First time sex

Me and my bf are wanting to have sex for the first time. He says he wants to do without condom also I fear about the pain in first time sex he says without condom is easier to slide in? He agreed to not cum inside me. I just want to get used to having sex off and on now. How to make it more pleasing and easier? I havent showed him my pussy yet he's too charged up I feel shy of how he'll see it and all. But i know once im with him he'll make me comfortable enough for sex