Dear Bearded Confidant,

I have a problem. Having anal sex has always turned me on. I have  gone as far as sticking a few fingers up my hole, or lubing something and  sticking it up my crack. Last time I tried, I wanted to orgasm just by the  anal sensation alone. I put a lubed condom on a short plunger handle, and  went to thrusting. The problem was is that it burned really bad, and just  made me want to have a BM. Needless to say, I was very disappointed. Am I  doing something wrong, or is anal sex just not for everyone? Please help.   

Dear Fire in the Hole,

Your problem is that you are shoving too stiff an object into your ass.  If you substitute the plunger with a soft rubber dildo or flexible vegetable, you shouldn't experience the burning sensation.  Anal toy play should never create discomfort when it is done correctly.  See my archives for advice on toy play.