Message: My Wife Will Try Anal—Now What?
Anonymous: Thanks to your blog and reading about all these other couples trying out anal only i’ve finally “come out” to my wife and confessed that its anal that i really want. It went down better than i dared to hope and shes said shes going to give it a try. I’ll do anything to make this work – so what lubes or positions or whatever will give us the best chance of success? I didn’t expect such a positive response from her but all the same want to do everything i can to ease her transition.
Congratulations! I wish the two of you luck and enjoyable experiences.
Lube is a very personal choice. Just about every lube out there has a number of people who prefer it above all else. Your best bet is to just try some different ones and see what you end up liking. Most of them will work fine, though there are advantages and disadvantages to each. Coconut oil is popular with a lot of people lately, but there are many water-based and silicone lubes that are good as well. (Note that silicone lube cannot be used with silicone toys.)
As for positions, many can work for first time anal. Spooning is fairly relaxing for anal sex, but cowgirl and doggy can both let her move while you stay still at first to help her control depth and angle.
Before you even try having anal for the first time, however, you should be enjoying anal play together for a while, starting her off first with small anal penetrations and slowly working up in size until she can comfortably fit something the size of your penis. Fingers make a good starting point for anal play. Start with one lubricated finger (be sure to trim and file your nails first!) during vaginal sex, or while eating or otherwise playing with her pussy. Gently move your finger in and out of her ass, stopping if it hurts for her until the pain fades and then starting to move again. Incorporate anal play with that one finger regularly into your sex life, playing with her ass as often as the two of you are both up for it. Try to always combine it with other stimulation she enjoys, especially at first. If possible, give her orgasms as often as you can while she has something in her ass. This will both amplify the strength of her orgasm and further develop the association of her ass being filled with pleasure.
When she feels very comfortable with the single finger, try adding a second. Take as long as she needs (it could be many sessions) between size increases, and back down for a while before trying again if an attempted increase causes her pain. Keep going until she can fit three or four fingers regularly. Each time you start a new anal play session, start back at the single finger and work back up in size to warm her up. The anus is a muscle, and a more sensitive and delicate one than most, so warmup is vital to painless penetration at larger sizes.
Once she’s easily handling multiple fingers during anal play, try some toys. Get her a butt plug, or several of a few different sizes. Don’t start too small with these, or they’ll quickly become useless as she becomes more accustomed to anal penetration. I’d suggest starting around the 1.5″ diameter point, with something like the Tantus Ryder, which is a good quality silicone plug and is very comfortable to wear, and will remain a useful toy even in the future. A dildo around the same size might be useful as well for practice before trying sex for the first time.
When she’s finally ready to try having sex with you, go through a normal warmup session first, maybe even giving her an orgasm beforehand to try and relax her more. Let her guide herself on to your lubricated penis. If at any point it hurts, she should just stop in that position and wait until it fades, then keep going, slowly working her way onto you until you’re fully inside, then pause again until she adjusts to you being inside her. She can then start moving, slowly at first, building up a rhythm. You should stay stationary throughout this initial process, letting her go at her own pace. After a few minutes, once she’s more used to it, you can try starting to move yourself as well.
The essentials: lube, warmup, training, and clit stimulation.
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