I never used to like anal sex.  I wouldn't let anyone near that part of my body.  There were all sorts of worries and thoughts running through my mind every time someone tried, from concerns about pain, to concerns about cleanliness, to not understanding, on a personal level, how stimulation to this part of the body could be enjoyed.

Shortly after I met M, He announced that I would, eventually, give Him that part of me.  That I wouldn't have a choice, and that I would, eventually, learn to like it.

I don't think I believed Him.

One of the many reasons this man is perfect for me is His occasional gentle application of new things.  He knows, whether I tell Him or not, when I'm hesitant, and need to be eased into something, and reacts accordingly.

Anal sex was not one of these situations, and so my introduction into giving Him what He wanted was, "This is mine, too, isn't it?" and in He went.  He went slow, and let me get comfortable before taking His pleasure from me, and before I knew it, I was in heaven.  However, there are other ways of involving yourself in anal play.  Techniques some consider much easier and healthier.  And that's what I've come to discuss today.

The "back door".  It's a place no man has gone before.  Or maybe he has, and that's why you're scared.  There are all sorts of things that can turn "Oh, yes!" into "Oh, no!" during butt sex.  So let's talk about a few ways to avoid them, shall we?

I almost always give myself an enema before anal play.  It's not required, and some people never do, but I'm a little squicked out by the functions that part of my body performs, and so I cleanse.  It's really not difficult, and it doesn't take long at all.  It's as simple as inserting a tube into your rectum and allowing water to transfer into your bowels.  Wait fifteen minutes, give or take, and expel.

I rarely wait more than five minutes.  Probably this makes it less effective, but I've never noticed a problem.

Extreme Restraints has a whole page of enema equipment if you decide this is the way to go.  I use the Unisex Douche System.  It comes with a two liter bag, a detachable tube, a closeable nozzle and two "heads".  One of the heads is short and thin and intended for the anus, while the other is sort of tampon shaped and intended for the vagina.

This kit has lasted us years, though the tubing isn't the easiest thing to keep clean.  Especially if you have hard water like we do.  Calcium tends to build up inside.  But generally speaking, it's easily dissolved with vinegar so long as you don't let it build up for too long.  And the kit is cheap, so it's not too painful to your wallet if you have to replace it.

Whether or not you decide to cleanse before indulging in anal play, you're going to want to go slow and relax.  I cannot stress this enough.  Toys can be intimidating, so start with simple touching.  Run your fingers (or have your partner do it) along your anus and get to know the sensations you can experience in that area.  You don't have to insert anything, yet.  Just see how touching feels.  And once you're comfortable with that, move on to insertion.

Use lube.  Lots.  There's no such thing as too much lube during anal play.  That's the toasted toads truth.

I tend to lean toward water based lubes because they blend well with my natural fluids, wash away easily, and are safe with all toy materials.  My favorites, so far, are Better Sex Essentials Liquid Lube and Toy Fluid by Fun Factory, but you could just pick up some Astroglide or KY from your local pharmacy.  Some people prefer oil or silicone based lubes, and those are fine, too.  However, make sure whatever lube you do choose is compatible with any toy you intend to use to protect yourself and your toy from possible damage.

Are you ready to move on to a toy? The only person who can answer that is you.  Some people go straight from touching to anal intercourse, but others prefer to experiment with anal plugs first to allow their muscles to stretch and get used to having things inserted rather than evacuated.  This is actually recommended by some sex experts.

Start small.  A diameter ranging between 1" and 1.5" is best for the anal beginner.  And the safest squishy material for a plug (or any sex toy, really) is silicone (Water based lube only for silicone toys, please!) because it's nonporous, phthalates and latex free, and hypoallergenic.  You can find some really great anal starter kits around the web that have, generally, three different sized plugs, which allow you to work your way up to the big stuff if that interests you.  This one by Trinity Vibes, (extreme restraints) with plugs ranging from 1.25" to 2", all made of silicone, is an excellent investment for the anal beginner, as well as the more experienced player.

Another good way to begin is with a slim, textureless, traditional vibrator.  Preferably something squishy, like silicone.  The vibration often aids in relaxing the muscles, which is always a plus.

Go slow.  Just as there's no such thing as too much lube, there is no such thing as too slow.  Take your time.  Breathe.  Relax.

There might be pain.  I won't lie to you.  The first time you insert something into your anus, no matter how slow you go or how relaxed you are, it might hurt a little.  If you feel pain when inserting your first toy, stop pushing.  You can either pull it back out a little, or leave it there.  Either way, wait till the pain subsides, and try again.

If there is resistance, however, don't keep pushing.  You could damage things.  You need to adjust your angle.  It might take a bit of practice to figure out which angle is best for you.  Hell, I'm an old pro, and I sometimes still go at it all wrong.

From here, it's smooth sailing.  If you're using a plug, your anus should close comfortably around the shaft just before the base.  I've heard of some people having trouble finding plugs that fit them comfortably, but all in all, that seems to be rare.  I occasionally come across plugs I just plain don't like, but it seems most often to be the texture or material I'm not comfortable with, not the design.

When you're ready, give intercourse a go.  This may take practice, as well, before you're completely comfortable with it.  It's easier on my psyche if I'm able to give myself an enema first, but we don't always schedule anal intercourse.  Sometimes it just happens.

We didn't always use lube either.  Till one day, my butt was nice and lubed up from extended plug wear and M decided He wanted to be where the plug had been.  And He loved it.  And I loved it.  We use lube almost all the time now.

Some people, once they're comfortable with anal play, find they enjoy a bit of anal stretching.  I've seen some pretty insanely sized toys  intended for anal play.  The glass plug I just received with a two inch diameter is as big as I've ever gone.  I don't know whether or not I'll ever go bigger.  I'm one of those girls who sets limitations for herself, then does everything in her power to exceed them.  So we'll just leave it at "Maybe."

Anal stretching requires nothing more than the steps I've listed here.  Sometimes it takes a little more patience and a lot more warm up.  It always takes a lot of lube.  But as long as you remember "Slow and steady wins the race." and relax, you'll do just fine.

Kink Academy Videos on Anal Play (affiliate)

Reference Material

For more information on anal play, check out Anal Pleasure and Health (amazon) by Jack Morin, Ph.D.  Mr. Morin covers just about everything anal you could possibly want to know, including, but not limited to, the history of anal sex, how to begin exploring anal sex solo or with a partner, and how to maintain healthy bowels.