True Anal Story

It started with a tentative slap across her backside as she leaned over the counter. Encouraged by her little yelp of delight, I cupped my palm and delivered another blow, and then another, each strike more furious than the last. Leslie joined me, each of us working a side. Our date’s cheeks turned crimson; my hand felt like it had fallen asleep. She gasped when I bit down on the pale, lovely flesh above the crease between buttock and thigh. She purred when I clamped my teeth around her nipple.

I am not certain what prompted the spanking but this pretty newcomer had coaxed something out of hiding. Like Leslie, she was agreeable and giving and just shy enough that her depravity was a delightful shock to me.

Men in relationships often outsource their perversions, or so I have read. This is not for me. My wife has always been my favorite whore. Over the years Leslie and I have done unspeakable things to one another. If I am not as open with our naked guests, it is less a matter of hard limits than of trust.

She is a rather perverted bitch, my wife. She thinks it’s funny, for example, when I try to make her gag while fucking her face. “Gok, gok, gok,” is all I have to say when I want to get a laugh out of her. As our guest looked on I pummeled the back of Leslie’s throat and waited for those lovely sounds: gok gok gok. She furrowed her brow when she disengaged. “Lex!” she protested in her sing-song voice. To our guest, she said, “That gives me the sniffles sometimes.”

The new girl nodded. “It makes my eyes tear up.” Her hair was not quite red and not quite blond. I grabbed what little of it wasn’t already gathered into a tie and pulled her to me, watching as her lips parted and slid down the length of me. Leslie slipped a finger up my ass. Tensing for a moment, I cradled our date’s head in both hands and flattened the tip of her nose against my abdomen. I held her like this, marveling at her ability to open her throat, and thought about what this might look like in x-ray vision. Her eyes were watery by the time she uncoupled from me. “See what I mean?” she said, blinking rapidly.

Leaning over her, I kissed away her tears, certain now that I had to do the thing that had been on my mind all day.

“I don’t know,” she demurred when, eventually, I made my intentions known. “You might be too big for me.” I smiled because I knew this game. It is the game Leslie plays with me: my wife, Our Lady of Perpetual Anal Virginity until I’m deep inside her and she’s begging me to pound her into oblivion.

Our guest uttered a breathy moan when her asshole gave way to the probing of my index finger. Rising from the couch, I let her gobble me up so that she was now impaled at either end. Not satisfied that our date was receiving enough attention, Leslie crouched behind her and lapped at her cunt beneath my pumping digits.

Such exquisite torture. I almost took pity on our new friend.

I still laugh when I think of what Leslie said years ago after I’d convinced her to give assfucking a try. That’s not bad at all! It’s like taking a shit over and over again. She knows how to relax for me now; she knows how to angle herself. I bent her over the easy chair, easing into her, and as I penetrated her ass I watched her round buttocks jiggle. There is something subtle, I think, in the way her smooth muscle wraps around the glans that makes our assfucking feel like love.

An ardent voyeur, our date sat some distance away and studied us as if she expected a quiz on our technique. When her turn came she made me wait, kneeling over her overnight bag and fiddling around with something in there. As she stood, stretching out her taut frame, I saw that she now wore eyeglasses.

I reached out to wrap my arms around her waist. “Oh my god.”

She smiled. “What?”

“How did you know I have a thing for hot lasses wearing glasses?”

She straddled me. My wife grasped my cock and slowly, delicately pushed me into our date’s lubed asshole. The girl closed her eyes and bit her lower lip. “Mmm.” I shuddered when I felt her capitulate and then tense around me. She lowered herself onto my lap, hesitatingly, the way one might step into a very hot bath. I rose inside her.

I had her lie on her back and our negotiations began anew. I ventured a little too far at first, causing her to wince, but soon she drew heavy breaths, her slender body melting into mine as I began to fuck her ass in earnest. I pushed my thumb to her lips and she opened her mouth, biting down on the nail. Leslie crept behind me and again stuck a finger in me, saying, “How do you like that?” The sensation was not unpleasant. I pressed our guest’s legs against her chest so as to get a better view of the in-and-out. “Careful,” she cautioned. “I am not as flexible as your wife.”

I am sure Leslie felt satisfied to hear this.

