Pity (The Pickup-Artist)

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Hi Kinky Reader! Thank you for dropping in on my first story. Hope you stick around :)

Dedicated to a certain one-night stand from several few years ago. We'll call him "Rich." He knows what he did. My fantasy spin on how it should have gone. His POV is more interesting than mine, because of how I want him to feel about it.

Honestly, I welcome criticism, suggestions, hearing what you like about my scribblings or don't. So plzzzzz drop a Comment, it helps keep me motivated :)))

You'll see, I may be Strict, but I'm sweet,

E.S.

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"Pity (The Pickup-Artist)"

by Emmalee_Strict

When the bartender swings back around, I ask for "same-again" for me and for the lady, Bacardi & Coke for me and another of whatever Emma is drinking. A twelve year-old Glenmorangie neat, it turns out, water back no ice. Classy.

I say, "Sounds like you're particular."

Emma looks me up and down like it's the first time she actually sees me, and says, "Very."

When I got here, she was sitting alone at the bar. I moved in on her cool and smooth. I took a stool next to her, acting nonchalantly unaware of her at first, ordered my drink. After the bartender left, I started chatting her up. She didn't tell me to get lost. So there was that.

Told me her name is Emma. Emma something, I didn't listen to her last name. I don't care. It's not like I'm looking to change it to mine.

So, the second round leads to another, then another, and by now we both pretty much know where this is headed. So, I don't feel crude or stupid about pointing out the pink and gold paper bag on the bar in front of her, which any idiot knows is from Victoria's Secret, and saying, "Is that anything you want to model?"

Pickup-Artist tricks: Embarrass her, see how she takes it. Give her a chance to talk about shopping. "Neg" her about it.

But Emma just shrugs and gets up off the barstool. She smoothes out her skirt, picks up her little clutch purse and the lingerie shop bag and squeeze them absently to her impressive chest. Scanning the Friday night yuppie meat-market on display in the bar, she has a sort of melancholy look, idly biting her lip, irritated or bored.

I wonder if I've put her off, if maybe I should say something. My PUA instinct says, If she's insulted, keep "negging" her, gauge how she reacts...

But at the moment, I can't think what to say because I'm captivated by Emma's looks... okay, mostly her boobs. I like how she fills out her black cotton, tanktop-style dress with a mid-thigh length skirt. Tight around her full tits and luscious ass. She's tall for a curvy chick. She wears her long strawberry blonde hair loose, wavy, kind of wild. Her face is more than passably pretty, complexion peaches and cream, lightly freckled, with dark brown eyes for a sexy contrast. A little on the thick side, but I don't mind that; big girls like to bounce, I can tell you that. Looking again, I notice a certain athletic power in her arms and legs. Like she works out, she's fit and all that... just naturally big-boned, I guess.

And again, tall. Almost "Amazonian," I think, which does something for me. I mean, I'm bigger, taller and stronger for sure, but I like the idea of the tussle we could have. And maybe I like the idea of not putting up much of a fight...?

She looks down at me with piercing brown eyes that could cut glass. "I'll stop off in the ladies.' Go out and grab us a cab."

She says it like it's more of an order than a proposition. But I mean, if this curvy blonde hottie wants me to meet her out front and go somewhere else, well, I don't see the need to object to the tone of voice.

I settle the tab and head out front. On my way, I catch sight of my buddy Devin working a slut by the jukebox. I pantomime melon-sized shapes with my hands over my chest, and mouth the words, Great ass. Devin gives me one of those slight back-tips of the head in reply, and turns back to his mark.

It's a hot summer night. I've got a cab running the meter by the curb when she comes out. I'm holding the door, like a gent, but my eyes are down on her shoes -- which are black, strappy and shiny, open-toed, four-inch stilettos. She moves in them with easy confidence. I feel a little stirring in my groin.

As she breezes by, ducking into the cab, she glances up at me. "My place."

I smirk. And it's not even eight o'clock yet. Slut.

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Emma hisses breathlessly into my ear, "Rich!"

Which is not my name, actually, it's Rick, I told her that... but hell, it's close enough for my present purposes. We were barely in the back of the cab when the necking and groping started. Our mouths and tongues are wrestling while our hands active elsewhere. Me, I'm feeling up her tits, which are large, responsive, and real. She fumbles with my fly, plunges inside the flap, into my tightie-whities, and gets a hefty measure of what she's doing for me. I moan into her mouth, while her free hand slides behind my neck and drags me deeper into the kiss.

