Hey dogmajay,

You want to take it very slow the first time you have anal sex. You want to have plenty of lube with you the first time. My suggestion is that you start by sticking your finger up her ass. Do this for a while, maybe 5-10 min. then keep adding a finger every 5-10 min. depending on the girth of your cock. After she feels very relaxed and you lube her ass and your cock up very good begin to stick the cock in. Do this inch by inch slowly until you have your entire cock inside her ass. Then slowly pump her and make sure you listen to her and don't hurt her too bad, because it is going to hurt her the first couple of times before she gets used to it.

Also tell her to rub her clit, and finger herself to offset some of the pain she might be feeling.

An alternate method would also be instead of using fingers, using different sized dildos, varying from small to about the size of your cock. And I don't condone this but it is also said that before you try anal sex the first time you should smoke a little of the wacky weed to relax yourself.

I hoped I helped you out man, and good luck to you and the lady!