Getting Started with Male Anal Sexuality

by Jason Stotts

Recently, a reader sent me this question and I’m very excited to get it.  It’s one of my favorite subjects and one that I think all too few people are willing to talk about.

My partner and I really enjoy anal sex, rimming, anal play with toys, etc, as long as it’s him doing it to me (female).  We are both open to me doing some anal play with him, but he has lots more hang-ups than I do (worried about cleanliness, more nervous and clenched, etc.) Any advice about how to get started with anal play with him?  He’s definitely open to the idea mentally, just not sure how to begin working past his worries.



I have so much to say, I don’t even know where to begin.

First, K., I want to say that you’ve already cleared the biggest hurdle, so, congratulations!  All too many men won’t even consider having their asses touched and will refuse to even talk to their partners about it.  The fact that your partner is at least open to discussion and is willing to consider trying it is a big step and puts you into a really good place to get started.

I’ve given advice on male anal sexuality a number of times, including (On Pegging 1, On Pegging 2, On Male Orgasm and Prostate Play, On Male Orgasm and Prostate Play 2, and Buttholes), but in each of these cases the advice was broad, so let me a different approach here.  First, if he’s like me and likes having a good resource to read that has lots of sound medical advice and good ideas about things to try to get started with anal sexuality, you should pick up the new edition of Jack Morin’s Anal Pleasure and Health, which was just recently re-released in a new edition.  Morin’s book is the best one I’ve found about anal health and eroticism, regardless of sex.

One of the things that I want to suggest comes from Morin’s book and it’s this: tell your partner to get acquainted with his own asshole before you start playing with it.  Tell him to start by carefully washing his asshole in the shower and once it’s good and clean, to explore it with a finger, perhaps with a little non-water-soluble lube (like a good silicone lube).  He should start by running his finger around the outside and feeling the skin of the asshole.  He should do this lightly and just focus on the external skin.  He should then start pushing in a little on the outside edges while going around it still, so that he can feel the sphincter muscle underneath.  It will feel like a ring of muscle.  There are, in fact, two sphincters, an external one that is open to conscious control and an internal one that is part of the autonomic nervous system and outside our control.  By focusing on the outer sphincter and rubbing it slowly, you should be able to feel it release under you finger.  Once you feel this, place your finger in the center of your asshole, not inside the internal sphincter though, and then tighten the external sphincter around your finger.  He should practice bringing the external sphincter more under your conscious control by focusing on relaxing it and then tightening it (like Kegels for women).  Once you have better control over your external sphincter, you can practice this at any time.  The more you do, the better your muscle tone will be in your sphincter and you’ll get a number of benefits, like things feeling better, it being easier to stretch the asshole (strong muscles stretch more than weak ones without damage), and gaining more control over the sphincter.

Once he’s got a better control of his external sphincter and he’s become a little more comfortable with having his ass touched, then he can move forward by massaging his internal sphincter.  While you can’t control this sphincter, it is sensitive to what the outer sphincter does and by relaxing the outer sphincter, you can relax the inner sphincter some.  Make sure that you definitely use lube at this stage and, if you’re going to be doing it in the shower, make sure to get a good silicone lube so it won’t wash off in the water (don’t worry, it comes off with soap).  Massage around the inner sphincter like you did with the outer one and once it starts to relax, you’ll be able to tell, you can try inserting a finger into your anus to see how that feels.  Now, for some people this will immediately evoke thoughts of pooping, but that’s a connection that if you have, will be broken with time as you learn to differentiate sensations.  Once you can insert your finger, try inserting more or less of it and exploring around a little bit.  It’s not going to be easy to reach too far in, unless you get into some awkward positions, but explore as you can.  If everything is still going well, then try adding an additional finger or fingers to see how that feels.  All of this should not be done in one session, but spread out over many sessions and done slowly so that you can adjust to it slowly

Once you’re at this stage, you could start partnered play, but I’d recommend waiting a little longer.  I’d suggest trying to incorporate anal touching into masturbation a couple of times to that you can experience while you’re being pleasured.  For the first times, I’d recommend going slowly and just massaging the outside of the asshole as you masturbate.  Note how that changes the experience of masturbating.  Does it make it more or less intense?  Does it make it feel different?  How does your asshole respond when you masturbate?  If you’re able to pay attention while you cum, you’ll notice that the anal sphincters contract with orgasm, since they’re part of the sexual system of muscles in the pelvis that are involved in orgasm.  Once you’re comfortable with touching the outside while masturbating, try penetrating your asshole with your finger and see how that feels.  Once you have some familiarity with anal play and masturbation, then doing it partnered will be easier.  Also, by learning more about his asshole and how he likes to be touched, he’ll be better able to tell you, K., how to touch him.

