It should ease up some. It wont ever be where you dont experience a little pain at that point, but thats part of the fun! Keep using your toy on yourself, it will get better.
But remember this, if you stop for a while, you're gonna have to start all over with stretching yourself out again. I used to be able to fit almost all my fingers in my ass, but then I stopped for a year or so and now I can barely do two.