High School Harem:
Mindy and Sheri
(Author’s Note: All characters, whether described as such or not, are all over 18 years of age. I’m drawing on fantasies from high school too many years ago to admit to, so some things may seem dated. This will hopefully be the first in a series, depending on reception.)
It was the summer after his junior year in high school, and for Rick Thomas, next year’s graduation couldn’t come soon enough. Rick was already 18, having started school a year earlier than his classmates. Classmates were a stretch to describe the dynamic between Rick and the other teens he went to school with. He had always been on the outside looking in. Tall, thin, gawky and socially inept, he was the stereotypical geek, but he didn’t even fit in with the science club dorks, only being of average intelligence. The previous eleven years had been a blur of last choice for sports, trippings in the hallway, and barely hidden giggles from girls as he slumped around the halls trying vainly to hide the erections that seemed to occur with more and more frequency. Hence the nicknames, which started with “Rick the Dick” and deteriorating from there.
It was one week before school started, and Rick was currently slumped against the snack bar wall of the small town’s local drive-in movie. His parents had forced him out of the house this Saturday night, encouraging him to “go make friends”, as if it was that easy. His parents were idiots, he thought, dropping him off at a drive-in, no car, so here he stood, not even able to enjoy the movie.
Rick had spent all summer in the city, working for his uncle’s landscaping company. As a result of the long hours of manual labor and a well-timed growth spurt, his thin frame had filled out considerably and was highlighted by his dark brown tan. He had been pleased to see in the mirror this evening that the end might be in sight for the acne that had plagued him for years. While still of only average looks, the face that had stared back at him from the mirror was only slightly recognizable as his own and he hoped the new anonymity might allow him to make it through a couple of weeks of his senior year untargeted. He slumped even lower, recognizing his neighbor Mindy’s car slowly driving past.
Mindy Cain was twenty and a sophomore in college. She was enjoying the last few days of summer break at home before returning to school. Mindy was blonde, blue eyed, beautiful, slutty and busty, the lethal combination ensuring that her teen years had been a piece of cake. A former cheerleader, popular with her classmates and the faculty, especially the male teachers, she was more than aware of her good looks and used them to her advantage. She had always dated whichever boy was the current season’s sports star and was not above popping open an extra button on her blouse in order to extract preferential grades. She had found that college wasn’t that much different than high school and was becoming more and more confident that her good looks would allow her to coast through life.
“Who’s the new guy?”
This came from Sheri Stilson, Mindy’s best friend and current passenger. Sheri was twenty as well and roomed with Mindy at college. Where Mindy used her looks to gain her every advantage, Sheri was much more self-deprecating about her looks, though of equally stunning beauty. Taller and slimmer than her friend, she had long black hair and big blue, almost violet eyes, which stood out in stark contrast to her mane. She had been on the drill team in high school, also popular, but relying on her intelligence to get through school, unlike Mindy’s shameless flirtations.
She glanced over at Mindy, as Mindy leaned over the console to get a look at whom she was talking about. Like always, Mindy’s blouse gaped open at the neck, giving anyone with passing curiosity an eyeful of her bountiful bosom. Sheri sighed, “Wish I had boobs like Mindy,” she thought. “But she doesn’t have my movie star mouth!’ It had recently been pointed out to Sheri that she and that new actress Julia something or other, had the same wide, full mouth, complete with straight, white teeth. She flashed a big smile at Mindy when Mindy noticed her glance down her blouse.
“Would you quit staring at my boobs, Sheri?” Mindy asked, feigning exasperation.
Sheri rolled her eyes. “Like you mind! Quit hanging them out if you mind so much!”
Mindy giggled and shook her shoulders, causing the exposed tit flesh to ripple and jiggle.
“You’re just jealous! Now who are you talking about?” she said, stopping the car.
Sheri turned and pointed out the window to where Rick slumped against the wall, trying his best to pretend that he didn’t notice the two girls talking about him, not thirty feet away.
“I don’t know, he doesn’t look fam…wait a minute! I think that’s Rick the Prick! You know, from down the street!”
Sheri looked closer now. It did look like Mindy’s neighbor, but he had definitely changed since she had last seen him over two years ago. She could remember the lustful gazes the gawky teen had given them as they lounged around Mindy’s pool while he sweated bullets, push mowing the Cain’s lawn. Mindy took endless delight in tormenting the shy boy, but Sheri had frequently taken pity on him, trying to carry on a conversation with him. These often ended awkwardly as inevitably he would sprout an obvious hard on and slump away with Mindy’s derisive laughter echoing after him.