“Oooh, her toes are curling!” came the cry from my wife. Our date was on all fours now, wrapped tight around me and receiving deep strokes, her head bobbing, her eyes closed. I studied the arc of her spine and the tempting mounds that cushioned my thrusts. Her puppy-like mewling only spurred me on. I felt my wife’s hands on me. When everything went out of focus I told the lovely creature pinned beneath me that her ass was surely about to make me come…

“It always hurts at first,” she was saying as the three of us lay entwined on the couch, “but then it feels great.” I knew what she meant, having been on the receiving end of Leslie’s toys. Pleasure has its price. My dick, for instance, was sore, and yet this did not stop me from having my wife again. In an effort to be a gracious host, I first handed our playmate a vibrator. As she pressed the buzzing chrome bulb between her legs and my wife wrapped her lips around me, I was struck by the decadent absurdity of this scenario.

Our calico kitten has a stripper name. When it was time for good girls to say night night, my anal princess held our kitten to her porcelain bosom. The two of them looked adorable together — innocent even, although neither of them really is innocent.

The contradiction gets me off.

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Met Art

Chapter Six: Let's All Come (Part One)

The Sex Box

The Sex Box (patent pending)

Suckin’ on my titties like you wanted me
Calling me all the time like Blondie
Check out my chrissy behind
It’s fine all of the time
What else is in the teaches of Peaches?
Like sex on the beaches. Huh? What?

-Peaches, “Fuck the Pain Away”

If I’ve learned anything during my stay at the resort it’s that wet, naked woman doesn’t join you for brunch unless she’s angling for something more than polite conversation.

Les and I were taking an early afternoon swim and Tammy asked me: “Are we allowed to have sex in the pool?”

“I don’t think so,” I responded. Leslie licked her cunt anyway, my little brown babe floating and lapping away while Tammy propped herself against the pool’s edge. And everything was so bright. And no one cared.

Tammy saunters up to us now, naked, beads of pool water rolling down the valley between her breasts, and the insouciant Cali blonde flops into an empty chair. Studying her curvaceous form, I feel the pangs of another kind of hunger.

After a few minutes there’s an awkward pause in the conversation. Here it comes: “Do you want to meet us in our room?” I smile but I don’t say anything. It’s not often that a man is propositioned for sex. I want to savor the moment. It also occurs to me that my fiancée might want to have a say in this.

Leslie giggles. “Sure, why not?”

The women both turn to me. “Like I’m gonna say no!” I intone, trying to contain my excitement a little. “But I would like to shower first.”

Tammy gives us her room number. We are expected in half an hour. When she struts away Les and I both watch her shapely posterior jiggle in the sunlight, then look at each other with raised eyebrows. “What is it about afternoon sex that seems so… indulgent?” I ask, not really expecting an answer.

We’re freshly showered and snappily attired in our birthday suits. The room key is in its proper place around my neck. I’m holding a recent invention I call the Sex Box, which is simply an empty pack of Benson & Hedges stuffed with condoms and packets of lube. There’s only one problem: neither of us remembers the couple’s room number. “Wasn’t it like thirteen-something-or-other?” I’m saying. “Let’s just knock on the door and fuck whoever answers.”

Leslie cackles. “Can you imagine that? But I seriously don’t remember the number. What are we going to do?”

“The girl in reception likes you. Give her a call and see if she can help.” My woman picks up the phone and after a couple minutes of Spanish chatter she has the right sequence of digits. It strikes me that ours is probably not an uncommon request at the front desk.

As Leslie and I stroll arm-in-arm to the other end of the resort, a terrifying feeling overtakes me: I am most definitely going to get a boner. I’ve been so good up to now—so in control—but as we approach our rendezvous Mr. Penis readies himself for the occasion. Leslie, of course, grabs at me, which does nothing at all to relieve the pressure building between my legs. And then… I realize I just don’t give a damn any more: I’m a man on a mission, cocked and loaded. In a world that’s so deathly afraid of hard-ons—yet, paradoxically, so in love with male power—how often does a man get to walk around in public with an erection, proud and yet humbled, powerful and yet vulnerable?

“Oh my!” says Tammy, casting her eyes downward upon greeting us at the door.

