She licked harder then returned to his balls, and eventually to his shaft, licking and sucking. She swallowed the large head of his 8” cock and sucked at the tip for a solid 10 minutes, making sure his rod had enough steel in it to fuck her proper.
Kim slid his cock down her throat, taking his entire length. Her hot mouth must have been driving him crazy. “Oh JESUS, oh fuck!” he grunted, lifting his ass.
“Mmmm,” Kim hummed, enjoying her tease.
Derek pulled her to her knees, kissed her deeply, and flipped her over again.
“Uh, Uh, not yet,” she said.
Kim got up, went to her bag, pulled out a glass dildo as long and as thick as Derek. “Fuck me with this,” she cooed. “I want you in my ass!”
“Oh god, you are so fucking hot!” Derek groaned, pulling her towards him. He stood and bent her over the bed, sliding the dildo inside Kim’s cunt as she groaned deeply, pussy slick and dildo glistening. He rammed it into her harder, making her scream, then took his cock and positioned it in front of her ass, as he gently probed her.
“Mmmm…yea, fuck my ass, fuck my hot ass!” she demanded. Derek slid inside her deeper, then deeper still, until he was buried to the hilt, with the dildo in her cunt filling her completely.
Kim was full to her stomach, with two steel rods inside her. “Oohhh” she moaned, cumming again. As she twitched, Derek went to town on her ass, holding onto her hip with one hand, while the other hand slammed the dildo into her fuck hole,
Kim’s ass was tight and warm, and squeezed his cock even harder than her cunt had. He kept fucking her harder and harder and faster and faster until she came again.
“Eeeeeeeee!!!” she screamed as he continued to mash her tight little holes.
Kim came again, and then again, until she finally screamed and released.
“FUUUUCCCKKKK!!!”
Derek dropped the dildo and grabbed her hips, slamming inside her until his second round of hot milk shot from his cock into her tight asshole, and emptied himself inside her.
“Oh yeah, oh yeah,” she groaned as he pulled from her hole and she collapsed onto the bed. He lay beside her, covered in sweat and cum, grunting.
Kim could feel him still buzzing beside her. She reached over and wrapped her arm around his waist, and moaned. “That was amazing.”
Derek agreed, then said, “Too bad I can never tell anyone.”
“You can tell me,” Kim said. “Next time we’re lying right here. I’ll be in town in three months.”
“I can’t fucking wait,” Derek said, rolling over and kissing her on the mouth.
XXX
Humiliated in an Alley
Forty five year old Jill Novak had just locked up her store for lunchtime. She was an attractive, single, small business owner who had been operating Jill’s Book Nook for nearly fifteen years.
Jill’s bookstore was located on a busy downtown corner and, despite the world going digital, had recently exploded in popularity, especially among the younger crowd.
Jill hid her smile several times as she walked toward the corner, catching a number of men, and a few women, running their eyes up and down the length of her body.
She was very proud of her figure, and should have been. Jill ate right, spent at least an hour a day at the gym, and visited her doctor regularly. She wasn’t self-absorbed or vane, but insisted on wearing clothes that accentuated her beauty.
“Excuse me, ma’am?” a young man waved at Jill as she crossed the street toward “The Brown Bag,” her favorite soup-and-sandwich shop. Jill recognized the man as a semi-regular at the Book Nook. He was tall and thin, with the funniest, almost random patch of facial hair she’d seen in a while, if not ever. Jill failed to understand why men who couldn’t grow a consistent beard still insisted on trying.
“Afternoon,” she said. “Sam, isn’t it?”
“Yeah,” he answered.
“Something I can do for you?” she said pleasantly, a few feet from the Brown Bag’s door, and not slowing her stride.
“I was wondering if we could talk about a business proposition.”
“I’m in a rush right now, but maybe another time?” She cast her eyes sideways toward Sam, but kept on walking.
“You bet,” he smiled, then handed her a business card. She stuffed the card into her designer purse, then smiled one last time before she disappeared into the Brown Bag.
