Another new series of stories. This one is a lot longer, focusing a lot on character building and romance, so if that's not your thing, I must redirect you to my other works, as you probably won't enjoy this(or at least skip forward if you don't care for characters much). This story goes into great detail about a friendship that flourishes into more. If you like long stories with lots of detail, etc, then please, enjoy the story:
The story starts in their freshman year of high school and lasts for many years thereafter. Justin and Brittany were complete strangers as they went to different middle schools.
Both kids lead very different lives. Now Brittany was a beautiful girl. She was short and petite, with long black hair, usually straightened. Being half Mexican and half white, she looked amazing. Her boobs were, of course, smaller, maybe Bs, but it fit her smaller frame well. Her ass was an amazing gift of nature, however, as her genes came together perfectly for her. She was ambitious and charismatic, and actually had gotten herself to be ASB president at their high school. By graduation time, she had a boyfriend, John, and they had been dating for a good two and a half years, and even though he was a year older and in college, it seemed they would be getting married soon after the ambitious teen graduated. Her life seemed to have everything going on for her.
Justin on the other hand was quite a bit different. Sure, he was fairly good looking; he kept fit and had a charming face, but he wasn't quite at Brittany's caliber. Justin hung out with people from all walks of life, from the varsity football team he was on, to the drama kids he would always "improv" with, to the nerds that he would debate and play video games with. Even still, it was more tolerance than kinship, as there were very few people that the semi-popular kid would actually call his friends.
When he first met Brittany, it was during her "campaign" for presidency freshman year. Before the first bell rang was one of the few times that Justin could talk with his group of "friends". There were around a dozen of them sitting and standing around the table, bullshitting about nothing in particular, when Brittany came up to the group, followed by her posse of friends. Brittany began a well-rehearsed speech right then and there, urging the group to all vote for her for obvious reasons. Striking up a conversation with Danial, one of Justin's closer friends, she acted like she was the boy's best friend. Concluding her speech to the group, and wrapping up her conversation with Danial, she gave him a hug, then parted.
"Woh man, gettin all cuddle cuddle with miss president-to-be, are we?" mocked Justin, hiding his respect for the nerd friend of his for even working up the courage to make eye-contact with the gorgeous girl.
"Yeah, we work a lot together in DECA, so we've become pretty good friends," Danial dismissed the jesting at his expense, switching the conversation back to the new video game coming out later that week.
Now Justin was pretty good at judging people. He knew that sounded bad, but his first impressions of people were usually spot-on. Now he got a strong vibe from Brittany and her close group of friends that she felt she was too good for most people. Maybe she was using Danial for a better grade, or maybe she actually saw something she liked in this friend, but Justin didn't count on it.
Storing the memory in the back of his head, Justin fast-forwarded to the next milestone in his and Brittany's relationship. Brittany had won the election, and was actually quite busy with her royal duties. Justin rarely saw her in the halls and Danial hardly ever talked about her in DECA either. Justin was sure that his prognosis was correct, that the girl was "too good" for the poor guy and that she was only using him.
It was the start of second semester that year and Justin filed into his new 3rd hour class. The teacher, Mrs. Hymes was one of the 'cool' teachers that let you choose your seats. The tables - as the school didn't use desks much - were arranged in islands, grouping four kids in each bunch. Justin was one of the first kids in the class, and shot right toward the back corner of the room, where his comfort zone was. His best friend Shelby came in, sitting right across the table from him, as to make the class much more tolerable.
Shelby was a gorgeous girl. The slender blonde was just a little taller than Justin. Her long legs met perfectly into a gorgeous ass. Her boobs would grow into large C cups, and her hair trickled down onto her shoulders. Sitting together at school whenever they could manage, they figured the class wouldn't be so bad.
The room quickly filled up, when Justin noticed Brittany enter the room. Making eye contact with Justin, she flashed a smile, then walked straight toward him.
"Hey there! Is anyone sitting here yet?" Brittany asked, signaling to the seat right beside Justin.
"Um, no. No, it's still vacant," Justin replied, curious why the girl would choose to sit by two complete strangers when there were surely a few of her friends in the class. Or at least people that she knew at all.
But sure enough, Brittany sat down, as if Justin and Shelby were her friends she had been looking for all day. "Oh hi! I don't think we've met yet. I'm Brittany," she directed to Shelby, shaking her hand like a businesswoman. Then she turned to Justin, "And YOU! You're Justin, right? You're one of Danial's friends. I hope I'm not imposing, you just seemed neat, so I figured we could sit together," she explained.
