CulDeSac Kelly, Next-Door Whore Ch. 01

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John talks 19 year old Kelly into liking sex, and sexwork!
4.1k words
4.36
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Part 1 of the 5 part series

Updated 02/26/2024
Created 11/14/2023
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It was my first summer back from college, and the ole' neighborhood cul-de-sac looked as shitty as ever. My pals and I who grew up there called it cul-de-shit, a cul-de-crap and a cul-de-let's-get-the-fuck-out-of-here-as-soon-as-possible. As for me, I did mange to get the fuck out of the cul-de-shit.

They didn't.

My college wasn't great, but I had a good scholarship, and when I learned how to work the system, I finagled a sweet work study deal that left me free most of the summer.

I was luxuriating in my brilliance until I realized...free to do what? I was stuck in the cul-de-shit for the entire summer, the friends I had made at school were all gone to their own homes, and a lot of my childhood pals were working their bullshit jobs with little time left over to party. And, I gotta admit, a lot of them had just become assholes. Or maybe I did. I didn't feel like an asshole, but assholes never do, do they? And how would you know? You, the reader, might be an asshole as well, so, who knows?

Whatever it was that had changed, me or them, I found myself not wanting to have anything to do with my old friends....with one skinny little exception.

Kelly lived across the street with her parents and an older brother. She was a razor cheeked brunette, skinny as a rail with huge blue eyes and she loved to be mean to everyone on the cul-de-shit. However, this summer when she started giving me attitude, instead of whining and taking it like I used to, I gave it tight back to her. And she actually loved it! And I did too! Trading insults, cut-downs and yelling friendly obscenities back at each other became my only pleasure, and though Kelly was dumb as hell in most things, she had developed some true talent when it came to crafting the scatalogical she was a genius, and therefore kept me on my toes all summer long with her frequent challenges.

One day I was going into Burger Yaga's Russian Burger Dojo, when Kelly almost knocked me over while bursting out through the 'IN' door.

"Watch where you're going, you blind piece of shit! What do you think you're..." Kelly's flaming eyes were able to see past her rage after a couple a seconds, which let her see it was me. "Fuck!". she yelled as she helped me up. That was her way of apologizing.

"What happened Kelly? Did they finally taste your cooking?"

"Not now John, okay? Just...." she stood there, twisting in place, clearly upset and stuck about what to do or where to look with her eyes. "This is the third time I've been fired in five months. I'm running out of places to work. Fucking McDonald's won't take me back after what I did with that ketchup spigot..."

The tears forming in her eyes gentled my tone. "Well, Kelly, the guy did have to get an operation to remove it from where you stuck it."

"....fuck.". She said softly, sadly, with all the remorse a remorseless bitch could muster.

"Would you like a ride home?", I asked.

"Yeah. Just don't gimmie any shit, at least for a while, ok?"

"Sure, sure. I declare a truce. Hey, I'll even let you play that shitty Stryper cassette you like."

She almost smiled. On the drive back, she started talking about all the jobs she'd lost since leaving High School. It soon became clear Kelly had no business being in the people business. Her disdain for tasks, bosses, customers, making things for other people and doing things for other people was tremendous ... and hilarious to listen to! I drove the long way home, picked up a six pack and headed to a nearby artificial lake in front of Sierra Chupacabra subdivision, parked near a picnic bench, got comfy and I just let her keep on yakking. To my surprise, she told me everything! I found out she had lost a total of twelve jobs in three years. And hearing each adventure, it was clear all of her firings save one, were entirely her fault, though that was not how she put it.

"I mean what did he expect me to do? Mop up the whooollle thing just 'cuz someone spilled it?!", her incredulous tone ringing across the suburban man-made lake as she swung her arms wide, spilling a little of the beer from her can.

"You know, he just might have, Kelly."

"Well....he's a dumbass then.". She walked around and stretched a bit, her languid twisting body betraying the fact that she was starting to feel the alcohol. Her nipples poked through her work uniform, showing that she wasn't wearing a bra. I ogled her lithe form which was sinewy, almost too thin, but still a luscious 19 year prize. She wasn't my usual physical type, but, shit, it was the summer, and she was drinking my beer by a lake, and what the hell. I wasn't going to force anything, but if the Wind of Easy Pussy blew my way I would catch that breeze and sail, brother!

"Fuckety fuck fuck!", Kelly babbled on. "If there was only a job I could do where I just sat there and stuff happened near me, or around me, on on me.... I don't know, JUST so I didn't have to move or anything much...".

"Ha! You mean like a prostitute?"

