Listening to Jack
Part 16
Things were mostly as expected as Emily returned to Jack’s basement of science and sin, with her best friend Donna lying naked once more on the bed in the middle of the room, her long, lean legs spread wide open and raised high in the air as Emily’s mother Chelsea ravenously feasted on Donna’s wet, eager cunt. Emily sauntered slowly over to the bed, thoroughly enjoying the lewd sight of Donna writhing about on the sheets as her mother’s tongue lapped away at her best friend’s creamy slit.
Donna’s so hot, Emily thought admiringly as she leaned over the side of the bed, putting the studded leather collar and leash she’d just gotten from upstairs around the dark-haired teen’s neck. To her delight, Donna barely noticed, lost in the deliciously decadent pleasures of having her pussy eaten by Emily’s mom, her eyes closed and her slim body shaking in ecstasy. And Mom … oh, Mom, you’re so sexy …
Chelsea wore a transparent black baby-doll teddy, and her curly mane of auburn hair was frightfully wild and messy, her blue eyes glassy with lust and her cheeks utterly smeared with Donna’s thick, musky juices as she knelt on the bed between the young teenage girl’s legs. Chelsea’s curvy ass was raised high in the air … so, with a wicked smile, Emily decided to take advantage of that glorious sight. She gently pushed up the hem of her mother’s teddy up over her waist, and playfully gave Chelsea’s round, jiggling asscheeks a nice, hard swat with the palm of her hand. As her mother let out a muffled squeal of joy, Emily knelt down behind her, spreading her mother’s ass cheeks wide open with her hands. Her mother squealed even louder as Emily’s fingers began invading her dripping cunt … and as Emily’s tongue found the tight pucker of her anus.
Mom always tastes so good, Emily thought happily, as she closed her eyes. Her mouth began to wetly slather over her mother’s asshole, probing it lewdly with her tongue. Dimly, she could hear Donna crying out in orgasm, even as her mom began bucking in ecstasy on her penetrating fingers and thick, messy juices began running thickly down her hand … and then, Emily let out a squeal of her own as she felt something hot and hard start to press between her legs.
“Hey, slut,” Jack murmured in her ear, as he leaned over behind her and roughly squeezed her tits, “miss me?”
Emily nodded. Eagerly.
Jack made good on his promise from the night before, making sure to fuck her good and hard first, making sure to make her cum hard twice on his cock before spilling his incestuous seed deep inside her pussy. Donna was next – after she’d dutifully cleaned all of Emily’s juices off Jack’s yummy prick, of course – and then Jack was nice enough to let his mother Chelsea give him a long, slow blowjob while Emily and Donna lay panting with exhaustion on the bed, their bodies shivering with blissful excitement as they stroked and kissed one another.
After that, Jack turned on the video camera surrounding the bed to make another sexy video, this one featuring just Donna and Chelsea, with the older red-headed woman made to wear white thigh-high stockings and a nurse’s hat while she ‘examined’ her eager teenage patient. Jack seemed to immensely enjoy recording their nasty little fuck session, at least as far as Emily could tell, barking orders and enthusiastically giving his mother and Donna directions as to how to use a thick, enormous double-headed dildo on each other while Emily gleefully sucked his cock. By the time his dick erupted in Emily’s mouth, Donna and Chelsea were crying out once more in orgasm … and the four collapsed on the bed once more, spent and content from their perverse liaisons.
“What’s that they say, about all work and no play doing something to Jack?” Jack said as he lay on the bed, his hands behind his head as his mother and his sister kissed his softening cock clean, while Donna rested her head on his abdomen. “Well, trust me, my lovely ladies … nothing’s ever dull when you’re around. And I don’t think things will ever be dull again, at least not for a long, long time.”
