Work for your money.
written by:
MSaintC

Greetings, dear reader. A friend of mine, an amateur writer like myself, recently proposed a challenge. She and I had traded erotic fiction in the past, and she's a big fan of this site. (I don't know if she submits stories here or not.) She challenged me to write one story for each category. The conditions were that I could not use the same characters/scenarios more than twice, and each story had to be a complete work in it's own right. So I hope you enjoy them. Feedback is always welcome, public or private (and hopefully positive ^.^)

This is my 16th submission. I hope you enjoy it. Sometimes the best surprises come along a little later.

Challenge #16: Older Women/Men

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"It's just a pile of shit..."

The speaker was an older gentlemen in a navy business suit. Barry Talbot was the executive managing partner at this firm that called itself in the realm of "Business Growth, Management and Consulting." A grizzled white haired veteran of nearly forty years as a professional, he was often considered to possess a genius level intellect, as well as an impressive foresight into the business world, seeing pitfalls others would miss, and finding opportunities out of thin air. In his hand, was a folder, containing a proposal agreement, drafted by the man sitting across from him. He looked at it again, shaking his head with disdain, and then throwing it carelessly onto the desk. The man sitting across from him looked off to the side, no doubt replaying in his head each typed word and trying to figure out what he could have done differently to keep his work from being such shit. But the speaker shook his head.

"Not this, Jackson. This is perfect, in fact, it's more than they deserve."

"Not sure what you mean." Came the reply.

"This proposal is perfect, it'll get accepted for sure. Then Sargrams Inc. can buy out another of its competitors and go on it's merry way. Unfortunately, I know where this is headed. I just don't like it, is all."

"Something against Sargram?"

"In a word, yes. If there was a company that was more sanctimonious and full of shit, I've never seen it. But, they're paying us to get this done, and I think you'll get it done."

"Part of my job. For what it's worth, I agree. And truthfully, I almost botched the assignment so it wouldn't go through."

"I almost wish you had. But.. what's done is done. Oh, I have a favor to ask."

"Sure thing, boss."

"Pierce is retiring at the end of the year, so that means we'll need a new office branch manager in the Boston office. I know you don't want it, so I've decided to hand the reigns of that office to my daughter."

Jackson arched an eyebrow. "I thought she was off saving the world or something?"

"Apparently the novelty has worn off and she needs a real job." Barry laughed out loud, possibly too hard. Jackson managed a small smile on his handsome face. "In truth I don't know why she decided to leave all her volunteer work behind. Maybe she thinks I'll retire soon and she wants to be ready to take over. As my only daughter it's a fair assertion that I will hand the reigns down to her."

"From what you said, she's also quite capable, so she would probably fit right in."

"Yes. While this surprises me, I can't say I'm upset about it. Anyway, what I wanted to ask you is, you used to live in Boston, right?"

"Sure."

"Good. I need someone to show her around the area for a few days, get her used to the city. I know her, she'll want to be fully acclimated to her new city as soon as possible, and I'm hoping you can help her since you know the area so well."

"I can do that, boss."

"Ok. She'll be in on Thursday. So I'll give you from this Wednesday till the next off. Is that enough time?"

"Should be plenty. Do you have her flight details?"

Barry slid a piece of paper across the desk. Jackson reached out and took it, looked it over, then folded it and slipped it inside his jacket pocket.

"Take care of her, Jack."

"Of course."

================Thursday

"Flight 9738 from San Antonio, now arriving at Gate 17."

Jackson looked up from the paper he was reading. Her plane was on the ground and passengers began filing out of the gate. Jackson put the paper down, holding up a placard that said "Miss Talbot" Jackson didn't know much about the boss's daughter to be honest, except that she was never married, and was a shade past fifty. Jackson's eyes scanned the crowd as they passed, and he saw one woman who looked like a possibility. She had greying hair, a conservative business suit, and a serious demeanor. He watched her, holding his sign, wondering if perhaps he should flag her down or say something to gather her attention, but she looked in his direction, then at his sign, and shook her head.

"You aren't who I'd thought you'd be."