The rest of the day was typical. Jill helped several customers, sold a few stacks of books, and set the brief exchange with Sam somewhere outside of her mind.
When closing time came, Jill closed shop then slipped into her back office to take care of the shop’s financials. She grabbed her purse, fishing for a pen, but found Sam’s business card instead.
She pulled it from her purse and stared in subtle wonder. The card was black with a red line through the middle. The only print on the card was “SLH Media Group” with a website address.
She opened Firefox to see what Sam and SLH Media Group were all about. It was odd that Sam chose to approach her during lunch rather than at her store, but maybe he was being polite and didn’t want to distract her from customers. Either way, Jill was curious.
She typed in the URL and a simple home screen loaded – a mirror image of the business card except for a “continue” link at the bottom. She clicked and waited, her eyes widening as image after image of nude women posing and having sex flooded the screen. While Jill wasn’t a prude, she wasn’t some horny porn-mongrel either.
She scanned the website, quickly realizing that all of the pictures were taken outside or in public places, many she recognized. There were several sections with pictures from each session to entice the viewer to purchase a full subscription to access all the related videos.
Jill grew increasingly shocked.
One scene showed a young, thin, black-haired girl sucking on some skater-looking guy’s cock on the subway while people stood in the background staring. Another showed a couple having sex outside on a second-floor balcony as passing pedestrians turned their heads. Jill browsed a fat handful of additional scenes before finally deciding it was time to go home. She felt a slight stir between her legs, with more than a hint of sticky. If she was going to take care of herself, which of course she was, she’d rather do it from the comfort of her couch.
She switched off her computer and headed for home. The entire time she fixed and ate her dinner, her thoughts circled Sam and his website, wondering what sort of proposition he had in mind. Surely he didn’t want her to be in any of the videos. Jill didn’t recall seeing a single older women featured on the website.
Curiosity claimed her, and she grabbed her laptop, along with a full glass of white wine, then plopped onto her plush couch to investigate. Jill had slipped into a comfortable pair of tiny sweat-shorts and a loose tank top, her usual sleeping attire.
She entered the address for the SLH Media group into Firefox, then started to surf through the site, slightly annoyed that the video previews were so short. Each clip was about fifteen seconds long, and wasted half that time with the young girl introducing herself. Jill wanted to see more, for curiosity’s sake of course.
A few minutes and one credit card number later, Jill was a full paying member of SLH Media Group. She settled into the couch with a smile.
Jill wasn’t truly surprised by a single video since she had already anticipated what she was going to see. Yet, she was still amazed by the audacity of the cameraman and the willingness of his subjects. Every video was virtually the same, except for the setting. The cameraman, who sounded like Sam, would approach a young woman, each one looking as though they were in their early twenties, offering them money in exchange for a display of the woman’s boobs. This proposition eventually led to the two of them having sex and the girl leaving with a wad of cash.
The taboo of having sex in public was exciting enough. The more videos Jill watched, the hotter she got. She ended her viewing session, as well as her evening, with a rather long mastu
rbation session spent with all four fingers of her right hand deep in her soaking wet pussy, while her left hand pinched her hardened nipple and her mind played a fantasy of her fucking Sam in the open.
She hoped the young man would come by her shop soon, hopefully the following day, to discuss his proposal.
Over the next few days, she went about business as usual, anxiously waiting for Sam to show up. Finally on Saturday, about an hour before closing, her prospective business partner appeared, dressed in his usual fashion: jeans, loose t-shirt, and carrying a black bag.
“Evening Ms. Novak,” Sam greeted her at the sales counter. Jill did her best to bury the anxiety that had welled up inside her when she saw him enter the shop.
“Hi there Sam,” Jill said. “How are you?”
“Great as usual,” he said from behind a sheepish grin. “I was wondering if you had a few moments.”
“Sure. You wanted to speak to me about a business opportunity the other day, didn’t you?” she asked as though she barely cared, and wasn’t already wet.
