Anal Sex with Older Women

Q: Dear Ava, I recently had anal sex for the first time, with a cougar, and it was awesome. To be honest, it wasn’t something I had given much thought to before; I was just happy to have sex of any kind. And this cougar was the first woman to even mention it. I’ve always been under the impression that most women aren’t into having a guy’s dick up their ass. All I know is that now I’m into it, big time! It’s so tight, and I’ve always liked taking a woman from behind. Unfortunately, my hookup with that older woman was a one-time thing, but I’m eager to have more anal sex. Is there any tips you can offer that will help me find it? -Al

A: Hi Al. I think there’s a couple myths around who likes anal sex. One: I think less men than you’d think are into it. I’ve met a lot of younger men who have no interest in exploring this region of the female body. And two: more women than you might imagine are willing to give it a go or are crazy about it. This should be encouraging to young men who love the bum action.

What you should know about anal sex with women:

  • wait until at least the second sexual encounter to bring it up, unless she does… then it’s full steam ahead, or behind I should say!

  • when you do bring it up with a new partner, be casual… like you’re into trying it, but it’s not a must. You don’t want to ruin any chance of sex by being too forceful or eager.

  • don’t emulate anal sex that you see in porn. Full-on thrusting without foreplay or lube isn’t cool. Go slow and talk your way in for her comfortability and pleasure.

  • older women are more likely to give you access on a first date because we are more comfortable with our sexuality and will know definitively if we like anal or not.

  • if she likes anal, she may be into exploring your nether region with butt plugs or a strap-on, so be prepared for the adventurous types.

Good luck finding a woman who enjoys anal as much as you do. We are out there!

Read: What Women Love and Hate about Anal

Cubs: Do you love anal sex? Is it easy finding a woman who will grant you back-door entry?

Need advice on dating, relationships, or sex? SUBMIT YOUR QUESTION HERE, and who knows, you may appear in the next Cougar World newsletter. -xo Ava

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