I'm assuming that you're a guy who's never done it and are worried about possible pain...
I actually asked my mum this question a long time ago and she said (now this is embarrassing and I'm only telling you this because we will probably never see each other ) that my dad had told her when they were younger that a man's first times, if he's uncircumcised, can be painful. Of course, I have no idea whether or not my father has been circumcised but when my brother was a few days old, they had him done, so maybe it's true and they wanted to make his life easier...
If your foreskin is bothering you, you could always book yourself in to have it removed once and for all; then you don't need to worry about this matter.
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