"No, by all means, you're welcome here. This here is Shelby. Any way that you can make English class more entertaining, I will welcome with open arms," Justin concluded, then broke into short conversation before the bell rang. The entire time in the back of his head, Justin couldn't help but think "What does this chick want with me? What is her angle?"
The class bell sounded and Mrs. Hymes was quick in diving into the ice breakers. The fourth seat in the group of desks was never filled, leaving the three of them alone in the corner of the room. Justin didn't mind, as was his preference. Most of the kids in the class were idiots. In fact, he thought, the three smartest minds were probably sitting at his table.
Mrs. Hymes continued her preaching at the front of the room. "Now I want each of you to turn to your neighbor and ask them three questions of anything meaningful. It could be a 'when you first saw me...' or whatever you'd like. Take your time, and get to know your peers a bit." She paused, before adding "Let's keep it friendly... and G-rated!"
Brittany took charge right away, "Okay, that's a good one. When you first saw me, what were your first thoughts?" She smiled, looking at both of her new partners.
"Well, you looked very pretty," Shelby said, being a little coy. Justin jumped right in with the blatant truth, as was his usual custom.
"I honestly thought you supercilious and stuck up. That you think yourself too good for most people. But now I'm not really sure..... You're a very curious girl," he explained. Shelby kicked his feet, staring daggers at him for his boldness.
"Well, that was surprisingly honest!" Brittany replied, still as chipper as before. "I do enjoy people who arn't afraid to speak their mind. Well when I first saw you," she turned to Justin, "I thought you were the kind of person who is easily irritated with the people. Not just stupid strangers, but peers that most would assume to be your friends. And you, Shelby, are the exact opposite, finding the good in everyone, right?" Justin smiled at her accuracy.
"Well now! Is this English, or Psych class?" Shelby jested, before adding "My question is this, what are you planning on doing after high school?"
"Well, you called it!" Brittany responded. "I actually would love to be a psychology major. But being a doctor is so expensive, so I have to get a LOT of scholarships," she continued. "What about you guys?"
Shelby countered with her aspirations. "I'm actually going the dentist rout. That's what my mom does, and she loves it." Brittany responded with her acknowledgements and praises, then turned to Justin.
"Me? I really have no idea yet," Justin admitted before adding, "I want to do something that keeps me entertained for 35 years, so I have to think hard about it. Maybe diagnostics medicine..." he trailed off.
"Oh my gosh, like Doctor House?!" Brittany responded excitedly. "That would be such a fun job!" Justin agreed, saying that the show was, indeed, his inspiration as it seemed there was never a dull day. They chatted for a bit about that, before Brittany dove into the final question, "Alright then! Third question..... Oh, so are you two together?" Brittany inquired. Shelby smiled as she looked at Justin to answer the question that was asked all too often.
"No, we arn't. We're just good friends here," Justin rehearsed. (Later on, they would attempt a friends with benefits role, but that's later in the story.)
"Oh, I see. Well you guys look great together. I mean as friends... You seem really happy every time I see you together. I wish I had close friends like you two," admitted Brittany.
Are you kidding me? Justin thought. You're followed around by your little group of friends that are inseparable to you. There were the girls: Alison, Jo, and Dee, and then the guys, Dakota, Kyle, and -if he was in town- her boyfriend John. They were always together, either hanging out, going to the beach, or partying with each other. And here the girl was claiming to be lonely. "You seem to have quite a few friends," Justin said, maybe a little irritation in his voice.
"Well yeah, and I love them to death. But I just... You two seem to NEED each other. I can go weeks without so much as a 'how are you' from even my closest friends. Sure, they think I'm fun to be around, but do they really love me?"
"That's.... pretty deep sharing for two people you just met," piped in Shelby, who was a little uncomfortable, and it showed.
"I'm sorry, this is kind of awkward isn't it?" Brittany apologized.
"No, no I get it," replied Justin. "Yeah, this is hella weird conversation for people you just met. But you WANT that vulnerability. You want to show your weakest side and still be accepted. You're tired of being surrounded by people and still feeling alone. I take it your parents are divorced?"
"Justin! Don't therapize her in the middle of class! That's rude," Shelby scolded.
"No, he's right. That was... harshly accurate. I don't know. I feel my idea of what relationships should be is too ideal to ever be real," Brittany admitted, truth bleeding through her words. Justin couldn't have agreed more.
