Message: Wife Hates Anal Discomfort
Anonymous: I love anal sex but am somehow married to my wife of over 3 years and she can’t take my cock in her ass. I have tried numbing creams and small toys. She hates trying and any bit of discomfort. What the heck can I do to get some anal?
If she’s willing to try anything anal again, spend a lot of time making it entirely about her pleasure. Don’t try anything penetrative at first, just ask if you can rub (and lick, if you’re open to trying that) the outside of her anus with a lubed up finger during oral and vaginal sex. No penetration at all, just external rubbing—and assure her of this. There are a lot of nerves in the anus and it can feel really good to have it externally stimulated, especially during vaginal/clitoral stimulation. If her only experiences with anal play so far have been painful or uncomfortable, she’s very likely going to be tense and fearful of further penetration, which will continue to make it painful. Beginning to associate that area with pleasure instead is a vital first step. But make sure you ask before, of course.
If she does enjoy this, make it a regular part of your routine. After a while, ask if you can try inserting the finger you’re using to rub her with. Don’t do this on its own, do it during something that’s already pleasurable to her, and possibly after she’s already experienced at least one orgasm in that session. For someone who is inexperienced, anal penetration can feel a lot better while while being pleasurably stimulated in some other way. If this works, build up to giving her an orgasm from oral/vaginal/fingering while also fingering her ass. Anal penetration during orgasm can often amplify its strength.
You can also do things like giving her a back massage that evolves into a butt massage and ends with you masturbating her to orgasm while fingering her anally. Again, she needs to know in advance that this is what you want to do and be okay with it. Never penetrate anyone anally without them being okay with it in advance—that’s the fastest way to get someone to lose interest in anal play.
From there, you could try a small butt plug during oral/vaginal, or anal beads which you pull out during orgasm.
Essentially, you need to focus on making the idea (and reality) of anal penetration appealing and pleasurable to her through very slow advances over a period of time. You shouldn’t even attempt actual anal sex with her unless she has become more comfortable with the feeling of anal penetration and is enjoying anal play. And then there’s the possibility that she simply doesn’t like it—not everyone does. A lot of the dislike comes from being improperly introduced to it, but not everyone is wired differently and some people just don’t get any pleasure from it. If she doesn’t like it, you’ll just have to respect that.