Dear Carol,

I know I'm late to the game here, but I have just made up my mind to explore anal sex. I have worried about its health risks and, to be honest, have been afraid of pain too. But I have a new partner now whom I trust a lot and whose health I am pretty certain of, so I am going to take the plunge - or let him take it, I guess. But I would like to ask for some handholding first, all the same. What should I be aware of? Any precautions you would recommend? How do I minimize pain? I hear such different things about anal sex that I am not sure whether pain is inevitable or not. I'd rather avoid it, if possible.

--Virgin Butt

Dear VB,

Late to the game? Do you mean that for the last decade-plus, it's been "all anal, all the time"? Everybody's doing it but you? But look at the bright side. You can explore guilt-free and legal anal pleasure now that the sodomy law has been overturned. Just a brief digression here before we get to technical info that will help you begin to explore: many people don't know that sodomy doesn't always or only mean anal sex - sometimes its definition includes oral sex as well. And many people have had the misapprehension that sodomy was by definition a gay male thing, but there have been sodomy laws on the books that explicitly banned heterosexual sodomy too. Yes, in some states, it's no non-procreative fun for *anybody*!

You don't say whether you're male or female - and, for our purposes here, discussing healthy and comfortable anal play, it doesn't really matter. Everybody (almost) has an anus, and therefore some subset of everybody will decide to explore anal eroticism. Let's get you ready to do it too.

First, before you offer your partner this particular virginity, consider playing anally when you masturbate, at least a few times. This gets you used to anal sensations, helps you recognize the line between comfort and pain, and gives your body a chance to trust the sensation while you're completely in control of it. You'll want to communicate clearly with your partner once he joins the fun, and it helps to know something about what feels good and not-so-good. Play with smooth, unbreakable toys that have a base so they can't slip inside or fingers with trimmed nails, plus plenty of water-based lubricant. The tissue of the anus and rectum is delicate, so nothing scratchy or sharp should be inserted - or even used for external stimulation.

Some people are very concerned about cleanliness and anal penetration. For the most part, it's enough to have an empty bowel. If you want to go further, use a saline-only rectal douche (beware of packaged enemas from the drugstore that are full of chemicals you don't need; the rectal tissue can absorb chemicals, so don't use them). Water in, water out - a couple of rinses like this and you'll be clean enough for almost any sort of anal play. You can also use a douche system for rinsing, but don't use too much water too fast. You do not need a classic enema for this, which involves a lot of water taken into the rectum over a fairly long period of time. All you need is a rinse.

To avoid pain upon anal penetration, you need three things: relaxation, lubrication, and communication. Relax by breathing deeply, making sure your partner's letting you call the shots as far as speed, when to penetrate, how much lube to use. Entering a person quickly is often a recipe for sharp pain, so start out slow, gradual, and in touch with one another. If you use alcohol, speed, or any other substance that affects your sensations, skip it. You want to feel what's going on so you can stay safe. You also want to be aroused - everything will feel better if you're at least as turned on as you usually are when you have sex. If you've played with toys before attempting penetration with your partner's penis, you'll have a better chance of accommodating him; if not, play with fingers first, and wait for penis penetration until two or three fingers feel good. Keep adding lube as you add more fingers. Once he's inside, keep letting him know how fast to go. Experienced anal players can have down-and-dirty, hard and fast anal intercourse - beginners are advised to take it slow until your body starts sending you signals that it wants more. Anal penetration can be exquisitely pleasurable - and as intense as anything you've ever felt. Hopefully you'll get these feelings all at the same time.

Experiment with different positions. Some people appreciate doggy style; this makes anal penetration very easy, though you are facing away from your partner and might prefer a more face-to-face position for intimacy and communication's sake. You might find it's actually easier to relax when you're on your back and he's facing you - sort of a missionary position, though the missionaries and their friends are the folks who gave us those just-overturned sodomy laws, so they probably wouldn't approve of lending their names to anything involving anal sex. Don't let that stop you from trying the position, though!

Males being anally penetrated will have one extra reason to try a few different positions - one will undoubtedly be the best for prostate stimulation. Which one serves this purpose will be affected by the way the two partners fit together, the length and curve of the penetrating partner's penis (or strap-on dildo), and similar factors - but many men (of all orientations) love anal penetration specifically for the prostate stimulation it gives them.

By the way, you mention your partner's health, and I assume you may be taking about his HIV status. But even HIV-negative folks sometimes decide to condom (or glove) up for anal penetration - it's one more level of cleanliness, for some. For men who are anally pleasuring female partners, using a condom makes it easy to switch to vaginal penetration without having to wash off between anus and vagina - just strip off the condom and continue! It's not a good idea to switch from anus directly to vagina otherwise; many women find it provokes vaginal infections, although some women don't seem to have trouble with these.

Dr. Jack Morin, who wrote *Anal Pleasure and Health* (great book, and you'll get much more detailed information from it than I have space to give you here), believes that virtually anyone can experience pleasurable anal penetration - as long as they want it. So your having made this decision, on your own time, is the most important part of your anal adventure.