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Thread: "Heartbreak High" with Loren Gray and Olivia Holt

  1. #1
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    fanfiction "Heartbreak High" with Loren Gray and Olivia Holt




    Heartbreak High #1
    With Loren Gray and Olivia Holt
    Written by TPG
    CODES: MF, blackmail, fingering, rimming, inc, voyeur, mutual mast
    DISCLAIMED: This FICTIONAL story was written for entertainment purposes only

    It had already been a stressful few weeks at home with dad's new wife and family moving in with us, and for me to discover that I now had a new step-sister in the form of one Loren Gray. All things considered it wasn't so bad, but right from the get-go Loren and I just didn't seem to get along, and to make matters worse we now attended the same school together.

    I mean considering all the fucking make-up she wore I thought she was a silly little slut who was devoid of any personality, and who only relied on her looks to get by. But that being said, I have to say that despite the "attitude" she did manage to clean up really well, and I dare say she could almost pass for someone several years older. In fact sometimes she managed to look more like a real life sex doll or pornstar than the average girl next door.

    I mean you'd have to be completely blind to not notice just how pretty she was, particularly as she started to grow more comfortable with her surroundings and began to wander around the house in next to nothing. It even got to the point where I'd come home to find her tanning topless by the pool, or sitting on the sofa painting her nails in nothing but her bra and panties. In fact she grew so cocky that one day I wandered into the shower only to find a huge black dong suction-cupped to the wall?

    I don't know what was funnier, the realization that she masturbated in the shower when no one was home, or the look on her face when I handed it to her with a loud "thud" and told her to clean up after herself. In any event, I assured her it wasn't a big deal and that I could be trusted to keep a secret, which she really seemed to appreciate. However things then went from bad to worse for her when a few days later I walked in on her rubbing one out to her laptop while watching porn. The poor girl just couldn't catch a break, but on the upside this latest calamity culminated in the two of us sending each other porn links which seemed to break the ice and bring us closer together, just as the links we shared grew increasingly more hardcore and taboo in nature.

    This arrangement went on for several weeks until one night Loren tapped on my bedroom door to seek some advice, and claimed to have some leaked footage of one of the more popular girls in school, Olivia Holt. Naturally I didn't believe her at first, but as it turned out Olivia apparently had a sex tape, and Loren wanted to know if there was a way we could blackmail her into becoming our friend - all in the interest of being "popular" in school. Even though I tried to talk her out of the idea, Loren seemed set in her ways so ultimately I agreed to go along, knowing she'd probably get into trouble without me.

    THE NEXT DAY at school I spotted the popular cheerleader from across the way and waited for the right opportunity to approach Olivia and give her the ultimatum. Right away I could see why Loren had such a crush on her, as Liv turned out to be drop dead gorgeous in person, and judging from the expression on her face I could tell no one had ever spoken to her like that, much less blackmailed her before.

    "What do you want, money?" she stated bluntly. "How much. What's your price?"

    I laughed at the suggestion and told her that all we wanted was for her to take Loren under her wing, and out to a few social events and allow them to be seen together so that it would help "my sister" climb the social ladder. To be perfectly honest I didn't know how Liv was going to react to this, but I was somewhat surprised when she seemed to agree to the terms and insisted that I help her find and delete copies of the tape. It was only later that same night that I realized just how vulnerable and accommodating Olivia appeared to be and that I could have asked for almost anything, including some sexual favors had I only asked.

    "You know, she probably would have blown you if you asked," Loren quipped. "Talk about letting a perfect opportunity slip by."

    Even though I didn't want to admit it, I knew she was right and the thought haunted me over the next few days until Loren and I finally confronted Olivia in the public bathroom between classes, where I decided to go off script and make a few demands of my own. I could see the look of concern on Loren's face as I spoke my mind and told Olivia that I too now wanted something out of this "arrangement," and wanted her to set me up on a date with one of her best friends, Paris Berelc.

    To my chagrin Olivia literally laughed in my face and refused, and for a moment there I thought I had lost all control over the encounter until Loren suddenly snapped into action and pinned Olivia up against the wall, and reminded her just what was at stake and who was in charge.

    "Listen bitch, we make the demands around here understand?" Loren hissed. "That's how this works, or say goodbye to your reputation!"

    To her credit Olivia didn't back down one bit and the ladies seemed to grapple for strength for a few moments before Loren actually appeared to come out on top, something I never imagined would happen.

    "Don't. You wouldn't dare!"

    "oh no?" Loren snapped. "Try me cunt. You have no idea what I'm capable of."

    "Excuse me, what did you say to me?"

    For a moment there I wondered if the two were going to come to blows, when out of the blue Loren abruptly kissed Olivia square on the lips, surprising and repressing any arguments from Holt, while running her hands all over her body. Things then took a turn for the surreal as Loren managed to stuff her entire hand inside Olivia's pants and playfully commented on how wet she was, before withdrawing her slick fingers and making Liv suck them clean. It was probably the most intense few moments of my life, and one of the hottest things I'd ever seen!