“We’re just here to fix your plumbing, ma’am. I think I brought the right tool for the job but you should have a closer look.” I grin, expecting some cheesy porno soundtrack to begin any minute now.

Bright and inviting, the couple’s love nest is a little smaller than ours. I set my stuff down on the counter and send Leslie in James’ direction with a pat on her marvelous rump. The four of us fall upon the bed, grinning at each other stupidly. Then, as if by a director’s cue, everyone reaches for tits and asses and cocks and cunts. “I turned up all the lights just for you,” explains Tammy, having thoughtfully made note of what I told her last night. In a show of appreciation, I sweep her blond locks to the side, grasping the back of her neck and pulling her lips to mine. My tongue travels downward, making extended stops at her nipples and curiously shallow belly button before finally coming to rest between her thighs. I drop to the floor to improve my angle of attack, the concrete hard and cold against my knees. I decide I kind of enjoy the pain, that it keeps me focused on my task. The room reverberates with a symphony of girl noises. After some delirious minutes have gone by I hear Leslie in the final throes of her ecstasy. My partner squirms beneath me but she’s not there yet.

Leslie rises from the bed and kneels behind me, flicking her tongue across my anus. “Is she licking your ass?” cries Tammy. “That’s so hot!” This is the hook that triggers her orgasm. Soon she’s shouting, outrageously, “Oh Lex! Oh. Lex!” Off in the distance, James quips that his wife can make any man feel like a champion in bed.

I feel a certain indescribable thrill when a woman seals her lips around me for the first time. Perhaps it’s just the way her face looks, her jaw slack and her cheeks hollow from the suction. Or else it’s my delight at her doing this very private thing for me, her tongue twisting around me in a selfless act of pleasure. I pull back and make Tammy open her mouth, gently tapping the head of my cock against her lips. She laughs. I lie flat across the bed and she straddles my face, her heavy breasts spilling over my midsection as she lowers her mouth to my helplessly twitching erection. Two lovely asses, hers and Leslie’s, white and brown, fill my field of vision.

Tammy comes again.

“You need to know a couple things about me before we get down to business,” says my blonde sex kitten as she curls up next to me.

“Do you have any extra body parts I need to be aware of?”

“Nothing like that. I just need you to go slow. And shallow. I can’t take you all the way at first but I’ll warm up.”

And so two very different scenes play out upon the same bed. James positions himself atop Leslie, thrusting as she holds her legs open and bites her lower lip. I plant one foot on the floor, push Tammy’s legs back toward her chest and carefully ease into her. “That okay?” I ask, and she nods. I pull out and go down on her, then push into her again, and while this is going on she’s trying to guess my ethnicity. We’re talking so much that Leslie and James begin to make fun of us. I suppose all the idle chatter is distracting, but then again group sex is not an activity I’d recommend to anyone suffering from attention deficit disorder.

To wit, James smiles and waves in the direction of the windows, which have been, I only now realize, wide-fucking-open the entire time. I peer over my left shoulder to see David hovering in front of the door with a giant shit-eating grin planted on his boyish mug. We all wave him in, but he holds up his index finger and scampers off somewhere with vaudevillian flair. Moments later David returns to the door with Karen in tow, but I see my English Rose whisper something in her man’s ear and they quickly move on.

“What was that about?” asks Tammy.

I cock my head and pull the corners of my mouth downward in an exaggerated frown—really, I know all too well what that was about but it hardly seems important at this moment. “We could have made room for them; you don’t seem to have anything in your mouth right now.” Tammy’s laughter sends contractions through her pussy. I like how this feels and try to make her laugh some more.

No sooner do I go back to ignoring the world beyond the windows than I hear the crisp rapping of knuckles upon the door. I look up to see the Mexican dude who stocks the mini-bar standing outside with a blank look on his face. The guy walks away after spending a good minute taking in the view and ignoring our attempts to communicate. I laugh. “This is getting ridiculous! Is your fridge empty?”

“We are out of beer,” goateed James informs me mid-stroke, wiping sweat from his brow.