She comes away with a sharp pant and a nip of my lower lip.

"Ow!" I touch the lip. I think she drew a little blood.

Emma slumps back into the seat, turns her head and looks away, watching the street scenes fly by along Springfield Ave. Absently, she finds her purse and lingerie bag on the seat, rests them on her lap, and crumples the bag in her hand. I notice, it looks like whatever's in the bag is kind of lumpy, which doesn't seem right.

I look down at my open fly and see the boner inside my briefs half-poking through. What kind of tease is that? Well, I'll show her later, I have ways to tame a tease.

Emma yawns and half-turns toward me, her fingers snaking out to grip my yellow power-tie. She talks to it, not me. "I hate ties."

I try and laugh that off. "What can I say, it's my uniform. I work in finance."

She shakes her head, disappointed, for some reason, tugs sharply just below the knot, then lets the tie fall. She looks away. "Bad answer."

"Hey, I'd take it off," I offer, trying to lighten things up again. "But that's exactly how I tend to lose these things when, uh..." I trail off.

When I shack up at the bitch's place, was I about to say? Which begs the question, You mean on your one-night stands? Ones where you forget your necktie and never get it back, because you were always planning to ghost the anonymous pussy attached to that phone number?

Which begs the further question, So, you have a lot of them? Which I do. But I leave it at that. Anyway, she doesn't seem to notice or care.

"Hey," she looks back at me, refocused and smiling mischievously at me. The sudden cheerfulness is a little unnerving. "Has it occurred to you, maybe you're going to regret you ever met me?"

"Uhh..." I'm stunned at the question, but I recover, PUA-confident. Hand on her leg, I purr, "Baby, that's the farthest thing from my mind."

"Hmm." Ignoring my hand, she turns away to look out the window, the scenery passing by. Finally, she sort of shrugs.

"Pity."

What does she mean by that?

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Emma's house is out in the toney suburbs, set back from the street behind a brick wall, wrought-iron gate and a line of sycamores. As I pay the cabbie, she is well ahead of me, already on her way up the brick path. She disappears inside. When I catch up and enter, she shuts the door and throws the deadbolt.

I catch just a glimpse of the long front hall -- Oriental runner stretching past side doors toward a dim light from the living room -- before Emma grabs and shoves me against the foyer wall and locks her lips on mine.

She's surprisingly strong. I almost think she's trying to push me around, take charge of things... We'll see about that. I put my legs into it and drive her back. We take a couple of spins, and when the dance ends, it's Emma who's got her back to the wall.

"Ooof!" she grunts. "Ahhh, Rich --"

I think she likes that, a little male dominance -- am I right? Her mouth is all over my neck and throat, breath hot and steamy, working her pelvis against mine, hands mauling at my collar. The big slut is hot and bothered and good to go. How far, that remains to be seen.

She likes things rough, I can see that. Maybe she wants to throw in a little kink? I've done that before. Maybe she likes a little restraint, spanking, name-calling, what have you...?

Which is okay, I can swing that way too, if she wants to be a good sport about it.

Her hands drop to my belt buckle, I step back a little to give her room to work, and she whips my belt out of its belt-loops. She undoes my pants and pushes them down over my hips. I feel the fine worsted wool of the Canali suit pants slide down my legs and bunch around my ankles. I try to kick and step out of them, but my Ferragamo loafers are in the way.

Her hands on my shoulders are strong. She pushes my suit jacket back over my shoulders. With my pants around my ankles putting me little off-balance, it feels like she's got an edge of control over me. I kick and flail uselessly at the pants in my way.

She pushes the jacket down over my upper arms When she's got it down to my elbows -- she stops.

There, she grips the coat tight. Her hands are strong.

Shocked, I open my eyes. At first, what I see isn't Emma... but a dead-eyed face in the glass-framed portrait hanging on the wall beside her head, and superimposed over that, the darkened blur of my own face reflected in the glass...

My eyes just as dead, I think for some reason.

And right here, I remember what Emma said in the cab.

Something about "regret."

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Emma is stronger than before. She pushes me back from wall, still gripping my jacket behind me, and spins me a quarter turn. She's quick, too, quicker than my response time, as she continues the the spin and ducks to my side, and --

And I'm not sure what happens next. She either pushes or pulls me -- I can't tell where her hands are -- and tripping over my own pants, I pitch forward. My knees fall onto the runner -- "OOF!!" -- which is mercifully thick, but the crash-landing jolts my whole body and knocks the wind out of me.

