Okay- I'm new here, please help me out.

So, I'm new to this whole thing. This app, masturbation, everything. I'm 16, and just started masturbating recently. I have tried previously but it either didn't do anything for me of I didn't identify the feeling I was having. I spent a lot of time being confused about the things my body was telling me, and being to nervous to do anything, even though I had my first period at 12. So now, I realize what arousal is, and I think I'm pretty horny. But. The problem is, I'm not sure if I'm orgasming or not, I'll stimulate my clit for a bit, and then ramp it up a bit and then I'll tense up and it will become super sensitive till I can't touch it. I also feel the urge to try penetrative stuff but when I've tried fingering myself but it hurts and I can't get in that far without feeling something stopping me. Am I aiming the wrong direction? And should it hurt? I think it's my hymen but does that hurt to break? Sorry this was long, I'm just really looking for answers.

Thanks!! (Also I'm posting Anon cause I'm not quite sure about this app yet)