“I … mmnnff … I know, Jack,” Emily replied softly, her fingers fondling his balls as she gave his inner thighs soft, wet kisses. “You’re … mmmm … so good to us …”
“Aren’t I, though?” Jack said with a laugh. He gently pushed Donna off his stomach and sat up, looking expectantly around the room. “Unfortunately, more work needs to be done. But I won’t be long. Mom, I need to talk to you about something important … so Emily and Donna, you just play with each other for a bit.” He winked impishly at the two teenage girls. “Don’t worry, I’ll get back to you both shortly.”
“Hear that, Em?” Donna said teasingly to Emily, as she ran her hands lightly down Emily’s slender sides. She gave Emily a firm slap on her toned, supple ass, making her shriek with shameless pleasure. “We’re supposed to play with each other. Think we can manage?”
“Life’s rough,” Emily said, nodding solemnly for a moment before leaning her head in towards Donna and crushing her mouth against her best friend’s, their tongues hungrily dancing with each other as they kissed each other hard.
The two girls played with each other for a sinfully good, long time, oblivious to just about everything but their insatiable need to wantonly pleasure each other. Briefly – and it was very indeed brief, as Donna was busy sucking on her tits and fucking her pussy with a very thick black dildo at the time – Emily vaguely noticed Jack taking their mother away towards one of his workstations. Holding their mother’s right hand, he pressed one of his weird little chrome boxes against her thumb ... and when numbers and wavy lines popped up on a nearby computer screen, they were accompanied by a bright orange box labeled NEGATIVE. After that, she watched as Jack put his lips to their mother’s ear, whispering something softly ... and watched their mother’s shoulders visibly slump in hurt disappointment.
Emily also thought she heard Jack muttering something under his breath about how Todd wasn’t getting the job done, which just seemed weird to her – what would Todd have anything to do with Mom’s test, anyway? she wondered in puzzlement – but then Donna started pumping the think black dildo even deeper and faster into her horny snatch, and then Emily was cumming hard all over the dildo, screaming and sobbing with joy, and then ... well, then, she sort of forgot about what she’d just seen.
For the moment.
Jack brought Donna and Emily upstairs shortly after that. Her mother Chelsea came up with them as well, and … well, Emily couldn’t quite put her finger on the reason why, but things seemed incredibly weird for some reason. Even as Emily absently stripped completely naked again as she got upstairs – and so did her mother – Jack immediately went to the hall closet and pulled out an outfit for himself. Nice shirt, nice pants, black silk tie … where is Jack going? Emily found herself wondering. Puzzled, she found herself watching Jack as he headed to their father’s empty office … and as he closed the office door behind him, without saying a word.
So Chelsea made lunch for the two teenage girls in the kitchen while Jack was otherwise occupied in the office. She stood there completely nude, casually chatting with two attractive teenage girls who also happened to be completely nude, like it was the most natural thing in the world. Chelsea asked Emily and Donna about their classes in school, about what they’d be doing with the cheerleading squad that year, while Emily and Donna asked Chelsea about some of the work she’d been doing at the community center – again, like it was the most natural thing in the world. And then Chelsea asked Emily and Donna for advice about giving blowjobs, since Jack still wasn’t satisfied with her skills at pleasuring him orally, and Emily nonchalantly gave her mother tips on how to relax her throat to deepthroat Jack, and Donna told her about how Jack liked the head of his cock sloppily pleasured with the tongue.
Like it was the most natural thing in the world.
Sort of. Kind of.
Not really.
Something seemed amiss to Emily … but for the life of her, she couldn’t think of what it could possibly be.
Fortunately, Jack wasn’t in the office for too long. He didn’t look terribly happy as he came back to his eager lovers, though, frowning and staring glumly at his smartphone. “Fucking Germans,” he muttered resentfully, “that’s twice the amount they said … and …” Shrugging, he looked up directly at Emily for a long, long moment before closing the phone and tucking it in his pocket. To Emily’s surprise, she thought he looked rather forlorn as he gazed at her – almost apologetic. “Well, that’s the price of doing business, I guess.”
