Need Advice on First Time Anal Penetration

Dear Dr. Betty,

My bf and I are attempting to have anal sex. I've tried explaining to him that prepping is needed ahead of time. The only thing is he's going by what someone else told him and that is to enter all the way in to get the pain done and over with.

He's length is 6 and a half inches, and he's girth is 5 and a half inches. What would you suggest on how to go about this? Any advice would be much appreciated.

Dear H,

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