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as time goes, your anus will get used to it.
always always use condom too
Re-think the kind of men you are sleeping with. A guy who is there for just one night probably isn't too concerned with how you feel the next day. If you want to try anal, do it with someone who genuinely cares whether or not it's comfortable for you. Don't ever do something that hurts and could potentially leave serious damage just because some one-nighter wants it. It's not worth the pain and discomfort that you and you alone will end up dealing with. My advice? Wait for a committed partner who will be patient in doing it right.