“Is there a problem, Jack?” Chelsea asked. “You know I’m here for you, darling. To take care of you, however you want, whenever you want … to take care of your, uh, needs.” She leaned back against one of the kitchen countertops, spreading her legs a bit wide to expose her bare slit to her son. “All of us are, sweetie …”
“I know, Mom,” Jack said. He walked right past his mother to the refrigerator, taking out a can of soda. “And actually, there is something you can do. I need you to go out … and I need you to dress nice. Not nice like last night at the sex shop … properly nice. Professional, and classy. Something like that cream pantsuit you wore to Dad’s awards dinner last Christmas would be ideal. Understand?”
“Yes,” Chelsea said, without any hesitation. Emily, though, could hear the crushed note of bitter disappointment in her mother’s voice, although Jack seemed not to notice it at all. “I … I know what you mean. And what do you want me to do?”
“Here,” Jack said. He grabbed a piece of paper from a pad hanging on the refrigerator, and a pencil from the counter nearby. “I need you to make a transfer … a couple of them, actually … from here … to here.” The pencil skritched across the paper noisily as he scribbled lots of numbers onto it. “This much. Then call Dad. He’ll know what to do next.”
Chelsea nodded. “Anything else, Jack … anything?”
“No, I don’t think so,” Jack said absently. He cracked open his soda can and took a long, slow drink. “Go. It’s very important, Mom.”
“Yes … yes, Jack.” Emily’s heart broke a little as she watched her mother slowly leave the kitchen, a look of complete and utter dejection on her gorgeous face. Emily loved Jack fiercely, more than anything in the whole world, and didn’t particularly want to share him with anyone else, but … I wish he would love Mom the way he loves me, Emily thought, her forehead furrowing in puzzlement. I don’t understand why he doesn’t, she’s so beautiful … and she wants to be his yummy fuck toy so bad, it hurts …
As Chelsea morosely left the kitchen, Emily craned her head so she could peer into the office down the hallway – Jack had left the door wide open, so the pretty blonde teenager could kind of see what was inside. She saw that a large video camera was set up on her father’s big mahogany desk there, next to the computer … and that there were a number of Jack’s special headphones scattered all over the desk as well. Some of the headphones looked identical to the ones Jack had so thoughtfully and kindly given Emily and Donna over the past few days, while others looked much larger and more advanced. There was some sort of presentation with pie charts and line graphs visible on the computer screen, but the words on the screen were too small for Emily to read, so she didn’t know what it might be about.
Still … a presentation? Emily thought wonderingly. I guess that explains the tie and the nice outfit and stuff … but who’s Jack presenting to? She turned to her brother, feeling even more confused than before, as several questions crept to the tip of her tongue … and then she forgot them all, as she noticed to her great delight that Jack was in the process of shedding his nice outfit in the middle of the kitchen, and that Donna was already on her knees in front of him, her small hand earnestly stroking his cock and making it nice and hard once more.
“Now, my sweet sluts,” Jack said, “where were we?” He grabbed the loop at the end of Donna’s leash – the one that Emily had affixed to her best friend’s neck the night before – and dragged the naked dark-haired beauty to her feet, making her yelp nervously with excitement … and just a hint of fear as well. “Oh, that’s right. I was going to fuck you both in the living room. Emily, come with me.” He pulled impatiently on the leash, dragging Donna along with him out of the kitchen as the girl giggled happily. Emily skipped along behind them, her face flush with lewd excitement once more.
Jack fucked his sister and Donna a couple of times there, letting each girl ride his cock until they came all over his shaft … and until he unloaded a nice, big load of gooey cum into their pussies. He was even sweet enough to finally take Emily’s anal cherry, bending her over one of the big, padded arms of the couch in the living room and shoving his big, beautiful cock right up his sister’s eager, willing rectum, hammering away at her sexy bottom until she screamed with depraved glee. Emily thought getting fucked in the ass was a little uncomfortable at first, and it even hurt a little, but it was a sinfully sweet hurt, one that felt incredibly good in a weird way as well … and by the time Jack’s hard dick had begun to twitch and spurt yummy hot semen deep into Emily’s ass, she’d grown to absolutely love it … not as good as when Jack fucks my pussy, but close, Emily thought happily, as she felt Jack’s jism start to leak out of the stretched pucker of her cock-stuffed anus … and especially as she felt Donna’s tongue start to lick it up.