Justin and Brittany had three classes together that term (both with and without Shelby), and their friendship flourished. Justin found it oddly comforting that their solidarity was formed by their solitude, which brought them closer together. Sure, they both had other friends, but there was no one with whom they shared so much. Family issues, emotions, sex. Nothing was off the table for these two, and it felt very refreshing to the both of them. Justin felt attracted to the girl, of course, as she was gorgeous, but he knew that she was committed to her boyfriend John, and he wasn't going to risk this friendship that he had craved for years for something that was ultimately going to fail. That never stopped either of them from flirting or joking around sexually with each other. In fact, Justin pushed the sexual joking maybe a little too far for most friends, but he knew Brittany's limits and knew what she enjoyed.
Now they were in their senior year and Brittany could not wait for her birthday coming up. In the (coming up on) four years that they had been friends, Justin had noticed Brittany grow into a beautiful girl. Her dark hair was long, stretching nearly to her waist. Her chest was still rather small, her boobs straining to be a B cup, matching her petite body frame. She was only 5'2, and chances were, she was done growing. Luckily for her, she was topped off with the most perfect ass you could imagine.
Having Brittany turn 18 in a few days meant that her and Justin would be going to Miami, a good hour or so away, where her boyfriend John was attending college. It would be a surprise visit to John, as he was fearing he would have to miss his girlfriend's birthday on account of work and school not allowing either of them to meet up. Brittany was hoping to solidify her role as a good wingman by setting Justin up with one of the countless sexy girls she knew would be at her boyfriend's parties. (John's class schedule was perfect, as his earliest class was at 12:30 in the afternoon, meaning he was clear for late nights whenever he pleased.
"What's up my beast of sexualness? What time where you planning on coming over?" Justin texted Brittany that Wednesday morning, verifying plans they had made earlier that week.
"Greetings sir! What time were you thinking? I have a mass murder to attend this morning, but that shouldn't take but an hour or two. Noon work for you?" Brittany responded with her virtual humor.
"Hell yeah, just let me know if things go south and you need to lay low for a while. I've got a nice basement I can tie you up in for a month or two, lol. Nah, 11 o'clock work for ya? That way we can get there in plenty of time." Justin countered.
"I'll be there Slim. Just don't tease me with that basement. You know how much I enjoy shit like that ; )" Reading the final text, Justin put his phone down, looking at the clock. It showed the time as 8 o'clock, so he had plenty of time to get ready. He recovered himself in sheets, falling back asleep rather quickly.
He awoke, however, only an hour later, as the clock informed him. Justin decided he might as well get up and get ready for the long drive. Stretching in bed, his arm gently bumped into Shelby, who was still asleep.
Last night wasn't the first time he and his friend had hooked up, but it was certainly one of the funnest. Shelby had just gotten out of an unfaithful relationship and, needing comfort, decided to spend the week-long break off of school at Justin's small townhouse. (Slightly well-off from years of under-the-table dealings around school, Justin was able to move out of his parents house only weeks after turning 18, where he now rented the townhouse from a family friend for close-to-nothing.)
Justin climbed out of bed, pausing for yet another long stretch. Waltzing to the bathroom, he quickly relieved himself, followed by his daily routine of teeth brushing and showering. He stripped down, climbing into the tub, and turned the hot water on.
Shelby slowly awoke, hearing the water run. Looking at the clock, she cursed the early hour, but decided it was better than her usual Wednesday wake-up time of six (in order to be to school on time). A smile on her face, she decided to surprise Justin as she crept into the bathroom. Ready to startle him, she tore open the shower curtain, yelling out "Oh my gosh!" to add to her scare tactic.
Justin nearly leaped out of his skin as his vision was filled with the bright bathroom interior and Shelby's screaming, as she was now laughing at his expense. "What the hell, girl?" Justin grinned, accepting that his friend had got him, but determined to get her back. He quickly grabbed Shelby, yanking her into the tub with him.
"NO!" Shelby screamed through her laughter. "You asshole, you're getting my clothes soaked!"
Justin merely laughed as the T-shirt and boy shorts that made up Shelby's nightwear filled with water. "Serves you right, I almost pissed myself, girl," he said with a smirk as he leaned in for a playful kiss.
"Well, since I'm already in here..." Shelby's tone changed to a seductive one. Her thumbs clipped at her waistband as she wiggled out of her shorts, tossing them onto the bathroom linoleum with a *FLOP*. Justin smiled between kisses as he helped her out of the T-shirt, which was soon flung across the room as well.
Justin could feel Shelby's hand creep up his thigh, finally resting on his package. He reached around her body, gripping her ass as he felt her hand cup his ballsack. He grabbed the back of her thighs, pausing momentarily so she could brace herself, then lifted her up, wrapping her legs around his own.
