> How do you go about thrusting!? In addition, I don't want him to feel degraded, as it took a long time for him to open up about wanting this kind of activity.
As for introducing anything into the anus, I recommend that you and others interested read this article listed in the Index.
"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.