Dear Lady Monster, My husband is obsessed with anal sex. At first, my attitude was “It's for exit only,” but I'm beginning to think more about it and want to tell him it's OK. Is it guaranteed to hurt? What can we do to make it feel as good as possible? Sincerely, Brown-Eyed Susan Hello Susan, Thanks so much for posing a wonderfully intimate question. You are being cautious and smart, asking the best way to make anal sex pleasurable. In the words of Nina Hartley, “You must earn butt, you cannot be given butt.” You obviously feel your husband has earned butt. This should be a great moment. Let me provide some tips. Lube. The anus has no natural lubricant, so you must provide it. Many people use silicone-based lube. Water-based lube is also good, but will become sticky more quickly than silicone. Crisco shortening is considered by many as the best lube for anal play. It is heavier, thoroughly lubricating the area for a long period of time, but will stain towels, sheets and blankets. Use ½ cup of Dawn liquid dishwashing soap in your regular laundry to remove the stains. When using condoms, use silicone or water-based lube. Crisco will disintegrate latex condoms. If you are using a different kind of condom than latex or are fluid-bonded with your partner, Crisco is an option. Do not use products with a fragrance, flavor or Nonoxynol-9. The tissue in the anal area can become very irritated by using these products. Also, NEVER go from anal to vaginal without first washing, changing condoms and/or gloves. Patience and Understanding. Begin with light touching of the area, gradually moving on to more probing techniques, checking in with your partner. You may never get past touching the outside, around the anus. Understand your partner's limits and accept them. Relaxing enough for penetration can be an issue for many in stress-filled lives. Take your time, communicate, listen, and only move at their pace. Knowing that one's partner is patient and respectful will help you go to the next level of trust. Knowledge. Teach one another the anatomy of the anus, how it differs between men and women, the vast amount of nerve endings and how pleasure and pain can be a part of touching and penetrating this area. It's important to note when using toys for the anus that the toy have a flared base. The anus can be a vacuum and will retract any object placed inside deep inside, requiring surgery for removal. Teach one another what feels good and what doesn't when touching the anal area. Discover each other's body, find excitement in this new area. Talk about using strap-ons, toys, butt plugs, vibrators – increasing sensations, pleasure and exploration. Anal sex is enjoyed more when partners can set aside their egos, to focus solely on pleasing their partner. Making friends with your asshole eroticizes the experience, and creates even more intimacy. The butt is very emotional – we carry many feelings of fear, shame, guilt, esteem issues with this tight brown ring. First shine some light and love there yourself, get used to the feelings and sensations, then show your partner what you have learned. There are a number of books and videos providing insight to anal pleasure and stimulation. I would not recommend most porn. Mainstream porn is unrealistic. It does not show the preparation that it takes to get an anus ready for penetration. It creates an illusion that people can easily accommodate any object into their rectum without hesitation. Please slow down and enjoy your journey to this new destination. Good Vibrations' How To Page on Anal Sex. Tristan Taormino’s The Ultimate Guide to Anal Sex For Women book (©1997) and video (©1999) Jack Morin, PhD's, Anal Pleasure & Health (©1998) Carol Queen, PhD's Bend Over Boyfriend I & II videos (©1998, ©1999) If you have a question or a topic you would like to have covered in this column, please go to: http://ladymonstersex.info and click on the link for the Google form. It is 100% anonymous. Thank you.