Anal Sex 101: Tips & Advice for Making it More Enjoyable for Both Partners

There are a lot of presuppositions and myths about anal sex: Men want it more. It’s not pleasurable for her. Everyone’s doing it apart from you. There’s no such thing as an anal orgasm. So on and so forth.

These sex myths are demonstrably untrue; all they do is expose the fact that people don’t talk about anal sex (oral, penetrative, or otherwise) well enough, because it’s still relatively taboo in mainstream conversation.

But why should this be? As part of a loving relationship, or even as part of a brief and hot encounter, anal sex has a lot to offer. Not to mention, the relative taboo nature of anal is part of its appeal for many participants.

There are two tricky obstacles to overcome. First, how do you initiate it when you want it and second, how do you make anal sex more enjoyable for both partners?

Anal Sex Tips

Initiating Anal Sex: Receiving

When you decide you’re ready to receive anal sex, you need to be in control of it from start to finish. That means you need to make it obvious that you want it, because your partner might be too uncertain to initiate it without your express permission.

The easiest way to tell your partner you want anal sex is, well, to tell them you want anal.

Many people aren’t so good at picking up dropped hints or reading the subtlety of your body language, so telling them directly and explicitly that you want it is the only failsafe approach, plus it means you’re able to talk about things like possible boundaries, previous experiences, etc.

Now, there are two ways to go about this. You can ask your partner explicitly while you’re already having sex, which many people might find feels more comfortable and natural. However, it doesn’t exactly make it easy to have an extended conversation about the aforementioned boundaries or reservations you may have if you’re an anal sex beginner.

You can bring it up before hand through flirty texting or emailing, which certainly sets up the anticipation, however it does have two possible drawbacks: one, you may no longer be in the mood when it comes to it, and two, they might think that’s all you want, so they’ll focus on that and leave the rest of your body wanting.

Another approach, particularly as you get more comfortable with anal sex, is to tell your partner by showing; start with self stimulation (or guiding your partner’s hand) or using a small vibrator made for anal play (ie: has a flared base).

If you’re trying pegging for the first time and your partner is not used to thrusting, this is a great time to talk about how you usually have sex, and what you think could work and what wouldn’t.

Initiating Anal Sex: Giving

Does anal sex hurt? Yes, it can. But is anal sex pleasurable? Yes, potentially. But you need to approach it… sensitively.

It should go without saying, but if your partner hasn’t initiated it or said outright that they are open to trying anal sex, you need to ask.

Generally speaking, anal stimulation during sex can be somewhat divisive, and ‘just going for it’ is not okay.

So exactly as above, there are several options available: ask them directly during sex or foreplay, bring it up beforehand via text or email, or show your partner what you want by paying their butt some extra attention during foreplay and gauging the reaction.

One of our favorite sex positions for initiating anal sex is in the spooning position. You’re both comfy and relaxed with all bodyweight is supported. Then pull out of her and rub yourself against them; they’ll quickly acknowledge whether it’s ok or not without having to break the mood.

But remember, there are no shortcuts and nothing beats good, honest bedroom communication – and good dirty talk does count as good communication.

Make Anal Sex More Pleasurable

While there are those rare times that, like stars aligning, the mood will strike both of you simultaneously and you’ll have the most incredible and satisfying anal sex imaginable, usually there is some preparation required.

Remember that if you’re receiving anal sex (of the penetrative or oral-anal variety), you need to be in control of it, to whatever degree you want. You will need to control the speed and he will need to listen to you, otherwise it will be uncomfortable and it will stop. The opportunity might be lost until some trust can be rebuilt.

Here are 4 things to try to help make anal sex better.

  • Lube. You probably already know that lube or a high-quality intimate moisturizer is essential for anal sex. The more the better. Apply enough to squeeze a manatee through a letterbox, and then apply more. The more lube involved, the more pleasurable it will be for both of you. It’s as simple as that.
  • Condoms. Condoms are great for anal, and not only because they enhance your sexual safety. Condoms actually make anal sex better because their smoothness responds better to lube than skin does. Condoms glide easier, and as a result are more comfortable. What’s more, they can help prevent the thrusting partner from climaxing too soon too.
  • Anal Sex Toys. Even anal sex experts find a ‘warm up’ to penetrative sex handy, so introducing some anal toys like a butt plug or vibrating prostate massager during foreplay can help ease the transition into anal sex.
    As a reminder though, any toy that is used anally should have a flared base to avoid it accidentally disappearing inside you, and anything used anally needs to be washed or covered with a clean condom before being used in another orifice.  During anal sex, try stimulating your clit or other erogenous zones with a vibrator while you’re having sex to double the intensity of the sensations and build up to a really fulfilling orgasm.

Check this out: Blended Orgasms – What, How and Why?

To Sum Up

The most important part of enjoying better anal sex, or any kind of sex for that matter, is talking. The most sensitive erogenous zone is between the ears, stimulate that one and the sex will always be mind-blowing.

Still Curious? You can read more expert articles about anal sex or go back to our Ultimate guide to everything about anal.

Written by: Katy Thorn

Katy Thorn is a post-grad writer with a passion for writing about sex, sexuality, and all things rated R. She received her degree in Women’s Studies with a focus in Intersectionality at the University of California, Berkeley (Go Bears!). She has a cat named Yoko, drinks too much black coffee, and hates writing bios.


