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“So today’s question on “It’s Probably You” is…”  Paul looked at the camera, “How can I get my SO to try anal sex?“”

“Man, how CAN I get my partner to try anal?” I replied. “Great question, anonymous internet friend.”

As part of “It’s Probably You,” a video webseries giving advice on relationships, sex, and dating,  I gave an unscripted, candid answer (that you can watch here and is NSFW). Afterwards, I considered the question in more depth — how can you have great anal sex with a partner… who might not be initially interested?

So here’s my ideas, in full, on how to have awesome anal sex with your partner. For the first time and for the rest of time. The text is a little racy if you’re at work, but there’s no scandalous photos.


Part One: Collect Information

(Admission: I am not a sex educator (though Lucy is, and wrote some smart thoughts about it). I am a sex advocate. My secret goals are to inspire less shame surrounding sexuality and bodies, and inspire consent, communication, and kissin’. I agreed to be on It’s Probably You to push my radical gay agenda, and Paul, the host/creator, agreed. Thems the facts.)

Okay. Let’s talk about anal.

First thing first: you’re going to have The Conversation About Anal. And that, my friend, is what I assume you need some advice on. How to talk the talk in a caring, charming, informed way. I’m assuming that you’d like to be the penetrator, not the penetrated, but if it’s not your intent, let’s talk about that later.

But but but *before* you start The Conversation, I’d solicit some damn good understanding about how your partner *already* feels about their most supple slope. Potentially awkward conversations are much less fraught when you have a solid basis of trust. When you have more information to frame your expectations, you have have a more vulnerable, intelligent Conversation.

And nothing is sexier than an intelligent conversation.

Because – spoilers – anal sex is something you really need to want. Anal sex is a process that requires due diligence, great communication, investment in safer sex supplies, and being on your best goddamn sexual behavior. It might hurt; be uncomfortable; be very, very intimate—and it’s damn crucial for you, as a partner, to be an excellent sex partner. Don’t be sloppy. Don’t be lazy. Don’t be quick. Consent doesn’t need to be sexy, it needs to be there.

I’m assuming you want to have amazing anal sex. If you want to have awful, abusive anal sex, please go away forever.

I’m also assuming that you want your anal sex to be so wonderful that your SO wants it all the time. Every night. Some afternoons. Before work, after work. Because, anonymous Internet friend, I’m in it for the long haul. I assume that me and my partner are gonna be together through thick and thin; I want them to find strength and security in our relationship. And I want them to come for me, over and over and over again.

I hope you’re on that same page with me. The page with the joy in it.

I’m serious about anal being a process. I’d think about building up to anal, in a gentle way that erogonizes the area, and makes your partner really thrilled about putting objects inside of themselves in a wholly new way. It’s not like trying a different flavor of ice cream (tangysweet! just try it, you’ll love it!). It’s more like trying figure skating. At first, you will be an awkward duck, clenching onto the sides, uncomfortable with your balance and your wibbly ankles, but after a bit of practice, you’ll be gliding along like Oksana Baiul.

It takes time. So you should do it right.

Information Checklist:

1. Why do you want to try anal?

2. What do you know about anal? (Consider learning more!)

3. How does your partner feel about their lush posterior?

4. Do they know that you fancy their fanny?

5. Are you prepared to have a few awkward, silly moments and purchase all the lubricant in heaven’s earth?

6. Can you laugh easily about silly butt things, and giggle about it, and not make your partner feel shame about their bum?

7. If you are asking to be the recipient (or the giver) of some fine anal loving, are you prepared to explore your own area and discover your own sensitivities and sweet spots? As they say in Buddhism and fisting circles: point one finger, and three point back at you.

8. Ask yourself: would I like some anal loving? What would I want to know about my partner before that happens?

9. Do you know how awesome the prostate is, and similarly, how happy-nerve-rich the anus is for women?

10. You’ve had a productive safer sex talk. If you haven’t yet, now is an awesome time to do it. (Read this post by M. Lunas for more details about how to talk that talk.)

Some of those questions are only questions you can answer (How sensitive is my own prostate/happy-butt-place? How many fingers can I slowly ease into my own entryway before it feels as crammed as rush hour on the 66?), others are one that might require some lengthy internet searches. But the really big question is to learn about your partner’s feelings on their butt *and* let them in to the truth: that you think they have one of the finest badonks in this land.

