So the other night the wifey and I were having sex where we would move all around the bed and change positions a lot. A couple of times I almost entered the rear and eventually she said to just put it in. I know she definitely enjoyed it especially since she can't seem to stop talking about it, but I have mixed feelings. For one, we didn't have any lube and I didn't want to hurt her. Second, she's had bad experiences in the past with it from way before me so I was kinda hesitant. We do plan on getting lube and I think it will feel better for me with it. Will it be a lot better with lube? Also should I be wearing a condom?