How to enjoy anal penetration

The most obvious possible problem with anal intercourse is that the man who’s receiving isn’t able to relax enough to take his partner’s penis.

It’s true that he needs to be relaxed in both mind and body to make it easy for his partner to enter him – the muscle ring around his anus will contract shut if he’s frightened of being hurt, or he fears being penetrated.
And for good thrusting which is enjoyable to both partners, he’ll need to be able to keep it relaxed – which is something that’s learned over time.

Not all gay men enjoy anal sex, and it’s fine if you don’t want to do it. But if you think you’re missing out on this source of pleasure solely because of feelings you have about your anus being dirty, then you might like to explore why you feel that way.

A lot of us have issues of shame around our anus – left over from all that repressive toilet training we received in infancy! Despite this childhood inculcation with ideas of dirt or shame or whatever, we can recover control over the muscles and learn to relax them at will.

So you might like to consider how you feel about your anus and rectum. If you think you feel bad about them, then you can begin a gentle exploration, perhaps when you’re in the bath or shower.
You can either do this on your own or with a friend (which may be much more fun, unless you need to get through some hang-ups first). If you want to avoid any trace of shit, just douche with a small douche bag before you try your exploration.

You’re in control, of course, if you do this to yourself, which can make this a safe way to find out what you like and don’t like. Try touching your anus while you’re in the bath or shower, or perhaps when you’re masturbating – if it feels good, try a little massage of your anus with a fingertip, or shift into a position where you can enjoy a little deeper penetration.

The objective is to monitor what you’re feeling, and how tight your rear end is when you try different things, like penetrating with a finger. You’ll have prepared for this moment by buying some lube or oil which will make penetration much easier; don’t use soap, shampoo or suchlike, it’s not good for the rectum.
Be careful, though, and don’t penetrate your anus with any sharp or potentially damaging objects, and use plenty of lube.

Once you have a finger or two (with well-trimmed nails) inside your anus, you can explore how it feels. Or you may want to masturbate with a finger deeper inside your rectum, and discover how that feels.
If you feel around inside your insides, gently, you’ll find a walnut-sized lump behind your testicles, which is your prostate gland. Pressure on this can feel very good, so if you’re masturbating, try a variety of movements with your finger and see what’s most enjoyable.

If you get onto familiar terms with your anus, it will soon learn to co-operate in admitting larger objects like a penis. Practice tensing and relaxing your anus around your finger. The nest step is to try a dildo; a small one to start with, obviously; you can go onto larger objects later.

If you’re playing with a friend, he can tongue or finger your anus, after washing it well, or he can masturbate you as he penetrates you with a finger. It’s not hard to get to a level of intimacy where you can do this – just say something like: “I’d like to try anal play, but I don’t know how. Can we try it together?” And it always helps to decide what you want to do before you start….

What if you can’t relax?,

This means that you’re still quiet anxious about being penetrated. Relaxation is the best way to deal with this; gentle sex play with a trusted friend helps as well, so that you work your way up to full penetration gradually.
If it proves absolutely impossible, then either this isn’t the form of sex for you, or you may need to see a gay counsellor or sex therapist to shed a few of your inhibitions.

And if you can relax?

When it comes to the time to try full-blown anal sex – that is to say, to have your partner put his penis inside you – you may find that you have to cover some of the practice ground described above again; after all, a penis is much larger than a finger! If you feel pain as he penetrates, take it very slowly.
He can enter you a little bit at a time so that you get used to the feeling of penetration and so that you can relax as he makes forward pressure against your anus. He needs to back off every so often so you can relax; little forward pushes followed by relaxation are the best way to get in for the first time. A lot of lube will make this much easier.

If you really want to be in control, squat over him and lower yourself onto his erect penis, holding it with one hand so it’s at the correct angle to go in. Or you can wrap your hand around his shaft so that he cannot force more of his shaft into you than you want to take at any time.

After he has his penis in you, it’s about relaxing and letting go, about enjoying the feelings that come as he thrusts or moves in and out of you. If you masturbate as he thrusts, you may find that the experience is very intense. Any slight pain or discomfort you feel will soon give way to pleasure – if it doesn’t, you may want to stop and shift position, or try again later when you’re feeling more relaxed.

Remember that you don’t have to be passive – indeed, the penetrator may even remain still while the penetrated man makes all the movements.

“Passive” and “active” are the wrong connotations: it’s more about receiving and giving, meeting in a sexual union which gives both of you pleasure and opens you to human contact – or, at least, a very powerful sexual experience!

Finally, as for the movements of sex, let them come gradually. Just do what comes naturally, and learn through experience.