“Wow, he’s really grown up,” Sheri said, instantly regretting the words as Mindy chuckled.
“Like what you see Sheri?” she teased, noticing the glimmer of interest in her friend’s eye. She leaned further over towards the open window. “Oh, Ricky!” she called.
“Stop it Mindy! I was just saying…” Sheri shrank back into her seat, horrified that Mindy was apparently going to get his attention
“What?! You think he’s cute, don’t you?”
“I didn’t say that! He’s just, you know, grown up…”
“Cut it out Mindy!”
Rick could hear the two girls plainly and cut his eyes to the car to see Mindy Cain waving him over. He groaned. Just what I need, he thought, more cock teasing. Mindy had forever wiggled suggestively in front of him or flashed him huge portions of cleavage when she knew he was staring, which was often when they had been in school together. He had filled up many a tube sock late at night, fantasizing about his sexy neighbor. He had been enormously relieved upon her graduation and studiously avoided her when she visited home.
“Hey Ricky! C’mere! We won’t bite!”
People at the snack bar were starting to stare, so Rick ducked his head and began shuffling towards the car.
In the car, Sheri turned to Mindy. “Don’t you dare embarrass him!” she hissed at her grinning friend as the obviously mortified boy walked slowly over. She turned back.
“Hi Rick! Long time no see! Whatcha doing?”
“Yeah, Ricky. Where’s your car? You do know this is a drive-in, right?” Mindy laughed. Sheri elbowed her friend as Rick stopped near the window, his hands shoved into his cutoffs. He shuffled his feet nervously.
“Hi guys,” he mumbled and wondered if his mom would come pick him up so soon or if he was expected to stay and endure this torment. From his vantage point, he could see right down Mindy’s gaping blouse and his cock began to harden in his pants. He discretely shifted it so it might not be so apparent, but Mindy noticed his furtive movements and teased a long, manicured nail down her collar and slipped it between her creamy mounds of flesh. She pushed her fingertip between the soft valley and brought it back out, before teasing the corner of her mouth with it. Sheri did not notice Mindy’s teasing, but Rick’s bug eyed reaction was evidence enough.
“Not wearing tube socks tonight, Rick?” Mindy giggled. She had overheard Rick’s mother complaining to her own mom about the plastered shut socks years ago and couldn’t resist the jab.
Sheri whirled at her friend. “Shit Mindy!” She made up her mind right then to somehow make it up to the humiliated kid for all the years of Mindy’s taunting. “Here, get in Rick. You can watch the show with us.”
“Sheri! No fucking way!”
Sheri was already opening the door and bounced out, leaning the passenger seat forward in order to allow Rick to get in the small back seat.
Rick blushed even more furiously. “Uh, aw, no thanks Sheri. I appreciate it though. My friends oughta be here soon.”
Sheri looked at the flushed boy. She could tell he was lying. She did feel really bad over the way she had allowed Mindy to treat the boy over the years and saw no better opportunity to right two wrongs than to let him hang out with them. She hoped that maybe just by being seen with the two popular former students, his coolness quotient might be raised.
It was a friendly, innocent proposal on her part, but to Rick, the idea of sitting in the car with the two beautiful girls was like a dream come true, he could feel his cock hardening even more. He kicked at the ground sheepishly.
“No, really Sheri. That’s super nice, but I’ll wait for them.”
Sheri huffed and grabbed his hand, pulling him into the back seat behind her.
Rick had to duck quickly to keep from getting brained by the doorframe as he was hauled into the car. He plopped into the seat, his bare leg contacting Sheri’s smooth thigh. When she leaned across him to pull the door shut, he sucked in half the oxygen for a mile radius, her small, soft tits pressing against his arm.
“There! Comfy?” she smiled at him. Rick grinned awkwardly back at the black haired coed.
“God, what a pair of lips,” he thought, looking at her full mouth, “I bet she could suck the chrome off a….”
“You’ve got to be kidding, right?” Mindy huffed from the front seat, turning around to stare at Rick.
