Dear Bearded Confidant,

I'm still a stranger to anal sex. I tried doing it with my friend. He inserted only two fingers and there was pain in that area. I tried relaxing and the pain still remained.  I tried using Johnson's Baby Oil to lubricate it. I want to know if there is any practice or lubrication that you can recommend to me? Thank you.

Dear Mark,

The first time you have a dick sliding across your prostate as you start to cum, you'll redefine the meaning of "orgasm" forever.  Anal sex may be fun for the man on top, but the man on the receiving end gets treated to an indescribably powerful orgasm because he gets stimulated in multiple ways.  If anal sex ever hurts, you're definitely doing something wrong.  The three real keys to pleasurable anal penetration are taking your time, relaxing, and getting slicked-up. 

Try starting out by giving yourself a oil massage (use vegetable-based massage oil such as almond or sesame and rub it all over your body), followed by a hot bath.  Next, moisturize your ass by gently applying some aloe-vera gel or water-based lubricant with just the tip of one finger.  You can then apply more lube with your partner.  Spend plenty of time lubing up.  Find a comfortable position, relax, and use just one finger to slowly insert more and more lube as your partner kisses and fondles your body.  When you feel ready, insert your finger further and further to get the lube deeper inside your ass. 

When your sphincter muscles have gotten used to the feeling of something inside you, have your man lie on his back, lube up his dick until it's slick and hard, and straddle his hips.  You will control how deep his cock goes.  Slide that shaft in slowly, half an inch at a time, and concentrate on relaxing.  When you get the whole cock inside you, sit there for a few moments.  To pass the time naturally you might want to reach down and play with your man's chest or ask him to pull on your dick.  Soon, you'll be ready to fuck yourself into a frenzy. 

Be forewarned that if you decide to change positions (such as lying on your back with legs in the air, getting on all fours, or standing up and leaning forward) you'll have to get used to the new sensations before your man starts thrusting hard.