I've heard it 863 times now (I've been keeping track). "I tried it once and it was awful." Or "My ex did it to me once and ruined it for me." Or "I'd like to do it again but I'm afraid it'll be as bad as the first time."

With a fervent desire to elevate butt-luv to the highest echelons of sexual experience for as many people as is possible, I would like to give you some ideas about how to make your first experience with anal so amazing that you'll want to try it again. And again. And again.

A caveat: I am not an expert. Read here for much more information on the topic in general, or take a look at this instructional dvd.

I have but one iron-clad rule which I will get it out of the way first. Both the giver and the receiver of the anal attentions must want it and want it badly. If this criterion is not met, nothing else will go well, no matter how hard you try.

If the penis-owning partner wants no part of inserting his willy into your ass, or if the ass-owning partner can't imagine being penetrated in that manner, you are SOL. I can't help you.

If the receiver really, really wants it, the first thing she (here I'm making the wild assumption that she will be a she; of course she needn't be a she, but I am a she, so there you go. Extrapolate at will.) must do is practice on her own. No partner. No audience. No help. Privacy is absolutely necessary.

To get comfortable with anal play, you have to convince yourself that you can have things in your ass without poo going everywhere and without horrific pain. You can--but you won't believe me until you try it for yourself.

For this part of the program, I suggest a very thin dildo or plug. Be sure to select a dildo with a flared base made specifically for anal play, as the last thing you want to do on the same day that you violate your own virgin ass it to have to haul that ass to the nearest ER for the surgical removal of a toy from your rectum. This would be exceptionally awkward. Flared base. Got it?

Also, invest in some high quality thick lube. Liquid Silk is nice, but Sliquid is even nicer. Conveniently enough, you can repurpose your unused Sliquid or Liquid Silk for any activities requiring lube, just in case your anal adventures are a complete bust.

Put the dildo and the lube within reach of the bed. Add to the pile your favorite method for working your body into a pre-assplay frenzy. I like a good strong vibrator. Do you like porn ? Turn some on. Will fingers suffice? So be it.

Toss down an old towel of a darker shade on the bed. I have a black towel expressly for this purpose. Place another dark towel near the bed. You'll need this later. Then hop in bed and make sure everything you need is within reach.

You may notice that I've said nothing about enemas. I've not yet tried an enema, although I'm not against their use. If you feel the need, go right ahead. If you've recently used your butt for its primary purpose, an enema's probably not going to add much to the cleanliness aspect, but if it makes you happy, enema away.

If you are multiply-orgasmic, get your bad self off in your standard way a whole lotta times before you even think about your bottom. If you aren't multiply-orgasmic, get yourself exquisitely, throbbingly close to an orgasm a few times before you even think about your bottom. Your goal is to be so achingly horny that your inhibitions drop to nearly nothing.

Then lube both the dildo and your ass liberally. Make sure the lube goes right up the shaft of the toy, as that part may eventually be inside you too. If the toy has a long enough handle, you can try inserting it while you lie on your back. If not, roll on your side with one knee pulled toward your chest.

When first you try to insert a toy, your ass will be very confused. It will be all agog with wonder that something is violating the rule (One Way Only!) that has been so strictly followed up until this point.

Asses can be stubborn creatures and comfortable in their habits. Your job is not to force your ass to bend to your will. You must coerce your ass. Romance your ass. Woo your ass. Nudge the toy ever so gently against the opening until it wants to open up.

It will help if you do two things at this point. First of all, if you can in any way manage it, keep up the stimulation you were using before. Can you wedge a vibe against the bed? Can you nestle a bullet vibe between your labia? Can you keep on watching porn? Good. We're not trying to pull a fast one on your butt. We're only trying to keep the level of happy relaxation going.

It will also help matters greatly if you push gently out against the dildo you are attempting to insert. Yes, push out. When a dear friend first explained this method it to me, I didn't believe him. But pushing out against your toy will actually open up your bottom wonderfully. Don't believe me? Try it.

You will feel some resistance, but if you are sufficiently lubed and horny as hell, the tip of your dildo should eventually make its grand entrance into your bottom. Go very slowly. Do not force it.

If this time it doesn't go, relube and try again. Or not. It's not a competition to see how much / how fast / how many / how large you can take. The more relaxed you are, the easier it will slide in. But if it doesn't, just finish getting off and try again another day. A not-forced bottom is a happy bottom. A forced bottom has the potential to make your life exceedingly miserable.

It make take you several sessions before you can insert your toy. That's all right. The goal here is to be able to have buttsex eventually. You may have to practice for weeks before you are comfortable enough to move past this point. If your partner is understanding, he'll wait. If he's not, then he doesn't deserve to get into your ass in the first place.

After you have gotten the toy into your bottom successfully, you'll want to play. Thrusting is nice, but it's not for everyone. Try it and see, because it's especially nice to be able to hit your g-spot from inside your ass. It's really especially nice.

But if you find this less nice than I do, think about experimenting with clitoral stimulation while your dildo simply rests inside your bottom. This also is amazing.

You may need to wedge your toy against the bed in some way so that it doesn't shoot out of you. Butt-muscles are surprisingly strong, and while it can be damned funny when your butt fires your toy across the room, your cat will be pissed as hell if he gets hit in the head with it, and you will be less than enthused if this happens right as you are about to come. To avoid this possibility, find a toy with a thin neck designed to stay in while you play.

Orgasms with something in my bottom feel completely different than orgasms without. I feel more opened, more exposed, more hot. Expect yours to feel different as well.

When you want to take your toy out, you again will need to work very slowly. Give your bottom time again to open up, and under no circumstances should you yank the toy from your body. Gently pull on the toy, going especially slowly when its head is coming free of your body. Push a little if you can.

It's not stuck. Really. Just keep working it.

When finally it breaks free, use the towel that is not under your bottom both to wipe up any drips (there will be drips) and to wrap the toy. Get that bad boy to the bathroom as soon as you're done cuddling with yourself. Give it a thorough wipe off and bath.

During my year-plus of playing with my bottom, I have yet to experience a feeling I'd describe as pain. Some people do. I'm just lucky, or have a high pain tolerance, or a slight degree of brain damage, or something. But if you feel pain that does not resolve almost immediately into intense pleasure, you should stop.

Don't for the love of God even dream of using any kind of desensitizing product. The point of buttsex is pleasure, not numbness, and if you even briefly trick your body into ignoring pain in the moment, you can rest assured that it will repay you with additional pain on the following day.

Later we'll continue our lesson on buttplay. We'll talk about how to incorporate your partner into your buttplay in such a manner that you'll both want to try it again and again and again.

Now get on outta here and practice. Then come back and check out our Guide To Buttsex (Pt. 2).