All characters are 18+. Please leave your comments and feedback below! Thanks! P.S. the bold and italicized text is someone’s thoughts/inner monologue, but can also be external actions.
Here is the background. This is a fictional story.
**Jessica**: F21. Main female of the story. 5’2″, blonde, c cup, petite, slender, athletic, great ass. Slutty at times, but loyal.
**Ben**: M18. Main male of the story. 6’1″, athletic build, brown hair, Kelly’s boyfriend.
**Kelly**: F18. Jessica’s younger sister. 5’4″, blonde, c cup, carefree, Ben’s girlfriend.
**Setting**: *Jessica and Kelly’s house*
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*Rules and responsibilities*
They were two separate families living in two different houses, but with a lot of overlap between them as they were close next door neighbors. Ben and Kelly were an item, and had been for years, but more or less only became officially boyfriend and girlfriend as of two years ago now. Since they were the same age, it was natural for them to gravitate towards one another as they went to elementary school together, rode the same bus, worked on school assignments, and now were nearing the end of their high school journey together. However, they also were each other’s firsts for a number of things, including sex.
Despite their undeniable bond and chemistry with one another, Ben always had eyes for Kelly’s hot older sister, Jessica. She came off as a bit of a princess to Ben given the way she treated him in the last several years, at least since Ben had made it to high school. However, since Jessica was an upperclassman in high school by the time that Ben and Kelly made it there, she and had little reason to interact with her younger neighbor. Plus, she was now a college girl, so she had even less of a reason to interact with him. Before that, the three of them would hang out and watch movies and such. Now, she had a standoffish demeanor towards him almost all the time for no apparent reason.
Whenever he would come over to the house, it was as though he was invisible; she just didn’t care for him at all, not even to say hello. In fact, since the three of them basically grew up together, Jessica probably saw Ben as a little brother more than anything else. Ben never made a big deal about the change in her attitude as he didn’t want to ‘rock the boat’ so to speak, for Kelly’s sake. To complicate matters even more, he was pretty much a household figure at their house, coming and going as though he was part of their family. He was essentially the son Jessica and Kelly’s parents never had, but always wanted. His relationship with Kelly was a big deal to both families as they all got along quite well, especially the parents.
Nevertheless, Jessica oozed a sexiness and a petite body that Ben simply couldn’t resist. He had caught himself staring at her on more than one occasion as her sometimes plain, but skimpy home clothes showed her off well. Her long blonde hair, feminine curves, and athletic body inspired the image of the ideal woman in his mind. Since he was pretty much always around their house, he was able to watch her physically mature into the beautiful young woman he knew today. Certainly, she was what he always hoped that Kelly could be to him. However, because of his relationship with Kelly and the dynamics between both families, Jessica was the very definition of forbidden fruit; she was strictly off limits. Looking was as far as he was ever going to get with her as she paid Ben no mind anyway and had zero interest in him. After all, he was only her younger sister’s little boyfriend and her otherwise annoying brotherly neighbor.
“Kelly! Jessica! Get your butts down here! Ben’s parents are here!” Mom yelled.
“Ugh! Why did she have to say it like that with company over?” Jessica muttered as she opened her bedroom door to leave, walking out across the hall from her sister who heard the same call.
“Hehe, I don’t know.” Kelly chirped back in response.
Both girls quickly made their way downstairs just as their mom was just about to bellow again. They were now standing in a bit of a circle with the four parents and only a few cases of luggage between them.
“Ah, there you two are.” Mom continued. “Okay, daddy and I are leaving now with Ben’s parents. Remember, we’ll be back in three weeks…so don’t burn down the house.”
“Hey, girls!” Ben’s dad interrupted, greeting them excitedly as he took a small step towards the pair.
“Hi!” Jessica and Kelly responded in unison with a smile and an overly feminine tone, concluding the pleasantries.
“Jessica, I left the hotel information on the fridge.” Dad said wanting to get going already. “Take care of your sister. I left some money on the dresser in our bedroom for pizza or whatever.”
“Yes,” Jessica said as she looked up at her dad, but was in the middle of her response when the front door behind the parents opened slowly and Ben stepped inside with a backpack slung over his shoulder, huffing a bit. “Daddy.” Jessica finished as her gaze naturally went to Ben, looking him in the eyes as she said it.
Ben, taken a bit back having seemingly been called, “Daddy” by Jessica, simply smirked at her in response to the unexpectedly warm welcome.
Jessica realized the unbelievably awkward timing of Ben’s arrival and glared at him with a sharp stare that caused the smirk on his face to evaporate quickly as he mouthed, “whoops.” Regaining her focus, she turned back to her dad and responded with a smile and her sweet voice again, “Yes, daddy.”
Ben surveyed the room and smiled at his girlfriend, Kelly, before looking at the other luggage.
