First Time Advice for Gay Anal Sex


Anal sex is often seen as the definitive form of gay love-making. You might think, and be pressured to think, that if you’re not doing it, be you top, bottom or versatile, you must be some sort of second rate closet case. But is it for you? It can hurt (a lot) at first, comes as something of a shock to the system, and might well be termed an acquired taste. If you fancy it, here are a few tips on how to begin to acquire it.

Spend time on your own discovering your anus before having sex with others. Run a bath and get naked. Go to the toilet. Then put some lube on a finger, work it around the outer anus, stay there awhile, and start pushing it in.

The sensations you get might already be quite intense. If you’re unsettled, use your other hand to masturbate and reassure yourself with feelings with which you’re familiar. Allow yourself to enjoy the new feelings. Relax and feel free to fantasise. Explore and get a sense of the shape and texture inside you. Then, when you’re comfortable, try inserting a second finger. Be careful, but rest assured your anus can certainly cope with this.

When you withdraw you might feel you want to defecate again. This is normal. Probably nothing will happen. If anything does, don’t worry. It will clean up when you’re done and there’s no shame attached. It’s just a reflex reaction.

You might also want to experiment with something more life-size. If so, use a proper dildo – not a deodorant canister or a cucumber. You don’t want to scratch the lining of your anus or have something nasty break off in there. And, yes, the guy in the sex shop may well take one look at you and know exactly where it’s going to end up. But so what? He’s seen it all already. Just acknowledge to yourself that you’re doing this as part of your exploration of yourself as gay.

When using the dildo, begin again with your fingers and use a lot of lube. You need to find a relaxed position. Sitting with your ass to one side can work well. If you’re standing, make sure your legs remain relaxed. If they tense, the sphincter will follow. Push it in slowly. Don’t force it. Don’t sit on it.

When you encounter resistance, pause, relax. If you push your anus towards the dildo, as if you were pushing faeces out, you might find you open more easily. Still, however gently you go, you can expect a pop. There might well be a moment of pain. After this, the rest will probably slip in a lot more easily.

The sensations that follow are complex. When you relax, the pain will probably abate and give way to a sense of elation. It can feel breathtakingly high, as if every connection in your body and brain just started firing. Your instinct might be immediately to masturbate and cum in a way more dazzling than you ever have before. One thing you are doing now is learning to ride this pleasure.

Move the dildo slowly and give yourself time to get used to it. It might be that’s enough for the moment, or it might be that you want to experience a faster pace – the pace of sex – and for as long as it would take a man fucking you to cum. If it’s the latter you want, be careful. The dildo can go as fast and as hard as you make it and experience no pain of its own. In other words, a dildo is NOT the same as a penis. Also, the loose skin around the shaft of a penis will lessen the friction on the anus, even though the head might be pumping quite hard and your buttocks might be getting a pounding.

Get ready to make some noise, and some pretty weird facial expressions. The feelings may become intense to the point of mindlessness. You might start groaning, shrieking, gurgling, sobbing…There comes a point when it is as if there is a barrier to cross. The feeling of being about to explode might make you stop. Or you can cross that barrier to find a further degree of elation.

At last, there is a point where you level out. It is as if a plateau has been attained and no further ascent is possible. You might want to stay there a little while, as it were to admire the view, then pause and prepare for the final shock, which is when you withdraw. It is possible you might make a mess. In order not to feel anxious about this, have a towel down or do it over a toilet or an easily cleaned surface.

Be aware that, after the high, there is a downside. After using a dildo, just as after having sex, your anus might take time to close. You might need to spend time sitting on the toilet relaxing and calming down. Also, the mess you might make risks leading to feelings of shame and humiliation. Mentally, you might feel unfocused and ‘spaced’ for hours to follow.

And when you first have anal sex (with a condom and water based lubricant of-course) be prepared to make further discoveries. On the one hand, if you’re the bottom, you are showing that man something intimate about yourself. You are experiencing ecstatic sensations – and making those noises and faces again – with him watching you. And you have to want him to do that. On the other, you’ll be seeing someone else working his way towards orgasm differently from what you’ll have seen and shared when masturbating or giving and receiving head.

Be prepared for the feeling of passivity. If you resist being passive and wanting him to do it to you, perhaps thinking that makes you less of a man, then, no matter your preparation, you’ll be in for a bad time. But if you accept all the feelings involved in having anal sex, then it can be wonderful.

9 thoughts on “First Time Advice for Gay Anal Sex

  1. Ben shirley says:

    Every time i have anal sex i allways bleed is it because my partner has a big manhood, he is over 10 inches long, or willit just take time to get used to it

    • Fraser Brown says:

      The length and circumference of his penis may make anal sex difficult at first. The secret is LUBRICATION and plenty of it. Use a good water based lube (water based will not rot the condom) and go slowly. You should find after a few times that the bleeding should have stopped. If not go to your doctor. Do not be embarrassed, he or she will have had to deal with this many times. Good luck and enjoy your anal sex.

    • Krys Storm says:

      I agree with you. My first time with my lover was awesome I was on cloud nine and it just got better the more him and I did it. I think I just use to his love member better it fit better

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