My boyfriend wants me to try anal sex on him

Dear Sex Educator,

My partner would like me to perform anal sex on him. I am willing but I have never done that before, and I am not sure how to proceed. Could you please give me some information on this?

Here are our guidelines on anal sex for beginners. For more information, we highly recommend the books Anal Pleasure and Health by J. Morin, and The Ultimate Guide to Anal Sex for Women by T. Taoirmino, which fully discuss every aspect of anal pleasure, and how to enjoy it safely and successfully.

When first exploring anal eroticism, please keep in mind the following:

  1. The person who is being penetrated should be in total control. This is their pleasure you are facilitating, and if they want you to stop, slow down, or increase the massage time, your job is to listen carefully to them and do what they say. Just because someone else “liked it that way”, doesn’t mean anything for this particular partner’s pleasure.
  2. The anus and rectum do not produce their own lubrication, so you should choose a good, thick lubricant to accompany your exploration. We generally recommend using a thicker water-based lubricants such as Sex GreaseSliquid Organics Gel, Slippery Stuff, or FleshLube since many people enjoy the cushioning effect of these thicker lubes. Other people like slicker lubes, such as UberLube or System Jo. You may like some other lube yourself – this is a great time for exploration. Do not use a desensitizing lubricant, gel or cream; it could block the sensation of pain that would tell you that you are hurting your partner.
  3. Start your exploration with your hands, covered in nitrile gloves. Non-Latex and lubricant combine to provide a very slick, sexy surface for the recipient. Also, your hands are protected from contact with bacteria that could infect them if you have any cuts. Hands are more sensitive, warm and responsive than toys or objects, and we think this sensitivity improves the massage as well as the connection between partners.
  4. Begin by massaging the anus and allowing it to relax. You should notice that the anal opening and pelvic floor muscles begin to feel softer to the touch. As the muscles relax, begin dipping the pad of your finger into the anal opening. Ask your partner to move on to your finger, rather than allowing you to “push in”. This way, your partner can invite deeper penetration if desired.
  5. Stay connected by communication with him; ask him if it feels good, or hurts, and ask him to tell you when he wants more. This will determine how deeply you will go, and how many fingers you will use to penetrate him.
  6. Be aware that if your partner is a male, you will touch his prostate about three to four inches in. The prostate is a walnut-sized gland made of spongy tissue with lots of nerve endings, and it might produce very pleasurable sensations when you stroke it. (This is a good time to ask him if he likes the stroking, and how he likes it …) Your attentions may produce an erection, if he doesn’t have one already, or may lead to orgasm for him.
  7. Does your partner want more? If this is pleasurable, there are anal plugs and anal vibrators they can wear during intercourse, or you can also choose to wear a harness and dildo to penetrate your partner. When using toys, keep communicating and using lots of lubricant so you’re certain you are providing pleasure, not discomfort. You will not have the same sensitivity with a toy as you did with your very sensitive fingers. Let him direct your actions as much as possible.

If you two decide to share your toys, please remember never to put anything into your vagina that has been in the anus – unless you’re consistently covering it with a condom, or washing it thoroughly with soap and water between uses. It’s probably easiest to use condoms on your toys, and change them when switching them from one to another person. We also recommend that you keep your toys segregated, so that each of you has your own toys, as the bacteria in your rectum could be different from that in his, and it’s best to avoid exchanging them.

So the main points are to communicate through the whole experience, use lots of lubricant, and take it slowly and gently. Anal sex can be very pleasurable for lots of people, men and women.

The Sex Educator (with some help from Dr. Myrtle)