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If it hurts you're doing it wrong. Why do people always want to rush anal? Trying that is something you should take your time for. Have a nice relaxing bath together, do some foreplay, have plenty of lube handy and spend as long as you need to make it work without it hurting.
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Well, damn. Havoc gave good advice. And about bumsex, too.
(I was going to write 'poojabbing' in reference to Alcar's sig, but it just made me feel nauseous)
The only thing I have to add is that it's a bad idea for your first attempt to be done with someone else. Leaving aside the fact that you're going to be tight, you'll probably be more nervous and that will make it difficult to relax. After all, it's a reflex for the sphincter muscle to clamp down and you need to train yourself to get past that. Best to try things out on your own first and get used to the feeling before inviting anyone else to have a go.