Dear Men,

So you want to have buttsex, do you? Perhaps you’ve seen the act depicted in porn and it seemed hot, eh? You thought you’d like to have a new passage, a tighter passage, a more forbidden passage into which to dip your wick?

Congratulations! This is a lofty goal, and I’d like nothing more than to speed you on your path with all good will.

But before you get too carried away with dreams of the ass, may I fill you in on some few small details? I may? Thank you.

For the love of pete please first banish from your mind the thought that you will be able to fuck your partner’s virgin ass tonight. You won’t. You can’t. At least, you can’t fuck her ass tonight if you’d like to be able to fuck her ass ever again.

Don’t ruin it for yourself, dude. Don’t ruin it for every other man she’s ever going to be with. Most of all, don’t ruin it for HER. What you do now can affect how she’ll think about buttsex—and about you—for a long time to come. Take it slowly and you will reap the benefits.

Next, don’t try to “numb her to the pain.” Yes there are products specifically for this purpose, but they are not a good idea. You don’t want her numb to the pain. In fact you don’t want her in pain at all.

What you want to do is introduce the idea to her gradually, as something you’d like for her to enjoy, not just bear. You want to go slowly, so that her body can learn to relax enough to accept first a toy, then maybe a finger, then after a long while and much pleasure, your body.

It’s slow, understand? It’s about trust. It’s about learning together that you can do this without pain and without the world coming to an end if things go awry—and trust me, when there’s buttsex happening, sooner or later things will go awry. Learning to handle these things is the difference between buttfuckery being either amazing or a complete disaster.

See what I mean? It’s not about numbing her up and jamming it in tonight, ok?

Your ultimate goal is to make buttsex so incredibly pleasurable for her that she’ll beg you for it. You want her wound up with enough desire that she’ll moan, “Fuck my ass, baby, please fuck my ass!” every time you have sex.

Or, you know, maybe every other time.

Oh, and may I make one final suggestion? You want your girl to take it up the ass? Have a thought about showing her that it can be done. Get yourself a sweet lil’ dildo and put it in your own ass. Show her how easy it is. Show her that you love it. Show her that you’re willing to do exactly the same thing you’re asking her to do.

If this thought makes you cringe, consider that perhaps that’s exactly how she’s feeling about stuffing your big ol’ sausage up there, you know what I’m saying?

Thank you for listening! Carry on now.

Sincerely,

aag

“I need you to fuck my ass.”

“As you wish,” he said, and he guided me into a new position.

On my knees, I leaned against the couch and presented him with my bottom. He poured over us a precious half-ounce of our co-owned lube.

“Slow, go slow,” I moaned. He went perfectly slowly, at least until I pushed back against him, the signal that all systems were a go for anything, anything at all.

He moves so well. How did he learn, I wondered. Did he go to school for sex? If so, he’d have a post-graduate degree in fucking. Did he have a coach, someone who coolly looked over his shoulder, critiquing his performance until it was perfect?

Or has he simply spent the past 30-plus years in careful study of what his partners like?

I reaped the benefits of his knowledge as I bent over the couch. I could do nothing but come and come and come some more.

My high-school friend and I used to say that a certain cute boy made us “wet to the knees.” We had only the very vaguest idea of what that meant. I understand it now, finally, twenty-odd years later. I understood it particularly well bent over my couch and gushing down my legs as he slid so smoothly into and out of my bottom.

Eventually my legs collapsed and my weak arms dropped off the couch. I ended up kneeling on the floor like someone praying, which seemed about right considering that I couldn’t stop murmuring “OhGodohGodohGod.”

He kept on fucking me right through the gushing, through the position change, through the praying.

Come to think of it, maybe I ought to consider kneeling in prayer one of these days. Maybe I should start thanking God that this man wandered into my life.

Once upon a time and a long long time ago, a girl named aag learned through a series of instructive events about the amazingly sensitive nature of the ass.

It became her quest to provide anal pleasure to her lover, who, despite his vastly greater experience in every other possible sexual endeavor, was almost a complete neophyte when it came to receptive anal luv.

He was almost a complete neophyte…and he wanted to learn.

So as time progressed, aag brought along a series of toys and other implements in an effort to catch her lover’s fancy. On their very first meeting, in fact, aag presented him with a large red dildo which she loved beyond all reason.

Her lover took one look at it and pulled away. “Too big, baby!”

Aag pouted prettily and tucked the toy into her own bottom. “See, lover? It fits!” But he remained steadfast in his refusal to allow the red toy entrance.

So aag went back to her toy box. Next time, she brought along a hard metal toy with a very small bulb on its end. After plentiful oral ministrations, her lover allowed her to slip the metal bulb home. “Too hard, baby!” he said.

Next aag brought out a very slim glass toy, which unfortunately came with a ridge of glass around the shaft. “Too…ridge-y!” said her lover.

Then aag attempted the introduction of her finger into her lover’s tight little hole. This was graciously allowed. It was in fact enjoyed immensely, most especially when aag also locked her mouth onto his hard cock concurrently. But still, the finger rankled. “It’s too rough, lover,” he pointed out.

Aag sweetly suggested that her lover search the internet for an appropriate tool. He dove into this enterprise with gusto, quickly coming up with a toy that was neither too large nor too small, too hard nor too soft, too ridge-y nor too…non-ridge-y, too rough nor too frictionless.

It was this, and it was deemed to be perfect. It was ordered.

And when at last the time came, aag bent her delicious friend over into the position he’d so often demanded of her. She knelt down behind him and applied her mouth to his freely hanging balls and her lips to his freshly washed bottom.

She thanked the stars and the planets, the gods and the goddesses, her agent, her friends, her family and the Academy for sending her a lover so very scrupulous about the rigorous washing of each naughty bit before playtime with her. Her lover likely had no idea how much this small gesture thrilled her.

Perhaps he does now.

She stroked, she nuzzled, she licked and she kissed each millimeter of his tender flesh, insinuating at intervals their new purchase into his bottom. She dribbled lube freely over him, then when he pushed back against the toy one last time, she drove it home.

Judging from the noises coming from the pillow, her lover adored it. Aag held the toy in place while her lover fucked himself silly; she added a stroke to his cock every so often.

The toy was just right.

After a pleasant interval spent in anal bliss-itude, he eased himself gently off the toy and demanded the instantaneous exchanging of positions. He spent his lust on aag, who was more than happy to be on the receiving end once more. Finally they collapsed into a happy groaning pile of twisted limbs, slippery fluids and raggedy breathing.

And they lived happily ever…ah, let’s not jinx it.

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 here for some panty-drippingly hot personal accounts and instructions.

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. 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. Maximus is nice, but the Sliquid line is almost as nice and it doesn’t have the drawback of an icky taste. Thus you can repurpose your unused Sliquid 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 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 my dear friend and butt-mentor first explained 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 alright. 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 tell me how it felt.

Part Two is here.