It will hurt like a bitch if you do it wrong. First, practice with dildos, vibrators, prostate massagers...anything that you can fuck yourself with that's safe. Use LOTS of lube and take it slow. Insert a little, pull it out a little, repeat until it goes in & out easily and doesn't hurt. The initial pain of insertion will turn to unreal pleasure, it ALWAYS does, and you'll be shooting off like you've never shot before! The people who say getting fucked is too painful have usually been fucked by a thoughtless top who hurt them. Don't pick a guy you don't trust, and tell him it's your first time. And don't just drop your drawers and let him bone you, foreplay is essential! A top who knows what he's doing (or is caring enough to be patient) will finger or rim you, maybe use toys on you, anything to get you loosened up and horny. And if it's still unpleasant, just keep trying. Once you get cum while a big hard dick pounds your prostate, you will want it all the time!