They talked for several minutes. To her surprise, Sam did want her to appear in a video. He said that they had wanted to feature some sexy, older women but hadn’t found any suitable prospects. He lavished her with compliments, sprinkling them through nearly every other sentence. He said he was hesitant to approach her since she was a well-known business owner, at least for the downtown area, and figured she didn’t want the adverse reaction to her appearance on his website.
Jill was flattered, and excited enough at the prospect that she had failed to consider the backlash her shop might endure. She agreed to be in the video, while trying to keep the giant smile from her face.
Sam said, “Great!” and offered her the fabulous suggestion of wearing a pair of large sunglasses to help obscure her identity.
After Jill closed shop, the duo retired outside to begin their filming. She started walking from the corner of the street while Sam recorded his initial attempt to grab her attention. She felt nervous but excited. If she hadn’t been wearing her jacket, she was sure her enlarged nipples would be fat and visible through her flimsy blouse.
“Excuse me, ma’am?” Sam called several times before she finally stopped.
“Yes?” Jill said casually, fighting the building urge to throw Sam to the ground and ride him like a pony beneath her.
“I couldn’t help but notice how sexy you are,” he baited her for his would-be audience.
“Well thank you,” Jill replied with a slight half-smile as though she were mildly annoyed. “Can I help you with something?”
“Actually, you can,” Sam said, digging a roll of cash from his pocket. “I’ll pay you fifty bucks to show me your breasts.”
Jill shook her head in mock resistance. He counted fifty dollars, then held the pile up to the camera. Jill took a step back, folded her arms across her chest and gave Sam a stern, almost professorial look.
“Sorry,” Jill said, “I’m not into being some bimbo on your website. I’m sure that’s what this is for.”
“Yeah,” Sam replied and counted out another fifty. “Come on, I’ll give you a hundred dollars, and all you have to do is flash me your tits.”
Jill shifted on her feet, playing up her contemplation, then snatched the cash from Sam, lifted her brow and said, “Just a flash, right?”
“Yeah,” Sam said, shaking the camera as if he were nodding.
They argued mildly about showing her breasts in public and Sam suggested, on film of course, that they could head down to the nearby alley. They would have a bit more privacy, while still staying in public. Jill agreed and Sam followed her with the camera as they disappeared around the corner, then down the alley, his camera trained on Jill’s round, shapely ass.
“Here is fine,” Sam said a few steps into the alley.
Jill looked around suspiciously, then unbuttoned her shirt, conveniently wearing a bra with a front clasp. Though she had been looking forward to the tryst, the red dot on the camera was making her change her mind.
Jill told herself that she’d give Sam what he paid for, but that was it.
She unclasped her bra and let her large, round tits free for the camera.
“Fuck yeah,” Sam said. “Now those are some nice tits!”
Jill had virtually no sag – a testament to her strenuous, regular exercise routine. She was in her mid-forties. Most women would have some sag, especially with breasts as large as hers. She stood still while Sam recorded, then wrapped her shirt around her body to cover up.
Sam could see that Jill was having second thoughts, but seemed intent on seeing the video through to its usual end.
“Well, you got what you wanted,” Jill said, suddenly annoyed.
“Come on,” he said. “You have the nicest rack I’ve ever seen. Show me again.”
When Jill didn’t move, Sam took it upon himself to reach out and playfully swat at her hands. Her body trembled; nervous and embarrassed and excited.
She allowed her hands to be pushed from her body and her breasts to be exposed again. The alley’s slight breeze made her large, erect nipples tingle.
She lightly shuddered. Sam reached out and grabbed her tits, one by one. He gave them a few quick squeezes, even pinching one of her nipples. Her chest slightly heaved as her breathing went deep at his touch. She tried to maintain her barriers but Sam was rapidly tearing them down. She wasn’t sure how far he would convince her to go, and wasn’t sure if she would be able to stop herself once he started.
Finally Sam let her cover her chest up and displayed another fist filled with dollars. Jill swallowed hard knowing what was next. He counted two hundred dollars and waved the splayed stack in front of the camera.
