Couple’s Couch: Anal Intercourse 101: Filling the gaping hole in our sexual education

Now that you’ve perfected your anal penetration skills with fingers and toys, you might feel ready to move onto a real, live penis. Horary! For an optimal first-time experience, I’ve organized some helpful tidbits of information to digest before you lube up and get down.

First and foremost, the cock sliding in and out of your tight little anus has nerve endings of its own. Even if your beau is totally in sync with your desires, he may find it’s substantially harder to control his movements when being inside of you feels so fantastic. Men, this is the ultimate test of self-control. If your sub tells you to go buck-wild and fuck them like an animal, go to town. But if at any moment they ask you to slow down, to not do that but do this instead, or pull out, it is vital, and I do mean vital, that you comply.

Unlike fingers or dildos that can start and stop with your every whim, the man controlling his member is unlikely to know how you want him to move. You are responsible for your own pleasure which may necessitate telling him how much to put in, how much to pull back, how fast he can thrust, how deep, when to let loose, when to freeze, and when it’s time to get the heck out.

What if my lover isn’t interested in having anal sex with me?
Simple. Find a new lover.
No, just kidding.

Many people say no to anal play because of their preconceived notions about what is involved. This goes for both the topping partner as well as the bottoming one. Sit your lover down in a non-sexual situation, over coffee and scones perhaps, and ask them (nicely!) if they will talk to you about their reservations. Most anal-negative people I’ve met have issues with some combination of the dirtiness factor, the potential smell, the STI risk, the fear of hurting their partner, or that doing someone in the butt will mean that they are gay.

It will help your conversation if you listen to these fears and not just shoot them down as inconsequential. After all, they make sense when we consider all of the societal messages we’ve internalized about our butts. Review “Myths of Anal Sex” from last week, talk about them together, and see what comes of it.

Running the risk of stereotyping my eager male friends, I would be remiss to not mention reciprocity. Men, if you are excited to anally penetrate your partner, you have to play fair. If they are reluctant to offer up the booty, take one for the team and let them do you first! There is no reason they should bend over for you unless you are willing to give back in kind and give it a try.

All of the proactive information in the world might not inspire them to have anal sex with you. If this is the case, it is up to you to get creative. Would they give consent for you to wear a butt-plug into a non-anal sexual encounter as long as they don’t have to insert it? Would they watch while you showed them that anal masturbation really gets you off? Would they settle for cuddling up on the sofa to watch one of the many fabulous “how to” anal movies? Demystify the act, talk about it, and hopefully y’all will come around to a satisfactory arrangement that gets you naked in one heck of a hurry.

Next step, getting tab A into slot B.

The big difference between anal penetration with fingers/toys and anal with a penis is more than the size, though the size matters. Penile penetration takes the pleasure of two people into consideration, thereby changing some of the movements and angles for the receptive bottom.

I simply cannot stress enough the necessity of moving slowly and breathing deeply. It might take numerous tries before his cock slides home without a fuss so don’t expect a perfect fit right away.

When you’re ready to begin, slowly tease the rim of your asshole with a lubed finger or tongue until it begins to relax. Foreplay here is important. If you aren’t turned on when your ass is approached, it will be exponentially harder to get your anal sphincter to relax. Interact with your lover in a way that you know will turn you both on. Even consider having some full-on genital play. The sexier, the better.

After getting good and hot, penetrate your anus with something slender; a finger, beginner’s dildo, or a small butt-plug are all great options. We do this to prime the sphincter, inducing relaxation with a pleasurably small item to warm it up for what’s to come.

When you feel relaxed and ready to proceed, do so with finesse. Press the tip of the penis against the edge of the asshole and press the tip in slowly. If you aim for the middle of the hole, your angle will likely be off. Press in at a 45-degree angle as if you are trying to bump the belly button via a route through the abdomen. If you feel pain, back off a few millimeters until the sensation subsides and take a few, deep breaths. Then press back in.

When I get nervous during anal, I often have trouble relaxing my sphincter enough to keep penetration from pinching. My trick to make everything relax is doing the precise opposite movement. Clench all of your anal muscles as tightly as possible for a few seconds, then let go. Clench again, then relax. After a few repetitions, I gain control over my sphincter and have an easier time accepting larger toys into my body a few millimeters at a time. It may take weeks of trying to get there, but practice will make the master.

Once you get all the way in, I cannot over estimate how nice it can feel for the top to just sit still and let the bottom adjust to the sensation. It is quite a personal thing, being inside someone’s anus. It’s warm and cozy in there, plush in a way that would make any vagina pink with envy. If you take some time to marvel in this sensation together, syncing your movements will be that much easier and your bottom will be substantially better off.

Most importantly, explore and enjoy yourselves! Anal play can be incredibly powerful, so don’t be surprised if you find yourself laughing or crying without having the foggiest idea why. Anal play forces lovers to be vulnerable with one another, and gaining sexual fulfillment while allowing yourself to open fully is a beautiful thing. Give yourself and your lover permission to explore your bodies and their many capabilities and you might be surprised at the many sensations that await you.

This entry was posted on Friday, 12 October 2007 at 12:00 am and is filed under Advice. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.


2 Comments so far

  1. My boyfriend LOVES anal. And I think the only reason is because we dont do it very often. I enjoy it as well, but again, because we dont do it very often it is often a painful process. My question is like other muscles in your body, is it possible for the muscles in your ass to have muscle memory? If we do it often enough, will it get easier over time?

  2. Yes! Not only will your sphincter get better at relaxing at your every whim, your muscles can be coached to slowly strech, allowing larger/thicker items inside with less resistance. (I find gradually introducing slightly larger toys every once in awhile can facilitate this process.) I can’t speak to your sphincter having true “muscle memory,” but you can certainly train your brain to act on behalf of your butt.

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