Tales of a Playboy - Downtown Anal

Down near Wall street about 2 years ago, late night, celebrating a friend's promotion at an investment firm. Some fancy gala type thing nearby just let out, and some of them invaded the little pub we were drinking in. Men in tuxedos, women all dressed in high end designer outfits and $1,000 heels. My buddy James (not the guy whose party it was) and I end up talking to two of the women who were clearly there after the event next door, without dates. Both in their mid-40's, corporate V.P.'s or such. I tend to roll my eyes at the "resume and credentials" chit chat that usually happens in these crowds, but this was nothing of the sort, but rather it was flirty and aggressive by the ladies from the start. Jill is the one next to me, clearly on purpose based on how they slowly eyed us over and then approached.

Tall, in shape, toned but not super skinny. Long jet black hair, tight and short red dress, studded Louboutins, oozing sexuality, already very drunk. After some banter among us 4, she's touching me up and down my chest and legs under the bar, and daring me to do some shots, with all sorts of dirty wagers offered in a not so quiet whisper in my ear. I warn her that I've never lost a challenge like that, and she's bound to regret it. After 4 tequilas and a Jameson chaser, she happily admits defeat, barely coherent, hands on my crotch above my pants, digging under my belt for more, mumbling in between drunken laughter that she wishes she could have me right there. I offer the bathroom, and we head that way. Small bar, long line. Major problem.

Before I know it, she's leading me towards and out the front door, and I assume it's to get a cab to her place. But she is wicked drunk, and clearly can't wait. After a glance up the block, we find the gap between the strip of bars, and she staggers us in the alley and behind the dumpster. I barely have time to push her down to her knees before she's got her dress hiked up over her ass and is crouching on her stilettos at my feet like a porn star. I'm quite sure it's not her first time giving head in heels, from her confidence, and her form. Even as drunk as she is, she balances perfectly and whips my dick out, is instantly taking down about 6 of my 9+ inches, and aggressively working my balls with her fingers. My hands are on her head, and I try to push more in to her mouth. She opens wide for it and gags a bit, finally giving up an inch or so from fully deep throating me.

As she pulls her face back, a trail of spit splashes across her chin. She licks it up greedily, using her hand to wipe it on to her tongue, and then sucking the pre-cum off my tip as well. I ask if she wants to finish me with her amazing mouth, and she licks her lips before replying "Hell no. I want it in my ass, damnit!" It's rare I'm shocked, but I was definitely not expecting that response. If I wasn't already about as hard as I'd ever been, I sure was then. In a flash, Jill is standing up again, dress hiked further up her back to fully reveal her worthlessly soaked black g-string and firm, toned ass, her index finger on her dripping slit and rubbing herself hungrily. She's looking for someplace to lean over, and spies a stack of empty crates nearby. Her hand grabs my cock and leads me along behind her. She finds a firm spot to brace her heels in the ground, and bends over, legs wide, back flat, holes wide open. "Fuck. Me. NOW"

I slide in to her drenched cunt to the hilt, one stroke, bottoming out as deep as I can. I hold still there and feel her spasm as she groans, but doesn't flinch at my size. This one is a real pro - most women cry or writhe when I go in fully that fast, She's already squeezing my shaft with her pussy, clearly wanting more, needing more. I take some wetness from her slit and rub a finger at the tip of her ass. She bucks back, trying to fuck my finger as i get her ready. I can't tell if she's more drunk or horny, but I know she can't wait for it. A few more quick strokes in her pussy makes my cock dripping wet as I pull out, and I pull her panties to the side just a bit more, as I ready myself at her tip. She's holding on to the far edge of the crate with one hand and fingering herself with the other, I've never seen a woman this hellbent on an explosion so fast, so desperately. I line up and edge in to her ass. Once i fit my thick head past the initial resistance, I slip in faster than I expected - is it possible she fucks more than I do? Have i truly met a porn star, or someone who could be?