“I have two hundred bucks. It’s all yours if you suck my dick.”
Even though she knew it was coming, Jill was insulted, and involuntarily shook her head. Sam held the money closer, urging her to accept.
Jill suddenly wanted no part of Sam or his video, and wanted to be anywhere other than the alley.
“It’s not like I’m asking to fuck you,” he said. “Just suck it a few minutes and I’ll give you two hundred bucks.”
Jill was already a step away before she reconsidered: Two hundred dollars was two hundred dollars, and it wasn’t like she would have to give him a marathon hummer.
He unzipped his pants and pulled out his cock. Jill was so shocked she couldn’t turn her eyes, even though she tried. Sam’s dick was only semi-hard but had to be at least eight inches, probably ten or more when fully erect.
She eyed his swelling meat, snatched the cash from his hand, then crouched to the concrete and curled her fingers around his bulging shaft. She leaned in, then hesitantly licked his thick, bulbous head looming in front of her face. Jill felt the heat building inside of her, imagining that she was being seen by passing pedestrians as she sucked on Sam’s cock.
Slowly she eased her mouth around the tip of his dick, trying to take him as deep as she could. He groaned dramatically for the video. The exaggeration made her wet pussy wetter.
Jill could only fit about half of his length into her mouth at first, but slowly slid her mouth back and forth over his throbbing dick as she swirled her tongue along the seam beneath. She felt so naughty and dirty, she almost felt filthy. She loved every second.
Sam began to buck his hips in time to her sucking. His rock hard cock glistened from her spit as the camcorder recorded it slipping in and out of her happy, hungry mouth. The audience could hear her sexy, wet slurp with every fresh descent.
Jill’s fingers wrapped around the base of his shaft, pumping his length with each bob of her head. She felt hot, wet desire building inside of her body, and reflexively hiked up her skirt and started rubbing her overheated pussy through her soaking wet panties.
She looked up into the camera as she continued to devour Sam, pulling his dick from her mouth, teasing his rim with her tongue, and then shoving her mouth back onto his massive throbbing cock.
/> Jill worked him like a pro and could feel him start to twitch. She felt suddenly for his cum, and started moving her face even faster. To her dismay, Sam suddenly pulled himself from her mouthcunt to keep from shooting his wad down her throat.
“Wow,” he said, turning the camera to his face. Sam smiled, giving her a nod of approval before turning the camera back on her.
“So how was I?” Jill asked, desperately caring from behind her sultry giggle.
“Fucking amazing,” Sam said, then zoomed the camera. “What are you doing down there?”
“What does it look like?” she said with a sexy gleam in her eyes, spreading her legs to give him a better view. Her hand was stuffed down her panties and she was rubbing her fingers up and down on her burning hot pussy.
“Why don’t you tell me?”
“I’m rubbing my soaking wet pussy,” Jill said to the camera before running her tongue over her lips, slowly followed by a moan, giving him exactly what he wanted and loving that she was.
Jill brought her free hand up and started squeezing her large, soft tits. She was on fire, hoping Sam wouldn’t ask for anything more, because money or not, she’d be perfectly happy to accommodate him.
“That’s fucking HOT!” he said, directing the camera back to himself. “Did you see that? This hot slut seems to be getting into the mood, eh? Amazing what a little cash and a fat cock will do!”
Jill watched Sam and waited. She felt slightly insulted even though she knew he was only playing it up for his viewers. She tried to stop herself and gather her poise, but her body wouldn’t allow it. She moaned softly instead, gasping as she slid three fingers deep inside her sloppy slut hole.
Sam quickly turned the camera back to her. “Since it seems like you’re really getting into the spirit, how about we make things a little more interesting?”
Jill continued to work her fingers in and out of her needy slit while all sorts of thoughts started swirling through her head. She was suddenly starving for Sam, and wanted him to fuck her on video like the countless young sluts before her. Jill wanted to show the world what an older woman could do with a cock as beautiful as Sam’s.
42 Filthy Fucking Stories Page 35