“I’m not. So you might as well find someplace to park. Rick is going to be our guest tonight,” Sheri said with authority. Mindy muttered under her breath and gunned the car towards the back row of the drive-in, hopeful that no one would see who was in her car. Flicking her eyes to the rear view mirror, as she listened to Sheri chat one-sidedly with Rick, she had to admit that little Ricky had grown up quite a bit since she had seen him last, but still…
Mindy found a parking place and shut off the engine. She rolled her eyes as Rick haltingly told Sheri about his summer. She could see that her friend was showing genuine interest in the geek’s ramblings and she threw open the door.
“I’m going to get a drink. You want?” she asked looking at Sheri.
“Yeah, you want anything Rick?”
“Uh, popcorn?” Rick could see the repugnance on Mindy’s face and scrambled to pull some money out of his pocket. She huffed and held her hand out, snatching the wrinkled twenty from his hand.
“Your treat geek,” she snapped and stomped off.
“I’m sorry she’s such a bitch to you Rick,” Sheri apologized when she turned back to the boy. “There’s no reason for her to act like that.”
Rick blushed even redder and shrugged. “It’s ok. I don’t even notice.”
Sheri patted his knee, her hand cool on his leg and didn’t notice his bugging eyes as she turned towards the screen and reached out to attach the speaker to the window. “You’re nice to act like that, but we both know she has been a shit for a long time.”
“You more than make up for it Sheri,” Rick said before he could catch himself. He braced himself for a slap, but Sheri just turned and patted his arm.
“Aww, you’re adorable!” She suddenly leaned over and chastely kissed his cheek. Her peppermint breath floated over Rick’s face and her hair brushed his face as she swung back around. He shifted in his seat, his cock at full mast, desperate that he not creep out Sheri with his woody. She was being so nice to him, he didn’t want to ruin it. He sat back and tried to concentrate on the previews, his nose full of Sheri’s clean, fresh scent.
Minutes later, Mindy walked back up to the car, struggling with the two drinks and large popcorn. She was disgusted to hear Sheri giggle from the backseat at whatever lame story Rick was stuttering through. She placed the items on the roof and yanked open the door, taking satisfaction in the way Rick jumped in surprise.
“Here are your snacks lovebirds,” Mindy sarcastically said, handing back the popcorn and drink. She got in and slumped as far as she could in the seat and still see the screen. A horror movie she had been dying to see was showing and this only pissed her off more. Rick’s presence was sure to ruin it.
Sheri giggled again from the back.
“Mindy! Did you know that Rick saw the first Star Wars twenty times?!”
Mindy rolled her eyes. “Why am I not surprised? Watch out if he wants you to put your hair up in buns.”
Sheri punched her friend in the shoulder and grabbed a handful of the popcorn Rick was holding in his lap. If Mindy would only give this kid a chance, she thought, she’d see he wasn’t the dork he’d been made out to be. While he would never be a suave jock type like Mindy went for, Sheri found his stories entertaining.
“Tell me more about this new Watchmen comic,” she prompted Rick.
Rick felt like he was rambling and he was, practically chattering non-stop once Sheri got him talking. He found her easy to talk to, once he got past her beauty, which was hard to do. Her huge blue eyes twinkled when she laughed at his lame jokes and every time she flipped her long black hair, his nose was filled with that clean, fresh smell. Their chatting trailed off as the movie started.
Rick’s eyes were glued to the screen, but he was painfully aware of how Sheri shrank against him each time the hockey mask wearing villain dispatched a victim. Her long, smooth legs rubbed against his as she shifted positions and her B cups brushed his arm from time to time. His dick had been hard for thirty minutes, and while he never wanted this evening to end, he looked forward to the chance to rub one out once he got home.
For her part, Sheri had no idea of the effect she was having on the horny boy. While not as well traveled as Mindy, Sheri had had her share of boyfriends over the years and had quickly gotten tired of their clumsy groping. She was enjoying Rick’s company, but only saw him as a friend, an innocent kid who she could maybe pump up their self-confidence with some conversation.
The next hacking came from a dark closet and Sheri squealed, pressing herself against Rick as the villain disemboweled someone on screen. Without taking her eyes from the screen, she reached down for some more popcorn without being aware that her startled jump had spilled the box on the floorboard.
Rick yelped when he felt Sheri’s hand close over the iron bar in his shorts. It pulled back for just a second and then closed back over the fat tube, squeezing tentatively. He cut his eyes at Sheri, whose eyes were no longer on the movie screen, but glued to the fabric stretching monster in his lap.
