aag

If you’ve closely followed the instructions given in Part One: How to Have Buttsex…More Than Once–congratulations! You are ready to move on to Part 2.

Eventually your bottom will decide that this buttfucking thing is pretty damn cool. Your bottom will begin sending you little mental greeting cards with messages like “You are the best. I love you. Will you fuck me tonight?” Respond appropriately. Step it up a notch. Find a larger toy that more approximates the size and shape of a penis. This is one of my favorites, but there are a vast number of alternatives scattered across the internets and in sex shops. Choose one that makes your bottom quiver with lust.

At some point, whether it is days, weeks or even months after your first forays into buttplay, you will compare your latest toy to your lover and realize that if you are comfortable with the size of your toy, you will also be comfortable with the size of your lover.

I’m hoping that by this point you have the kind of relationship with your lover where you won’t worry that the world will fall apart if the buttsex goes awry. I had complete confidence in the one person (to date) whom I have allowed to enjoy the pleasures of my bottom; before the buttsex was even under discussion, he’d proven himself to be warm, calm, kind, accepting and all those other lovely characteristics that showed me that he’d accept and even love that part of my body no matter what little tricks it might play on us.

Buttsex seemed–and still seems–far more intimate than vaginal sex. It’s not something I’d do with just anyone. It boils down (for me) to the fear of two things: Pain and poo.

The fear of pain and the fear of poo may make you very cautious when you decide to give your ass. If you have any question about your partner’s ability to deal with either your pain or your poo, you should probably hold off.

When at last your ass begs you to fill it with actual (as opposed to silicone) cock, choose a night when there is utterly no rush. Assemble the necessary supplies and then have fun together. Only after you’ve both gotten completely worked up (and had many orgasms already, if you can) should you think about the butt. Have your partner use a condom. Lube, then lube again, both your behind and his cock. Then add more lube. Really, you can’t have too much.

I’ve preferred buttsex in the doggy-style position because it lets me both relax into the bed and also push back against my partner. I like to be very very still as he gently enters me, a millimeter at a time. Here’s where trust is so important. You must be able to trust that he’ll go as slowly as you need him to, and that he’ll stop if you want him to. If you can’t trust absolutely that he’ll do this, then you’ve got some conversing to do before you lube up, sister.

Have your partner stand behind you and very…very…very slowly nudge his cockhead into your ass and then pause. You will feel extremely stretched when he enters you. You may also feel the need to poo. You almost certainly don’t need to poo; that’s just the confused message your behind is sending to your brain. Breathe out slowly and keep calm. The feeling will pass.

If it hurts for more than a moment, add more lube. Ask your partner to go even slower. If it’s still uncomfortable, congratulate yourselves for a good first effort, clean up, then turn your attention to other fun activities.

Remember…there is no rush. There are no prizes for buttfucking successfully on the first attempt. Just try again another night.

If you can relax with your partner’s cockhead inside of, it’s time to move deeper. Push back gently onto your partner. As the butt-fuckee, you get to control the pace. Really, once your body has accepted his head, it will probably be more than happy to take the rest of his cock.

That’s why you practiced on your own for so long. Remember?

Once you’ve assured yourself that you can take your partner’s entire cock without the world coming to an end, it is time to turn over the responsibility for thrusting to him. You trust that he’ll stop if you ask, right? And that he’ll pay attention for signs of distress on your part, eh?

‘Cause if you have any questions about those two things, you shouldn’t even be thinking about giving him your ass.

If you are enjoying having your butt taken by your partner, experiment by gently tilting your pelvis. This should allow him to hit your gspot harder, which is REALLY REALLY NICE. You can also try slowing down and then squeezing with the same muscles you contract during a Kegel.

He’ll probably love it.

If you get close to coming (I so hope that you do!) you can try pushing out when the orgasm approaches. This may make you gush. Or it might not. Either way, it’ll be a different and interesting sensation for both you and your partner.

Your partner should NOT pull out of you without warning. If he’s ready to pull out, either before or after orgasm, he should do it very very gently. Plan on going twice as slowly as you think you should. Jerking it out will be painful and potentially messy.

The second the cock comes out, it’s nice to have a dark towel nearby for a quick wipe-up and for condom removal. Just a once-over will suffice for now. After you’ve regained your senses and cuddled for a bit, then you can clean up more thoroughly in the bathroom.

The fuckee gets first choice on who goes first.

Once clean, you both must return to bed for additional cuddling. Forgo any discussions of the raw mechanics of what just transpired. You can do that later, after everyone’s emotions have settled down. Just cuddle, and talk, and touch, and maybe move on to more sex.