    "You guys are fucking crazy," Olivia gasped while Loren repeated the action and proceeded to finger her again. "You two deserve each other!"

    "Just do what we say and no one gets hurt," Loren smirked. "Heck if anything you might enjoy yourself, and learn something new."

    All I could do was stand there stunned as my "kid sister" essentially took charge of the situation and helped herself and now probed and fingered Olivia Holt to the point where the blonde cheerleader actively squirmed against her digits. Even though she didn't say it, or would never own up to it, I could see Loren's fingers were having an effect on her by the way Liv's hips moved involuntarily, whipping gently from side to side as her blonde counterpart twiddled her clit.

    "You're really getting off on this huh?" Olivia sniped before she was forced to lick Loren's fingers again. "Taking advantage of me like this."

    "Not as much as you are I right now, I bet." Loren grinned. "You might act all sweet and shit in public, but deep down you're just a little slut like me."

    "Ha, speak for yourself."

    "Bro, keep a look out yeah?" Loren directed at me, reminding us that we were still in a public place during class, and at risk of being walked in on.

    I leaned around the corner to check if we were alone, only to glance back and find Loren and Olivia locked in a heated kiss, their tongues flicking and wrestling for domination in each others mouths. Watching them together like that, made my cock twitch with excitement since it almost seemed like the more time they spent together the more willing Olivia appeared to be.

    "You won't get away with it you know," Olivia said between kisses. "Someone will find out that you're blackmailing me."

    "Ah I dunno Liv, I think I'm pretty much getting away with it right now," Loren boasted. "And doing all the things I want to do to you."

    It was at this point that Loren kissed the side of Olivia's face and neck and licked all around her throat, all the while as she continued to shove her hand deeper inside her pants and finger-banged her against the bathroom wall.

    "Please, don't leave any marks on my neck." was Holt's only request, which made Loren giggle.

    The entire scene was just mind blowing-ly hot, particularly since I was starting to get the impression that despite all her whining Holt was starting to enjoy our company. Unfortunately for us, Olivia was then saved by the bell and we let her fix her appearance and rush off to class while I spent the better half of the day thinking about the encounter, and how hot and unexpected it was to see Loren take charge like that.

    Try as I might I just couldn't get the image out of my head, and I'm not even sure what turned me on more, watching Olivia Holt get fingered like that in public, or seeing that side to Loren's lusty personality. In any event I found it hard to sleep that night and had Loren decide to pay me a visit, and slip into my room while still clad in her sleep attire that left little to the imagination, and clearly showed off her latest nipple piercing.

    "Are you still thinking about today?" she teased while noting the tent in my pants. "It was pretty intense huh?"

    Loren then went on to describe just how soft and wet Olivia's pussy felt against her fingertips and all the lewd thoughts that had been swirling around in her head since the incident had occurred.







    "We should have done more things to her," she proposed. "You have no idea how fucking wet it made me touching her like that."

    "I have to admit, watching her lick your fingers was pretty fucking sexy," I admitted. "Who knew she was so submissive."

    "Seriously, I don't know if I'll be able to sleep tonight, so if you hear some buzzing from across the hall you know why." Loren giggled. "cos tonight I'm going to break my fucking vibrator!"

    Just hearing this tone from her made my cock swell, much less the notion that Loren was going to go back to her room and spend the night jilling off in bed and riding her toy until she came again and again.

    "You have no idea how worked up I am right now," she sighed. "I've already masturbated like four times today."

    "Jesus,"

    "What are you gonna do tonight, beat off too?" she grinned. "Maybe we should just join forces and do it together, I mean since we both know we're doing it and thinking about the same person."

    There was a long awkward pause before I took the chance and invited her to stay.

    "Well, you're more than welcome to sleep in here tonight if you want?"

    "-seriously!"

    I barely finished the sentence before Loren squealed with delight, then ran out the door and returned a moment later with what looked like a small bottle of lube and a vibrator. I couldn't help but laugh at her enthusiasm as she shut the door behind her and switched off the lights, then climbed into bed with me. We then spend the next twenty minutes or so just pursing several porn sites and tried to find a blonde that remotely resembled Olivia Holt. Ultimately we just gave up and settled for some lesbian porn, with her laying beside me in bed as the sound of buzzing could be heard.

    "Having fun over there?" I chuckled.

    "This is kinda hot, I've never done this in front of anyone before." she said. "It's actually making me really wet."

    "Really? Prove it." I dared.

    With that, I flicked the sheets off her body to leave Loren laying there naked from the waist down, her legs spread wide with her pocket rocket vibrator jammed against her teenage sex. All I could do was shake my head in disbelief, amazing at how incredible she looked in that moment. Her entire crotch glistened with excitement.

    "You have to do it too," she teased. "You have to show me how you jack off."

