Phone Sex, I Like a little mystery
WYR read sexy story alone and masturbate or with have a someone read it to you while you both masturbate?

Quote by Dancing_Doll
Ask her if she is interested in trying anal again.
If she is, it might be worthwhile to get her a butt-plug, an anal vibrator and a bottle of lube, and let her experiment on her own a bit. She'll probably feel more comfortable going at her own pace at first so that she can have a good experience with it and understand how amazing it can feel. It might also help if she's experimenting without the pressure of you sitting there with a hard-on, wanting to speed things along. If she experiments on her own a few times, she'll probably be more open to trying again with you.
Because she had a painful first attempt, she will be all nerves at this point. If she's the one lubing a butt-plug or toy and inserting slowly on her own, she has the option to go as slow as she needs to.
I have a friend who is "trying to get comfortable with anal" and this is what she's doing to relax herself to the experience, after several failed attempts with her man... A bit of anal-training without any pressure from you is probably the best way to go with this...