Down and Out

Story Info
When all is so wrong, she finds it can be so right.
4.1k words
4.23
56.3k
25
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Deadwood
Deadwood
74 Followers

Leslie James hesitated for a moment inside her Lexus even as the alarm beeped twice giving her a thirty second warning to remove herself from the vehicle. It was the best system money could buy, but even then Leslie knew this was certainly no place to leave a vehicle of this caliber. It's asking price was probably twice the yearly income of the residents of this neighborhood, and stealing cars was a mere past time of the elementary school kids, to say nothing about the professional thieves that lurked about the many dumpsters and vacant warehouses. Leaving it was a huge risk, and yet as the timer wound down, she knew it was for that very reason that she had to leave the safety of her car, the safety of her gated community and the safety of her father's all-powerful political friends.

She had but a few seconds left when she stepped out of the vehicle, slammed the door and retrieved her keys from the lock just as the tiny red light on the dash began to flash its visual warning to any would-be thieves.

"I should not be here," she mumbled under her breath as she made a step from the lavish Sport Utility Vehicle, then another and another as each step bore her further away from her only safety. With each step she also announced her vulnerability, her high heels clicking loudly upon the broken cobblestone paving, the sound echoing softly off the brick buildings as well as she stepped around broken pallets and trash drifting about in the wind. Her high heeled pumps echoing loudly, spoke volumes about her vulnerability; that she was a lady that would not be able to run from any stalkers. Her shoes also announced that she was dressed for pleasure, for no woman wore such senseless shoes with jeans and a sweatshirt. For all those who looked, Leslie did not disappoint, for under the shoes she wore black stockings, their wide elastic tops just visible under the hemline of her dress.

It was an evening dress at that, a short black number that was the staple of every ladies wardrobe. She could see her own image reflecting off a rather large mud puddle that was frozen solid to its core as she skirted past it, fearing she could easily slip in her cumbersome high heels. She paused for a second in front of the ghetto mirror and saw her pale reflection glimmering on the silky smooth ice. Her pale skin glowed in the moonlight against the stark contrast of her black dress and dismal settings that surrounded her.

She wished she could have at least worn a jacket, her favorite long mink coat at that since it was incredibly warm, but knew she had to be dressed just as she was a week ago so that she would be recognized. Instead she froze, letting the icy wind hit her legs that were only covered by the thin fabric of her black nylon stockings from her mid thighs to her black pumps. Even then there was an inch of exposed skin where the tops of her black thigh high stockings stopped and the short hemline of her dress. From there the meager dress only rose to the height of her navel before splitting again. Here the fabric rose up into two slim pillars of material, covering her chest before encircling over her arms and across her back. Only the shiny chrome buckle of a belt stretched tightly across her waist gave the outfit a hint of color.

Leslie wore it well, her pedigree mandating that she wear it to cocktail parties and benefit dinners for the wealthy politicians that feasted far too often at her father's estate. While fitting at such events, in this neighborhood, such a dress had no use. It was far too eloquent to be considered slutty, and thus no one was about to confuse her with the many prostitutes that lingered about the neighborhood. Instead, she looked out of place; a sophisticated young lady that looked lost and scared.

The latter she was, for her hands twitched more out of nervousness than from the cold, while the former was another story altogether. She had been here before, a week to the day no less and accompanied by a man at that.

Fifteen degrees was what Leslie remembered the Time and Temperature building stating as she drove through the downtown portion of Portland. Now it felt much colder as the wind easily whipped through her meager satin dress as she rounded the corner of the forlorn brick building and took the heavy sea breeze straight in the face. There would be half a block of walking through this before she would turn out of the wind, duck through a side alley and then emerge just on the south side of the railroad tracks.

That was, if she could make it that long. Already her feet were beginning to feel like blocks of ice, her legs getting the sensation of needle pricks from the wind, and while she could have turned back to her vehicle at any time, some inner drive pushed her on. It pushed her on to make the turn half way down the block. It pushed her walking down the dimly lit alleyway, and it even pushed her until she was stepped from the giant brick archway and faced the chain link fence of the railroad yard.