Or maybe, if you’re both so inclined, it’ll be his turn to experience the pleasures of buttsex.

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.

Two and a half years ago, the thought of having a penis or even a fingertip embedded in my bottom horrified me. Eighteen months ago, someone jonesing for my ass made me blush and cringe. By a year ago I was mostly cured, having experimented enough with solo butt-play that I felt nearly ready to give it up when the time was right.

I’ve since given it up, of course, and even though I’ve been giving it up for a little while now, I thought there existed butt-things that were still beyond the pale. Like, for example, doing the butt-thing in a room with other people.

“They know we do…that, right?” I asked him apprehensively in the days preceding our meeting.

“Yes, they know,” he told me. “They don’t do buttsex themselves though.”

“Oh. So they probably would be grossed out to see us doing it, right?”

“I wouldn’t necessarily say that,” he answered, smiling.

“I don’t know, baby. I don’t think I’m quite ready to show that off to other people.” I was nervous.

“As you wish, sugar.” And that was the end of the conversation.

But then the night in question arrived. We’d played with bottoms before we were joined. We’d had a nice giggle over bodily oddities. And I’d been getting the ever-loving life fucked out of me so thoroughly that my inhibitions had packed up and departed for parts unknown.

The other couple was on the opposing bed. My friend had me bent over our bed, face in the pillows, bottom upturned, his hand wrapped in my hair and pulling hard. I’d come so much and so hard that I feared I’d pass out from the pleasure.

Suddenly his mouth was right next to my ear. Even though we were being observed (closely), he was quiet enough that I’m sure they couldn’t hear what he said. “Do you want this in your ass, my little slut?”

I would have robbed banks for him at that point if he’d asked. I would have drunk the blood of infants. I would have voted Republican.

I would almost have given him this url.

“Yes Daddy,” I whimpered.

The room was silent as we followed our routine. He ever so slowly entered me, letting me adjust to the feeling of his big cock. It must have taken an extra-long time. It must have worried our friends. When finally he began fucking me in earnest, I could almost hear their mutual exhale.

And then one of them spoke quietly to me. “Does that feel good, XXXXXX?”

A thousand thoughts flashed through my mind of just exactly how good it felt, but I could put none of them into words. I suppose I could have nodded, but I was face-down in the pillows.

So I gave them the sign that in all languages and across the globe represents yes-oh-yes, this buttfucking does indeed feel good.

I think they all might have laughed at me, but I was in no shape to care.

So the moral of the story is this: If you give me many many orgasms, you can do just about whatever you’d like to me and I will not care. You could rip my limbs from their joints and suck the very marrow from my bones (if that sort of thing gets you off), and if you rub my clit in just the right way throughout, I’ll say nothing more than yes yes yes please more ohhhhh god yes.

It’s an amazing power. Use it only for good and never for evil, please.

“Face down ass up, my little slut,” he requests, and as the ever-compliant lover I strive to be (and because I love doggie-style anyhow), I obligingly assume that position in the middle of the bed.

“Move back baby,” he demands, his long fingers pulling gently on my thighs. I shuffle somewhat awkwardly toward the edge of the bed, trying not to position either knee in the suspiciously-large wet puddle that appeared on the bed a half-hour earlier.

He pushes my head down more thoroughly into the pillows then dips his long cock into me just once. He withdraws and settles it against the opening to my bottom. His hands move off my hips; I want to turn and see what new devilry they are up to but I obediently keep my face in the pillows.

Lube. He pours it generously down the cleft of my bottom, then uses his finger to rub it inside me. A finger inside my bottom makes me blush and squirm (odd, then, that a cock doesn’t), so I beg him to exchange finger for cock.

“Be patient, little girl!” He continues for an almost embarrassingly long time, until finally I feel the head of his cock once again push against me.

This has become our routine: He makes the first gently stretching pushes into my bottom, to the point (I imagine, though we’ve yet to attempt photographic preservation of this moment) that his cockhead is nearly engulfed in me. He pauses then as I become absolutely silent in concentration. I breathe deeply and feel nothing but the all-consuming (but not even slightly painful) sensation of opening up my body to his. It requires quiet and complete stillness, the sexual version of a Zen meditation exercise. I breathe out very slowly and think of nothing but opening up.

He waits, not moving, not speaking, not touching me any more than is absolutely necessary.

When I’m ready I push back against him, glad for the lube he put inside me. I don’t understand why (and I prefer not to know), but each stroke in feels hot, so hot, and each stroke out feels cold. I think of asking him if he feels the same, but I cannot speak.