“Okay I’m going to drag his ass back here. Well, uh, not literally.” I uncouple from an incredulous Tammy and run out to the balcony, waving the mini-bar guy in. I must look like a madman. To my surprise, he returns to the room and begins dutifully restocking the fridge. I hop on top of Tammy again and impale her, neither of us put off by the absurdity of the situation. When the mini-bar guy gets up to leave he tells us to have fun and the room echoes with the sounds of our laughter. I’ve stopped pinching myself; I’ve stopped asking myself whether any of this is really happening. If a 30-piece marching band were to come crashing through the door I’d probably just shrug and get back to business.

I’m behind Tammy now with my feet planted upon the floor and I’m ramming her the way I want, slow and shallow be damned. The birthday girl bucks against me and gasps. I look down to marvel at the sight of her cunt grabbing at me over and over again. Across from us hangs a small mirror. I look into Tammy’s reflected eyes and watch her reflected breasts sway to and fro. She watches me take a swig from a large water bottle. “You can do that and fuck at the same time?” she says, breathless.

“Baby, if you balanced an ashtray and a plate on your back I could probably smoke and eat a sandwich too.”

“That’s so hot!” It takes me a moment to realize she’s totally serious.

James, standing diagonally across from me, pulls out of Leslie, yanking the condom off with a sharp snap and stroking himself over her back (“You better not hit me,” I warn him). When he comes I’m genuinely impressed by his prolific splatter. A true gentleman, he wipes Leslie’s back with a washcloth before disappearing into the bathroom. My fiancée then joins the action still in progress, smacking Tammy’s buttocks before spreading the rosy cheeks apart. Leslie then disappears somewhere beneath me. The heat of her breath against my balls and the tickle of her hair against my thighs send shivers up and down my legs. When she comes up for air I lean back a bit, making space between Tammy’s ass and my hips. “Lick her asshole,” I growl. Les complies, slathering my date’s puckered button in saliva. Suddenly inspired, she wets her index finger and pistons it deep into Tammy’s ass (what a joy it is to be engaged to such a naughty girl!). Doubly impaled by us, our date cries out in what could easily be pleasure or anguish or a bit of both. Her head drops to the mattress as she slips a hand between her legs and furiously massages her cunt.

We’re taunting her now, mocking her pleasure, daring her to give up and come for us. When the poor girl can’t hold out any longer I let myself go too. My orgasm comes on like vivid fragments of a half-remembered dream, rising up from the base of my spine and taking my shuddering body for a ride. “This little bitch is gonna get me off,” I hiss, almost surprised at my dirty talk.

“Oh yeah baby,” Tammy cries, her voice rising an octave. “Let’s all come!”

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I'll take the filet mignon, please!

Effortless music from the Cameroons
The spinning darkness of her hair
A conversation in a crowded room going nowhere
The open palm of desire
Wants everything
It wants everything

-Paul Simon, Further to Fly

She positioned herself astride my cock, facing me, leaning back with her arms braced against the coffee table, and we both gasped when she lowered herself onto me, the smooth muscle of her little puckered asshole stretching to accommodate an unwelcome intruder. I pressed an index finger to her clitoris as she impaled herself over and over again. Leslie’s mouth was open; her eyes were shut. That old saw came to mind again and again like an incantation: why fuck around with hamburger when you have steak at home?

Why, indeed. I haven’t been terribly interested, lately, in what anyone else has to offer. Oh, I’ve looked—it’s a man’s evolutionary burden, after all—I’ve flirted, I’ve teased, I’ve even tweaked a nipple here and there, but I have not done these things, as a lawyer might say, with intent. Like window shopping on the day after Christmas, my forays into the world of extracurricular sex have felt a little pointless, a little indulgent. Double blowjobs notwithstanding, there’s nothing about my sex life right now that cries out for the addition of a third. Or fourth. And so on.

This revelation first struck me at one of Porno Jim’s legendary soirees. Les and I were fooling around with a young, busty babe from Chicago (in the bathroom no less, after watching her take a piss) and at some point I realized I was done; I didn’t need to take it any further. Jim was surprised when we decided to leave just as the orgy was heating up, but all I wanted to do was take my girl home and have her good and proper, her face in the pillow and her big round buttocks in the air, beckoning me to do my worst.

We talk about our best sessions for days afterwards, Les and I do; I call her at work and remind her of all the dirty little details, egging her on until she’s begging me to stop.

