When it comes to older women and anal sex, the rules really aren’t any different than they are for women your age. There are two important things to remember: a lot of women just aren’t into anal, and it’s not something to be brought up lightly.
If you’re lucky, your cougar will let you know that she’s into anal sex, because the best way to find out is to have her take things in that direction while you’re already in the throes of passion. Most of us aren’t that lucky, however.
If you’re wondering whether a woman likes anal, or is at least open to taking it up the ass, it’s probably best not to just come right out and ask her, unless the two of you are already pretty damn comfortable with each other at that point. You also don’t want to find out by sticking your finger in her butt during sex without warning. The best way to approach the subject is as a part of a larger conversation about sex – one of those “what’s the dirtiest thing you’ve ever tried?” sort of talks. Those don’t usually happen in relationships right away, and you don’t want to rush having them, so patience is often an important part of the equation here.
If you find that she does like anal, remember the importance of going slow; despite what you see in porn, you can’t just plunge your cock inside a woman’s ass without plenty of lube and foreplay. This is especially important if your partner isn’t experienced with anal. You want her first experience with anal sex to be as pleasurable as possible, particularly if you want it to be shappen more than once. Take it easy and go slow, count on her to let you know if and when she’s ready to take it harder and faster.