QUESTION
My boyfriend asked if I would be willing to have anal sex with him. He knows that I used to like this but after being raped several years ago, I have never tried again. I trust him and know he would stop if I asked him to. When we use small toys I'm fine and remember why I used to like it. Is there any position we could try that would be easiest to help me enjoy this again? Anything else we could try to help me relax?

ANSWER
Working through any kind of sexual trauma takes time and patience. It is great that you are able to talk to your partner about why anal sex might be difficult for you now.

As for position, with your partner on his back, you might try straddling your partner so you can sit down on his penis. This allows you to stay in control during anal sex and makes it more enjoyable. Once you are relaxed while straddling him, changing positions will come more naturally. Don't forget to use lots of lube, go slow and don't force it. Remember that anal sex is all about your pleasure.

The Ultimate Guide to Anal Sex for Women, by Tristan Taormino is a great guide and confidence-builder.

To your health,
Dr. K