Jackson looked to his left. If he wasn't a master at keeping his poker face solid, he would have stood open mouthed and stared. She wasn't just beautiful for being over fifty years of age, she was just beautiful. She was 5'6", he guessed about 130 pounds, and the business suit she wore was professional, but clung tightly to each curve like it was going to fall off if it didn't. Her legs were long and shapely, roving upwards to a perfect hourglass figure with wide hips, a sculpted rear, a narrow waist and a full bust that seemed to defy gravity, either by the work of a bra, or perhaps augmentation. Jackson had originally thought that he could spend the week with her and avoid thinking of her in a sexual way, but even as he looked at her now he felt a twinge in his cock as it started to gauge interest.

"Who did you think I'd be?"

"Harris." She said simply. Her eyes roved him with the same brief analytical appraisal she saw in his eyes. He was roughly six feet tall with a solid build of around 175. He looked much like the actor Ryan Reynolds, with a certain boyish charm and undefined innocence, with an undertone of rugged manliness. Harris, she knew from experience, was a pot bellied slackjawed lazy chauvanist. She wasn't looking forward to spending a week with him. This guy, however, opened up a few ideas and fantasies that quickly ran through her head. "Harris Monroe"

"I don't know anything about that, but I'm here."

Merry Christmas to me, she almost said aloud, it was like putting on an old pair of jeans and finding money in the pocket, a lovely surprise. Behind her, the porter came up, dragging behind a luggage cart with her bags. Jackson turned on his heel, and the trio strode out of the terminal and into the open air. A short walk across the roadway, and they were in the parking garage. Jackson didn't drive a Mercedes like most businessmen, instead he had a pristine Pontiac Grand Prix. She had to admire a man that bought a car based on what he wanted, rather than what stature dictated he should have. The porter loaded her bags into the trunk, except for one particular one she slipped into the backseat, and she tipped him a rather generous hundred dollars. Jackson held her door open for her, a surprising gesture she clearly was not expecting, and she slipped into the car. It was neat and pristine, the faintest trace of a lime smell from the freshener hanging from the mirror. Jackson slide into the car, started it up, and soon they were leaving Logan airport, headed for Boston.

"Do you know where the apartment is I'll be moving into?"

"Yes, ma'am. It's in fact why I'm here. I used to live in the city."

"Oh, I have a tour guide then."

"Yes, ma'am."

"Please refrain from the ma'ams if you will. We're professionals. At work I'm simply Miss Talbot or "boss" if you prefer. Outside, you can call me Janet."

"I understand."

She studied him for a moment. He was staring ahead, eyes focused on the road, not looking around or suffering distractions like most men. He was either a very careful driver, or he was focusing on the road to keep his eyes from wandering. Either was just as likely a scenario.

"Is Jackson your first name or your last name?"

"First name. Jackson Castle, actually."

"Is that a place or something?"

"Nah, they wanted to name me Micheal Jackson Castle, but for some reason or another, it changes everytime I ask, the Micheal was left out."

"Interesting parents you must have had."

"Yea."

They drove on. She watched him, watched the way his eyes moved. Jackson didn't seem to want to talk much, at least not while she was a stranger, but he seemed like an open person, albeit reluctant to actually start conversations. Her head buzzed with a few feelings. The first was a general sense of relief that her guide about town was a laid back young man, rather than that oaf Harris. After Harris, in a drunken haze, got himself a nice big handful of tit at her father's last house party, she very much doubted he would of behaved himself with this assignment. Jackson seemed to be a respectable man, who was doing his best to ignore his male impulses. Another major feeling swimming in her head was lust. The way he was avoiding looking at her and trying to be professional, rung a bell that said he found her attractive. A young stud thinking an older woman to be hot, would make any cougar wet. Though she'd never refer to herself as a cougar.... out loud.

"How are you with the direct approach?" She asked. It never hurt to know how someone is going to react to your attitude, right before you gave it to them.

"Honestly, I prefer people to say what they mean. People have grown a thin skin, especially in our line of work. As long as a person means what they say, no matter the intent, I can accept what they say. Even if I don't particularly like what I hear."

"My thoughts exactly. Why I ask, is that I need to be comfortable, so I'm going to change clothes in the car. I've been in this all day, and it's driving me crazy. You will probably see parts of me that aren't for the public eye. I don't mind you looking, but please try not to wreck the car."

