"the trick to painless anal is to just sit on the tip of the cock for about 20min, it will sting a little at first, after the 20min the rectum muscles relax an it starts to stretch to accept the cock, let it slowly slide in til its balls deep then start with slow long strokes. as the muscles relax more the cock will go in an out easier, then the cock can gradually build up speed til he cums balls deep. after the first load the rectum will be stretched enough to take more."