"Huh?"

"You just described what a prostitute does."

Kelly looked around a little wildly, trying to disagree with me, but she couldn't come up with anything.

"...Fuck you, John...", she said without gusto.

"How much?". I retorted.

She didn't tell me to go fuck myself harder, as I expected. A thoughtful look crawled onto her face.

"I mean, shit, if sex wasn't so shitty, I'd maybe think about it..."

She trailed off and turned away from me.

"Sex isn't supposed to be shitty, Kelly."

"Not for guys, duh."

"Nooo, not for everyone. I mean, not shitty for everyone. Women are supposed to enjoy sex."

"Bullshit."

This was weird. Could could foul-mouthed Cul-de-sac Kelly really be this naive, or was she just fucking with me?

"Uh...so you've had sex...?" I asked her cautiously.

"Of course, dipshit."

"How many times? Or how many guys, what ever applies?"

"Once was enough for both."

What the fuck, I thought to myself.

"So, you've never had an orgasm?"

"What? I don't have a dick, dumbass, how can I cum?"

You gotta be kidding me, I thought once again to myself. But when I thought about it, it started to make sense. Her parents were dumbasses so they wouldn't have taught her anything about sex. Also, Kelly was as mean as they come so how many guys are gonna try to fuck her. And any number of guys in the cul-de-shit could have been the kind of shitty lover that would make Kelly hate sex.

"Kelly, I swear, women are supposed to have orgasms. I promise you on a stack of Stryper Cassettes."

She turned back to face me, and looked my up and down. "Your girlfriends... cum?"

"Uh, yeah.... most of the time."

"How do you know they're not faking?"

"Because she told me what to do to get her off. You don't give instructions and then fake it."

Kelly looked at me right in the eyes for a little bit. Then she started nodding to herself, as if she had made up her mind about something.

"OK, Johnny-Boy, let's get me a six pack of beer and head home.", she said in an upbeat voice. We drove off, got the beer and pulled into the Cul-De-Shit. Kelly got out of the car almost before it stopped.

"Come on, and keep quiet.", she whispered over her shoulder. I hustled out of the car to catch up with her as she fast-walked towards the old Freetowski house, which was for sale and had been empty for six months. She made straight for the back and stopped in front one of the side windows, gracefully pried off the screen, slid open the window and climbed inside without a single word to me. What else could I do? I climbed inside after her.

The room was dark except for a little moonlight coming in from the window. Kelly replaced the screen and closed the window, then hooked an old Star wars blanket onto two nails sticking out on top of the window frame, making the room pitch black. There was the sound of a few steps, a rustling of some paper and then a lighter came to life in Kelly's hands, which she used to light two nearby candles.

The light revealed a room with an old mattress, an over-turned cardboard box with two candles on it. There were magazines and junk food wrappers scattered about the floor, showing someone had been coming here for a while.

"Allright, make me cum.". Kelly said, sitting cross legged on the mattress.

I blinked a couple times. "Uh, ok... "

"What's the matter? Ain't it nice enough in here? I come here a lot. I need a place to go when my parents are all up on my ass. "

"...no, it's just.."

"Oh, yeah, hold on...". Kelly stood up on the mattress and took off her shirt and pants and threw them in the corner. Completely naked, she turned in a complete circle, her arms akimbo, practically challenging me with her slender body, B cup tits and her muscular ass and thighs. She didn't pose or stretch, she just turned around a couple times and then let her arms flop to the side.

"That's what you guys like, right?"

"Kelly it's not just about that. It's about what you like."

She looked confused.

"Here, let's try something.". I took off my shoes and joined her on the mattress. I put my hands on her ass and caressed them. Kelly rolled her eyes.

"Oh Jesus Fucking Christ, are you going to be all handsy and touchy feely?" she sneered.

"Well not for long if you don't like it. How about this then?". I grabbed one of her nipples and gave it a squeeze. She yiped and jumped a little, but she didn't get angry and before she could say something stupid I took a light hold of both her large, red nipples.

"Ok, now tell me if I squeeze too hard.". I then began to increase the pressure my fingers were applying to her nipples. Kelly blinked, and uttered little gasps as I ever so slowly squeezed harder and harder, but she said nothing. I kept on, her nipples flattening out between my thick fingers I smiled as she stayed silent, throwing her head back, her mouth hanging open. It was only when I gave them a little twist that she cried out and her hands flew up to mine, grabbing and holding on to them, but not pulling them away from her sweet titties.

I laid her back on the mattress and took off my clothes. When I turned around her eyes grew wide at the sight of my dick.

