i occassionaly have anal sex with my girlfriend but its something we keep for special occassions.i personally find it great cause it has this really narrow feeling and she likes it as well. i figured out that for a girl to like having anal sex she has to be really really arroused. Try it with a girl that just wants to have sex and it will fail. Try it with a girl that is craving for sex at the time and it will succeed. A tip for couples that have tried and found it painfull at the first time of later : Try different positions! . For us doggie almost never seems to work , on the other hand she standing up and leaning forward and me coming from behind works great all the time . So if you are certain that you didnt go in too fast , or didnt use enough lube , try a different position.