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Homewrecker, Episode Two: Raymond

Caitlin the homewrecker by Tori Hamlin

Raymond was a friend of Caitlin's father and a contractor for his business. He ran a small operation but had recently upgraded some software that necessitated a deal of manual labor. In order to get his information from a set of old spreadsheets and into the new program, a great deal of copying and pasting information had to be done. It was boring busy work that was necessary, but Raymond just didn't have someone that could sacrifice the time to do it. Caitlin listened to her father and Raymond discussing this over dinner one night, as the three of them shared a meal at Caitlin's home.

Raymond was a big man with a weathered tan and calloused hands that was far more comfortable working outside with those hands, than he was sitting behind the desk in his small office. Caitlin greatly enjoyed cockteasing Raymond. She'd often fantasize about the big man picking her up and tossing her onto his desk, then folding her legs back like some kind of slutty pretzel, while he pounded her into submission. Under the guise of her father's longtime friendship of the man, Caitlin would often pop into his office unannounced with a lunch. On occasion, she might stop in to deliver something from her father pertaining to their work.

During her visits, Caitlin would dress cutely in skirts or short dresses, sitting in the chair across from Raymond's desk to eat her lunch and giving him the odd glimpse of her panties. Other times, she would put her computer skills to work to help Raymond solve some baffling computer issue, which he was not suited for troubleshooting. During these incidents, some of which Caitlin herself would cause, she might lean over the keyboard and present him with her ass as she worked. Other times, she would seat herself on his knee and correct the problem, often leaving something that would, inevitably, cause another problem for her to fix later.

Raymond would thank her, flushed, his cock obviously hard, sometimes placing a hand on her hip as she worked. Caitlin would always leave his office by giving him a hug and leaning up on her toes to put a soft kiss on his cheek. She would always ensure, somehow, that her tummy or her hand would brush against his erection, while never making a comment about it.

While these little teases would always leave her cunt very wet, Caitlin also enjoyed delivering things to Raymond at one of his job sites. It was here that she could cocktease his construction crews, as well, all the while fantasizing about them losing control, tearing away her little dress, and forcing her to service them all in a filthy gangfucking that would leave her with semen dripping from every hole. The fantasy always had her panties drenched with girl cum, which she knew was evident whenever the wind, invariably, blew up her skirt as she blushed furiously or, innocently, gave the men flashes up one of her short dresses.

Now, as Raymond related his tale of woe to her father, Caitlin saw an opportunity to finally get her father's friend to give in. The work might take several days, but Caitlin knew it would be easy to do. In fact, she knew that Raymond was just inept when it came to the software and she could likely just import the spreadsheets into his program and have the problem solved in a matter of hours.

"I could do it for you, Mr. Raymond," she suggested, stopping the conversation.

"Really?" Raymond asked.

"Yeah. If you don't mind me spending a few days in your office, I could do it pretty quickly. Copying and pasting is pretty fast."

"Jesus, that would be great, Cait! You don't mind? I mean, I'll pay you for it, of course, but it would be a huge help."

"I don't mind," she said, accidentally spilling a bit of her water as she raised the glass to her mouth.

The eyes of Raymond and her father followed the small trickle of water as it rolled down her neck and into her cleavage, where she wiped at it with her napkin for a little longer than was necessary.

"It's no problem," she said, "When do you want me to take care of you?"

"Are you busy tomorrow?" Raymond asked.

"I babysit in the evening, but I don't have class. I could work on it tomorrow," she agreed.

"Well, shit! You're a life saver, girl!" Raymond exclaimed.

Caitlin beamed.


Caitlin arrived in Raymond's office wearing a pleated skirt and pink top, with frilly sleeves that hugged her rack tightly. She carried a small lunch bag, which she deposited into Raymond's little office refrigerator, bending over to do so and allowing the skirt to ride up and show the man her panties. Finding a place to put her lunch took a bit longer than it should have, and there was no real reason to wiggle her bottom as she did this, but Raymond did enjoy the view.

"Good morning, Mr. Raymond," Caitlin said cutely, and deposited herself on his knee, giving him a quick hug and a peck on the cheek.

"Morning, sweetie," Raymond said, casually laying a hand on her hip.

"Ready for me to get busy?" she asked.

"Sure. Just do your thing. I'm going to run out for a bit to visit a job site. I'll be back by in a couple of hours."

"Sure," Caitlin agreed, and allowed him to get up.

When Raymond left, Caitlin examined the new software. As she'd suspected, there was an import feature. She arranged the file import and let the software process it in the background, then took the time to look through Raymond's browser history. The man's ineptness with computers made finding the porn he watched, while alone in his office, an easy thing.