At the end of her graceful turn, Emma is back in front. Athletically throwing her right leg over me like a rider mounting a horse, she straddles my chest. When her meaty thighs tighten, I feel my chest and shoulders pinned between her legs, arms trapped behind me, arching me backward...

I regain a little composure, tense up and struggle, trying to rear up and push her off me. I manage to slide my jacket off my arms, but it doesn't help. With her big-boned frame and strong thighs, she easily has all the weight and leverage over me.

Fuck! Pinned!

And all of this happens in a second. Before I can even think of resisting.

She takes her Victoria's Secret bag from the little foyer table beside us, and she reaches inside.

Breathless, I look up at her. "Emma, what the f --?"

Her hand comes out of the bag and wads a large ball of black cloth into my open trap. " Nooo-NNGH! Mmmfff!!"

Panties, as expected. Satin. Not so expected -- they aren't new, but used.

"I've been looking forward to shutting you up, Rich," Emma laughs, "since the minute you started talking me up at the bar."

Something else comes out of the bag next, and it's not lingerie. It's a large, red rubber ball connected to straps with rings and buckles. She forces the ball between my teeth, using the heel of her hand to jam it in good.

What is she doing! Is she insane!?

"Bitch, hold still!" Emma barks.

She buckles the main strap at the back of my head, then loops a thinner one under my chin. As he tightens this, I feel my teeth clamping tightly on the ball, which is huge, my lips stretching around it. Packed behind the ball, the satin fills my mouth. I can taste it: Fresh pussy juices, with a hint of piss. Fuck... now I see why she stopped off in the bathroom before we left the bar.

"MMHHH!?" I test my voice, which is hopelessly muffled, feeble, and... I admit, scared.

"You're doing just fine, Rich." Smiling down at me, she giggles and winks. I realize then, her skirt is hiked up, and while flexing her thighs, she's also grinding her bare pussy into my chest. I feel her hot pussy juices seeping through my shirt onto the skin of my chest. "Stay nice and cooperative like a good boy, and I'll let you in on my plans soon enough."

She picks up my belt from the floor, eases up her thighs a little, wraps it around my upper arms, and buckles it over my chest, squeezing my arms tightly to my sides. Next, she opens the drawer of the foyer table, reaches in and takes out... handcuffs? No, it's two pairs of cuffs. What the fuck? How kinky is this bitch?

She eases off my chest and slips behind me. Restrained by the chest-strap, I can't fight her as she closes the cuffs around my wrists and ratchets them tight.

Click-click-click.

"Mfff!" I protest.

My only answer is Emma's soft, breathy laughter as she pulls off my loafers and socks, then yanks off my pants. That done, she cuffs my ankles, click-click-click.

I don't have a second to process my growing helplessness, before she takes hold of my boxers and yanks them down my thighs. Twisting the crotch-part of the briefs, she ties off a knot that binds my knees together. Dammit, I shake my head, struggling uselessly, she knows what she's doing. She's got me good!

I feel the force and motion behind me suddenly cease. A breathless pause. Then, when Emma walks around in front of me, all the urgency in her coiled frame gone, replaced with casual, no, arrogant cool. She's right to feel that way, too, because there's nothing I can do about my predicament, pretty much, except wrestle with my bonds until I fall over. And I'm not going to give her the chance to laugh at me for that. Fuck that, cunt!

So I lower my face, denying her the satisfaction of seeing a frightened or pleading face.

"NNGH!" I grunt defiantly.

When she pulled down my drawers, I discovered the painful way that my penis was still full-on engorged from our making out a few seconds earlier. It still is now. I should be terrified at what she plans to do with me in this state, but the fear is overpowered by the red-hot outrage and humiliation of my predicament, and more than that, at how my dick won't calm down despite that. Made helpless in seconds flat, by a girl? I've never knelt at a chick's feet in my life. Picturing that through her eyes scalds the skin of my face with impotent humiliation.

Mostly, I am pissed off that despite the way Emma has taken me down and humbled me, I've still got a boner for her.

From the way she laughs, I guess she is thinking the same thing. But she doesn't say so. Instead she says, "Stand up."

"Nngh?" I snap my head up, shooting her a hateful look like she's crazy or stupid.

"Do it," she purrs, "pet."