I urge my weight forward as she struggles past 5 inches, then 6 and 7 - I think it's the girth that is slowing her down. Her hips have finally stopped bucking back to me, and I know she is aching for more, but her body has finally said "no" to my size. I lean forward towards her bowed head, her breathing slow and deep. "That enough cock? You want more, slut?" She whimpers for the first time, and pauses before replying. She's been greedily in control until this very moment - and I've finally cracked her confidence. "Yes please. Yes yes yes. Fill me up. I want it all. I can handle it. Give it to me." She is saying all the right things, but I can hear the wavering in her tone, the gasps between phrases as her body adjusts to the onslaught. I've been slowly working my cock in and out ever so slightly as she struggles to keep up, and I can feel her legs tremble every few thrusts.

I grab her hand from her clit, and have it pull one ass check wide, as I steady my arm on her back, bunching up her expensive dress in my palm and using it as an anchor. I slide out most of the way and feel her hole clench at the emptiness. Before she has a chance to relax or recover, I rock forward with all my weight, and I slip almost completely in, 8 or so thick, throbbing inches, her wetness allowing me to enter in swiftly, deeper than she has ever had a cock up there, I'm sure.

"I warned you not to make bets your ass can't cash, Jill. I own it now, bitch." A hard slap on her check punctuates my whispering this in her ear, as I give her every inch she can take.

Her coos and groans are all I need to hear, and I begin to work back and forth inside her now, sliding out 2-3 inches at a time before pushing back in urgently, confidently.

She finally gets comfortable again, steadies her body on the crates, and lets out a string of obscenities as i pound her. "fuck fuck fuck, ow, don't stop, fuck fuck fuck, yes, fuck fuck yes, oh god it's so huge, fuck fuck, yes. oh god. so good. fuck fuck fuuuuuck."

The first orgasm wracks her body, her hands long ago having left her clit, but not being needed anymore. Her pussy spasms - I can feel it on my balls and up my shaft. I pick up my pace - her asshole is totally used to my girth now, and her will is broken. She's just muttering gibberish, I'm sure no one has ever had her like this. Whatever veneer was left of her career and title, her huge paycheck and her high fashion - all gone. She is a crazed slut now - my crazed slut - desperate for a huge load of cum in her ass and nothing else. I am emboldened by this, and rear back, forcing every bit of myself in to each thrust. I can feel her ass contract as I pull out each time, leaving her empty and wanting. She is rocking her hips and ass back to meet me now, trying to control the action again. I pull out to my tip, smack her cheek roughly a few times, and then plow back in fully, to her surprise. She whimpers loudly once more, and I can tell she is now fully mine. I thrust hard and quick, leaving my shaft in as deep as possible as much as possible, and feel her orgasm again, the second one more intense than the first. It's only been 10 minutes since we left the bar, but it feels like hours. Her perfectly done hair is a mess, I'm sweating through my shirt, her expensive cocktail dress is crumpled and battered around her writhing body.

I catch my breath once more, lock both my hands on her hips, and give everything I have left. a few more deep stroked and I feel the cum churn up in my shaft. I grab her arms and yank her body halfway up towards me, her lower back hitting my abs, shocking her as it locks my rod up at an angle she can't control. I thrust up instead of forward, once, twice, on the third one i let her fall forward and shove my whole body forward, crashing on to her as she braces against the crates and her knees buckle. The first shot is a canon blast, as deep in her ass as possible, and then another jet, and another. I roar in her ears as she cries in pleasure, her whole body going limp under my assault. The cum is still pumping, she shifts her weight to allow herself to lean forward, and she quakes once more, an aftershock now, her body limp under me.

We slowly catch our breath and come to our senses, I slip out, and she slowly stands up and leans her back on the wall. She takes the sight in, her thighs slick with her own juices, panties around her hips, ripped and ruined, she can feel her ass gaped and dripping with cum, my cock covered in a mix of both our juices. She begins to walk forward, finds herself deeply unsteady, steps back to the wall. I pull up my pants and offer her assistance, we laugh and kiss deeply, our first romantic moment in a frenzy of lust.

I fix myself first, wipe my brow, head in to the bar quickly to grab some napkins. I return to meet her in the alley, help her fix herself best we can, then she tells me to grab her friend and meet up back in the alley.

Once we have Susan out front, along with Jill's purse, she takes my number, kisses me once more, thanks me again for the "drinks". I flag them a cab, and off they go. I receive a picture 30 minutes later - of Susan in lingerie licking my cum off Jill's thighs, and a promise to meet them both for more soon.