A couple weeks after the Porno Jim soiree we were juggling invites to a few different events, trying to figure out how to spend our weekend. Les asked me whether I wanted to go to the bukkake party or whatever the hell it was and I said, without really thinking about it, “Oh it’s just a sex party.” My fiancée cocked her eyebrow at me as the import of what I’d just said finally sank in. “Wait, did I really say that?”

It’s just a sex party. A few years ago I was burning with curiosity about this debauched world and now its rhythms and peculiarities are familiar to me, comforting yet also mundane. It’s a queer reversal of our culture’s conventional wisdom: sex with your partner is supposed to get boring, to the point where you go into therapy or else buy marital aids to spice up your sex play, to the point where you have to train yourself to avert your eyes from the forbidden fruit. What the morons who dispense relationship advice don’t realize is that freedom has a funny way of making a man content with what he has, that sometimes he tastes the erstwhile forbidden fruit and finds it’s gone rotten.

A the Chemistry party a couple weekends ago, someone who’d never been to a sex party before asked me whether people go for reasons other than winding up on a bed in a sweaty tangle of bodies. I explained that I for one enjoy the permissiveness of an anything-goes atmosphere, and that there are nearly as many reasons for going as there are attendees at any given party. Les and I had spent most of the night catching up with friends and flirting with a pretty Russian MILF, yet in the end we went home to have our own fun.

There is a vast and largely unexplored wilderness between lock-step monogamy and indiscriminate hookups, a place Leslie and I call home. I’ve come to understand that what I enjoy—again, double blowjobs notwithstanding—what I enjoy most about our “lifestyle” is going on the occasional date (even the weird ones can be fun), going out on the town with other kinksters, and generally engaging in behavior that would be scandalous to straight-laced couples. I’ve come to learn that simply having sex with other people does not a kinkster make, and that standing in line for the next available orifice only to tap in like a professional wrestler is not my idea of a good time.

On the relationship-oriented end of the continuum, dealing with other people’s sexual and emotional issues can be exhausting. Like, a massive pain in the ass. Leslie wrote about her disenchantment with the male of the species, and I’ve experienced a similar disenchantment with the female of the species—the young, urban North American female being an erratic and capricious bird indeed. Although Les and I have agreed, in principle, to dating separately should the right moment arise, I still haven’t bothered asking anyone out.

As Les and I cabbed home the other night I asked myself a simple question: How many of the women Les and I have dated together would I have dated were I single at the time? The answer is a disturbingly small number. Which is not to say that none of the others were attractive enough, or nice enough, and so on—indeed, most delivered what the situation called for—but there was always something lacking. A profound lack of the kind of sexual creativity I’m accustomed to enjoying at home, or else a profound lack of the kind of affection I suppose I’d taken for granted.

And most women here, most people here, are lazier than long-haired cats on a hot summer afternoon. They’re all waiting around for someone to come along and tell them what to do, what to think, how to feel. New York spoils us with convenient access to everything, the result being that anything not within the immediate reach of our fingertips is seen as too much work. There’s always someone else, something else; some shiny new object upon which to squander one’s attention.

At first I was concerned about my lack of interest in other women—frankly, I was even a little embarrassed, ready to see a doctor or a shrink and get a prescription for anti-apathy pills. Now I realize it’s just that I know what I want; I know what turns me on and what turns me off; I know what I’m looking for in a relationship or a casual encounter. And I’m willing to forgo hamburgers indefinitely. As I told Les, we’ve had some great lovers and some truly wonderful experiences. If I’m thrilled again by someone or something there’s nothing to stop me from acting on my desires, but in the meantime I’m as happy with my relationship as anyone has a right to be. To torture a metaphor, Abu Ghraib style, if I’m going to head out for seconds, that meal damn well better complement the steak I have at home.

So, as a beautiful summer afternoon gave way to a beautiful summer evening, I fucked my fiancée in the ass, with my finger pressed against her clitoris, and I watched, fascinated, as she rode me like one of the girls from those naughty videos, impaling herself over and over again. Her smooth brown skin glistened with sweat and her pretty curls, some of them matted to her face, rolled to and fro. When I came I groaned and panted and clawed at the furniture, lost in my animal self. And as my heart pounded away it crossed my mind that this was the best sex I’d ever had, or ever will have, with anyone.

