Dear Molly,

If sex is meant to share intimacy and make babies, why is it that some girls do anal sex? I think anal sex is not natural, where vaginal sex is, and also painful. This is my thought only and I respect every individuals personal choice and preferences.

In my opinion, anal sex is fine. People like it because there are lots of nerve endings that make it feel good. I don’t believe sex is just for procreation. That belief tends to create a lot of guilt and shame surrounding sex.

Hence your question and comments like anal sex is unnatural and sex being for reproduction. Those mindsets make sex less enjoyable and lead to things like sex shaming and slut shaming and gay bashing. Not my jam. Saying such things about sex tends to show a lack of experience, bigoted ideas, and a reliance on traditional gender roles and stereotypes.

Plus, anal sex takes away the risk of pregnancy for a lot of women, especially if she’s in a culture where birth control and premarital sex are stigmatized. Many women will opt for anal for that reason alone.

But I think if I try to insert my penis into her anus, and it is too tight, it will cause her a lot of pain. Is this true?

Well you don’t just shove it in. Shoving a finger or dick into a dry vagina is also painful, so don’t just go around sticking fingers and dicks into things without preparing them first.

If you don’t want to have anal sex, that’s perfectly fine. Lots of people are uncomfortable with the idea. But if your lady wants to try it,  you’ll either learn to push beyond your comfort zone or you’ll leave her unsatisfied. That decision will be yours to make.

If my lady really wants it then I’ll do anal. But how to do without hurting her?

You take it slow. Very slow. And use lots of lube.

And start with a finger. Then two. Before you even think about try a dick. The sphincter muscle needs to relax and that takes time. So you go a little bit and wait. Then you go a little more.

Once you do start to engage in penetration, you let her move on it. If you’re in doggy style, you let her push back against you. Or, even better, have her on top and she can control the depth and the pace.

Can anal be done in missionary ? I kind of like missionary so would like to do missionary if it’s possible.

Anal can be done in missionary. Have her rock her hips up a bit and you have plenty of access.

Can I just ejaculate and rub the semen on my glans and then insert in her anus for additional ease? Semen is sticky, plus there’s no risk of pregnancy in anal, right?

I would not recommend doing that, as it could create a risk of getting semen into her vagina. Chances are slim, but it could happen.

Plus men tend to lose some of the firmness of their erections after ejaculation, which makes anal penetration more difficult.

Instead of using semen, try to get your  hands of some lubrication. If you can’t, try coconut oil. But be careful. It will stain your sheets.

Also consider the fact that STDs are transmitted at a high rate during anal sex. Be certain to wear a condom or get tested to protect both you and your lover.

Will anal sex hurt her? Once we do it, will it not hurt again?

Sometimes anal hurts a lot and sometimes it doesn’t. The secret is she needs to relax. If she’s worried about it and clenching, it will be very hard to accomplish penetration and if you do, it will hurt.

And, as I mentioned, start slow!

If I could ask a personal question, do you enjoy anal?

I like it sometimes. Sometimes I don’t.

Womens bodies change a lot in what feels good over the course of their monthly cycle (although most don’t realize the connection). So sometimes I want sex that is hard and fast. And sometime I want it rough. And sometimes I want it soft and slow.

In this same manner, when it come to anal, sometimes it feels great and sometimes it hurts like hell.

I will say that I tend to want it more when I’m drinking alcohol, which tells me I probably like it more than I realize if I’m all about it when my inhibitions are down.

Has a man ever thrust too fast or deep and caused pain? I think that would be a deal breaker.

Oh yes. Plenty of times. And sometimes it’s me. I push into it too quick myself. Sometimes it’s a deal breaker for that time, but never has it been a deal breaker for the long haul.

Is eating her anus considered okay in the West? Do men do this to women in real life?

Yes , it’s totally a thing. We call it rimming. And women do it to men too. Even straight men can enjoy it.

The only prerequisite is to be clean. If you’re apprehensive or squeamish about the hygiene factor with anal or rimming, keeping things trimmed and shaved can help.

Have you had your anus licked? How does it feel?

I’m not a huge fan of it myself, but I know a lot of folks who are and it’s a completely normal to enjoy. As a matter of fact, I have no problems doing it. And I have no problems receiving it if my lover enjoys doing it. But, like I said, I have inhibitions about anal play, unfortunately., which probably halts much of the pleasure I would normally receive from it. It kind of makes my belly clench and gives me anxiety.

That’s it for this week’s reader question! If you have a sex question, email it to me at!


Leave a Reply

Avatar placeholder

Your email address will not be published. Required fields are marked *