Reader question: I’m interested, but nervous, about trying anal sex.

The taboo nature of butt stuff is no doubt one of its biggest selling points.

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Reader question: I don’t know where to start. Basically: I’m interested, but nervous, about trying anal sex. My partner is a very giving lover and he’s made it easy for me to try new things sexually. We’ve tackled role play, bondage and spanking (which I never thought I would do, much less enjoy). He has expressed that he wants us to try anal. He’s very, very interested in it and has never gotten a partner to do it before. He’s offered up letting me do stuff to his butt first — which I think is not only fair but quite sweet.

But it wouldn’t be my first time with anal. I tried it in high school exactly one time. It was with my first boyfriend and to say it went poorly would be an understatement. We were in a truck, which was our first mistake. I was pretty drunk and didn’t do anything to prepare for it. I’ll spare you the gruesome details, but it was a mess. And it didn’t even feel good!

Since then, I’ve been fairly traumatized about anything approaching my butt. One other partner asked but I haven’t tried it again. I’m only considering it now because my current partner makes me feel genuinely safe. He isn’t putting pressure on me, but I do know he wants it.  If wonder if it could be a chance to work out some of the trauma by doing it again under better conditions. Is that crazy? What should I know before trying again?

Humans of all genders have been using the anus for sexy reasons since time immemorial. That’s presumably because it’s both an effective means of not getting pregnant and because butts are chock full of nerves, so there’s potential for a great deal of pleasure. But(t) something happened in the last few decades in America that took the practice even more mainstream. Hint: that thing is probably internet porn.

The taboo nature of butt stuff is no doubt one of its biggest selling points. All body parts can ostensibly be sexualized but we have tended to be pulled to some spots more than others.

According to Joe Duncan in “The Psychology of Anal Sex,” “There is no possibility of pregnancy resulting from anal sex, and on a deep level this resonates with many men who consider it more carnal, just done for the sheer pleasure of it without even a hint of being something more.”

Meanwhile, there are the humans on the receiving end. What it means for a person to be penetrated anally varies dramatically. For some, it’s just another enjoyable option on the menu. For others, it’s perceived as a romantic gesture. As Dr. David Ley says, “In many relationships, anal sex is perceived as a type of “gift” from the woman, given out of love and regard, and a desire to give her partner something special and rare. When a woman is willing to engage in anal sex with a lover, it usually comes from a place of significant trust and love.”

For others, though, the act cannot be disentangled from dominance and degradation. From this vantage, the increased fascination with hetero anal is just the rebranded patriarchal desire to control women, packaged as sexual freedom. And to be fair, a lot of the advice written for and by straight men is decidedly coercive (and weirdly homophobic) in nature.

I can’t tell you how to feel about it. And while I can offer advice for minimizing discomfort and maximizing pleasure, I can’t promise you that trying anal again on your own terms will ensure that you enjoy it, especially given your aversion up to this point.

Let me be clear: regardless of if you had ever done it before, you’re entirely within your rights to do or not do any sexual act for any reason. Whether it’s because you have trauma from the past or you simply are not fucking interested: you don’t have to do anything you don’t want to. And not pressuring you is the absolute baseline minimum for your partner.

If you feel confident that you want to take another crack at this, we can aim to make this time about pleasure. Here are some key considerations:

Try it on yourself first. Toss in a little gentle touching and rubbing while you’re masturbating and see if you can find a pace and pressure level that feels good. Insertion into the rectum isn’t even necessary. Play around with a toy or a finger and see what happens when you add in backdoor action — and this is critical — while you’re already aroused.

Prepare your body and your space. Enemas and anal douches aren’t required, but if it makes you feel better: go to town. A regular old shower or some time with the bidet is probably sufficient. You can use nitrile gloves and lay down a dark-colored towel if you want.

Safety considerations. Unlike the mouth and the vagina, the anus is not self-lubricating, so be generous with lubes, both on you and on any objects. Any toy that goes in the butt should have a flared base, so it doesn’t get lost in the vacuum of space that is the colon. Condoms are a great idea. Sanitize anything you end up using.

Go slow and feel free to bail out. Max pleasure is not achieved quickly or with massive objects. Penetration of any kind is NOT supposed to hurt, so don’t push through pain. Stay in communication with your partner about how it’s going — what you like, what you don’t. If it feels good: great! If it feels uncomfortable either physically or mentally, then say fuck it and try something else.

Basically, remember what Erika Moen’s Anal Sex Safety Snail says: lots of lube, go slow and communicate with each other.

Have a question for Dr. Timaree? Send an email to asktimaree@philadelphiaweekly.com.

  • Timaree Schmit Headshot

    Timaree Schmit is basically an episode of Adam Ruins Everything, but in the shape of a person. She has a PhD in Human Sexuality Education and years of experience in community organizing, performance art, and finding the extra weird pockets of Philly.

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