I also only started to think about bottoming in my late 40s. Before that my only attraction was to shorter guys with really big bubble butts and they always wanted me to top. And it always felt great to do so. At any rate, besides cleaning out and fingering myself with a good lube as described above, I also try to loosen myself up by using a 3 - 5 " dildo (I want to make sure they have to do some of the work). But I always had a problem because the dildos tended to burn the tissue it rubbed against when it was being used. However, once I slipped a condom over the dildo I could go to town on myself. The downside is that I always had to make sure that I have some condoms for smaller cocks. Generally I only had Magnums. Oh, well, we do what we must.