Other problems with anal sex

There’s a saying that “the penis never lies.” What this means is that if you’re penetrating for the first time, you’re likely to have an attack of nerves which results in you coming too soon – or, worse, your penis wilting, and your erection disappearing!

Talking about this with your partner is essential, because explaining how you feel and what you’re experiencing will take away a lot of the pressure.

What makes this worse is when you worry that it might happen again next time, because you’ve established the association of sex and erection failure. Just laugh about it if you can; it happens to everyone (fact!).
Losing your erection isn’t a failure, you’re not a failure, and the problem will go away as your confidence grows.

Being relaxed and intimate with your partner is often all you need to get over erectile difficulties: although men are often supposed to be rampant sex machines, ready and erect to go at a moment’s notice, this is in fact rarely the case, and some men just can’t get it up for a casual encounter with someone they are unlikely ever to see again.

Instead, find a friend you trust, who’ll help you. Go back to anal play with a finger, and when you’re comfortable with this, try lying on your back, and inserting your penis into your partner as he lowers himself onto you. You don’t have to move at all; just relax and enjoy the way it feels.

And then don’t worry about what you do after penetration! Instead, let your partner move as he wishes while you just enjoy the feelings you get from it.

When you’re comfortable with the sex so far, try a different position: side by side, either facing each other or facing away from each other, is good, because it’s less demanding, and you can relax or thrust without much danger of losing your erection.

What you’ll find is that the way you move will probably have a lot to do with your emotions. You might thrust your hips slowly, fast, hard, softly, simply, in complex movements – whatever feels good.

And moving in synch with your partner is something you’ll gradually learn how to do as well. For example, you could thrust while he moves his pelvis in a circular way.

And if you’re trying positions like rear entry or missionary, you can either thrust in opposition to him, so that your bodies come harder together, or you can thrust in synch and time with his rhythm, so that you move in the same direction at the same time: the first method holds much more energy between you, and can be good for two men who want to express their masculine energy during sex at the same time.

The question of force sometimes arises in gay sex. The answer is very simple – unless you’re into some of the darker sides of sex, anal sex should always feel good; it should not hurt (beyond maybe a little at first).

If your partner is trying to force his way into your anus, and it feels bad, stop the sex. He’s not considering your feelings, nor your body, and you need to ask if this is the kind of sex you want from anyone.

And since an anus is only as loose and open as its owner, if you’re the person entering it, always be considerate and kind. You should use gentle pressure to start with: if there’s any pain beyond a little at first, it’s a bad sign, for the receiver is not ready to have sex, to be penetrated, and you need to stop and work towards it more gradually.

Deep thrusts and strokes can be good for both partners once the bottom is opened up and loose; at first, shallow strokes and gentle pressure are more appropriate.

When things loosen up and get going, and both partners become more aroused, you can increase the the speed and depth of your thrusting until you reach the point of ejaculation.

There may be more satisfaction to be gained from anal sex than masturbation because the friction of the anal canal may be considerable: this may mean you ejaculate fairly quickly.

Experience and self-control (not always easily acquired, it has to be said) may be helpful in slowing down your progress towards orgasm and ejaculation; this may be one occasion on which men with delayed ejaculation actually have an advantage over the rest of us!

Finger play with your partner’s anus

As you press in (with plenty of lube), you’ll feel your finger pass the muscular rings of the outer and inner anal sphincters. The inner wall of the rectum feels ridged, soft, muscular and warm.

Once your finger is inside, move it around, curling it around the inner edge of his anus and feeling his prostate.
Stroking or massaging his prostate as you masturbate or fellate him will increase the strength of his ejaculation many times (if it hurts, it’s probably infected; if he doesn’t feel much, he’s probably nervous).

Putting two fingers up him will increase his sensations, and you can move them around independently to add to his pleasure.

Just having your finger(s) positioned inside him while sucking or jacking him off will feel good for him, and if you massage his prostate gently by sliding your fingers up and down at ejaculation, you can double or quadruple the intensity of his orgasm. When he’s ejaculated, you can simply pull your fingers out gradually.


Rimming – (also called “analingus”) is licking and tonguing your partner’s anus. To make this a pleasant experience, good hygiene is essential, so cleaning up beforehand in the shower or bath is a good idea – just run your finger inside the anal canal to make sure it’s clean. An enema or douche can also be reassuring.

The reason this can feel good is that the anus is well-supplied with hundreds of erotically sensitive nerves, all of which will register the pleasurable sensations associated with a tongue licking or caressing the anal area. It might not be to everyone’s taste, but it can be fun to try it.

Another way to enhance a man’s enjoyment of analingus is to lick and nibble at his balls and cock at the same time.