As she approached her destination, it took her a moment for her eyes to grow accustomed to the bright flickering yellow light and the raw smell of burning wood in the air. She approached slowly, two men huddled around the fire, warming their hands and tearing apart a pallet to make sure their only supply of heat did not die.

"A rich bitch huh?"

"Yeah a real rich bitch. And she wanted it hard I tell you."

"Hard huh? And what was the rich bitch's name?"

"Leslie," he said making Leslie draw in a breath upon hearing those words and cowered against the dark brick wall to over hear their conversation.

"Oh she was good. Young and hot..."

As the man went into detail about their sordid affair, Leslie slowly drew her hand up under her hemline and began to massage her pleasure point with increased intensity, her own mind beginning to spin back in time to a week earlier when she had slipped into the darker side of her sexuality.

It was not hard to drift back in remembrance, for she wore the same dress, the same shoes, the same purse clutched tightly in her left hand. Only the location was different, she realized as she began to think back to the quaint and charming bistro on Mason Street. It was her father's favorite restaurant, and a favorite locale that had managed to maintain it's upscale patronage despite it's location in a neighborhood that was slowly dwindling into poverty. If the Bistro was in a desolate part of town, at least there was an unspoken agreement that left the wealthy patrons immune to the criminal activities of the other sections of the neighborhood. Cars could be parked without fear of being stolen, muggings were rare and trash quickly cleaned up.

Leslie managed to order an appetizer before her Fiancée arrived. In fact she managed to make it through the bread choice, main course and dessert before coming to the conclusion that he once again had stood her up. Such an occurrence was becoming increasingly common. It was the second time that month and it she began to get cross as she stirred the cream in her mug of coffee. Her anger only increased as she looked up at the Waitress who had a look of pity in her eye. There was no denying that she had been stood up, her formal black dress, stockings and hells, could only have been worn for the benefit of a lover, while the seat across from her still had its place settings undisturbed. With a cross look, she paid for the meal, the act itself only making her bitter at being slighted by her Fiancée, as she rose and left the restaurant.

"Please Miss, can you spare a little change?"

Leslie had not even seen the man, an older gentleman that had been sitting just outside of the Bistro's building, slightly obscured by the shadows as she walked by. It jumped her slightly, but no enough so that it stopped her strides towards her Lexus.

"Get a job," she cried over her shoulder.

"Yeah, I would, but maybe you should look around here and see the jobs that are leaving the great State of Maine in such haste!"

At this Leslie halted, and then spun back around. Perhaps it was her father's efforts to improve life in Maine through the legislature, or perhaps it was the man's brazen critical statement, but Leslie was not about to let the bum go without at least having a piece of her mind.

"Oh you could get a job if you wanted to," she said strolling up to him. "You're just lazy. A worthless bum that has to beg to subsist.," her anger spewing out of her lips as she got within a few feet of him. "You're a worthless piece of shit that chooses not to work, that's all. Go out and find a job and quit begging for money."

"Yeah, and how would you know what it's like to find a job? I bet you have never even had to try. Rich Bitch."

"How dare you question me, because here is a thought, what if you cleaned yourself up? That wouldn't hurt your chances of getting off the street and making something of yourself," she said, her words of anger really stemming from her Fiancés inconsiderate behavior, more than it came from his words.

"You would not understand."

"No, I probably wouldn't because my family chose to make something of themselves, to do better, to work."

"Miss I just want ten dollars to get something to eat, that's all," he said lowering his voice in trying to de-escalate her anger.

"What, ten dollars of my money, so you can go out and buy booze with it...or cigarettes...or drugs?"

"I just want something to eat Miss. That's all, I swear."

Leslie could not help but smirk at his words. She had heard this so many times before; a feeble attempt at deception just to gain a few dollars. She had heard stories of beggars making an average of fifteen dollars an hour pan handling, while the working poor worked and made even less. Despite his weak pleas, she knew he had no intention of buying food with her money any more than she did in giving it to him.

"You're hungry you say huh? Then I'll cook you dinner," she said knowing full well that he had just gorged himself on the soup kitchen just down the street.

