Nothing but Agony--Help?

I'm a very petite teen (barely 100 pounds, small boned and slender--if any of that helps) and a virgin.
I got a free sample for the Softcup and wanted to give it a try. I'm also planning on purchasing a reusable cup, but I've been having a horrible experience with the Softcup. I REALLY, REALLY want this to work out, but I'm at a loss with what to do next or which cup to choose.

Last month, I tried to insert the first Softcup (the free sample included 2 Softcups)--I read all the instructions, watched the animation online to make sure I knew what I was doing. I even used lube and relaxed my pelvic muscles, but it wouldn't go in and hurt REALLY bad. I gave up on the 8th try.

This month I was especially determined to make it work, so I put a towel down on my bed, laid down in front of a mirror to make sure I was doing it right--it still didn't work. I tried to fit a finger in and felt a lot of rough-spongy tissue in the upper wall (which I'm assuming is my cervix?) I kept trying to get the cup in (at least 11 or 12 times) and just gave up. It hurt so bad and I'm still burning.

Has anyone ever had this issue? What did you do to make the cup work out and which cup do you use?

I've worn slender compact tampons a few times--they also hurt, but I was able to insert them.

I've never been to the GYN, should I go? I've also had excruciating cramps which is more common in smaller people and people that never delivered vaginally or are still virgins (or so I've read .) I don't know if there's anything they can do for me? Could there be something wrong? All the websites say anyone (even younger people and virgins like myself) can use the cups. I really want this to work, as I love the benefits (especially the environmental benefits) of the reusable cups.