Menstrual Cup First Timer Nightmare. Send help.

So I just bought a diva cup. I spent an hour trying to insert it to the point where my legs were trembling. I was so frustrated that I decided to take a breather and come back later. Now it's later and I still can't insert it.

I do the push down method to make the tip smaller and as I slowly work it in, sometimes it starts to become painful. I let it stand for a minute to relax and I continue. If the pain subsidies and I'm able to push it into the correct-ish spot, the cup won't pop up to its position. I tried twisting it 360 degrees and the "run your finger along side of it and press gently" but when I do that, I feel the pain again.

I think that the cup might be too big/long on me. I bought the size 1 diva cup and I'm 19 years old so technically it should work. I watched many videos about the insertion but none of them had a problem I had with the pain and the "pop" thing, so I turn to the real men and women of eve and hope that any of you have an answer I might be looking for. Is the pain normal? How can I avoid it? How do i get it to pop out? And also, does the tail thing have to be inside of your vaginal opening?