the lower portion of the vaginal canal. You can get a visual here (as well as learning more important information about your anatomy):
Innies & Outies: The Vagina, Clitoris, Uterus and More. Also here's a bit more about different ways that people masturbate:
How Do You Masturbate?
It sounds like overall you have found things that make you feel really aroused, have found an activity that gives you pleasure, and have reached orgasm multiple times. That's all great! What is that you are looking for moving forward? More activities that bring you pleasure? Reaching orgasm more often? Something different? Let us know and we can go from there!