He glanced over at her, brow raised in confusion, then looked back to the road. There, she thought, now you're intrigued. She unzipped the skirt and untucked the blouse from it. She lifted her hips off the seat, enough to slide the garment out from under her. Jackson tried to fight it, she noticed, but his eyes betrayed him and he stole a glance at her shapely legs, covered by black stockings that led up to a garter belt and black silk panties. The skirt was folded neatly, and set on the center console The stockings were slid off her legs, slower than normal, but not so slow that it would be an obvious seduction. She wanted him thinking he was getting a show without her intending to give him one. Her hips rose again, and both the garter and her panties were pushed down until they were off of her body, also being folded neatly and placed on the center console. She crossed her legs demurely, but her eyes glinted with a mischeivous fire. Yes, she said as Jackson stole another quick glance, I'm sitting here, naked from the waist down. Making you hard is it? Good. A few seconds later, the traffic on the highway lightened, and she had her opportunity. She unbuckled her seat belt, and turned in her seat, on her knees. She rummaged in her bag for the clothes she intended to change into, then counted to 20, giving him ample time to turn and glance at her bare ass, and maybe see a hint of her slick lips. Then, with her prizes in hand, turned and settled back into the seat.

"Was.. was there a reason you started to get undressed before you did that?" He asked, hesitantly.

"Didn't want to tear my skirt, which may have happened." Not a lie, but a mistruth. Sure, she didn't want to ruin a seven hundred dollar skirt, which may have happened. But she couldn't very well just say I did it so you could look at my pussy, now could she? At least, not yet.

"Makes sense.." Was the cute reply, before his attention became locked on the road again.

She reached down, taking a frilly white thong and stepping through it. Janet hadn't grown up with this kind of racy underwear, but when she saw how good it made her ass look, she was hooked at a moment. She wore less slutty underwear at work, but at home, it was game on Tiger. Next followed a pair of khaki shorts, and soon both were pulled up over her hips to cover her nudity. She also slipped on socks and changed her heels for a pair of sneakers. Jackson had to admit that her skirt had accentuated the length and smoothness of her legs, while the shorts showed off their sleek muscle tone and form. He found both to be irrisistably sexy. Her business suit jacket came off and was folded into the pile of work clothes.

"You don't have anything against naked female breasts, do you?" Honestly, a silly question, but she was enjoying the tease, seeing how flustered he would become.

"Not a thing."

Then check out these titties, she almost said out loud as her fingers undid the buttons of her blouse. Janet was a stacked 36DD, and unlike most women her age, never went through a phase of saying no to bras and yes to gravity. So even after 50, her breasts were still firm and proud on her chest. One of her favorite sayings was even at 50 she had better tits than two 25 year olds combined. The blouse was removed and folded, leaving on a white lace bra. That was then removed, and sure enough, Jackson was looking again. His eyes lingered for longer than previously before he could tear them away. She made a big deal about the t-shirt she had selected, intentionally mind you, to leave her breasts in the air just a tad longer. The cold air brushed across her already hard nipples and turned them even harder. The shirt was slipped on, after a truck driver passed in the right lane and let her know he enjoyed the view with a single short burst of airhorn. Not something she'd ask for, but a small price to pay to make the young stud want to fuck her silly. She made a big production of stretching back, arching up and thrusting her breasts forward, the nipples poking out obviously through the fabric. The decision to remove the bra was perhaps a bit out of character for her, but she was entranced in the game of teasing him.

"Much, much better, thank you for putting up with that."

"You're welcome."

"Did you see anything you liked?"

"Yes."

She wanted to giggle at the terseness of the short exchange. Here she was, a business professional with a stack of degrees and awards in her long career, not to mention possibly old enough to be his mother, and all she could think about is more ways to show off her body and make his cock hard. The highway gave way into the city of Boston, but traffic remained light as it was a work day and in the hours between work beginning and lunch.

"Can I see something I'd like?"

"What?" His answer came with a puzzled glance.

"Your cock."

"Huh..? I.. uhh.. is that.. are you sure that's appropriate?"

Her reply came with a shrug, as if nothing could be simpler. "I was a part of the sexual revolution. I stopped trying to pretend to be a prissy prude a long time ago. You got to take all sorts of glances at my body, is it unfair to deny me the sight of yours?"

"I.. umm... uhh.."

"I just want to take a look. Nothing all that devi..." She was leaning over as she started speaking, her hands groping about his groin. She'd gotten his fly undone and was reaching inside when she felt it's length. Her words stopped and she quickly pulled the monster free. It laid against his stomach, not completely hard but rapidly engorging further at her touch. He was at least ten inches now, and still had room for growth. "Oh my god..."