"Well that's just great Miss because I am starved," he said calling her bluff as he started walking towards her sport utility vehicle. For a second Leslie was speechless. She never considered her next move if he actually took her up on it. Now she considered her options and produced a twenty dollar bill.

"Here, go get something to eat. I don't care what you do with the change."

"I don't think so. I love the sound of a home cooked meal."

"I'm not taking you anywhere," she said firmly placing her hands on her hips to verify her steadfast resolve.

"So you're word is no good then? You know what though, you think you are all that, but you are no better than that useless boyfriend of yours that stood you up tonight. I mean that is what you are really mad at anyway isn't it; him, not me, but I'm an easy target so you started slamming my unfortunate situation?" Leslie looked at him with a look of utter animosity. It was the second time in two hours that a man had offended her and she was not thrilled about being portrayed as the bad person now.

"Fine, if you want dinner I'll cook one for you. Hell maybe then you can get cleaned up and you can get a job."

"That would be nice too," he said making sure he countered her every statement with one that was just the opposite.

Leslie made for a lousy chauffer as she drove up the darkened streets of Portland. She had placed an empty shopping bag underneath the seat so his soiled pants would not ruin her expensive leather upholstery, and made him hold his shoes in his lap as well. It was only a half hour drive to her Townhouse by the sea, a true requirement of being influential in the State of Maine.

She hardly spoke a word to him as they drove there however. Other than demanding he wear his seat belt and giving him a stern warning about ever remembering where she lived, she said very little. She was glad however that most of her neighbors had turned in for the night and would not see such a bum being escorted into her home.

"Take your shoes off," she demanded as they reached her front door. She ignored her own advice and stepped inside to snap on the dining room light and punch in the security code, leaving him to untie his muddy and greasy boots by the door.

She turned back to watch him after she was done. It was the first time she had really seen him in any kind of light. It certainly was not flattering. His socks were nearly as dirty as his boots with grass and dirt stains making his white socks look more of a grayish color than any resemblance to white. His hair was just as unkempt, having been uncut for several months and sprawling out in clumps that would not stay flat. Particles of food and dirt stuck to it, while his matching gray beard was just as shaggy, and equally unflattering.

Leslie did not bother to review much of the rest of him. His blue jeans matched his unclean socks, while his red and flannel shirt was ripped in two places. A pack of cigarettes bulged one of the breast pockets out as he stepped across the threshold and into her small kitchen.

"Well you are here. What would you like me to cook you," she asked upon ushering her arm toward her well stocked cabinets and refrigerator? As he opened the cabinets and inspected the cupboards carefully for his meal choice, Leslie began to take note of his age. With his unkempt look, it was hard to calculate, but she considered him to be in his late fifties or early sixties.

"Mesquite chicken sounds good," he said upon a rather long review of her pantry. Leslie merely nodded and began to grab the contents she would need as he placed himself at her oak table and watched her rush about the kitchen in a flurry of activity. She wanted to get her obligation over as soon as possible and return to her rather nonchalant lifestyle. As the frying pan began to heat up on the stove however, he dropped a bombshell onto her.

"Nude," he finally said after a long bout of silence.

"What?"

"I want you to cook me my dinner nude." Leslie just looked at him with utter bewilderment.

"I'm not cooking you dinner naked if that's what you think. How dare you even come into my home and demand such...", but her words were cut off when she looked down upon the table and saw a steak knife in close proximity to his knotted up hands. "Your dress, please," he asked, as if such a request was as nonchalant as asking a waitress for a shaker of salt?

Leslie's stomach cramped up in instant nervousness, as much from him speaking her name as she did for his outlandish request. She was about to ask him how he knew her name, but as she looked towards him, she could see the mornings mail sitting just in front of him. She silently cursed herself for getting herself into this predicament.

"Please don't hurt me okay. Please, I'll cook you a nice dinner, just like you wanted, chicken, potato and everything."

"I'm not going to hurt you Leslie. Hell you've invited me into your fine home, offered me a nice meal, but taking of your dress isn't going to hurt you either is it?"

"I don't know?"

