I was wondering what the best way to start a women into trying anal sex is? I have always fantisized about fucking a woman in the ass but am not sure how to go about it so that I dont hurt her. I know she loves it when I rub her ass hole and lick her but i have never tried to penitrate her? Any suggestions?

SAME situation bro!

I have rubbed my girlfriends asshole and slipped a finger in maybe an inch during sex. Licked her asshole like crazy during a 69.. but when I mention anal sex she says shell NEVER try it...

I would suggest that the next time you two are playing around , and you are licking her anus, simply wet or lube a finger and as you are rubbing slowly push into her and let her tell you if it is something that she is enjoying. I think it is important to have open communication, and simply ask her if she is likes that, and if she would like to progress things up to anal sex at some point, if she says it is something she wants to try. Then I would suggest you learn all you can about anal sex before you try it, there are several great web sites that are very informative, and proceed slowly as you are both comfortable and she and you will have a great experience

Mikey-
Yeah I will try that next time we 69..