"...Yea. Well, there it is."

"I'll say.." The words came in a throaty whisper as her fingertips caressed his member. They found each ridge and vein and felt them pulse into life as she crossed over them. His cock started to stand upright, physically pushing back against her touch as it hardened into it's full vibrant life. His cock was a full foot long, 12 glorious inches of meat ending up at a bulbous head that was a dark purple. A deep angry color at being roused from it's peaceful slumber. "It's.. beautiful.."

"It's just a dick.." He said with a shrug. For a brief second she wanted to slap him for his modesty. It was like someone putting a Piccasso in your living room and you treating it like it was an everyday water color.

"This is a gift from God..." She said, giving it one long glorious stroke as the car came to a stop at a red light. The stroke caused Jackson to shiver and close his eyes, long enough not to notice the two young ladies that pulled up beside them. They looked like vibrant twenty something college kids, either returning home or returning back to school. The one in the passenger seat glanced over quickly, then a second later turned and looked more fully. Janet locked eyes with the young lass and saw her pupils widen as she realized what she was seeing. The girl stared for a few frozen seconds, then reached over and shook her friends shoulder and soon the other girl was staring wide eyed as well. Janet gave the pair a knowing smile as her hand gave long slow strokes from top to bottom. Janet had a brief thought to tell Jackson that they had an audience, but why ruin his mood?

"That... feels good.." He spoke in a breathless whisper.

"Light's green.." She said, removing her hands from his lap.

Jackson opened his eyes and looked up. Sure enough the light was green, and he started driving. His female secret admirers in the other car drove off as well, giggling and no doubt discussing the show they'd seen, maybe even talking about what they would do to a cock that big. Janet continued to watch him as he struggled to drive and put his massive erection out of the view of prying eyes. He succeeded in doing so, but the sight of the huge bulge in his slacks made Janet a little giggly. She studied the look on his face, wondering if perhaps he was thinking of unpleasant things to diminish his hard-on. It must be a tad bit embarassing to try and walk around in public with that huge noticeable bulge.

"When was the last time that cock saw some action? Other than me of course."

"About eight months ago."

"What was it? Pussy, ass, tits, mouth?" The dirty talk was very intentional. She was going to keep him hard and wanting. Make him want it, then when he got it, he'd be hooked on it. All part of an older woman's seduction.

"...Mouth.."

"I take it she didn't deep throat it."

"Ah, no.. not even close."

"Color me unsurprised."

"We're here."

"Oh good." He started to stop in front of a huge high rise building that dominated the landscape around it, but she pointed ahead to a side street. "Pull down there, I have reserve parking in the garage."

He obeyed, turning down the street. The garage itself was massive, nearly solid concrete, and what wasn't was a steel mesh grate to keep people out. Two guards were in the booth, controlling both a heavy steel bar gate, and retractable pillars. Janet leaned over him to show the guard her ID and her property lease, at the same time her free hand touched his erection again, rubbing it very gently. It took a concentrated effort for Jackson to keep his expression unchanged. A short exchange informed the guard Jackson would be needed every day for the next week, and the guard placed a temporary pass on the dashboard, which would allow Jackson to come and go any time for the next 8 days. Janet sat back in her seat as Jackson pulled into the garage, but her hand remained to brush up and down the length of his cock. It was so massive and strong, and she wanted very much to see a huge cock like that cum, up close. Then maybe again, in her mouth.

"Go up to the top, that's where the loft parking is. I have the whole eighth floor to myself."

"Can you.. not do that?"

"Stroke you?"

"Yes."

"Going to cum?"

"If you keep that up, yes. And I'd rather not do it inside my pants."

"Ok, then." She took his cock out again, stroking it's full massive length. Jackson was having a difficult time focusing, and because of that he made it up the garage in record time. They saw no-one on the way in, not that Janet would have cared if someone saw her stroking this super studs huge dick. Jackson slammed into a parking space crookedly, just before a pleasurable spasm overtook him that might have caused them to hit a wall. Yes, she thought to herself, the woman who's going to be your "boss" for the next week is giving you a nice slow handjob, just enjoy it, because you have no idea what I'm going to do to you when we're actually in private.

"Better?" She asked.