It’s a sensation completely unlike that of vaginal fucking. It feels hotter, dirtier, closer, more extreme. I soon beg him for the entire length of his penis; he gives it to me with a vengeance. And soon I’m screaming into the pillows.

If he moves just right (and oh this man can move, God can he move), he hits my g-spot with his cock from inside my bottom, which just may be my favorite feeling ever. If he does this, and if I’m sufficiently hydrated, and if I have the wherewithal to push at just the right moment, I gush. Fountains, rivers, torrents of hot fluid run down my legs, and if he’s lucky enough to have his hand in the right spot, he catches drops of liquid on his fingers and offers them to my mouth.

I love that.

Right before he comes, he pushes me down on the bed and crawls between my knees. I think he wants to wear me at that point, as if we could unzip our skins like two sleeping bags and zip us up back into one. I speak a string of meaningless noises and rock my hips; he bites hard into my shoulder before collapsing onto me.

Then we pray: OhGodohGodohGodohGodohGod.

He shifts slightly, concerned for my well-being below him. I beg him not to move, please don’t move.

We lie still for five minutes.

Eventually bodies move despite our best intentions. His cock works its way out of me, making me groan in dismay. The condom is discarded. I clean myself in the bathroom. We meet back in bed, twist around each other again, and lie still for five more minutes.

But then my hand softly strokes down his belly and his hand slides between my legs, and we start something new all over again, something that once again leaves me screaming into the comforter or the sheets or the pillows.

And I wonder the next day why I have such trouble speaking.

————

I redid the Photos page with a cool flash thingie.

Lubeless, pre-1991: I scoffed at lube. I though only women who were uninterested in sex (and therefore not making the proper natural lube) needed lube.

Come on, I was young. I didn’t know anything then.

******************

KY Tube #1, circa 1991 – 1997: My friends gave me an economy-size tube of KY Jelly as a gag gift before I was set to meet a man for a long weekend.

We didn’t use the lube. I blamed the inevitable chaffing on my inexperience. He was unaffected. I married him anyway. The lube mouldered in a bedside drawer, entirely unused.

******************

KY Tube #2, circa 1997 – 2006: Even after several years of marriage and the birth of my first child, I remained cluelessly lubeless.

When my postpartum check-up rolled around, I asked my doctor why it hurt so much to have intercourse. He asked if we used lube. “Of course not!” I answered. “I don’t need lube!”

He gave me a funny look, presented me with another economy-size tube of KY Jelly (wrapped in a brown paper bag for discretion’s sake) and ordered me to use it.

A couple of times I tried to use it, but the consistency and taste of KY were just awful. The husband hated it. I abhorred how sticky the stuff felt.

So we plodded on, having mostly-dry sex (when we managed to have sex at all). I did not consider that there might be alternatives to KY.

Were there alternatives to KY in 1997?

******************

Lube Epiphany, late 2006: Somehow I acquired a tiny bottle of KY Warming Jel. I don’t recall the circumstances of the acquisition. I experimented with using it during masturbation.

What a revolution. My fingers slid over my pussy instead of rubbing it raw.

I needed to know more.

******************

Lube Epiphany Continues, early 2007: The occasional lover arrived armed with a small tube or bottle of something. I became less and less shy about asking for its use–its liberal use. I scrutinized labels whenever I could to find out what I liked.

******************

Water-Based Lube Experimentation, late Winter – early Spring 2007: I began looking at websites and sex toys for Jane’s Guide. Babeland sent along various types of lubes they wanted to see featured on Jane’s.

I got to try a healthy handful of different varieties, noting their subtle differences in quality, texture and taste.

For example, Maximus feels great, especially for butt-play, but you wouldn’t want to taste it. Entice doesn’t taste bad and it’s beautifully packaged, but it’s a bit thin. The flavored Sliquids are fairly thick, have pleasingly subtle flavors, and dry cleanly.

******************

The First Taste of Heaven, Silicone Lube, Spring 2007: I read this impassioned love-letter to silicone lube; at the very same time, I tested a toy that came with a tiny bottle of silicone lube.

I was instantly hooked.

Silicone lube is so slippery, so rich. You can keep fucking yourself for hours with a butt-toy if you’d like. Hours, I tell you!

Not that I tried. I’m just theorizing.

******************

Fisting Takes a Lot of Lube, Late Spring 2007: So does butt-sex.

My friend and I went though vast quantities of lube. It wasn’t unusual for one small bottle to last only through one or maybe two sessions. The idea of having sex without lube? Unthinkable.

