i guess the idea of enjoying having any kind of bum fun is scarry to alot of men though alot of these same men will very happily give the g/f one round the back door,lol,i really dont know why we have this problem!!i go with all the other advise take it slow use plenty of lube and make sure hes very relaxed.i know it drives me wild when my g/f has her fingers up my bum wanking me off.Go for it.