Welcome to the SI101 Board and its Forums. I hope you enjoy participating. Please begin by familiarizing yourself with the FAQs, the Posting Guidelines section, and especially the Index, all found at the top of the main screen. The Index lists links to helpful informative insightful as well as how-to articles.
Here is one that will help with your concern:
"Playing Ball" and How To Tips for Prostate Massage
This is also an excellent tutorial for people interested in and concerned about the how-to of Anal stimulation as well as play.
There is so much the two of you can do. Please do your homework by reading the articles listed in the Index. After that, pick up the book "The Joy of Sex" at your library or local bookseller.
Anal does not need to include intercourse. More often than not anal play is just that--fingers and dildos. Before you engage in anal stimulation, read the article on it as well as all the others listed in the Index and discuss what you have learned. Then apply what you have learned and expand upon what you are already doing using this new information.
If you decide to try anal intercourse, the article will explain how to go about it safely and without discomfort. However, having said that, read the part about there being a fine line between pain and pleasure. He may just change his mind regarding pain.
I believe if you learn how to make out in all of its progressive stages, and work together in partnership, understanding that making love is not what we do to each other; rather, what we do with and for each other, that you will find a new appreciation for what you already do.