As well, your sex toys may well be larger and are certainly far less flexible than a partner's fingers or penis. Anytime it doesn't, you not only don't need to just find a way to make pain go away so you can have it regardless, you're much more likely to have a sex life that feels good all around if you listen to and respond to what your body wants and needs than taking something so you can't hear its messages. If yours haven't so far, good on you. Anticipating pain actually makes it more likely we're experience it. Those things can absolutely help to make it more likely vaginal-entry sex with a partner is pleasurable, rather than painful. But the long and the short of it -- or the tight and the loose of it, as it were -- is that the vagina and vaginal opening are never one static size, save the size that is the closed position of both.
I'm not going to go into detail on why here, because this question and answer from the other day goes very in depth as to why, and it's also explained in-depth in this article here.
I feel too tight: should I use painkillers during sex?
If yours haven't so far, good on you. As for your other question, not all vibrators are meant to be used penetratively, and certainly not in the anus - anal toys need to have a flared base so they do not get stuck or lost which can happen. I sure wouldn't, even if she cleaned it like it had never been cleaned before. Masking pain with sex with a painkiller so you just don't feel pain not only could mean sex won't feel as good, it also could mean you don't notice when you or a partner are doing something your body isn't up to, which is a way to get hurt. I have 2 vibrators and a dildo.