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It helps to be really turned on and he should move slowly. My first time was with someone who was very experienced and I'm not sure that a better first time exists. Leading up to our meeting, I did use butt plugs a bit, just wearing them a few times a week for a few hours each time to get used to it. I never could do more than the size medium. You need lots of lube with butt plugs. You also need lots of lube with a dick, with any anal play.
That first experience started with him going down on me and making me cum. He played with my ass all along, one finger, then two, then three - stretching me and slowly getting me used to the feeling. We were in missionary position when he entered me (he wanted to see my face) and he went slowly and then paused inside to let me get used to it.
I would encourage him to go slow like this. It made for a very positive first time for me and left me more than eager to do it again.