Pet? Stubbornly, I convince myself I'd rather be on my own two feet, facing her, than kneeling at hers. So I try. I get the balls of my feet under me, and try to squat back so I can push off the carpet. But as soon as my knees leave the floor, I lose my balance, overreact, and tumble heavily onto my side. "Mfff!"

"Clumsy little boy," Emma scoffs, and I can practically hear her eyes rolling. She moves behind me, plants her foot on my arm and kicks me onto my front. Ouch! The scratchy wool runner scrapes my still-hard penis. Why won't the little fucker take a hint that it's not fun and games anymore?

Emma rests a foot firmly on my upper back, and I feel the dig of a stiletto-heel between my shoulder blades. "Looks like you'll need my help," she laughs, "if we're going to get you up."

The pressure of her heel abruptly increases as she bears all her weight on it, stepping over me. Next, I see her feet strolling around in front of me, coming to rest under my face.

"You need to do something for me, though, if you want my help." She extends her right foot, placing her big toe just beneath my ballgagged mouth. "Kiss."

I groan. I confess it, when I first saw those open-toed pumps on her -- back outside the bar, before my evening plans went, um, sideways -- I'd fully intended once I got her alone, to lick and suckle each and every one of those toes, see what that did for her, and for me. But not like this, bitch, no way.

"Tsk," she scoffs, irritated. "For hesitating, pet, you just made your job a little more demanding."

"Nngh!" I snort.

She lifts her other foot and plants her heel on the back of my neck, gently, for now. "Oh, I haven't forgotten about the ballgag in your yappy, yuppie mouth. But your lips are available, aren't they? Use them, pet. Both lips, all five toes. I'll be counting...."

I grumble and begin. I touch my lower lips to her big toe, then my lower, then move on to the next one down. The truth is, she has gorgeous, sexy feet, her toes are immaculately manicured, with the nails painted fire-engine red, and the sight of them fill my eyes as I acquiesce and give her what she wants.

"Oooh, that's it, pet..." she breathes, deeply aroused, whispering, "worship me... ooh!"

There's a motion above me, and I can tell she's stroking her pussy through that tight skirt of hers while she looks down on me degrading myself.

"Five... six..."

Slowly, I realize I've been unintentionally grinding my junk into the carpet as I slobber on her toes with my ballgagged lips, and for just a second, I consider getting myself off that way. I think I could. That way, my emptied, satisfied cock would finally settle down, and she'd lose the fun of ogling and snickering at the unwanted arousal of her humiliated captive.

But then, I imagine the heartless way she'll mock and scold, even punish me, for leaving a mess on her fancy Oriental runner. So I quiet that urge and hold my hips still.

"Seven... eight... nine..."

Emma doesn't bother with the "ten" as I finish her pinky toe. She reaches down, grabs my shoulders and lifts me back up on my knees. Showing me a cruel grin, she crouches in front of me and takes hold of the belt buckle at my chest... and my penis.

"Ready or not," she winks.

Using both handles, she hoists me upright. Between my bare feet and her four-inch stilettos, I have lost my height advantage, and she is staring me level in the face. She lets go of me, and I teeter a little, before she reaches out and steadies me. Again, with my penis.

"Mfff."

She licks her lips. "Follow me."

Turning on her heel, Emma starts away. I freeze, panicked.

She stops and glares at me back over her shoulder. "You hesitate again, clumsy boy, and it'll be your balls I use. Don't be stupid and boring, pet, you know how..." She gives my penis a little shake to demonstrate. "Hop," she giggles.

"Nngh?"

"Hop like a bunny. Like my cute little pet bunny-toy." Emma shifts her hand and cradles my balls, the tips of her nails digging lightly into my scrotum. "Don't be a difficult toy, and make me wind you up."

"Nnngh" I groan in frustration, seeing no other way out.

So I hop. Following Emma's irresistible lead up the hall toward the living room, I hop on bare feet, the links of my ankle-cuffs clinking with each little jump. I try not to picture the pathetic sight I am, but I can't help it: cuffed hand and foot, ballgagged, my own belt strapped across my chest, briefs tied around my knees, stripped naked except for my dress shirt and tie. My manhood in her hand and at her mercy.

"Follow me, funny bunny," Emma giggles like a schoolgirl. "Hey, you should be used to following your dick around everywhere. Huh, Mr. Pickup-Artist? I mean, think about it, that's what led you here."