When I insert a new ring it does not feel like it is that far in... however, I don't feel it. That is the whole point, it is in far enough as long as you don't feel it.
Also, when you and your bf have sex, he may feel it but he will also push it in further. You still shouldn't feel it though. Let me warn you though, certain times of the month you will feel the ring during sex. Don't know why, just is.
So, enjoy enjoy enjoy... I love the convenience of the ring and hope it works for you.