I completely agree with Tommyhot and would add two more pieces of advice. In his advice he suggests using a latex glove about 10% of adults, including myself, are allergic to latex. For me, if my skin comes into contact with latex, depending on the length of exposure, it varies from anything extreme itching to where my skin breaks down and begins bleeding. My point here is make sure he is not allergic to latex. Second point is from my experience anal play works the best when foreplay has been occuring for a while. If you just dive it to it you may not get the response you are wanting.