Dear Bearded Confidant,

As a newcomer to anal sex, I wonder, how deep can a dick be planted up the ass?  My partner's is a 9 incher and I'm worried if he gets it more than halfway in that it will damage something.  How far can it safely be put in? 

Dear How Far,

At nine inches, your man's tool (or should I say crowbar?) is more than adequately qualified to keep your ass well-fucked. Most guys should be physically able to handle taking in a nine-inch cock, though it might require a little time to get used to feeling that much man inside of you. The key to anal sex is taking it slowly, relaxing, and using lots of lube. You'll need to get lube all the way up nine inches of your ass, and that will take some time in itself. Work some lube in your hole with your fingers, then lube up your man's cock and have him stick it in as far as it feels comfortable to you. (That will probably be just an inch or so at first). Then have him pull out and repeat the process. Eventually, the head of his shaft will push the lube all the way up your ass. If at any time you experience discomfort, have your man pull out, re-lube, and try again (perhaps in another position). If the pain intensifies or persists, be honest with your lover and tell him that he's just too much man for you to take right now. Then suggest jumping in the shower and blowing him while he sprays his balls with hot water.