"Holy shit, that's way bigger than Jimmy's!". she exclaimed.

"Jimmy Brannigan? You let Jimmy Brannigan fuck you?", I sneered at her.

She shrugged. "I lost a bet. He got me drunk."

"He's got the smallest dick in the whole Cul-De-shit, Kelly."

"Yeah? Well, he's also a dumbass."

"That sure as shit helps explain why you don't like sex. Now, let's get back to business." and then I lunged between her legs, grabbed a firm hold of her skinny pale thighs and started licking at her hairy pussy which made Kelly start yelling.

"Whoa! Shit! What the fuck are you doing! That's fucking gross!! Oh! Ungh...oh shit, that feels....oh fucking shit!"

Her clit was tiny and a little hard to find. But once I got it in my sights, my tongue gave it a good working over. I caressed her little nub back and forth and up and down, until she was wriggling at my will, like my tongue was a joystick and her clit was the interface. It was like no one had ever touched her clit before and she was barely able to contain her pleasure.

"Oh gawwwwdd....Fuckfuckfuck John. That feels so, that feels so fucking.....ungh, ungh, ungh....oh God!". Her hands were now on my head, keeping me between her legs. Her hips were bucking up toward my face, matching the pace of my tongue lashing. Her moaning, screaming and swearing echoed in the candle-lit empty room as I kept licking and sucking at her pussy, until she started to tense up.

"Oh Jesus, what's happ...oh God, oh fuck, oh FUCK!". Her body convulsed and shook as my face got soaked in her sweet pussy juice, as she came for the first time in her life. She kept holding my head hard to her pussy, moaning incoherently and fucking my face. When she had settled down, I extricated her bony fingers from my hair, moved up so I was face to face with her, and then placed my cock at the head of her pussy.

"Did you like your orgasm?". I asked her in a flat, confident tone. The candlelight made her sharp features even more so, but her razor cheekbones couldn't hide the pleasure and contentment that shone from her eyes.

"You haven't even...fucked me yet.", Kelly said in a soft, raspy voice. "Is that gonna hurt, since that other thing you did felt so good?". She sounded so vulnerable, and a little afraid, which coming from a bitchy in-charge shrew like Kelly was a big turn on.

"I don't think so, let's find out.". Without another word, I started to slide my cock into her tight pussy. Inch by inch I gave it to her, her eyes growing wider and wider, her jaw falling open, until I had my cock all but an inch or so in. Kelly's arms were wrapped around me, and her little hands were splayed flat against my back. I then pulled out, and poked at her clit with the head of my cock. Kelly grunted in anger and kicked at my ass with her feet, like a cowboy spurring a horse.

"Hold on there, Girl! You don't go kicking at me like that.", I chastised.

"But...but..."

"But what? What do you want?"

"I want... your cock back in me.", she pouted.

"I beg your pardon? What was that?"

"I want your fucking cock! Fuck me, John! Fuck me hard with that big cock!", she snarled like an animal. I slammed my cock all they way into her, making her shout with satisfaction and pleasure, and then I began to give her a good solid fuck. Her tight pussy felt great, and I have to admit, fucking the neighborhood bitch in an abandoned house was nasty, dirty, filthy....and so fucking hot!

"Gaaawwdddd! John you mother fuckin' beast, fuuuck me! Ungh Ungh Uncgh!" Kelly howled into the litter strewn room, her breath stirring the candle flame and making the shadows dance across our sweaty skin. I started to fuck her harder and faster, which made Kelly start gasping and shaking again.

"Oh shit, John you're gonna make me cum...fuck... with your cock... AAARRRGGhh!". I had started to rabbit pound her hairy cunt, which made her lose all sense of words. I felt her pussy tighten and tremble around my cock, which made me groan out loud in pleasure. I was able to keep from cumming, but only barely.

"OK, my turn.". I told her as I flipped her over on her stomach, grabbed her hips and pulled her up to a doggy style position. She didn't resist me at all, and stuck her skinny 19 year old ass high in the air for me. I plunged my dick into her and she screamed into the dirty mattress. I held her ass tight in my hands as I plowed into her from behind, first with long strokes, but as I got close I started fucking her deeper and deeper, with shorter strokes. She was grunting with every one of my deep thrusts, her hands balled up in fists. My cock became a glowing wand of pleasure, pulsating an tingling! Finally, I pulled out and shot a huge load all over her ass and back. I flopped down next to Kelly, both of us breathing hard. Several minutes went by, silent, neither of us touching each other, despite the fact we were on a twin mattress. Finally she rolled over to face me and blurted out while gasping for air, "So why come...can you do all that... and Jimmy can't?"