When her hand first contacted the huge, hard lump, Sheri instantly knew what it was; having had her hand forced into enough slobbering boys’ laps to know. She jerked her hand back quickly, but curiosity brought it back. “Damn, he’s hung!” she thought, her nipples instantly stiffening inside her tight, white T. Small enough that she rarely wore a bra, she could feel the scratch of her shirt against the sensitive tips as they strained outwards. She timidly gripped the thick shaft, feeling its heat burn her palm through the denim fabric. Even in the darkened interior, she could see the length of the broad cock snaking down his thigh. She ran her hand down the pulsing cylinder to where the corpulent head lay, not two inches north of where his cutoffs ended. Slowly she slid her cool fingers under the edge of the fabric.
When she dropped her hand down on his hard cock, Rick was sure that he was going to shoot off in his pants. This was only the second hand to ever touch his hard on, the first being…well, you know. Sheri seemed to be fascinated, not disgusted by his erection as she slid her hand down, squeezing the bursting tube tenderly. It took all of his self-control not to cum at the first touch of her cool fingertips as she slipped her hand underneath his shorts.
Totally unaware as to what was going on behind her, Mindy called over her shoulder, “Don’t let him try the hole in popcorn box trick Sheri!” This startled the two, not enough that Sheri withdrew her hand, but enough that she raised her eyes to look at Rick. He was breathing heavily through his mouth, his eyes wide, and the whites of his irises visible in the dark. When she withdrew her hand, he was sure that his first, albeit abbreviated, hand job was done.
Sheri raised her finger to her lips to shush him and felt the heat of his cock still on her skin. Shocking herself with her boldness, she reached down and began to unsnap his pants.
Rick’s heart pounded wildly in his chest as Sheri slid his zipper down and folded back his pants. He watched as her hand slid into the opening and closed around his shaft. His eyes flicked to hers, but her attention was focused on the big tube she was hauling out into the opening.
“Fuck me, that’s huge,” she whispered as the enormous pole waggled in her fist. It jutted above her fist menacingly and she was sure that there was room enough for her to stack her other hand on top with room to spare. She licked her lips unthinkingly, further inciting Rick’s passion at the sight of her pink tongue teasing her impossibly full lips. She looked at him again.
“Can I?” she asked. Not trusting his voice, Rick adamantly nodded his head. It would take an army to stop him at this point. He bit back a whimper as the sexy girl began to slowly whip her hand up and down his aching pole.
Sheri couldn’t get over how fucking big the hard cock felt in her hand. The skin was smooth and soft, underlain with his spongy hardness. As her hand crested the top, a big droplet of cum oozed from the tip, she opened her hand and spread the goo over the tip with her palm. Sneaking a look at Mindy, who was engrossed in the movie, Sheri risked licking her palm, intending to only lubricate her act. The salty flavor of him was a pleasant side affect as she began to slowly pump him, her eyes glued to the towering prick.
Rick’s eyes rolled back in his head and he groaned, much louder than he intended. This unfortunately got Mindy’s attention and she swung around.
“What are you two…?” Her words trailed off at the sight of her best friend’s hand filled with Rick’s pink missile. She looked at Sheri who seemed to not even notice their discovery. When she looked up at Rick, his mouth dropping open in shock, she overwhelmed his attempts at holding out and his hips pumped up off the seat cushion.
“Fuuuuuuuck!” he gasped.
“What the hell?!” Mindy managed to get out before the first salvo leapt from his blooming cock and splattered wetly against the ceiling of her car. With a barely stifled whimper, Sheri dropped her head, her full lips parting wide to encompass the exploding cock. She had never had a cock in her mouth, much less one shooting glob after glob of cum onto the back of her tongue. His output quickly overwhelmed her and she pulled back, the last shot grazing her cheek and clinging stickily. She continued to pump his reeling snake, her mouth still full of his hot, salty load. She closed her eyes, moaning in lust as she struggled to swallow the immense load. She opened her eyes to see Rick staring at her with something like reverence.
“Have you two lost your fucking minds?!” Mindy screeched, looking at the big wet stain on her upholstered roof. “You’re paying to clean that shithead!” she said to Rick.
Sheri’s voice startled Mindy out of her rant. “What!?!”
“Drive to the park. Now.”
“No fucking way. Were not leaving ’til…”