Satiated for the moment, the two girls finally curled up next to Jack as he sat on the couch, both their heads in his lap, both taking turns gently sucking and stroking his cock, which was still hard and ready for them. Emily couldn’t help but staring at her brother’s stiff manhood with lustful admiration. When he’s inside me, it just feels perfect, she thought happily, I wish I could just fuck him all day … I love him so much …
“So, Donna,” Jack said casually, as he reached over to slide his hand between the dark-haired girl’s slim legs, “after this weekend, when you finally go home … make sure to get the first pair of headphones that Emily left for you in your locker at school.” He turned his head to kiss and nibble the side of Donna’s neck. “I know you don’t need them any more – trust me, I don’t – but they’re important to me. I need them back.”
“Oh, Jack, I … ooohhh!!!” Donna squirmed excitedly on the couch as Jack’s fingers slid into her slippery slit. “I … but I … OOOHHH!!! … but I don’t have them anymore, Jack, I lost them …”
Jack’s fingers abruptly withdrew from Donna’s wet, slick pussy. He pulled his lips away from Donna’s neck.
“Say that again,” Jack said. Emily’s eyes widened in fear as she heard a cold, vicious fury starting to build in her brother’s voice. “Say that again, bitch.”
“I … I lost them, Jack,” Donna said. Her voice quavered slightly as it dropped to a low whisper. “Please, I didn’t mean to …”
Jack snapped his fingers irritably. “Both of you whores,” Jack said icily, “on the floor, and on your knees. In front of me. Now. Fun time is over. You better explain what the fuck is going on, and fast.” He pointed angrily at the circular shag rug just a couple of feet in front of the couch, and Donna and Emily practically leapt off the couch to kneel on it, facing Jack as they rested their pert bottoms on their heels, clasping their hands nervously behind their backs.
“Jack,” Emily said uncertainly, “I –”
“Shut up, Emily,” Jack said. “You’ll speak only when I want you to speak. Understand?”
Emily nodded.
“Now … Donna,” Jack said, as he turned his attention to the dark-haired girl. “Explain yourself. What happened to the first pair of headphones that I gave to you?”
“I told you, I don’t have them,” Donna repeated. She gave Jack a timid smile, shifting about nervously on her heels. “I thought you knew that. I thought that’s why Emily gave me another pair – to replace them, since I lost them. Isn’t that right, Em?”
Emily nodded. “Yeah, that’s what I thought, too,” she said.
The lazy, cocky smirk on Jack’s face abruptly faded away.
“You dumb, lazy, cunt,” Jack hissed at Donna. “How could you be so goddamn fucking careless?!”
“I didn’t mean to Jack, I swear!” Donna’s eyes darted all around the room as she spoke, looking everywhere but in Jack’s direction. Her hands twisted about nervously in her lap, her pretty face pale as a ghost, her eyes filled with fear. “It just happened … I had them in school, I was listening to them, like you told me to – I always do what you tell me to, Jack, I do, I promise! – but that awful Mr. Hill, he made me take them off, he made me, I would’ve gotten in trouble if I didn’t, I wouldn’t have be able to try out for the cheerleading squad like you wanted me to, Jack, so I put them in my purse and when I looked for them at lunch they WERE GONE!!!” Donna wiped tears from her eyes. “I’m sorry, Jack, I’m sorry, I’m so, so sorry –”
“Well, I don’t give a shit about your ‘sorry’, you stupid twat,” Jack hissed at Donna. “You better find those headphones, and fast. If you don’t, I’ll … well, I’ll make you sorry. Very sorry. You’ll wish you’d never been born if you don’t find those fucking headphones.” Emily watched Jack’s shaking hands clench tightly into fists, a dark look of anger lurking in his eyes, as well as … he looks afraid, Emily thought, her eyes widening in wonder. Afraid, uncertain, and … nervous? What’s making you so scared, Jack?