He quickly inserted his hardening tool into her pussy, now wet inside and out. He was met by a sigh of relief as Shelby immediately started grinding her hips as to maximize pleasure. Justin humped as hard as he could while standing stationary, but alas, it was not enough to keep him satisfied. "Alright, switch it up," he ordered, much to Shelby's dismay. He lowered her back onto her feet, then turned her around, so she was facing away from him. Putting both of her hands on the wall she was facing, Shelby smiled, bracing herself for impact. She was greeted by a now fully erect cock plummeting into her from behind. She cried out as her body was pierced with the foreign object, her pussy welcoming the alien resident.
"Fuck yes, baby. Harder!" she beckoned as Justin began slamming into her at full speed. She grunted with every thrust as he plowed into her backside. His arms quickly encircled her body, finding rest on her dangling tits. He squeezed them, using the handles for more leverage, forcing Shelby to cry out in pain and extacy.
Justin loved how tight Shelby's pussy felt. Almost two years ago now, he had taken her virginity, but even now, it was still just as tight as that first time. He fucked her mercilessly for quite a while before he finally was ready to unload. Announcing his upcoming arrival, Shelby replied by pleading for him to cum inside of her. Justin quickly obliged, grunting as his dick erupted into her welcoming pussy. Shelby swooned as her insides were filled with the hot spunk, closing her eyes in pure bliss as Justin slowly pulled out. Feeling him turn her around, she was met by a cute little butterfly kiss.
"That was amazing, Shelby," Justin complimented. "Have I ever told you that you were just... perfect?"
Shelby smiled shyly. "Once or twice I think," she winked, playfully gripping the boys butt. "Now, look, you go get dressed, and let me finish up in here, and when I'm done, I'll make you some french toast."
"It's official. I think I love you," Justin said gawkingly as he kissed her. "You sure you don't want me to... 'finish you up'?"
Shelby laughed a little, "No sweety, I don't mean sexually. I'm still recovering from last night, you stud, you," she said in an overly feminine voice. "I just mean take an actual shower. Besides, I was up one last night, so now we're even," she explained with a wink.
"Oh, I get it. Alright, well I'll see you downstairs!" Justin said, stepping out of the shower. He dried off his body, then proceeded to his post-shower clean up. He shaved, put some deodorant on, and lastly, got dressed. Finally finished, he started for downstairs, bidding Shelby goodbye as he left the room.
Flopping down on the couch, he turned on the television. Quickly finding there was nothing on, he decided to watch a pre-recorded Two and a Half Men while waiting for Shelby. Looking at his phone's clock, he was amazed at it still being only 9:45, time moving incredibly slow for some reason. Luckily, he heard the shower turn off upstairs, meaning breakfast would soon be started. He smiled at his fortune for having such an amazing relationship.
It took Shelby another 15 minutes, but finally, she deemed herself acceptable to be seen. Climbing downstairs, she found Justin staring at his phone, begging time to move faster. As she took her final step, she announced her presence, asking Justin the unnecessary question of "Are you ready for something to eat?"
Justin turned around, mocking Shelby's need to ask such an obvious question. As he turned, he found she had gotten ready quite well. "Damn, girl, you clean up good!" he said smiling. "Don't get me wrong, I love waking up next to you with your natural look, you still look amazing, but right now, you just look... breathtaking!" was the only word that came to mind. Shelby, in the short amount of time in the bathroom, had let her hair down, as it now dangled wavingly past her shoulder blades. She had also done her make up, accenting her already-positive qualities. Her blue eyes sparkled brightly as her tone was set to a perfect color. She smiled at Justin's baffled complimenting, making her even more irresistible. As if it wasn't enough, she had on a sexy little top, intended for night use, as it was a pink nightgown with a black lacy outline. The material struggled to cover her lower half, and every time she lifted her arms even slightly, Justin could see her matching pink lace panties.
"You're too sweet!" she told Justin as she kissed him softly before heading to the kitchen. Justin debated following her, but before he even stood up, he was shot down. "Don't you dare interrupt my cooking!" she demanded playfully. "I'll be out there soon enough, so your stomach and your penis can both wait!" She giggled at Justin's moans, then disappeared behind the kitchen corner.
It didn't take long for the aroma of cinnamon and maple to fill the entire townhouse. Justin heard sizzling, which meant that the french toast would be complimented by bacon. He cheered internally as Shelby announced that breakfast was almost ready. The clanking of plates gave hint that the dishes were ready to be served.