"Yes..." His reply was meager and weak and she could feel the throbbing pulse against her palm.

"Let's go inside then, and don't you dare put that away. I'll have someone get the bags later."

Jackson slipped out of the car obediently, and walked around to open her door. She had pulled her top up, exposing her firm breasts, with a knowing "I see you, now you see me" smile. She stepped gracefully from the car, her hand finding his thick rod again and holding it gently as she lead him towards the private elevator, her thumb making soft circles over the engorged helmet. The private elevator was not in use, and came quickly when it was called. She held him as they rode the elevator up, finding that a thick droplet of precum had oozed from his member. She held it in front of her face, then slowly, seductively, licked it off her finger, before placing her hand back around his cock.

"Now that's good stuff." She said, almost giggling at his only response being a pleasured groan.

The elevator stopped at the eighth floor, and a LED display over the panel indicated that a key card was needed to access the private floor. Janet swiped her card and the door slid open, revealing a lavish apartment. The main sitting room was just ahead, with two leather couches, black plush carpeting compared to the rest of the apartments tile, and a hearth fireplace of polished white marble. An island bar stood off to the side, acting as a partition between the main area and the kitchen. The walls were a perfect alabastor, making the scene a stark contrast in blacks and whites. Janet led him inside, still holding his achingly hard cock in her hand, and the door behind them closed, the auto elevator security giving them complete privacy. She pushed him down onto one of the couches, and then sat beside him, her hand still on his dick.

"Do you want to cum, Jackson?"

"Yes.. please..."

Her hand stroked him, slowly at first, then fast for a time, then slowing down again, the teasing art of the perfect handjob. Jackson leaned back, his head resting against the top of the couch, his eyes closed. With her free hand, Janet took out her phone, and focused it's camera to watch her stroking this huge cock. She took a video, focusing on it's bulbous head, the long thick shaft as her hand moved up and down, his big balls that were together the size of an average tomato. The video lasted a minute or so, about as long as the camera would actually allow, and she quickly sent it off to one of her best girl friends that she'd known forever. Sandra was best described as a horny old slut, who in her near sixties still had an amazing body and fucked a lot of younger men. She'd appreciate this kind of dick, and would probably fly from her home on the other side of the continent just to suck and fuck it. If she did, well, six inches each wasn't too bad, right? She finished sending the video and put her phone down, focusing her attention on stroking the cock in front of her. She watched the massive head throb with her strokes. Her phone beeped, and she picked it up. The message from her friend said simply.

"Skype, now."

Janet giggled to herself, and opened the app. Skype on a smart phone isn't the best quality, but for what was desired, it would be enough. She connected in a video call with her friend, then set the phone up on the coffee table, where it faced the action. The camera on this phone was on the front, so two parties could see one another in just this way. Everything connected well, and Sandra appeared in frame. She was almost six feet tall, statuesque with perfectly tanned skin. Her hair was a mass of brown sexy curls that framed a beautiful, if a little aged, face. She could only been seen from about the waist up. She was wearing a black sweater, the right side of which showed that she had big full breasts, possibly an E cup or bigger, the other side was a bit larger because her hand was underneath her sweater, caressing and kneading her breast. Her other hand was out of frame, but stuck down not so subtley in her crotch. She moaned aloud as her phone received the image from the other end.

"Ohhhhh yea.. fuck that's a big cock. You lucky bitch.."

"Jealous much?" Janet said, emphasising her words by giving a gentle lick to Jackson's huge cock head.

"Mmmmhmmm.. fuck, I'm wet.. put him in your mouth.."

Janet leaned down, taking a few inches of the thick meat into her mouth, sucking away delightedly. Her hand stroked the remaining skin, and Jackson shuddered so hard she almost feared he would choke her with his cock involuntarily. But the wave passed and he settled back, she settled into sucking him. There was no way she'd get all of it in, not even close, but then again, all she wanted was what came from the head. Janets eyes looked toward her phone, watching her friend watch her. Sandras hand came out from under her sweater, and grabbed the phone, tilting it down to show between her legs. Her pussy was shaved, smooth and looked like a fresh twenty somethings, a result of cosmetic surgery. Sandra rubbed her snatch furiously, then would slam three fingers inside several times before withdrawing them and returning to the rubdown.

"Yea, fucking suck that cock you sexy slut. Mmm, I'm gonna cum, mmmmmm..."

