I'm not a doctor... but I can tell you from my experience that if you're not comfortable about engaging in anal sex (for any reason) then avoid it. And, simply tell him... no. Most men, at least the more sensitive or caring ones, will understand and not press the issue... few would take it personally.
My guess is that his hints may actually be hopes. And, maybe he figures that if he brings up the subject often enough that one day, you'll change your mind and say, yes.
I can fully agree with iam1butterfly!!
He is waiting for you to give in, but if you don't feel comfortable with it just tell him in all honesty that this is not what you want to do and that it will never happen.
If he does not understand and does not respect your wishes, you might want to think about if he is serious and respectful to your feelings!!!
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