“Hey, dad, I loaded those in, do you want me to grab these too?” Ben asked his dad as he motioned to the remaining luggage.
“No, son. We’ll get these last few. You take a break and settle in.” Ben’s dad said in a conclusive fashion.
“Yeah, son, you’ve helped plenty.” Dad added, patting Ben on the back as he walked on in towards Kelly.
Jessica seemed out of the loop at this point, not quite realizing what was going on with her dad’s inviting gesture towards Ben. Although, she reasoned that he could have come by to work on some final school assignments with Kelly since he did have his backpack with him.
“Hey, babe, can you get me some water?” Ben asked Kelly nicely, as he walked closer to the girls.
“Sure!” Kelly responded as she turned and walked off to the kitchen.
***Huh? Why is Kelly so overly excited?***
“What’s going on, dad? Is Ben hanging around until you leave?” Jessica asked, seeking clarification, though she already knew that the parents were just about to head out the door.
Dad looked at mom puzzled before he realized that Jessica wasn’t told yet. Jessica looked at her mom and then back to her dad.
“Oh, sweety, I forgot to tell you, but Ben will be staying over with you girls and checking up on you both from time to time while we’re gone.” Mom said, a bit apologetically, realizing that Jessica’s frown was growing.
“What? Is this a joke?…You mean like a babysitter? I don’t need a babysitter!” Jessica pleaded in the direction of her parents as she then turned her attention to Ben, who was standing next to her now with his backpack on the floor leaned up against the wall near the stairs.
“…I…come on, he’s younger than me!…This is so humiliating!” She added, hoping that a dose of reality would change the parents’ minds.
As her words fell on deaf ears as no one responded, she looked at the faces of all of the adults for sympathy before she hopelessly and desperately added, “…he…he’s never even babysat me before!”
***Wow, great…that sounded so much worse out loud than in my head!***
“It’s okay. We trust Ben to look after you and Kelly while we’re gone. He’s a very responsible young man, Jessica.” Mom said with a hint of pride regarding the neighbor boy.
“What about me? Am I not responsible?” Jessica fired back.
“Of course you are, sweety, but we just wanted a man in the house with you both for safety.” Mom said to pacify her, hoping that she would understand. Using her better judgement, Jessica kept her mean thought to herself as to not ridicule Ben out loud in front of everyone.
***A man? Little Ben is who comes to mind, mom???***
“Plus, it will be a new experience then for him to babysit you and Kelly.” Dad chimed in and added with a bit of a chuckle, but not helping the situation as the look on his face conveyed that he really didn’t know what to say to appease the girl now. “I mean, just think of it as you three hanging out together for 3 weeks.”
“Ugh! I can’t believe this…” Jessica muttered, now blushing slightly and stomping her foot on the ground in defiance like a child as she crossed her arms to show her disapproval. Up until now, Ben had been standing quietly staring at the floor as the whole conversation was a bit awkward and seemed more fitting between their own family than with him and his parents around to hear it.
He then leaned over slightly towards Jessica and muttered quietly under his breath with a grin, “Well, you did call me ‘Daddy’.”
Enraged, Jessica pulled her head away from Ben and looked up at him as she muttered back, “I so did not!”
Kelly came back in with the glass of water and stood alongside Ben so that he was standing with one girl on each side, Jessica to his right. Ben took the water and started drinking it happily as Kelly wrapped her arms around his left arm, showing their closeness in front of the parents.
“Did you know about this?” She leaned in towards Ben slightly to get closer to her sister, Kelly.
“What? About Ben staying over? Sure.” Kelly said innocently, not realizing what had transpired in her absence.
“Jessica, enough. Behave like a mature, young lady. Girls, this is the arrangement that your mother and I and Ben’s parents agreed to while we’re all gone. You can all look out for one another.” Dad said sternly as he had enough of her miniature tantrum.
“…Yes, daddy.” Jessica replied in a defeated tone, realizing that it was a done deal. “Yes, daddy!” Kelly added, clearly excited by the prospect of having a free pass to have virtually unlimited sex with her boyfriend at her house with both sets of parents knowing about it.
After a few more minor exchanges by the parents with Ben and the girls, they began to depart.
“Okay, kids, bye!” The parents said as the dads carried the luggage out and the moms waved.
“Ben…” Mom said somewhat sternly as she turned to face him partially as she was in the doorway. She then smiled as she turned and left, shutting the door behind her.
“Yes, ma’am.” He responded politely as he understood that Kelly and Jessica’s mom was saying ‘goodbye’ and ‘take care’ in that one gesture.
Still standing there with her arms crossed, Jessica pouted about the situation and rolled her eyes at that last exchange between her mom and Ben as she also knew that her own mom was undermining her age and authority. It was another final gut punch. Ben handed the glass back to Kelly as he went to take his shoes off, leaving them by the front door with the rest of the shoes. He locked the door as he was going to stay for a while, probably the night.