Raymond had an affinity for cute teenage girls, which was no surprise. She watched several of the videos in his history, her pussy getting wetter and more excited. Big men pounded their cocks into squealing teens, who struggled to take the full length of their big shafts. More submissive teens knelt and sucked on cocks, sometimes more than one at a time. Yet more girls had their bottoms spread open as older men fucked their asses. One of the more curious finds, though, was an extensive playlist of pregnant teens fucking older men.

Caitlin tabbed over to the software every now and again to check the progress of the import, then flipped back to the porno. While the software chugged away, she began to rub her cunt to the porn. She was knuckle-deep in her twat with one hand, when Raymond opened the office door and stopped. Their eyes met. Raymond blushed as he took in the sight of Caitlin's nude fuckhole, her panties on the desk, and her fingers in her cunt.

"Oh!" he exclaimed, his cheeks coloring.

"Oh my gosh!" Caitlin snapped, feigning surprise, "Mr. Raymond! I'm… I'm so sorry!" she wailed, yanking her fingers from her cunt and snatching her panties from the desk.

She fumbled them up her legs as Raymond stood, shocked, in the doorway.

"I'm… I'm so sorry!" she said again, blushing, "I… Oh my gosh!"

Raymond shut the door.

"Caitlin, what on earth are you doing?" he asked, as though there were some question about her activities.

"Oh my gosh," she said again, wringing her hands, "I was just waiting for the program and… and I was doing some shopping online, but then I saw a video and… and…" she stammered, then asked, "You won't tell my dad, will you?"

Raymond cleared his throat and said, "I… No. I won't. Just… you can't do that in the office, Cait."

Caitlin blushed and fidgeted, looking from Raymond to the monitor, where the porno was still playing, then back to Raymond.

"I'm so sorry," she said again, "I promise I won't. I just got curious about, you know, what they were doing in the video."

"Oh, fuck! Fuck me, daddy!" the porno girl suddenly screamed, "It's so big, daddy!"

Caitlin gasped and looked at the screen, breathing, "Oh my gosh! How did he make it fit?"

"Caitlin!" Raymond growled.

"Oh!" Caitlin exclaimed and reached over to pause the video.

Raymond rounded the desk and looked at the monitor.

"Look," he said, "Let's just close this and forget about it, alright?"

He sat down in the chair and adjusted his hard cock, then moved to close the video. Caitlin gasped and covered her mouth, drawing his attention. He followed her eyes to his cock, tenting his pants.

"That's… Mr. Raymond, it's really big!" she said.

Raymond colored and moved to cover his crotch with his hand. Caitlin's hand covered his.

"I can't believe it," she whispered, awed, "It looks like it's as big as the video."

Her hand tightened on his and forced it to massage his aching cockhead through his pants. Raymond moved his other hand, groaning, and put it on Caitlin's, gently pulling it from his cock.

"You shouldn't do that, Cait," he said.

Caitlin allowed him to pull her hand away, and then she moved it under her skirt and thoughtlessly rubbed her cunt once, as though scratching an itch.

"Oh! Oh my gosh," she said again, dumbly, "I didn't… I didn't mean to, Mr. Raymond. It's just… big."

She sat back on his knee, his cock pressing against her leg and she put her arms around his thick neck.

"I'm really sorry for playing with my pussy in your chair," she said, "You promise you won't tell my dad? He'd spank me so hard and I hate that. It makes my pussy feel wierd."

She felt his cock twitch against her leg as his hand rested on her back. He patted her gently.

"I won't tell your dad," he said, clearing his throat, "Just… you shouldn't be watching that stuff."

"But you watch it, Mr. Raymond," she said and one hand fell from his neck to his stiff cock once more, "You watch it and it makes your cock really hard."

"Cait…" he said and put his hand over hers again, "You shouldn't do that either."

Caitlin giggled and said, "It feels really nice. I like how it feels in my hand."

Raymond inhaled the scent of her and, against his better judgement, allowed her to continue squeezing his cock through his pants, his hand over hers as her fingers flexed.

"Is this okay, Mr. Raymond? Could I just touch it a little bit, like this? I just want to see how it feels. I won't tell anyone. Is this okay?"

She continued groping and tugging his cock through the pants, her soft breath in his ear, tits pressed against his chest and her bottom wiggling on his knee. Raymond groaned, his will to resist draining.

"Does it feel good, Mr. Raymond?" she asked, "Does what they were doing in the video feel good?"

Raymond nodded.

"Can we watch it a little more? Just me and you?" she asked, her fist encircling his cockhead, "Can you play it a little longer for me? I want to see."

