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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