    I did as she asked and gripped my tool and proceeded to stroke my cock as I watched the toy gently massage the lips of her cunt, her eyes locked to mine as her mouth parted and she moaned softly.

    "Damn it Lorie, how are you this evil with such a sweet, angelic face?" I said while caressing her cheek with my free hand.

    The stunning blonde giggled as my thumb brushed across her chin and lips, before she sucked it into her mouth. I could feel her wet tongue swirl around my digit causing me to groan with delight.

    "Seriously, that mouth is gonna get the rest of your body in trouble," I told her.

    "Mm, don't tempt me." she purred. "I'm that fucking wet right now, if we weren't related I'd totally bury that fat cock into the back of my throat."

    "Really?"

    "-fuck yea."

    To prove her point, Loren then spat a hefty amount of saliva on her hand and reached over to smear it all over my junk, making sure to spread it all around with her fingers before gripping me in her fist. Her actions literally caused me to twitch in her hand, before I reaching over to caress her sex, which really seemed to set her off – her hips twitching wildly the moment I made contact with her clit.

    Loren clearly enjoyed this touch as she ultimately tossed aside her toy and now allowed us both to get each other off with our fingers, as we were now forced to huddle closer together on the bed while we manipulated each other.

    "ugh, I can't wait until I see her again." she cooed, her face just inches away from mine. "Next time I see her I'm going to make her go down on me."

    "Yeah I bet she'd like that – Liv on her knees between us both, being forced to lick your pussy and suck my dick."

    As I spoke, I continued to play with Loren's cunt-clips and now used my index finger to smear her juices around her clit.

    "I bet she's at home right now," she added. "Rubbing one out and thinking about all the things we could have, and are going to do to her."

    "Now there's an image, her lying in bed naked with her legs spread while she's rubbing hard and fast."

    "Mm. I wonder if she has any idea what we're doing right now too, and how shocked she'd be if she knew – you were playing with my clit like that."

    "I'm only teasing your clit cos you're stroking my cock, sis." I grinned evilly. "It's only fair."

    "It's so big," Loren grinned.

    As Loren spoke, she drooled all over her hand again and applied it to my prick, making sure it was well lubed. I followed her actions and smeared some of my own saliva all over her sex, not that it needed it, but just as I proceeded to play with her pussy again she bucked her hips upward which caused my fingertips to brush against her backdoor, and caused her to moan out loud. Noting this I stared right into her eyes as I gently caressed and prodded her backdoor. Even though she didn't say it, I could tell she was extremely self conscious about having someone touch her bunghole, but that only made me want it more.

    "Stop it," she objected briefly.

    "Hey don't get shy on me now," I teased. "Besides, just close your eyes and imagine it's Olivia's tongue down there."

    "ugh-fuck yea." Loren moaned. "I'd give anything to have her eat my ass. God knows I'd happily eat hers."

    "Now that'd be hot to watch, you two locked in a hot and heavy sixty-nine together."

    This comment really seemed to turn her on and she moaned audibly to the premise. Suddenly, without warning Loren got up and leaned over and slipped the head of my fat cock into her teen mouth, taking my breath away. I was literally rendered speechless by the action, something that was so unexpected that I almost came right then and there. Somehow however, I held off long enough to watch her bob her head up and down before she pivoted her head and stared up at me while she ran her soft tongue along the length of my sword – almost worshiping it with her lips.

    "Grr now imagine if I was Olivia," she teased back while licking my shaft.

    I lay there enjoying the sensation of her young mouth for several minutes until I finally reached over to grab at her legs and pulled her on top of me to place us into a sixty-nine, where I immediately began to lick and suck at her young slit, as we both attempted to get the other off first. I initially concentrated on her clit, but soon realized that if I dipped two fingers inside her cunt while I licked the rim of her ass at the same time, it really seemed to set her off and caused her to groan with a mouthful of cock.

    Noting this, I ultimately wrapped my entire mouth around her tiny bunghole and licked her asshole like a man possessed, while she responded to this by groaning out loud while she deep-throated me on the other end of the bed.

    By my count Loren came at least three times in quick succession, filling my mouth with her warm tangy nectar before I finally lost my nerve and abruptly exploded into the back of her throat, slamming my hips again her face and causing her to gag and choke on my rod and spew my spunk all over the bed. There was no doubt about it, things at school (and around the house, for that matter) were about to get a whole lot more interesting to say the least.

    "We should do that more often," she panted beside me, at one point.

    "Sure. Why not." I agreed. "From now on you should just sleep in here with me now."


    ...to be continued.




  2. #2
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    Fark.

    That was incredibly hot, can't wait for more.

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  4. #3
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    All in on Loren !!

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    Loved it TPG. Great writing and looking forward to the next chapter.

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  8. #5
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    Thanks guys, yeah I have to admit this Loren girl is really growing on me by the day.
    She's definitely inspiring me to write again.
    This definitely won't be her last story from me by a long shot.
    Might even try to turn this into a series?

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