Janet watched as her friends body convulsed in the throes of sexual bliss. She imagined her face, locked in the silent cum scream. Janet released Jackson from her mouth, returning to stroking him fully with her hand as her friend came down from her orgasmic bliss. Janet felt the cock in her hand buzzing and reacting to her touch, feeling like it could explode at any moment. Sandra recovered, pulling the camera away from her throbbing cunt and back towards her face.

"Mmmmmm.. god that's so hot. Can you make him cum?"

"Do you want to see it?" Janets hand quickened her pace ever so slightly.

"Fuck yes. Make that big dick cum all over the place."

Janet quickened her hand, stroking rapidly while her free hand held his tremendous ballsack. Jackson groaned, his breath coming quickly, his entire body tensing. He was going to cum, and it was going to be massive, judging by the buzzing she was feeling from his immense balls.

"Diana, come here, you have to see this!" Sandra yelled towards someone not on screen.

Janet smiled to herself, and slowed her teasing, just to hold off the flood. Diana was Sandra's personal assistant. That was a broad term in and of itself. Sandra had no occupation, as her husband was filthy rich, so all she did was sit at home and keep herself wet and ready for his quick in and out of the house fuck trips. Mainly, he was on the road a lot, gone for two or three weeks at a time so his loving and horny wife was forced to employ toys for her own amusement. Sandra, tired of the lack of human contact, found a young cashier at a local grocery store. Diana was 19 at the time, fresh out of high school and no prospects except a long road of simply working for a living. Diana was also pretty hot, 5'3" 118 ibs, with a small frame, most of her weight packed into her big heavy D cups. Her hair was short, and a combination of blue and purple. Her lip, nose and eyebrow were pierced, and that gave Sandra an idea. She asked if she was into "alternative things", and Diana responded that she'd be into anything. Sandra laid it out, keep my house in order, spend time with me, and eat my pussy, and I'll give you a comfortable job and a place to live. Diana finished the transaction, agreed to the proposal, flipped off the old woman in line who glared at her, then quit. Now, she lived with Sandra as her playmate and friend. Her face appeared in screen, and she gasped.

"Holy shit that's a big dick.." She stared, transfixed.

"Mhmmmm. It's going to cum soon, watch it.."

The two stared as Janet sped up her hand, stroking fast and hard. Jackson grunted, and a few seconds later cum exploded from his huge dickhead, splattering on Janets cheek as well as his pants and the couch. Janet kept stroking, milking and pumping his balls for all they were worth. He kept cumming, some spurts leaping a few inches, some dribbling and leaking out, but by the time he was finished, Janets hand was covered in cum, and there were several drying pools on his clothes and her couch, even a few on the floor. All three woman stared in amazement at the sheer amount of the sticky fluid. Janet licked across her hand, tasting his seed. It tasted like normal cum, and since Janet loved the taste of normal cum, she began finding ways to clean up the mess he made with her mouth. Sandra had her head leaned back, and her eyes closed as her assistants head moved towards the bottom of the screen, her face buried in her employers crotch. Jackson hadn't moved, his breathing slow and labored, in a state of recovery. His cock, hadn't lost so much as one ounce of stiffness. Janet, finished in her cleaning, caressed his big balls, and found them heavy and ready. Wow, she mused to herself, huge dick, huge loads and he could go more than once at a time? She almost turned off skype to call her dad and ask if she could keep him.

"Fuck, he's STILL HARD!?" Sandra had opened her eyes and was staring wide eyed.

"Yes.." Janets hand stroked the now cleaned shaft, marveling that it felt just as solid as it had just a few short moments ago.

"Diana, go get your computer.. we need to check flights to Boston."

"Before or after you cum?" Was the slightly muffled reply from the young girl.

"Hmmm.." Sandra pondered for a moment. "After.."

Sandra and Janet shared a knowing grin with each other, and then the call between them was closed. Janet knew that her friend would easily make the cross country journey for this cock, and probably stay until Jackson left. Probably bring Diana along as well. Jackson's cock was about to sorely be tested. Janet sat there a few moments, her hand slowly stroking the behemoth dick in front of her, contemplating giving a second hand job to see if the second load would be as massive.

"Your friend seems nice.." The words were quiet, and subdued, like he hadn't quite caught his breath yet.

