Three things you need to do to prepare for anal sex:
Use lube. Lots of it. It will be very painful for her the first time.
Poppers. Gay guys often use mild amounts of poppers (http://en.wikipedia.org/wiki/Poppers), which supposedly helps to loosen the anal passage. I'm not saying you should, but it's an option :)
Go slow. You should take it very, very slowly to begin with. Once the head is inside, then wait for her to adjust, and I would even suggest telling her to back herself on to your shaft (again, very slowly), as this will allow her to remain in control. This is important if you ever wish to have anal sex with her again :)
Good luck! It's actually pretty fun.
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Answered: 15 Apr '12, 16:57
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Yikes! Dude, you didn't say whether you'd be giving or receiving, LOL... I won't be too much help for you in the "receiving end".
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Answered: 26 Apr '12, 13:58
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