My# 1 tip for pleasurable anal sex is to do it doggy style, and while your man is thrusting away (slowly at first! ) use your hand to stimulate your clitoris. If you can bring yourself to orgasm this way during anal sex, you'll see why people like it so much. This post was originally published in 2014 and has been updated. Follow Anna on Twitter.
Get or make yourself a cock ring that is about an inch wide and sits comfortably at the base of your cock when semi erect. I made one with layers of cling film. Follow the tips on this forum to get the head of your cock into your ass then slide a lubricated under the cock ring.
Anal plugs are also an excellent idea for those just beginning to explore anal masturbation, as they slightly help dilate the anus while enjoying a discreet pleasure. You will get maximum pleasure from this toy if you wear it while masturbating vaginally, so this will also help you get used to anal pleasure.