Dating an anal virgin?

So, long story short I fell hard and fast for this guy. We've done mouth/ hand stuff a bunch already and he hasn't ever bottomed (or topped, but he wants to bottom). I've never slept with a "virgin" before, and while I'm fairly comfortable with my end of the bargain, I really really care for this guy and want to know how I should handle his first time.He keeps saying how bad he wants it, and I'm holding back because I want to wait until we have a house to ourselves and not just the back of my car, to make it special for him. I want that first time to be as special for him as he is to me.Do I bring up douching? Do I start with a toy? Do I let him ride me to control it himself? This is a brave new world for me, and obviously for him, and I want to make it as good for him as possible.