Emily couldn’t remember the last time she’d seen Jack look so flustered and rattled. She knew that it had to be a while ago, well before she’d started listening to Jack the way she was supposed to listen to him – before the conditioning, and before he’d started being the best brother in the whole wide world to Emily. Seeing her brother Jack like that, when he usually was so confident and handsome, and so very, very smart … it scared Emily a little, too.
More than a little, actually.
“This is what I get for making my dreams come true,” Jack muttered darkly. He started to pace nervously between the couch and the kitchen door, running his fingers through his hair as he skulked about. “I turn two of the hottest girls I know – two girls I’ve fantasized about fucking – into my perfect, obedient perverted fuck bimbos, and what happens?” He threw up his hands in the air in exasperation. “They turn too horny and stupid to notice the obvious!”
Emily said nothing, just the way Jack had told her. She bit her lip nervously, looking back and forth between Jack and Donna, wishing desperately that Jack would stop berating her best friend. They’re just a stupid pair of headphones, Emily thought, you’ve got lots of them … why are you so worried about one missing pair of them? Again, the question crept to her lips, but it simply remained there, silent and unspoken.
“Go home, Donna,” Jack said. “I want you to go home to your sad, empty house and be all alone there.” A wicked gleam crept into his eyes. “Go home tonight and think about what an awful, careless failure you’ve been. Go home and think about how bad you want to fuck me, and about how much you want my cock inside your tight little pussy. How much you crave it … how much you need it. But no matter how bad you want to, you won’t be able to play with yourself. You won’t even be able to touch yourself, not in any sort of way that brings you any sort of pleasure. You’ll only be able to think about how much you’ve disappointed me, and how badly you want me … and that because you’ve been such a selfish, stupid slut, you can’t have me. Understand?”
Dully, Donna nodded, her eyes glassy and filled with disappointment.
“And tomorrow,” Jack continued, “you’ll go to school. And you’ll find my fucking headphones. You won’t go to any classes, though, not unless it’s to help you find them. You’ll do whatever it takes to find them, Donna … what. Ever. It. Takes.” He spit the last four words out with venomous contempt. “Now get the fuck out of my sight. You’re a completely worthless failure, Donna, and until you get those headphones back, I want nothing to do with you. Nothing.”
Donna burst into tears, sobbing hysterically. Emily watched helplessly as Donna half-ran, half-stumbled out of the living room to the entrance foyer, barely remembering to throw on her clothes before awkwardly leaving the house. Emily wanted to say something to Donna – it’s okay, we’ll find them, Jack will forgive you, I know he will, I know it – but again, the words seemed to be trapped inside her, doomed to remain unspoken, unable to do anything to comfort her best friend as the front door slammed shut.
“As for you, Emily,” Jack said, as he got up from the couch, “you’re just as stupid and selfish as your slut friend Donna, and you should be punished just as bad as her, if not worse … but I need you right now … for certain things.” He strode back to the kitchen, gesturing to Emily to follow him. Emily followed without hesitation, watching as Jack picked up his clothes from the tile kitchen floor and started to get dressed. “But don’t worry, slut, you’re still going to be punished. Make no mistake about that. You may speak now … but only to answer my questions, and to acknowledge that you understand what I’m telling you. Got it?”
Emily nodded.
“Good,” Jack said. He quickly opened the refrigerator again, taking out a glass carafe of orange juice. “My work … everything I’ve been doing for months, sweet sister … it’s all hitting a very critical stage right now. More than ever, everything needs to be absolutely perfect. If it’s not perfect …” Jack sighed, pouring himself a tall glass of juice. “Well, let’s try not to worry about that, shall we?”
Emily nodded. Even though she had absolutely no idea of what her brother was talking about.
