With my first regular anal partner, the key was teasing her mercilessly about it and refusing to do anything for her until she begged me for it.

She wasn't comfortable with me licking her down there, either, but lovebites on her ass really got her going. Tying wrists together behind her back also helped, as did clamping the left hand across her mouth... every time I set that scenario up, she was sure that this was the day I was going to do it. Eventually, she raised her hips on to me as I teased my cock at her anus. I wish I had stayed still and let her do the work!

If I had used a vibrator to stimulate her clit and toyed with her the way Cindylu's partner did, it probably would have sped things along tremendously.