Nearly a hour after he first entered me things showed no signs of slowing.

I love it and find it exhausting, these marathon beginnings to our meetings.  In the midst of twists and turns and position changes and orgasms, I could no more stop than I could turn my skin inside out, though sometimes that’s how it feels as he pumps into me slow and fast and every speed in between.

I somehow wound up with my knees barely perched on the edge of the bed while he stood behind me.  Could anything have been more natural, more expected, more necessary at that moment than for me to beg him to take my ass?

I did, and he did, but that pleasure after so much other pleasure quickly became too much.  My knees slid off the bed.  With tiptoes on the floor and only fingertips propping me up, we must have given off the illusion that he was supporting me primarily by means of his cock.

And then he pulled me upright, hands cupped under my breasts.  Chance had put us at that moment in direct line of a mirror where our images blurred in the dim light.  “Look in the mirror,” he said in my ear with his voice no higher than a growl.  I didn’t or couldn’t look, loath to see the grimace from coming, the sweaty hair, the round tummy.

He gently (more gently than usual) grabbed a handful of my hair and pulled so my chin tilted up.  “Look in the mirror,” he demanded.  “Look at the pretty girl getting fucked.”

I had no choice but to look, and for just a brief moment I caught a glimpse of her too.

“When you have a chance,” I whispered to her during a child’s birthday party at my house, “look in the china cabinet.  Top shelf, extreme left.”

——

Later, when it was her turn, my friend stroked between G’s legs as she reclined shyly on her stomach.  Before long she thrust her bottom into the air and instead of touching, my friend switched to licking her pouty, swollen lips.

I supplied dirty talk, tit-pinching and the occasional cock stroke.

G didn’t realize it, but as her arousal increased, my friend lengthened his tongue-strokes to cover everything from clit to ass. He’s a master of working me up to the point that I lose all sense of the outside world; I become only a clit, a pussy, and a screaming voice.  His talents worked the same on G.  I had to smile as I watched her enjoyment, a sharp contrast to the nervousness she’d expressed earlier.

“Do you know what he’s doing to you?” I smoothed the hair back from her forehead.

Up popped her head.  “No, what?” Her voice was as confused as if she’d just woken from a hundred-year nap.  She rolled to her back and looked at us down the length of her bare body.

My friend told her.  “So that’s what that feels like,” she said.  “Do it some more.”

So he did.  And when the time was right, I lubed up that pretty blue plug and asked her if she wanted it inside her.

“Go slowly,” was her only caution.

I went as slowly as I could with shaking hands, watching all the while my friend’s fingers circle over her fat little clit.

She loved it.  It was in a minute without her knowing.  I let her come and come more before letting her in on the secret; when she knew (and satisfied her disbelief by feeling for herself) she screamed loudly enough that I thanked the universe for giving us a day warm enough to force the shutting of windows and the switching on of air.

I’m not absolutely certain that we replaced her previous bad experience, but I’m satisfied that when her mind now runs to anal play, she’ll have something very pleasant to picture.

——

When the kids were absorbed in crafts, she sidled up to me.  “I love your collection of blue glass,” she said quietly.

“Yes, isn’t it nice?  I’ve been collecting for a long time.”

“I saw your newest piece.”

“I thought you’d like that.” I grinned at her, and then we turned our attention back to the kids.

So I was on the IM the other night, negotiating a meeting for the following evening with a friend of mine. We’d been working up to some lovely buggery for ages, and finally we possessed both the heart and the means to make his wish a reality.

But as happens in my little world, even the most ardent conversation can get derailed by life’s other demands. In this case, the demands came from a child up in the night with a cough and a bubbling pot of chili. Listen in?

Me: Sorry to have disappeared. I’m back and forth between the child and a pot of chili.

Him: Yum, chili.

Me: Oh, you like chili? You want that I should bring over the implements of assfuckery and some chili for you?

Him: Nah, best be one or the other.

Me: Well then. Which would you prefer?

Him: I can make my OWN chili. Bring the damn strap-on!

So I made a mental note to lay off the chili past noon the next day, and I packed up my little bag of sodomy goodies.

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.

The other day, a sweet reader named Annie left me this question:

“…Anal sex seems to be all the rage. Is it really worth it? As a woman, you are obviously able to compare with vaginal sex. I mean, is it not a fad…? Why would a woman need anal sex, when she’s got a vagina, the ideal self-lubrified device that mother nature specially crafted for the purpose?”

Dear Annie,

Anal sex may be all the rage, but it is not for everyone. If it squicks you out to think about it, you shouldn’t do it. You especially shouldn’t do it with someone who tells you that everyone else is doing it.

‘Cause someone who tells you that is just trying to pressure you, and asses don’t respond well to peer pressure.

Anal sex might be a fad; I can’t answer that question. I have no idea. Let me tell you what. I’ll keep on having anal sex for the next 50 years, and then I’ll get back to you on whether or not it’s a fad. Do we have a deal, Annie?

Now as far as “needing” anal sex. Do you mean would your average woman die without it? Of course not. Humans need physical contact, emotional bonding, and a healthy dose of lurve, but all that can be obtained in ways other than by putting something up your ass.

And sure, Annie, you’re right; the vagina does generally self-lubrify (love that!) quite nicely. It does a wonderful job of welcoming in hard cock and (in my experience, at least) it seems to enjoy the presence of hard cock immensely.

Shall we summarize? Anal sex could be a fad, and it’s certainly not something you need, because (as you so rightly point out, Annie) the vagina is a right nice place for sex.

But sometimes, sometimes we do things not because we need to, but because we want to. Because we really REALLY want to. Because for months or even years, we’ve wanted to. Because something deep inside our tiny reptilian brains screams out in a voice that cannot be ignored, “Penetrate my bottom!”

And if you are wise, if you love your ass (and why wouldn’t you love your ass?) you will listen to that part of your brain, because (and this is the secret) ass sex feels really great to some people. It feels really great to some men and some women. It feels really great to some straight folks and some not-straight folks.

It doesn’t feel better than vaginal sex, nor does it feel worst than vaginal sex. It just feels different. It feels different in the same way that oral sex feels different than vaginal sex. It feels different in the same way that blue looks different from red. It feels different in the same way that lasagna tastes different from steak.

None of those things are intrinsically better or worse. They are just different.

If you are among those folks for whom anal sex feels really great, you’ll know what I mean, Annie. You’ll know exactly why it’s worth the effort to prepare your ass (and your mind) for anal sex. You’ll know exactly why you devote the time to working with your partner toward anal sex.

You do it because buttsex feels really great, and it feels really great to share that really great feeling with your partner.

And the only way you’ll know if you are one of the folks who loves anal sex is if you try anal sex.

But Annie, please don’t have anal sex until you know you want to try. When you are ready to try, a small voice in your head will start begging. You’ll be enjoying your traditional sexual activities when suddenly you’ll hear, “Play with me, please!”

And you’ll discover that it’s your ass begging for attention. If that happens, consider exploring buttsex.

If that never ever happens, don’t worry about it. There are dozens if not hundreds or even thousands of other quite wonderful sexual activities you can enjoy without ever bringing your ass into the mix.

Does all this help, Annie?

Readers, any other suggestions for Annie? Leave them in the comments, please.

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.