I don't know if this applies, but on me there's a flap of skin across the bottom of the vagina. I have to insert the dilator at quite a steep angle (as Choloe said) to get between that flap and the top of the opening. It's really tight, but the angle also helps get it under the pubic bone. Once I get it started it slides in fairly easily, but getting it started can take some moving around. I kind of put it in an inch, withdraw a half inch, put it in another inch, etc., while wiggling it around the long axis until it feels right and then slide it in the rest of the way.
One of my GG girlfriends was interested in the dilators. She asked how I'm doing. When I said I was having trouble getting the big one started, she said "of course" like she would have the same difficulty.
- Kate