Part Two: Erogenize the Area

Many of us have divided thoughts on our bums. We can’t really see them too well, and many people might not see their butt in a sexy way. For our partner, you might want to change that – help them see the sexiness of their lush bottom.

And one of the easiest ways to do that is to stare at it.


Stare at that hot thing.

Appreciate it. Gaze. Oh yeah.

Romance that bottom with your pretty eyes. Bat those lashes. Bat.

How round is it? Does it kinda peek out when they bend over? Can you see its shape in cargo pants, in boxer shorts, in bikini bottoms?

You want to be a goddamn expert on your partner’s booty. You want to be able to tell them about how much you like those dimples they have, and how strong it is, but how soft that skin is, and how sweet it jiggles. How much space do they have in their pockets? You might want to ask to cup it and feel how juicy that is. Try that out. You want to be the Indiana Jones of that Hidden Temple.

If your partner seems uncomfortable with all this attention, you need to leave best enough alone. If they get kinda into it (hint: they might touch your butt, bro) then… lay on, Macduff.

Maybe, before you have the conversation, get some fine butt-touching in while you’re doin’ whatever sexy things you do. We all see sex differently, but maybe as your teasing their downstairs, you wanna grip onto that fine bottom and give it a pat. A good squeeze. Maybe a jiggle.

As Ally McBeal taught us (and kinky folks would *confirm*), it’s in poor form to surprise-spank your partner. But, maybe ask them if they’d like that? They might. Ask them. They really, really might like that.

They might also like having a tiny vibrator against their butt as you do your sexy business. Ask them. They really, really might like that.

Your partner may love all this, and still not want to have anal sex. You may love some nice squeezes but not want the whole enchilada. And that is totally cool.

Other data to collect? It helps to read about bottoms and learn about their cool features and how they work. There’s a bunch of butt-related resources at the bottom of this post that you might want to check out, but here’s one teasing thing you’ll get to learn in your anal-exploring journey: you really need lube. The anus does not create its own lubricating fluid (unlike mouths or front-side genitals). No matter how excited someone is, their bum will not create a happy-slime for pleasure-making. It’s crucial to your partner’s health that you lube that butt up so you don’t create tiny tears in the anal cavity that are both painful and a health risk.

Part Three: Talking the Talk

First, watch this NSFW video (after work) about one way to have The Conversation:


Obviously, in The Conversation, you will not attempt to weedle (bad form), coerce (that’s repugnant), guilt (most dastardly), or annoy your partner (just plain obnoxious) into trying anal. To take advantage of your partner’s vulnerability and their desire to please you and do things your partner isn’t quite on board with…. That, dear querrent, is a nasty move. So, let’s just take all those ideas out of this process.

So, right now, you have more information about your partner’s views on anal. This can affect the tenor and tone of the conversation — can you breezily mention it on a Sunday morning while you’re considering where to get breakfast (“Hey, babe, do you ever wanna try anal? I think it’d be fun, but if you’re not as into it, that’s cool. Just wanted to see if you’d thought about it before. Do you want to get Five Guys? I have a major peanut craving right now.”), text them (“Hey u wanna try anal tnite??? xoxo”) or would it be better to be more formal, more informed, and provide much more data on the excellence of the buttlove? What style of language will let your partner think about it and have a consent-filled, excited response?

Conversation checklist:

* why their butt is a special place that you fancy

* that you’ve fingered your own butt and found it scintillating

* that this is a process and you’re gonna do all the nicest things to your partner and they’re gonna be busting down the doors to get some more salad-tossin’, light butt entry, that might, several nights later, evolve into some more serious Things In Booty play.

* ask your partner what they think is hot about this concept- have they had any dreams/fantasies about it?

* you will not drink before trying out all your fancy new moves

* at all times when you’re in them, they are in control of the situtation and can ask you to withdraw.

* “Consent is keeping a hold of your partner’s hand, agreeing to go with them, agreeing to not leave them behind.” Hold their hand, bros and bras, and read this post by Rosie Franklin about how to incorporating consent in your sex.

* you have lube. all the lube. many types of lubes. that butt don’t lube itself.

* you have gloves. sexy gloves.

