try a glass toy. Only a little lube goes a long way. Super slick surface. I would pick glass over silicone any day. Just look at the sizes and try something small first.

I was given a couple of silicone plugs, but I didn't like them. I recently bought the luxotiq anal plug. I love it! The top is the size of a fingertip, the taper is gradual, but it is big enough that you aren't longing for the next bigger toy and it stays in nicely. It does everything I was wanting. I may not get anything else for a long time because I am very content with this one!