“I don’t have time for games, Em,” Jack muttered darkly. He sipped at his orange juice, not even bothering to look up at his naked sister. “You have a lot of things to do tomorrow. Very important things. But most important of all, you better find Donna’s headphones. I promise you, if you don’t … you’re going to regret it. Understand?”
“Yes, Jack,” Emily said quietly, “I think so –”
“DO YOU UNDERSTAND???” Jack bellowed. Glass shattered and orange juice sprayed everywhere as Jack abruptly threw his glass into the sink as hard as he could. Emily flinched, her hands trembling as she wanted to run up to her bedroom and hide under the covers of her bed … but she stayed where she was. She couldn’t move. She knew she couldn’t.
“Yes, Jack,” Emily repeated, her voice shaking hard as she vigorously nodded her head. “I understand. Completely. You’ll have the headphones by tomorrow, I promise.”
Jack smiled thinly. “Good,” he said calmly, as if he’d just been casually discussing the weather with his twin sister, and as though he didn’t have a care in the world. He reached into one of the front pockets of the pants that he’d just put on again, and took out a folded piece of paper, handing it to Emily. “You’re going to read this. Once you’ve read it, I want you to look at the school sports schedule. Figure out what’s possible, and when the things I want can happen … and who’s going to be doing them. Especially if it’s you. Understand?”
Emily nodded, as she wordlessly took the paper from Jack, tears brimming in her eyes.
“Which reminds me,” Jack continued, “I need to get rid of the stupid cum dumpster upstairs, too … no point in keeping her around right now, especially since Todd isn’t getting the job done.” He shook his head, a look of resigned scorn on his face. “Without him, uh, getting results with Mom, I can’t compare that to what you and I have done, Em – and that means I can’t move on to Stage Three of my data analysis. And I need that before I can move forward to even more important things. So there’s no point in rewarding Todd for anything … he’s almost as worthless as you and Donna right now. He doesn’t deserve any sort of extra rewards. Here’s hoping that he’s, um, a little more potent over the next few days with Mom … I’m already too far behind schedule as it is. Understand?”
At that point, Emily didn’t have the vaguest idea of what her brother was rambling about. But she nodded vigorously anyway, desperate to please him.
“Anyway,” Jack continued, a note of malicious joy creeping into his voice, “while you do your work for me … you’ll do it in your room. Alone. And I want you to think about what a terrible, stupid failure you’ve been. I want you to think about how much you love fucking me, and about how much you love it when I cum inside you. And how bad you want me – you need me – to make you cum. But no matter how bad you want to, you won’t be able to play with yourself. You can’t touch yourself, not in any sort of way that brings you any sort of pleasure. You’ll only be able to think about how much you’ve disappointed me, and how badly you want me … and that because you’ve been such a selfish, stupid slut, you can’t have me. Understand?”
Emily felt her whole body go numb with dread as she nodded. For some reason, his words sounded familiar, she just didn’t know why …
“Good,” Jack said. “Now you may leave.”
Emily barely noticed the contemptuous, dismissive wave of Jack’s hand as she ducked away from him and scurried as fast as she could back upstairs, back up to her bedroom. Tears spilled down her cheeks as she threw herself on her bed, her cheeks burning with shame and disgust. Her pussy tingled wildly as she thought of Jack … and how much she wanted to tell him she was so, so sorry for letting him down, and how she desperately wanted to make it up to him, and how she wanted to ride his cock until she screamed out his name at the top of her lungs for the whole world to hear, cumming all over his big, beautiful dick as he spurted his semen into her pussy over and over and over again …
Fidgeting, Emily opened Jack’s note and began to read it, writing some names down, writing some ideas down, checking the sports schedule … it wasn’t easy. For some reason, it was incredibly difficult to stay focused on doing what her brother Jack wanted. Her body kept shaking uncontrollably, she kept crying, and it seemed all she could think about was Jack, her sexy brother Jack, how wonderful he was to her, and how she’d totally disappointed him like the dumb, self-centered, ungrateful whore she was …
The rest of the day was long and miserable for Emily – and that restless, sleepless night was even longer for her.
And even more miserable.