* if you are asking to put a toy or a penis in them, you have condoms for handy clean-up and safer sex reasons. Even if you’re fluidbonded, consider condoms for cleanliness. Believe me.

* you are going to go slow.

* you are going to listen to them. butts have moods. sometimes, butts want lots of love sometimes, only a little bit of love.

* if you are putting a toy in them, that toy has a flared base (and is not a hamster or lightbulb.)

* that you’re excited and you love them and if they really aren’t into it, that’s totally fine. You can lay in bed and rub bellies and make out forever.

If your partner is charmed by your care, attention to detail, and ability to recall in instants the finest aspect of their fine behind, you’re on your way.

If your partner still seems wishy-washy, but still game, double-affirm their ability to opt out and control the experiences.

And you’re on your way.

And by that, I mean, you’re on your way to encorporating the butt into your sex life. After the Conversation, I would not bee-line to butt-fuck that night. Let it settle. Give them a day or two to fantasize about that firm finger of yours inside of them. Touch their butt a little more often. Help them know the beauty that they cannot see.

And when you ask them, a few days later, “Do you want to try anal tonight?”

And they say, “Yeah, sweetie, I’ve been dreaming about it my whole life.”

Be slow. Be careful. Be attentive. Think about their enjoyment as much as your own. It should not hurt.

Be on your best goddamn sexual behavior.

Part Four: Is it you?

* Let’s think about the original question: “How can I get my partner to try anal?”

I’ve gotta say, the word “get” is a bonercrusher for me. I don’t like to feel “sold to” in a relationship, and anything that feels like that makes me really uncomfortable. If you’re in a relationship where you’re regularly “convincing” your partner, instead of suggesting things to your partner, I think you should check yourself.

I’m also a bit bonercrushed by the word “try.” I can try some vegetarian lasagna, I can try on some Sketchers, but I wouldn’t “try” anal sex. Do or do not, padawan.

And, as we say on this show, “It’s probably you.”

* I really appreciate how unclear you articulated your gender and role in anal sex would be. I really dig that ambiguity, because I think it belies one of the primary greatnesses of anal sex – everyone can like it! It’s great for everypony forever! I love that men have delightful prostates that act like secret, hidden clitoruses inside of their bottoms.

And I’m sad that most men are taught that anal play *on them* is a gay thing. A very very gay thing. And thus, a very bad, nasty, emasculating thing.

Clarification: gay sex is when gay people have sex.

So straight fellas, that surge of warm delight you feel when some lady is patting down your booty, that’s a damn hetero thing to feel. (Not that it really should matter, but if you base your masculine identity in your heterosexuality, we can let you off the hook here, for just a moment.)

Repeat: gay sex is when gay people have sex.

And if you, dear querrent, are a gent who’d like to have some more direct anal delights, let me take a minute to applaud you.

Because it’s awesome, and you’re gonna have a great time if your partner is caring, attentive, and slow. And I’m happy you’re busting through gender stereotypes to bring the butts back home. Being penetrated does not make you submissive, gay, or feminine (you can read this if you don’t believe me, fellas.) Though those are all awesome things to be.

* I would replace the word anal sex with anal play. There’s so much to do with butts! So much! We all interpret sex differently, so I’d steer away from just focusing on the male orgasm, and a little more on mutual pleasure.


Part Five: What should I watch + read?

1. Go watch Bend Over Boyfriend, the first and best film about pegging. It’s a docu-porn!

2. Take a look, it’s in a book! A reading rainbow! Read The Ultimate Guide to Anal Sex for Women by Tristan Taormino. If you have a Kindle, you can read it on the metro, and no one will know you’re a little pervy. And read Charlie Glickman and Aislinn Emirzian’s The Ultimate Guide to Prostate Pleasure, which is more for folks-born-male who have prostates.

3. Take a class with Strap-on Jo, who’s a professional teacher of prostate stimulation. (I took a class! It was great!) You can also take classes at some local sex stores like The Garden (washington dc, it fits me to a tee) or Good Vibrations (west coast). Sex toys and butts go together like jelly and toast, making gift-buying for Christmas/anniversary/birthday/Friday a million times easier.

4. Consider thinking about sex as a performance, or music jam, as articulated by this awesome video on Yes Means Yes.

5. And consider this:  “The ass is the face of the soul of sex,” sayeth Charles Bukowski. Preach, Chuck.