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A Spy in the House of Ass

Leslie’s in her white wig and retro Seventies shades. She looks like a porn star. It’s appropriate for where we are, at Crash Mansion, with its stuccoed slate interior and subdued lighting. Producers, genuine porn stars, vendors and press people flit about. A young woman asks us if we’re part of the production and we both laugh. Someone else corners us, plies us with champagne, promises to send us a lifetime supply of sex toys.

“How did my life turn into Boogie Nights?” I ask my fiancee.

Perhaps it’s just that I have a hard time saying no. My default setting always seems to be “why the hell not?”

I run into Dacia and the two of us chat for a while; I tease her about being a porn celebrity. “So how do I compare to my blogging persona?” Dacia asks me, her breasts threatening at any moment to tumble out of a corset that barely contains them.

I think about her question for a moment. “I guess you’re more charming than I thought you’d be, and, um, well,” I pause, smiling, looking her up and down, “you’re even hotter than I expected.”

Tired from partying all weekend, Les and I pack it in early, grabbing a couple schwag bags on the way out. I rummage through my goody bag as we cruise uptown; among the many promotional items are two butt plugs and a bullet vibrator. I have an idea.

The next evening, after Les calls to tell me she’s on her way home from work, I try out one of the butt plugs, intending to surprise my babe upon her arrival. Now I’m no stranger to ass toys (I’ve indulged Leslie’s curiosity on a few occasions) but I’ve never had anything up there for an extended stay. The butt plug isn’t painful really, just mildly uncomfortable. I try to do a little work and find myself unable to concentrate on anything other than the thought that I have something up my ass.

And this is just a wee little thing, squat and fat, sure, but small compared to the ones you might find in a Chelsea sex boutique.

The minutes tick by. I fidget.

And then the phone rings: it’s the Swedish girl. I take a deep breath and answer. While we talk I have to fight the temptation to conclude every sentence with: “and by the way I have a butt plug up my fucking ass!”

I wonder what she’d think of me if she knew?

When Leslie finally arrives I promptly drop my trousers. “Touch my ass,” I command.

She appears confused at first but then palms a cheek. When her fingers tap against the flattened base of the buttplug she squeals with delight and begins to giggle uncontrollably. Her girlish noises cease when my cock enters her mouth.

“Don’t get too excited yet, babe—I’m gonna try your toys on you.” I lead her into the bedroom, undressing her, pushing her onto her back, warming her up with my tongue and then slathering her jiggly behind with lube. I insert the silver bullet into her cunt and hand her the controller: “Go ahead and turn it on.” As she cranks up the amplitude she squirms and laughs. I take advantage of her distracted condition and push the long, slim, jelly-like buttplug into her ass.

“Oh this is fun,” she says.

I pull both toys out and reinsert the silver bullet, this time choosing the narrower opening.

“Hey!” Les says.

“What’s wrong?”

“Nothing. I want you to fuck my pussy and see if you can feel the vibrator.” And sure enough when I enter her I feel the silver bullet buzzing away in her other hole; the vibration doesn’t get me off, exactly, but it does add something. With each thrust my butt plug threatens to fall out and so I take a break to remove it—I find it too distracting to try to hold the thing in—and as soon as the toy vacates my ass a feeling of relief washes over me. Why do I bang my head against the wall? Because it feels so good when I stop.

My girl’s eyes grow wide as I remove the fatter butt plug from its packaging and brandish it before her. “You wanna put that in me?”

“C’mon, it’s not that big. I had mine in for like half an hour.”

She relents. I watch, fascinated, as her little asshole expands to accommodate the plug at its widest cross-section and then collapses around the narrow neck above the base, locking the toy into position. Leslie sighs. I pull her to the edge of the mattress, push her legs against her chest and plunge into her cunt. “Now you have both holes filled, you little slut!”

And when she comes the butt plug shoots out of her, bouncing off the wooden floor like a rubber ball. We both giggle. I switch holes—if the butt plug won’t keep her rear-end occupied I will—and it’s not long before I burst inside her, my knees threatening to buckle.

We’re both looking forward to more pervy schwag. Sure beats the hell out of an iPod.

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Abby Winters

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