The Other Way In: Making Anal Work

Ok, so I know this isn’t the most creative, but I really want to do it in my wife’s ass. She’s kind of interested, I’m very interested, and we both want to be safe and for both of us to enjoy it. How’s she going to feel good? What are ways to ease up to, yanno, something bigger? And lastly, do you guys have any toys you’d recommend?


james_nelsonAnal sex has so many possibilities, and yet is prey to so many misconceptions. There are still people out there that believe that anal isn’t something straight people do — at least not respectable straight people. Luckily more and more straight men and women are curious about experimenting with anal, both boy-on-girl and girl-on-boy using a strap-on.

But many people refrain due to another misconception: the belief that anal must hurt. Some people just assume — after all, you’re sticking something up your ass! Others may have tried anal without being prepared or doing it properly, resulting in a painful experience.

It is unfortunate but not tragic that there are people who don’t try anal because they think it will hurt. But this myth has more dangerous consequences. Some people attempt to dull the pain of anal sex by getting intoxicated first, or by using “numbing” lubricants. Do not do this! Pain is your body’s way of saying ‘stop’, and if you ignore (or dull) the pain, you can injure yourself, perhaps without even knowing it.

Luckily, it’s not hard to make anal safe and enjoyable. First, you need good communication between the person penetrating (who I will henceforth call ‘Top,’ borrowing from gay parlance) and the person being penetrated (‘Bottom’, of course). Then you need my four P’s’: Passion, Position, Patience and Participation. And of course, you need lots of lube; I recommend a water-based lubricant such as Probe Classic. This is especially important if you’re using a condom (which you should be if you’re not in a long-term monogamous relationship), because oil-based lubes will eat through latex.

The first ‘P,’ Passion, is the easiest. Basically, the more turned-on Bottom is, the easier anal will be. Whether Bottom’s male or female, when they’re horny their body becomes more relaxed and ‘open.’ If Bottom is a woman she might warm up by sitting on Top’s face; if Bottom’s a man, a blow job might do the trick. Or penis-in-vagina sex might be a good starter either way.

The second ‘P,’ Position, comes next. Most people assume that the standard position for anal sex is on all fours, i.e. ‘doggy-style.’ In fact, this is not the easiest way to do it. The most comfortable way to start is for Bottom to lie on one side with knees curled up to chest. Another good position for Bottom to kneel with chest and head bent all the way to the bed, similar to yoga’s “child’s pose.” Basically, the closer Bottom’s knees and chest are the more open Bottom will be.

The best way for Top to start is with a finger and some lube. You’ll find a finger goes in quite easily. Top should do this until Bottom gets used to it; this is where the third ‘P’, Patience, first comes in. The first few times you experiment with anal, this might be all you want to do. As Bottom gets accustomed to it, they will be ready for something bigger.

At this point Bottom is unlikely to feel any pain. But if you do, Bottom, say “stop” right away. It doesn’t mean you have to quit altogether; you just have to back up and try it slower. Top, you should always be checking to make sure Bottom is okay. This is standard operating procedure with any sex act, especially one you haven’t tried before.

Once Bottom feels ready to try something besides a finger, the final ‘P,’ Participation, comes into play. Top should lie back, while Bottom kneels with knees on either side of Top and anus right above Top’s penis (whether biological or a dildo). In other words, Bottom should be on top. Rather than Top fucking Bottom, Bottom can ‘participate’ by fucking themselves on Top’s member.

This is a good time to add more lube. Then Bottom can slowly slide onto Top’s cock. If Bottom’s been warmed up with a finger and is turned on, then the cock should easily penetrate the anus and go up several more inches before coming to a second obstruction. This is the inner sphincter, and it doesn’t open as easily.

In fact, it may feel to Bottom like there is no way that the cock can go further without hurting terribly. And it will hurt if you force it now; it could cause injury as well. But this is where Patience takes over again. Just stop there for now, Bottom. Pull yourself most of the way off the cock, then go down again until just before it hurts. Do this for as long as you need to.

Top, you should have nothing to complain about at this point. Just relax and enjoy it.

Eventually, Bottom should start to get a sense of relaxing and loosening up further. Eventually the cock might just slide in the rest of the way naturally. If it doesn’t, Bottom can open up by the counter-intuitive step of trying to ‘push out’ the cock like taking a poop. This can be hard to do at first, because Bottom might feel like they really are pooping, but they won’t.

It may not work the first time you try, or the second. That’s okay, because every step of the process is pleasurable. The more you try it, the easier it gets, and the more fun it is. Once you’re more comfortable with anal you can try other positions, such as from behind on the side, or with bottom lying on their back with knees to shoulders.

Some people are afraid of anal because fear of poop. There may be a little — that’s where it comes from! — but not a lot. There will be less if the bottom has recently done a number two. Either way you should clean up well afterwards, maybe take a shower together.

JoSchmo, I hope your wife is open to enjoying this. But then, she might want to strap on a Claire Dildo in a Commando Harness and do you the same way. And then I hope that you were as open to the idea as she was!

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