I grinned and poked her clit with my softening cock which made her squeal. "Jimmy's a small dicked asshole and... now don't get mad, but you're naive as shit. Girls are supposed to know how to cum on their own."

"Well, my family's all fucked up.". she answered flatly.

"Mine too. Glad I got out."

"So all guys other than Jimmy can do that or are you special and all?"

Now here, Gentle Readers, you may condemn me if you wish, but I was lying next to a skinny Mean Girl, my cum on her back, in an abandoned house on a dirty mattress. So my impulses were already not leaning towards the pure and righteous.

"Oh, um...I took classes in college."

"No shit?"

"No shit. I minored in coitus, that's Latin for fucking. And I also took some classes in Pornological labor studies. That's college talk for sex work, um, whores and prostitutes."

"Damn. They have classes in all kinds of shit now, don't they?"

"They sure do, Kelly. Would you like to learn a little more?"

Her eyes lit up.

"I think I would, 'especially if whoring..."

"Sex work, we call it it sex work in the profession..." I corrected her with my best stern Teacher tone.

"...oh, yeah, like a professional, sex worker...so if being a sex worker means I can feel like that, like this, and get paid, then why isn't everyone doing it? I mean, fuck, screw flipping burgers, right?" She looked incredulous and innocent, but wisely suspicious, and started to answer her own question, reasoning it out, getting up on well elbow to look me in the eye. " Okay, so first off most chicks are ugly, so guys won't won't to fuck them as much. And me, I'm alright, but not like a model, so maybe guys actually go for me more because I'm easy to approach or some shit like that, hunh...." Her frank and accurate self assessment of her looks was a small shock. Kelly wasn't dumb at all, she just hadn't found the way to make this fucked up world work for her. It can really mess with a person's head to see so many others finding all kinds of mundane happiness and never finding your own. It can fill you with negative bullshit, and make you blind to what's actually going on in your life.

"And I bet most guys you fuck won't be as good as you, and may be even bad at sex... ", both of us joined in unison, ".. Like Jimmy!" We laughed together, and smiled into each other's eyes, like in a coffee commercial.

"Look Kelly, If you think you could perform sex work on a professional level, I think I could set you up safely and profitably."

"For a cut, like a Pimp."

"For a big cut, yes, but no, not like a pimp, like a manager. There's a lot you need to learn..." I smiled slyly. "Do you think you can handle the lessons?" She grinned like the devil in the candlelight.

She breathed the words softly as she giggled, "There's only one way to find out.."

TWO MONTHS LATER.

Kelly and I had got a lot of things figured out in the last two months, but instead of dryly describing our glorious eschetologica process of learning, growing and profiteering I think it best to simply describe our Monday morning routine.

It was 8 am and I was leaning in the corner of old man Smith's living room while Kelly was kneeling and slobbering all over Old man Smith's cock, who was standing dead center, fully dressed in slacks, white shirt and tie with a skinny blonde wig wearing Kelly on her knees in font of him passionately sucking his dick. Over on the couch, Mrs Smith was sitting on her Ethan Allen green floral couch, her legs splayed wide open. The black hose and garters than ran up her shapely legs led you to a hairy pussy that had no panties to get in the way of her furiously flicking fingers. The rest of her was as Betty Crocker as they came, a pale blue dress with no cleavage and a sweet face with full red lips and green eyes, all framed with a hairstyle Patty Duke would have been proud to wear, except for her open legs and bare ass lifting off the couch as she grunted and moaned while watching her husband get his cock sucked by a 19 your old skinny prostitute in a pink halter top and tight cutoff jeans with red leather lace up boots... just as Mr Smith specified when he made his appointment with us.

Kelly was on her knees in front of the slightly fat Mr. Smith, both of her hands on his stubby cock while her tongue ran tight circles around the head of his penis. Saliva dripped down Kelly's chin as Kelly kept her face on Mrs. Smith. Their eyes were locked onto each other.

"That's it you little tramp! You nasty little trollope!" Mrs Smith yelled at Kelly. "Suck his dirty cock, i want to see that nasty spittle of your yours covering all of his manhood! Oh that's it! Ungh....ungh!"

As Kelly started to swallow her husband's cock, pistoning up and down the shaft, Mrs Smith came all over her couch, her body and thighs all thrashing against themselves. Old man Smith was watching his wife cum like a freight train, a sight that always made him ...

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