  1. First timer-How do I go about doing anal on him with a pocket rocket w/prostate massager, my finger or one of my g spot vibes? We’re excited!

    • Hey y’all,
      I was very very late in discovering the mind blowing intensity of a blended, prostate and penis orgasm. My ex wife was big time into male male sex and that is my limited experience. But she knew exactly where what when to the extent that I became addicted almost. I certainly was not being fair. But I couldn’t believe that the big I could possibly get bigger or more Oish. It is an actual FULL BODY CLIMAX ORGASM. My wife would just use her finger. One finger. And every time it was bigger by far. I would say 80% of the time it reached epic proportions. I would be on my back with her sucking my cock knees bent and spread. Easy access is a must. But she would use her index finger and said that she hit my prostate very easily every time and she was only going just past the first knuckle of her very tiny hands. Now she she has used was more then one finger and gone way farther then a couple inches. But at the critical moments it was hard enough for her to keep that finger inserted as I become like a big flopping fish fresh out of a mountain stream hitting a hot ass asphalt road. Good luck enjoy. Would love to hear back as to how he took it and what did y’all think. Especially to hear from him.

  2. after you share with him that you are excited about experimenting with him
    then take his que and i bet you’ll be trying all 3 before the evening is done

  3. Patience is key. If you and your partner are willing to try, then start off slowly…Caress any play with all areas surrounding before getting to it…start to tease the area while playing with others, use a well lubed finger or small toy before moving onto bigger things…And communicate every step of the way. let her take the lead, listen when she’s ready, slow down if she’s not,and have fun.

  4. Anal sex is amazing.. I am lucky enough that my partners have all loved it too, despite some having bad prior experiences that turned them off…
    It just shows that its critical how you do it if it is to be enjoyable…

    My recipe for mutually incredible Anal sex is that the man should stimulate his partner to orgasm before anal. This means the woman is very relaxed and aroused before anal takes place.
    A full body massage with the woman lying face down is also a sure fire relaxant and arousal before anal.

    Second, the type of lube counts.. Personally, one lube changed the whole experience for me and my partner and that is Coconut Oil!! Cant say enough about it, its natural, discreet, tastes great, is a wonderful massage oil, is healthy and a natural anti-bacterial. The only caveat is that as a natural oil, it is not suitable for use with latex condoms, so for monogamous partners only.

  5. It’s nice to see more discussion happening on the topic of anal sex. Its interesting that it is still perceived as taboo in todays society. We dont blink when we hear about so many things in the media but bring up anal and no one will meet your eye. 🙂
    I personally love it and am able to orgasm from it. I am lucky enough to have an adventurous personality and a partner who is more than willing to try most things and take the time to make it great for both of us. He’s a gem.
    Having worked in an adult store for a number of years though, I was surprised to realise that a lot of guys had no idea how to approach their partner and ask for this. I found after a while that a lot of couples were coming in to talk to me about it and ask lots of questions….I’m not shy about discussing sex.!

  6. Anal sex is very pleasurable. I ve been doing it since I was seventeen. I am well experienced and wide enough to take any man. At times I don’t need lube. I am still tight though but when I want to take something big, I kind of push out. I once swallowed a cucumber that is slightly thicker than my wrist and 10 inches long.

  7. This was. Great. To read. Confirmed. A lot. I was thinking

  8. What is the best way to clean the back door to avoid any nasty surprises prior and during anal sex?
    I have used my billy solo but want to step up with my partner but want to make sure it’s pleasurable for us both and nice and smooth and clean

    • Hi there! One of the best ways to make sure you won’t have any unpleasant surprises during anal play is prepping before hand: make sure your diet is full of fiber and your BMs are regular and non-messy, and have one about half an hour before you plan on having sex. Our bodies don’t always cooperate with us so you might still run into surprises, but if you or your partner are a bit squeamish, you can make sure you use a condom (good practice anyway) and move things to the shower. All sex is a little bit messy, which is good to keep in mind as well!

  9. know the people know how good it is

  10. Hi Katy,
    Great advice, thank you!
    Good to see this article got another run, I have tried anal with a few partners and they all have loved it, unfortunately my current partner does not, I was hoping if she can see I like it, she might relax also, some great advice on approaching subject gracefully 😉

  11. Very good advices, thank you!

  12. Hi guys. I have been having sex with other men for the last 3 or 4 years now. I have never found it painful or uncomfortable to have a penis inside my anus, even with bigger penises. If you let the guy use a finger or his tongue first, it helps you relax and makes the sex more pleasureable. Also, make sure you douche before penetration.

  13. Thanks again great article

  14. I’m a female and I have experience anal sex with both of my partners.and my guys and I have a threesome and they have a good lube and I have many Orgasims . And I like it Doggystyle or rocking horse. Thanks for the article

  15. Anal sex is great!! My partner and I have been enjoying anal sex for a year. I’m a female and I ask my boyfriend let’s try anal sex. At first it took time . So once we found that Cocnut oil is great . Now my boyfriend enjoy it as much as I do I have so many Orgasims . I invited another guy for a threesome with use . And I had two cocks for double Pentration . One guy penetrated in my vagina and my boy friend penetrated in my ass hole. It’s hard to explain when both guys are fucking you and they are going in and out and I’m exploding with cume . You have to pepare for double Pentration as well . Thank you for the article

  16. Hey I love this can you teach me more?

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