Finally

Dear internet,
I finally had sex.  It wasn't great, it wasn't that comfortable, he didn't go in that deep but it was something resembling sex without me crying in pain.  I was crying, grinning, shaking, very emotional.
We were fooling around and I felt ready so I tried going on top, and all the muscles tightened and I started crying in frustration, sitting on top of him.  It was ridiculous.  I was just sobbing and angry.  He held me and stroked my hair and after a long time, he started slowly touching me again and after a lot of that, he put his body over mine and gently pushed against me, without the intention of going in, but it did.  We put a pillow under my hips and we were able to go a little bit deeper.  I said, 'This is SO EXCITING!" and he said I was a strange and wonderful woman.  I told him he'd just taken what was left of my virginity.
Still a ways to go, but a huge step forward.