Anal Sex 101

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 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.

al Sex 101

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 pleasurable and enjoyable?

Initiating Anal Sex: Her

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 he might be too uncertain to initiate it without your express permission. The easiest way to tell him you want anal is, well, to tell him you want anal. Many men aren’t so good at picking up dropped hints or reading the subtlety of your body language, so telling him directly and explicitly that you want it is the only failsafe approach.

Note: telling him very explicitly that you want anal while you’re already having sex with him will have the best results. That’s like a golden ticket for most guys.

There are alternative ways to start anal sex, though. Texting or emailing him your desires will let him know your intentions long in advance, but this has two drawbacks: one, you may no longer be in the mood when it comes to it, and two, he might think that’s all you want, so he’ll focus on that and leave the rest of your body wanting.

A sexier approach to telling him you want anal sex is not to tell him, but to show him. Let him watch you play alone, perhaps with a small vibe or even a plug, and put it everywhere you want him. It’ll drive him crazy, and you’ll certainly get what you want, where you want it.

Initiating Anal Sex: Him

Does anal sex hurt? Yes, very often it does, even if it doesn’t hurt for long. But is anal sex pleasurable? Yes, potentially. But you need to approach it… sensitively.

If she hasn’t initiated it or made it obvious that she’s open to anal sex, or if you’re not 100% sure she’s given you the green light, then you need to make sure it’s ok before you try, otherwise it’ll be a while before you can try again.

So exactly as above, there are several options available: tell her directly during sex or foreplay, tell her beforehand via text or email, or show her what you want by paying her butt some extra attention during foreplay and gauging her reaction.

There is a slightly more adventurous way to initiate anal sex, providing you’re having sex already. Find a comfortable position – we suggest a kind of spooning position, with her laying on her side with her back to you, and you behind her. This position is good because it’s comfy, all of her bodyweight is supported and her muscles are relaxed. Then pull out of her and rub yourself against her butt. She’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 three things to try to help make anal sex better.

  • Position. You already know that all positions are not created equal, so explore some of the anal sex positions that are best for beginners, as they let the receiver take more control.
  • 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 him climaxing too soon too.
  • Anal Sex Toys. Introducing some anal toys like a butt plug or vibrating prostate massager can help ease the transition into anal sex, and by using toys of increasing size during foreplay you’ll find it much easier when his turn comes. Then, try stimulating your clit with a small external vibrator while you’re having sex to double the intensity of the sensations and build up to a really fulfilling orgasm.

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 mindblowing.

So how about you? What tips do you have to make anal sex more enjoyable?


About Katy Thorn

Katy Thorn is a post-grad writer with a passion for - and a history of - writing about sex, sexuality and all that it entails. She spends her time running, reading, writing and socialising. Katy has a cat named Feargal, she loves coffee and hates writing bios.

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  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!

  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. This article is a wonderful source of information. Ignorance, poor communication, and absence of foreplay plagued many of us back in the day.

    My one and only experience with anal sex was excruciatingly painful. As a newly wed I was held down as I resisted and penetrated without foreplay, lubricant, or advanced warning.

    Today, I can’t imagine attempting anal sex. Doctors says there are several anal fistulas after 4 pregnancies which become inflamed after eating spicy food and/or bouts of diarrhea caused by tape worm infestation and amoebic infection common in Southeast Asia.

  4. 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.

  5. 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.

  6. 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.!

  7. 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.

  8. I don’t get why you all only are focused on -her- anal? I mean, men have a prostate, guys! This artical is just full of heteronormative crap!! and it makes me really sad that you think that men have to be “dominant” and women have to love it (it = mens dominance). :( anal could be a pleasurable exploring loving thing for people who like it, but it’s sex-positive/sex-liberal ignorant people like you who just reinforce rape culture that force girls who don’t even like anal to “put up” with it so that their boyfriends will like them. Shame on you!

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