Raymond's trembling hand moved the mouse and played the video. The girls excited moaning and squealing came from the speakers. As Caitlin massaged Raymond's cock through his pants she watched the little slut on the screen get her pussy opened up by the porn star's big dick, his hand roughly squeezing her tit.

"Geez," Caitlin breathed, "It's really big, like yours, Mr. Raymond. How does he make it fit? Her pussy is really small."

Raymond did not reply. Caitlin slowly slid the zipper of his pants open and slipped her hand inside, another barrier gone. She slowly groped his thick shaft through his underwear and breathed raggedly in his ear.

"Is this alright, Mr. Raymond?" she asked, "Is it alright for me to just touch your cock a little bit? I like how big it is."

"Yes," Raymond agreed, breathing heavily, his eyes on the screen, where the excited little slut humped her pussy on the man's cock.

"When I was watching it earlier," Caitlin whispered, "When I was touching my pussy, she put it in her mouth and sucked it for him."

Raymond groaned.

"Could I do that for you, Mr. Raymond? Could I try to put yours in my mouth, so you won't tell my dad I was touching my pussy in your chair?"

"I… We shouldn't do that, Cait," Raymond protested, weakly.

"Alright," she said, and slipped her hand into his underwear, wrapping her hand around his naked cock and pumping it, "You don't have to let me suck it for you, Mr. Raymond. I like it in my hand, though. Is this alright? It's alright if I just touch it like this?"

He nodded, gulping and rested his hand on her leg. When she did not object to the touch, he began to lightly stroke it.

"I like that, Mr. Raymond," Caitlin purred, "That feels really nice."

The girl on the screen orgasmed loudly and a moment later the man's cock twitched and jerked. He pulled it from the girl's tight hole and splashed her naked tummy with a hot wash of cum. Caitlin gasped and began to pump Raymond's shaft with more vigor.

"There's so much," she hissed, "That's so much! Look! I think he got a little bit in her pussy."

The camera's close-up view showed that, indeed, a bit of the man's spunk had squirted into the girl's cunt.

"Do you think it felt too good to pull it out?" Caitlin asked, "It looked like it felt really good."

She extracted Raymond's cock from his pants and continued to pump it as the video faded and a new one in the list began. This one showed a petite blonde on her knees, lovingly sucking a man's erection as she looked up at him submissively.

"She looks really cute like that," Caitlin whispered, "She looks so cute sucking on his cock for him."

Before he knew what was happening, Caitlin had slid off the chair and onto her knees. Raymond opened his mouth to argue, but the girl quickly sealed her lips around his sensitive head and tongued the underside of his crown, giving a happy purr as she looked up into his eyes.

"Oh my god," Raymond said, his head relaxing back into the chair, "Cait… you… you shouldn't…"

Caitlin put her hands on his legs and lovingly suckled on the head of his cock, massaging it gently with her lips. Raymond set his hand on her head and Caitlin took him deeper, her tease as polished as his cock was about to be. Her lips glided slowly down the first couple inches and then she made a little gagging noise, drooling a bit around his cock before she pulled back and sucked in a breath. She jerked his cock slowly with her hand.

"I'm sorry, Mr. Raymond," she said, her eyes watering, adorable little face so wide-eyed and innocent, "I don't think I'm very good at it, yet. Can I try some more?"

Raymond nodded and guided her mouth back over his cock, a bit more firmly.

"That's good, sweetie," he said, "You're doing good. It's okay if you choke on it."

Caitlin gave a nod, her pussy wet as she made a little choking sound around a few inches of his cock. Those wide eyes showed a look of disbelief, as though Caitlin could not believe how naughty she was being. The look tripped that switch that she knew it would. No one could resist it. Raymond gave a little push of his hips and injected her throat with another few inches of cockmeat, making the girl drool and sputter.

Caitlin gave a little shocked squeak and her eyes widened further, a tear rolling down her cheek. Raymond firmly pushed her mouth further down his jerking penis, growling at the sight of her watering eyes. Her grip on his legs tightened and Raymond's hand in her hair tightened in return. Caitlin gave a slutty little moan around his dick and choked. Raymond's open hand lightly slapped her cheek and Caitlin moaned again, this time with pure want as her pussy gushed.

"That's so cute," Raymond said, and slapped her cheek again, harder.

Caitlin responded by taking his cock deeper, stopping just short of the final inch, her eyes trained on him. Raymond pulled her head back up the length of his cock and then pushed her back down, roughly. Caitlin squealed unhappily, as though displeased, but one of her hands went between her legs and she touched her wet panties. Raymond took long, shallow breaths as he masturbated his cock with her mouth, the wet sound of her sealed lips an undertone against the porno that still played on the computer.

Finally, he yanked her head up roughly by her hair. A long rope of spit trailed from his cock to her quivering lip and she huffed in air, tears on her cheeks.