"She is." She almost said, you'll find out soon enough, but she decided to let that be a surprise. "Can you go again? Can you cum again?"

"Yes."

"How many times?"

"My record is four..."

"Are you serious?"

"Yes. I don't know how or why, but I just can."

"Does it hurt? I've heard that men can cum multiple times in a short span, but it hurts."

"No, not really. Not that I've found anyway."

"Do you want to fuck me, Jackson?"

"Yes, I do."

Janet stood up, and quickly stripped off her shirt and shorts. Jackson felt her movement, and opened his eyes to watch, and she slowly stripped off her panties to tease him. She spread her arms out, and then turned around slowly, to let him take in all of her body.

"Am I hot or what?" She asked with a grin.

"You are incredibly sexy..."

"Say it. Say you wanna fuck my old body."

"I want to fuck your body, Janet. But mostly.. I want to make you cum."

"In due time." She smiled, and climbed back on top of couch, straddling him. She slowly lowered her hot throbbing cunt over his dick, and slide a few inches inside her. In recent years, Janet had rediscovered her sexuality, and thus her pussy was experienced, but even she had to stretch to fit his cock inside, even only a shade less than halfway. "Mmmmm.. how far are you in?"

"About half way..."

"More than I thought. You.. you feel so good inside me."

"You're so wet and tight, Janet. It's amazing."

"Ah, well." She giggled. "I'm tight because your cock is fucking huge."

Jackson gave her a sexy, Sorry my dick is so big, kind of grin, but said nothing. Janet started to ride him, each thrust inside filling her up to maximum, even though he still had so much more to stuff inside her. Each bounce made her wetter, and ever so slowly, another inch disappeared inside her. Then another. She had him two thirds of the way in, but that was her body's limit. She began to ride him faster, now that she knew how much she could take. Jackson grabbed a hold of her firm, perfect ass, and used his arm strength to support her, and help her bounce.

"Fuuuuuuuck... so good. So fucking wet..." She moaned. Jackson couldn't speak much, instead he attached his lips to her breasts, licking and sucking her aching nipples. "Mmmm yea, suck my tits. I love it."

Janet felt the surge of pleasure as she climaxed once, a quick little burst that caused her mouth to stay frozen in an O for a minute or two. She didn't want to stop, in fact, it was quite the opposite, she simply wanted more.

"God.. Jackson.. too good. Can you fuck me all day..? Pleaaassseeeee...?"

"As you wish." Was all his mouth left her greeding attention demanding tits to say.

Janet's hand fell between her legs, rapidly rubbing her hot clit as she fucked the huge cock she rode. She climaxed a second time, and she stopped riding for a moment, convulsing as her orgasm took hold. She felt lighter, distended somehow, and realized it was because Jackson had picked her up and laid her on the couch, taking control and fucking her slowly. Her arms wrapped around his neck, holding him against her chest, as her legs locked around his waist, keeping him buried inside her. Janet couldn't be sure if she was taking in more of his cock than before, and frankly, she didn't care. His cock was pounding away at her box, stuffing her up and making her feel good, and making her cum again, and again.

"Talk... dirty... to... me.." Each word came in between a breath as his cock slammed into her.

"Oh, you'd like that.. like hearing me talk about this big cock fucking that tight pussy, hmm?"

His words were soft, and yet commanding, each one settling in her ear, and the sound waves shooting right down to her hot cunt, making it spasm with more pleasure. "Yes. Oh, god yes, fuck this hot slut. Give it to me."

"Oh, you're a hot slut, baby. Nice big tits, round ass, fucking tight wet pussy. I'm gonna cum all over you. Going to cum all in you, too."

"Fuck yea.. cum in me.. cum in me until cum comes out my fucking mouth.. Ahhhhhhhhhhhh.."

Janet's entire body convulsed and shook as she came again. Jackson held her to him, pumping away at her cunt, feeling his balls signal that he was going to unload again. He lifted her up, and turned their bodies so she was on top again, his cock buried deep within. He thrusted a few more times, causing her body to bounce on him, and then he grunted as his cock exploded again, dumping spurt after spurt of hot, sticky cum deep inside her pussy. She was coming down from her high, and felt the heat of his seed fill her up, and slowly leak out. He held her trembling, spent body in his arms, neither moving for a few minutes.

"Jackson, that was.. incredible." She whispered, breathlessly.

