Trouble inserting anything down there

Hello, this is kind of embarrassing but I think it’s time to ask a question that has been on my mind for a while. Ever since I started my period in 6th grade, I have been unable to comfortably get a tampon in. I’ve tried almost every period from then until now, (I’m 18,) but I still cannot get them to sit comfortably. I feel like I am getting it in far enough, just no luck.

On another note, not too long ago I was doing a little experimenting with a dildo and it ended horribly. It was not going in and suddenly I felt a pop and a shooting pain, and then there was blood everywhere and I blacked out (lol.) My friend who I told said I could have popped my cherry, but I’m actually pretty sure I had already done that years ago and I didn’t think it could happen again. I’ve been so scared to try again and it makes me really nervous knowing I’m about to go to college and I don’t know if I can have sex. I don’t want to make it a big deal if it isn’t one, but I would like to have it fixed if it is. Thank you guys in advance, I’m just really nervous!