Dear Carol-

I would love to have your advice and tips regarding the best tool or way to achieve full relaxation of the anal sphincter allowing penis insertion. I am sharing anal games with my female partner. She likes anal sex very much but despite extended warm-up sessions, a lot of lube and communication, she cannot accommodate my penis every time. This situation is happening two times out of three and it makes me feel frustrated and wondering what is wrong. I am pretty sure that she is doing her best but it is a kind of "rejection" of the penis by her (it may be that her anal sphincter is still not relaxed enough). The situation is even more frustrating for me (and maybe for her too) as we have to stop *after* the tip has successfully passed the anal ring. I am always very gentle and caring about her comfort. We are not having anal sex every day.

I do not need general advice (I know a lot about anal sex: I got Bend Over Boyfriend, have read Tristan Taormino’s and Dr. Morin’s books, learned a lot from the GV Magazine, etc.). I am mostly asking for some advice or tips regarding this specific situation: i.e., how to guarantee a fully relaxed sphincter and a wide anal opening.

Something that works well is a vibrating toy but maybe I am using some very large toys while she needs to start with something more progressive. Any vibrating anal toy you may recommend specifically and which in your experience works nicely? Thank you in advance for your reply. Please tell me also if you have published a new book or appeared in a new video?

Your faithful “AAF: Anal Aficionado in France”

Dear AAF –

How nice to hear from you again! I’m glad you’ve found someone who likes anal play too, but you have to be patient with her – you have a head start, you know. Here are some specific tips for relaxing anally that you can share with her and keep in mind yourself. First, her ability to relax anally might have a lot to do with her tension level in general – so if she has had a rough commute on the Metro, a frustrating day at work, or a fight with her mother, it may be less likely that she will successfully relax into anal penetration. The secret: Work on making her more relaxed before even beginning to play. Rub her shoulders, draw her a warm bath, share a glass of wine. Also make sure she’s very turned on before beginning anal play, because that can make a big difference too. It’s common for people to have a hard time with anal penetration unless they are aroused.

As you know, a lot of lube is important, but perhaps trying another sort of lube will make a difference. I’m not a big fan of the silicone lubricants for vaginal play – I find them hard to wash off my hands, never mind other areas. But for anal play I think silicone is often a good choice – it is extremely slippery, and while it will not prevent a tight sphincter, it may make some difference to her comfort, penetration-wise. Also, it may make a difference to lube ahead of your penis, rather than just putting lube *on* your penis. (This is true of any sort of lube, water-based or other.) To insert lube ahead of your penis (or a toy), use either a bulb syringe, available at the pharmacy, or a vaginal cream applicator, the kind that comes with contraceptive foam or vaginal cream medicines. Put lube into the syringe or applicator, slide it into the rectum, and release the lube inside. This way, even if lube has a tendency to come off because her sphincter is tight, there will still be lubricant inside her.

Note: If she complains of a burning sensation once the head of your penis is in, it could be simply that she is too tense; there is also a possibility she’s experiencing a sensitivity to the lube you are using now, or even to latex condoms. If latex is a problem, the Avanti or Reality condoms are both poly and shouldn’t aggravate sensitivities the way latex sometimes can.

Your insight about the size of your vibrating toy is a good one. If it is close to the diameter of your own penis, it may be too hard for her to accommodate it, and you should go for something a bit smaller. Using a vibrating toy is, however, a really good idea. I’d suggest you have a look at the P-Spot Plug, which is available at the Good Vibes website, and compare it to the size of the toy you’re currently sharing with her. Also, because this is an anal plug rather than just a dildo, she can wear it while you do other erotic things, which may help her more readily relax anally – and she may also find, since she likes anal play, that wearing a plug during other kinds of sex really turns her on.

It would be a good idea for her to visit a proctologist for an exam, to make sure she has no underlying medical condition that is being aggravated by anal penetration, like polyps. And if she is not rinsing her rectum before you play, depending on her diet, there may be some fecal matter left inside which is causing irritation for her. In such a case, stimulating foods (like coffee and spices) should be avoided, and she should eat a diet that includes more bulk (but fewer seeds and nuts that might cause internal scratching or irritation).

Finally, the secret to many sorts of sexual success is time – meaning that even if she feels emotionally willing and eager to have a good session of anal play with you, it may take her body more time than either she or you realize to prepare and relax. So try spending even more time in “foreplay” – which brings us right back to the point about arousal I made earlier. Perhaps wait to penetrate her until she has had an orgasm or two. They are, after all, among the most relaxing of experiences!