"You were amazing." Was the terse reply. He was back in "recovery mode", not speaking much, and using as little breath as possible to convey what he had to. Most of his energy was used in keeping his breath steady to recover his wind.

"I think feel you leaking out of me."

"I'm... sorry?"

She supressed a giggle. "Fuck, don't be. It feels so good to be full of cock by a hot stud who still finds me fuckable."

"You'd be fuckable no matter what age you are."

"You're sweet. Now..." She shifted her body so his cock slid out of her with a slurping sound. She reached down and grasped it. It wasn't soft. but after two orgasms it lost a little of it's stiffness. "Oh my, still ready. But, that can wait. We both need showers and then we can see about dinner."

"Yes, boss."

They went out and had a nice dinner, slowly getting to know one another. Jackson purposefully tried to avoid talking about their past sex lives, while Janet seemed to make every effort to keep the flow of conversation teetering near the gutter. For Jackson, this whole scenario seems a bit unreal. He respected the hell out of his boss, and here he was, on an errand as a favor to the man, and all he'd actually done is chaufer her to her apartment and then fuck the hell out of her. Janet was acting like nothing could be more natural. They were in the middle of dessert when Jackson's phone informed him that he had a text message. Janet excused herself to use the restroom before they were to depart, and he checked his phone. It was from his boss, and was one simple line.

"Did you fuck my daughter yet?"

Jackson stared at it for several heartstopping seconds. What should he say? Deny that anything happened? And.. "yet"? Was the man expecting him to fuck his daughter. Jackson didn't really want to upset his boss by telling him that he'd done so, but he didn't want to lie either. So with a clear concience, and thoughts of what he was going to do if the man fired him, he simply sent back "Yes." The reply was almost immediate.

"Good, happy hunting."

Janet came back to the table, and after paying the bill, she asked to be driven home. She spent the rest of the night on her computer, doing business or ordering some things for her apartment online. Jackson wasn't sure what to do, and as the late hour drew near, was contemplating leaving to check into a hotel room when she came out with two throw pillows and a blanket.

"Sorry I don't have a spare bedroom or anything, but this couch folds out."

"Oh, you don't have to.. I can get a hotel."

She turned to stare at him like he'd just refused a second helping of his favorite food. Like he was out of his mind. "Nonsense, you will be staying here. No sense in having you sleep elsewhere, as I will not know when I need you. Besides.." The next statement was accompanied by a slutty grin. "I'd like to keep you close in case I... need your services."

Jackson chuckled to himself, partly at the innuendo, and partly at his being trapped. "Ok, you win, boss."

---Next Day---

Jackson woke up in the pre-dawn hours, with the sun just barely up over the horizon, causing the sky to be an orange color. He'd woken up, because he felt a powerful mouth sucking his cock to life. Janet's mouth the day before was gentle, teasing, this one was raunchy and wet. She either had two modes, or it was somebody else. He opened his eyes and looked down to see a petite girl with dual colored hair happily sucking away at his growing member. She stopped for a second and looked up at him.

"Oh, hey sexy.. you're awake." She said with a lusty grin, her tongue dancing around the head of his stiffening prick.

"I see you've met Diana." A voice called from his left. When he turned to see, he saw the same woman he'd spyed in the video call the day before. She was naked from the waist down, and slowly straddled one leg over his chest. "Good, now you can get to work, licking my pussy."

As she lowered her musky cunt to his lips, he could make out from the corner of his eye, Janet standing in a corner, setting up a video camera. She was also naked, and when she finished checking the focus, starting walking towards where he laid.

"Ok, girls. He's hot, hunky, has twelve inches and says he can cum four times before stopping. I say, we make him break that record."

All in a day's work.

-End-

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I hope you enjoyed this story. If you want to see more from these characters, or continuations of the other stories I publish, feel free to request them and I'll try to get around to it. As always, feedback is welcome, public or private. But try to be somewhat constructive. It you loved it, tell me what you loved. If you hated it, tell me why. I can't be a better writer if all you tell me is how much I suck. Until next time.

Also, I recently lost a bet with a female fan, and have a new profile picture. Part of the agreement also says I put a reminder in every story for you lady readers to check it out and say what you think. So, there is your reminder. :)

In a few weeks or so, my author interview should be posted as well. Thanks to Naughty Miranda for setting that up. :D

-Mark St. Claire.