"I… my pussy feels really wet, Mr. Raymond," she whispered, "Am I a slut now?"

Raymond stood up, his wet cock smacking her cheek, and then he hauled Caitlin up with him. He spun her around and pushed her face down on the desk, reaching under the skirt to yank her panties down just far enough to expose her puffy little cunt. His hand rested roughly on her back. Caitlin wiggled, her bottom moving from side to side as she pretended to weakly struggle. Raymond gave a low growl and pushed his cock into her, making her gasp.

"Oh! Oh, Mr. Raymond! It's… it's in my pussy! Your big cock's in my pussy!"

Raymond began to thrust his cock into the girl roughly, taking a fistful of her hair and jerking her head back up. Caitlin's fingers clawed uselessly at the desk for purchase, but there was none to be found. The big man dominantly fucked his whole cock into her, roughly banging her against the edge of the desk with one hand on her ass and the other holding her hair. Caitlin made little grunts of displeasure, egging him on, her legs quaking.

"Oh! Oh! It hurts!" she squealed, "It hurts but if feels so good, Mr. Raymond!"

"Fuck," Raymond replied, and continued to batter her tightly gripping fuckhole.

His hips made her small ass jiggle each time he bottomed out in her pussy, moving the heavy desk forward a slow inch at a time. The porno videos continued playing, adding a further fucktrack to Caitlin's grunts and squeals of pleasure.

"I'm gonna... gonna cum… on your… cock… Mr. Raymond!" Caitlin said and Raymond fucked her even harder, the words giving the man a second wind.

Caitlin's wet and squishing cunt around his cock, the pained little squeals she made each time his length filled her, just made him want to hurt the pretty little slut with his penis. He didn't want her to cum. He wanted her to cry, to see those wide eyes and pouty little face in pleasurable agony as her confused body couldn't decide what it wanted.

Raymond yanked his cock from her before she could get the orgasm, easily flipping her around, slamming her onto her back on the desk and pushing Caitlin's legs apart like she were just a toy. He put her legs on his shoulders and roughly shoved his cock back into her. This was good. This was right.

Now, he could see that cute little face, the small tears in her eyes, the flush in her cheeks. He could look down and see the tight, bald little hole stuffed so full of cock. Her slutty cream coated his shaft and the slick, wet sounds from between her legs mingled with the sharp grunts each time he buried the length of his cock into her, until his balls slapped against her skin.

Caitlin bit her lip cutely, her eyes still wide and shocked as the big man repeatedly used her cunt for his pleasure. He leaned forward, pushing her legs back painfully, folding her nearly in half, so that he could keep those legs on his shoulders and get his hands on her tits. Caitlin groaned as his hands squeezed her melons hard. Her stupid face, flushed and so innocent looking just begged to be slapped, and so he removed a hand and did it, leaving a red print on her cheek that made Caitlin's pussy spasm and then cum on his roughly thrusting cock.

"Fuck," Raymond said, "Fucking cum, you little slut. Fuck!"

Caitlin's whole body convulsed and he watched the girl begin to buck and squeal, making little animal noises. It was just what she needed, a rough fucking from a man that she'd teased, until there was no choice but to batter her fucktunnel and hurt it. With a roar, Raymond fed the full length of his prick into her and let it go, releasing a gush of hot cum that pasted Caitlin's wet little sheath.

"Oh, no, Mr. Raymond," Caitlin hissed, "Oh… oh my gosh! You're gonna make a baby in me! Oh!"

Raymond's cock hardened again, even as it continued pumping cum into the girl's pussy. The thought of knocking the little slut up, watching her carry around a big belly and even larger tits just made him fuck her all the harder. Someday, Caitlin decided, she'd make that little fantasy of her own come true. Someday, when she was ready, she'd play roulette with a string of big, pussy-hammering older cocks, letting them juice her up and impregnate her.

The idea made her cum again on Raymond's renewed hardon. Today was not that day though. Raymond didn't have to know that, of course. Raymond just needed to manhandle her and keep pumping her full of cock cream, then go home to his fat wife, unable to wait for the next chance he'd have to roughly shove Caitlin's prone body over his desk and vigorously use her like a sex toy.


Enjoy stories of slutty seduction? If you like it with a incest twist, you'll love Tempting Trevor, a story of sibling manipulation. This lengthy novella details the seduction of Trevor and his girlfriend Mary at the hands of his manipulative and twisted older sister, Stacy.

Care for a long form tale of sexy teen seduction of an older man? Look no further than Love, Lust, and Erin. This story follow's Erin's seduction of her best friend's father, along with Casey's pursuit of becoming a real slut.

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