I'm a little confused about how sometimes it's painful, but you also say you can't feel him sometimes. I'm assuming this is during different sessions. Is that correct?

A product for making the vagina flexible and helping with vaginismus is available. One type is "vaginal stints". They are insertable cylinders in graduated sizes from very thin to 2 inches in diameter. I've often thought that they are a great product for those that want to work on it at home.