"No it's not," he said and began to stand up. The knife was not in his hand, but Leslie knew it was extremely close by.

"Okay, okay, I'll take it off. Just sit down huh? If you want to see what I look like undressed that's fine, I'll take it off. No one but you and I will ever know I did this right? Just don't get any ideas huh?"

It was all Leslie could do to work her arms behind her enough to grip the zipper and ease the constricting fabric from around her torso. She knew posing nude for the man was only a temporary reprieve from his demands, but as her dress dropped away, a new sensation began to fill her. She could not explain it, nor the smile that spread over her face as she turned from his view, then she let the dress puddle at her feet, only to step out of it a second later. Next she stepped out of her thong with a hint of flair to it. She still wore her black stockings and shoes, but when she went to remove those, the transient stopped her.

"Those you can keep on." Leslie nodded, her heart beating a thousand times a minute at what she was doing. With one hand, and an outstretched finger, he made a revolving gesture. Leslie nodded understanding full well what he wanted, and spun around on one foot so that the man could see all of her, including her backside. Her bottom was not exceptionally full, but then again neither was her chest, but the man smiled indicating he had no objections to her fine form.

Leslie feigned interest in her cooking of the chicken, but her provocative pose had an unforeseen effect...it was turning her on. There was no mistaking it as she cooked up the kitchen, teetering on her heels as she swooped from the stove to the sink to the refrigerator trying to prepare the man a decent meal. As she did, she was becoming increasingly aware of the dampness in her sex.

"Smells like you are cooking Haddock not Chicken," he commented as Leslie brought out the Mesquite Chicken he requested. She could not help but turn a dark crimson red, but as she went to serve him a helping; his hand reached out and touched the wide darker bands of her nylon stockings. Surprising even herself, Leslie did not move from the geriatrics touch.

"After I am through with the chicken, I want you for dessert," he said in a line so lame that if any one else had spoken it, Leslie would have burst out laughing. Instead, she spoke one herself.

"You can have me for the main course if you want."

Leslie was not sure where such bravado came from. Obviously what she was doing was wrong; so very, very wrong. He was three times her own age, dirty, lazy and derelict, and yet she felt him whisk her up and easily lug her small frame into the bedroom. Long forgotten was the eloquently prepared chicken, the fresh split peas and the hot coffee, the latter still steaming on the table. Dropping her down onto the bed, Leslie's legs immediately splayed wide in an unmistakable open invitation, and grinned as the man hastened to push down his pants.

It was raw sexual energy that passed between them, as Leslie opened her mouth up wide and accepted his greedy lapping tongue. Dipping in and out, lashing her teeth against his, she could taste his vile breath, a seedy mixture of stale cigarettes and cheap booze. She kissed him again, an equally powerful French-kiss that was entirely reserved for lovers. Like their love-making, it too was wrong, but Leslie swooned at the pleasure of it, the pleasure of doing something so wrong, that for once in her life, it was right..

"Do you want me to wear a condom," he politely asked, hesitating at his entry into her as he loomed above her fragile body. Leslie tossed her head back and forth on the bright white sheets.

"Oh God no. Put it in me. Put it in me and fuck me hard." It was not her that was talking, but her darker side. A side she never knew existed until now.

What should have been young and clean shaven was old and hairy. What should have smelled like cologne and fresh flowers smelled like gin and locomotive exhaust? Mostly though, what should have been isolated and rubbery, was hard and natural, for it had been years since Leslie had sex without the benefit of a condom.

"You want to get pregnant don't you," he lamented as he began to thrust harder and harder inside her. Already Leslie had moaned from one orgasm and was quickly approaching another.

"Yes, yes, yes," she moaned for more than one reason as her pelvis rocked with an orgasm. It had approached so quickly, a flash and then it was upon her. It occurred so quickly that as satisfying as it was, she wanted another, and another, and another...

After a moment of raw passionate sex, the transient sensed her needs and slowed his rhythm, settling into her with more steady, powerful thrusts that sent her back pressing down into the satin sheets again and again. Leslie moaned, a deep full moan that indicated she was enjoying everything she was receiving.

Deadwood
Deadwood
74 Followers
12