Kelly smiled as Ben made himself more at home and then shoved her sister playfully to snap her out of it. “Hey, take it easy. It’s not a big deal.” She said.
“Sure, you don’t see it as babysitting because you two are having sex! It’s just you having your boyfriend over for 3 weeks! It’s totally unbelievable!” Jessica roared.
Ben made his way to the sofa and sat down with Kelly in tow as Jessica looked on at the couple. Kelly curled up into his right chest and shoulder area, making herself comfortable as he wrapped his right arm around her.
“Ugh!” Jessica voiced her displeasure, not really concerned at this point about manners in front of a guest, since it was after all, just Ben.
“So, do you want pizza?” Ben asked a bit quietly, aiming his attention at Jessica, but was probably muffled by Kelly’s general giggling and cozying up as his voice trailed off quickly. Preoccupied by her anger, and having had enough of seeing them, she turned around and started back up the stairs.
“Jessica!” Ben called out with a stern voice, simply wanting to get her attention.
***Ah! What the-?***
Jessica hesitated and stopped dead in her tracks, startled a bit, before she turned around slowly to face Ben. Kelly, raised her head up from Ben’s chest and glanced at Jessica before looking back at Ben’s face, noticing his commanding voice out of nowhere. She bit her lower lip, turned on by her boyfriend’s sudden dominance and how it actually worked to stop her sister in her tracks. The added fact that it made Jessica obey made Ben even more attractive to her now.
“Do you want pizza?” Ben repeated.
“Sure, whatever!” Jessica retorted, embarrassed by the exchange. She turned around and continued back up the stairs.
***Ugh, why did he have to scare me like that? I could have slipped on the stairs or something***
Ben watched as the girl’s figure disappeared out of his sight. Jessica’s cute, form-fitting white tee and pink shorts left a lingering impression in his mind. Now, fueled with some pent up sexual tension, he gazed down at Kelly who was one step ahead of him, as she slid herself onto his lap and begin to kiss him passionately. Ben and Kelly continued their heated make-out session as Jessica went up the stairs, hearing a bit of her sister’s giggles fading out as she finally made it back to her room.
Back in her room, she realized that she could simply ignore Ben and just invite her boyfriend, Todd, over as well. However, not wanting to chance it as Ben might report her activities back to her parents, she decided to have Todd come over later on after her sister and Ben turned in for the night, just to be on the safe side. After all, her parents were not exactly fans of her boyfriend as he wasn’t quite as upstanding as they would have preferred for their daughter. Kelly knew it too even though she didn’t really care, but knew that her dad had already told Todd not to come by in the past.
***About 20 minutes later***
She laid down on her stomach on her bed to text Todd with her body facing away from her partially closed door. Jessica had her knees bent with her feet crossed over in the air behind her as she pulled up her last text with Ben, realizing that the last time that she had spoken to him before today was when she had asked him to mow the lawn the other day at her dad’s request. Suddenly, she heard the voice of her sister behind her, pushing her door open.
“Hey, Jess, where did dad say he left money for food again?” Kelly asked in a hurry. “The delivery guy is at the door.”
Jessica turned on her side to face Kelly and then hopped up from the bed. “It’s on the dresser. Let’s go find it quick.”
The girls raced over to their parents’ room to get it as Jessica mindlessly began to type out her request to her boyfriend.
>*Hey, babe, can you come over tonight around midnight? Horny and pissed. Neighbor kid is babysitting here and I don’t want him or my sister to know that you’re coming over. I’ll leave the front door unlocked.*
“There!” Jessica pointed at the stack of twenty dollar bills lying on top of the dresser in plain sight as she sent off the text, only partially looking at she was distracted by the money itself.
***Guess dad expects us to buy a lot of food while they’re gone.***
“Great!” Kelly responded.
She grabbed the money and ran back down the stairs as Jessica wandered back to her room to relax.
***Later, downstairs in the kitchen***
“What’s the matter, Ben? You don’t like the pizza? You only had one slice.” Kelly asked, wondering why her boyfriend seemed noticeably distracted. She herself already had two and found it uncharacteristic for him to be behind, not that it was a race.
“No, it’s good. I’ll get another slice in a minute.” He replied back enthusiastically as he sat with crumbs on his plate, staring at the phone in his lap, which was out of sight.
Ben quietly set his phone to vibrate so that Kelly wouldn’t be bothered by it as he began to look on at the screen and lose himself in thought. Something was weighing on him, but Kelly let it go rather quickly as she was now distracted by her own phone. Seemingly at a crossroads, Ben took action as he was tired of the deliberations in his head as he looked on at the text that he had crafted in response to a friend who had texted him earlier. With the conflict unresolved, he went for it and sent it anyway.
>*Sure thing.*
Source: reddit.com/r/eroticliterature/comments/olaqbs/an_uneasy_proposition_mfdomsubblackmail_part_1