Now, doing all of this solo is different than doing it with a partner, so let me address some of the concerns you might have with someone reaching into your ass.  I’ll limit myself to those you address in your message, but if you look at the linked posts above, you’ll see more discussion of problems that people can have with anal pleasure.

I’ll start with the issue of being nervous and clenched.  If you followed the advice above, you should find yourself much more relaxed and open to experiencing pleasure from your ass.  If you find that your ass is more clenched up when playing with a partner than it is when you play with it alone, then it means your ass is worried about how your partner is going to touch it.  Don’t worry, though, this can be overcome.  First, and this is very important, it’s much easier to know how much pressure to use, what angles use, what feels good and what doesn’t, when it’s your own ass.  When someone is playing with your ass, you need to give them this information by either explicitly telling them (which is what I recommend at this stage) or conveying this information via your body language and noises (which requires lots of experience together and a perceptive partner).  If you don’t tell them what feels good and what feels bad, they won’t know!  You have to let your ass get used to being touched by others and this involves going slowly and not over-shooting where you are.  You’re not going to go from not ever having someone play with your ass to pegging in one night!  Start by just doing external touching for the first few times you let a partner play with your ass.  Then slowly move to penetrating the outer sphincter only, then the inner sphincter, then exploring inside the anus.  Make sure you use lots of lube at each stage and limit yourself and your partner to not rushing ahead, even if you want to.  It’s better to go too slow than too fast, because if you go too fast, your ass will take a lot more encouragement to open up to your partner the next time: your ass will remember pain.

Also, and this is very important to anyone who wants to put a finger in any ass, make sure that you have well groomed hands and nails and that you don’t have any hang-nails, rough patches, or anything that might hurt an ass.  If you’re not sure, use gloves to make sure that the ass isn’t injured.  There’s nothing worse than having a scratch in your ass, you’ll feel it for days as it heals.

In terms of your worries about cleanliness, you shouldn’t worry too much.  In terms of your ass itself, you don’t actually store any fecal matter right inside the anal opening (or in the places you might end up using).  Furthermore, if your diet is good and your poop is generally solid and comes out neatly, then you shouldn’t have any remnants hanging around inside your ass.  If your diet isn’t good and your poop is loose and doesn’t clump together, you should reevaluate your diet.  If you’re really worried about anal play being messy, then you can always do an enema before anal play to rinse out your ass.  To perform an enema, all you need to do is get an enema kit from a pharmacy, make sure you will it with warm water (no laxatives, so empty out what’s already in there) and empty it into your ass.  Repeat until the water comes out clear, then wait at least an hour, although preferably two, to make sure all the water has come back out.  Enemas are super easy and you can guarantee a clean ass that way.  If you’re worried about the outside of your ass, a little soap and water is all you need there.

Hopefully this will be enough to get you going.  I have just a couple of final thoughts, though.

All too many men feel shame over their desire for anal play or the thought of getting pleasure from their ass, feeling that doing so is effeminizing or means that they’re gay.  This is a silly worry.  Sexual orientation, insofar as it is a useful concept at all, is only about the sex of people we are attracted to.  If a man is only interested in having women play with his ass, then it’s not gay.  Everyone has an ass and asses have lots of nerve endings can feel very pleasurable if correctly stimulated.   Furthermore, men have prostates and stimulation of the prostate can lead to some of the most intense orgasms possible.  Once you get more used to anal play, then prostate stimulation will become an option.  Self-stimulation of the prostate is exceedingly hard, you really need to have a toy or a willing partner.  To stimulate the prostate, all you need to do is insert a finger or fingers about two inches into the ass and make a “come here” motion towards the belly button.  You’ll feel a small lump under the skin of the rectum that’s roughly the size of a walnut.  This is the prostate.  If you reach slightly farther, you’ll feel a larger organ, which is the bladder.  When you start stimulating the prostate, it will grow in size as the man approaches orgasm.  If you can’t find it at first, try stimulating the man close to orgasm and then finding it while it’s swollen, which will be much easier and allow you to more easily find it next time.  While some men can orgasm from prostate stimulation alone, most can’t and require some kind of penile stimulation to get them to orgasm.

I hope this helps you guys get started.  Please write update us with how things go and what helped and what didn’t.


FCC (Federal Censorship Commission) warning: if you buy Anal Pleasure and Health using the Amazon link, I will make some small amount of money.  The federal government is very worried about this and wants you to know that they’re “doing something” to protect you against my machinations.

6 Responses to “Getting Started with Male Anal Sexuality”

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  4. WD

    Good article!
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