******************

Silicone Surfeit, mid-June 2007: Armed with a brand-new bottle of premium silicone lube, I met my friend for a long session of fun. We used the lube for hand-jobs. For fisting. For vaginal sex. For butt-sex.

We showered.

We next employed the lube for a long slow back massage. Then a drawn-out hand massage, which ended in some surprisingly hot finger-sucking.

Which moved right back into another hand-job. Then more sex, only this time with hair-pulling.

Then there was some erotic photography, with a hand-job given for the sake of fluffing. Then more sex, with more hair-pulling.

Can you imagine the state of my hair at the end of this? Sex-hair, full of silicone lube?

******************

Thus ends this short history told in lube. I can foresee many more raucous episodes where I end up with a happily lube-drenched body.

And now that I’m done writing this history, I’m going to attempt to take care of a small problem with my camera. The photos I’ve taken over the past few days look slightly blurry.

Silicone lube on the lens will do that, I guess.

It was with the greatest reluctance that I put my clothes on at midnight. I’d been naked for the previous five hours; my body screamed at the pain of covering up again.

I looked myself over in the mirror as I dressed. A pair of bruises bloomed on my left breast, near the nipple. Some tiny maroon marks marred the outer curve of my right breast. Another bruise developed later on my upper arm, a deep purple and green flower, a reminder of the night visible to anyone who might care to see.

I love the bruises. I love the intensity. I love the fact that even now, days later, there’s still a gentle ache deep in my pelvis from where the bones gently spread and adjusted to his fist in me.

Did you hear what I just said? My bones spread open for his hand. The ligaments stretched and expanded under his influence. My bones moved for him. God.

I love these things: A mouth opening up for his mouth, or his cock. My bottom raised high in the air, open and exposed for the plundering. His ass opening for my finger. My throat opening, allowing the tip of his cock to rest gently against the place that should trigger a gag reflex. Arms opened wide, welcoming him into a house, or a room, or a bed.

Eyes wide open to see pleasure.

It’s a wonderful thing to open up for a lover, to adjust my body and allow him do what he will. The times I’ve been pushed (or have pushed myself) to open more and wider and deeper, I expect to be permanently marked—left gaping, raw, ruined.

I’m not. Things close up again, gradually shifting back into place. My bottom goes back to a tight little dot. My throat relaxes. The ache in my jaw subsides. Torn skin heals. Bruises fade. A ragged voice becomes smooth again.

Even my pussy, stretched full by a fist inside, goes back to normal: a tiny, tight opening, barely wide enough allow my finger entry as I search for damage while showering. And my bones? Doubtlessly the ligaments will contract, shifting my bones back to where they belong.

There’s no damage. Nothing is permanent.

I’ll take it all in, enjoy it while it’s there, enjoy the pain of it leaving, and then it’s gone. And after it’s gone–after he’s gone–I’ll go back to normal.

“Are you trying to lick my eyeball?” I asked.

“No, just your eyelashes.”

“Why are you trying to lick my eyelashes?”

“Because they’re there,” he told me.

“That makes sense.”

“It does. And if I actually do lick your eyeball, I will have had my tongue on every square inch of your body.”

I ran through a quick mental inventory. “That’s actually true. You’d better lick it then, just so the evening can be complete.”

“You don’t mind my tongue on your eyeball?”

“Did I mind your tongue here?” I wiggled a certain body part that had received oodles of tongue attention earlier. “Or here? Or here?” More wiggles.

“No, you didn’t seem to mind at all.” He placed his fingers back on one of those spots. My voice was destroyed from coming so loudly before, so we were both very very quiet for a few moments.

Eventually he spoke again. “It’s really too bad that I haven’t been able to make you come tonight.”

It took a moment for the joke to sink into my serotonin-flooded brain. “Yes, yes it is. Things just don’t seem to fit for us.” Bear in mind that as I spoke, we were wound around each other like snakes.

Regret hung heavy in his voice. “Right. We don’t click. Not at all.”

“Some people don’t. It’s just the way life works.”

“Well, what are we going to do about it?” he asked. “We’re naked…”

“That we are.” I squeezed one part of him that was particularly naked.

“And we’re together.”

“Yes, yes we are.”

“We have time to try again. Maybe it’ll be better this time.”

“I don’t have high hopes,” I told him. “The first time you gave this to me in the ass,” another gentle squeeze from my hand, “it felt just awful. I can’t imagine that doing it again would feel any better.”

He said, “All we can do is try. Are you game?”

I sighed. “If we must.”

So we did. And it was of precisely the same quality as the first time.