Shelby came around the corner sporting two plates full of french toast, bacon, and scrambled eggs. Setting them down on the coffee table, she quickly turned back toward the kitchen. Appearing again, only seconds later, she brought two glasses of orange juice. A third and final trip included syrup and powdered sugar. "THERE!" Shelby concluded, finally sitting back on the couch next to Justin. She gave a content, albeit tired sigh, as Justin repeatedly thanked her for the bounty she had prepared.
"You're so fucking amazing. Do you understand where I'd be without you?" he asked, leaning in for one last kiss before they would divd into a feeding frenzy.
"You probably wouldn't survive," she jested. "Oh by the way, there is a lot more in the kitchen if you want seconds or if Brittany is hungry when she gets here."
"I wouldn't survive at all," Justin continued. "You are the Pepper Potts to my Iron Man," he smiled, then finally dove into the plate of food.
Every bite, dipped in the warm buttery syrup was matched perfectly with a coating of powdered sugar. The consistency of the bread was perfect as all of the flavors had an orgy in his mouth. Justin moaned his praise, to which Shelby merely answered by winking as she joked, "Wow, deja vu, huh?"
The pair continued to eat like starving men, returning to the kitchen for seconds the both of them. Finally satisfied, Justin pushed his plate away, patting his belly and lounging back onto the couch. "That was delicious, girl," he complimented again. "I'd make sure to thank you properly, but you made it so I can hardly move."
"That's okay sweety," Shelby toyed. "Every man has problems every once in a while," she continued to tease. "Let me go into the bathroom and brush my teeth, then I'll be right back down here."
She walked back upstairs, moving her hips seductively as she passed Justin. He reached into his pocket, pulling out a stick of mint gum to help absorb some of the syrup in his mouth. A few minutes later, he heard Shelby climb down the stairs once more. She quickly jumped over the back of the couch, landing directly beside Justin who let out a grunt from the bouncing on his full stomach.
"Aww, big boy must have eaten too much," Shelby teased, bending down to Justin's crotch. "Just lay back, and allow me." She pushed his body so he was leaning against the back of the couch, creating plenty of room for Shelby to maneuver.
She unzipped his jeans, tugging them down just enough so his crotch was well exposed. She fondled his limp cock until she was able to push it through the hole in his boxers. Immediately, she licked the head with her tongue, darting quickly back and forth over the pisshole, only to run a long lick up the entire rod right afterward. She quickly changed her tactics however, as she held the base of his dick with her hand and started bobbing down on it, wrapping her lips around it's circumference. Her tongue made contact with Justin's shaft as her lips continued to suck, the friction of her mouth becoming more and more rapid.
Shelby looked up to Justin, seeing his eyes closed in pure pleasure. She felt overjoyed at his happiness, and knew how to keep it going. She removed her hand from the base, using only her mouth now. Both hands she locked together behind her back, as if she had been tied. She started moaning as her mouth enveloped more of Justin's prick. Taking more with each bob, she soon found the tip of his member at the back of her throat. Relaxing her muscles, she continued to bob down, receiving the invading substance despite her body's physical rejections.
Shelby gagged slightly, but held true, until her lips made contact with Justin's pelvis. Retreating only slightly, she shoved her face right back into him, as she fucked her face with his stationary dick. "Ah, fuck yeah baby, I'm getting close!" Justin announced.
Shelby pulled back a bit, resuming her softcore oral assault. She replaced her hand at the base of his cock, then proceeded to jack him off as quickly as she could, all the while keeping her lips surrounding his head. Her hand and lips synced perfectly, as her speed increased. "Come on baby! Cum for me! Cum all over my face baby!" she beckoned, quickly sending Justin over the edge. Grunting loudly, he painted Shelby's face, splurting wave after wave of cum onto her. The first stream landed in her mouth, leaking onto her lips. Quickly pulling the dick out of her mouth, the second jet of cum shot up onto her upper lip and cheekbone. A third wave struck her in the eyelid, forcing her to glue her right eye shut. a final, less powerful, fourth wave dribbled onto her chin.
Now completely spent, Justin sighed contently. "You are just too perfect," he concluded. "Just wait, I'm going to marry you one day, and you're going to be sorry for being so perfect, cause you're gonna have to keep it up," he joked with a wink.
"I wouldn't mind sweety," Shelby replied. "You're going to have to make an honest woman out of me sometime, though," she teased with a smirk. "Now I'm going back to the bathroom..... AGAIN. To redo my make up that you ruined." She laughed as she bounded up the stairs. Justin merely leaned back, putting his feet on the coffee table. He was amazing at how great his life was going. And to top of his wild sex-filled week with one of his best friends, he was leaving on a road trip with his other best friend, filled with booze, fun people, and (if Brittany's party predictions were accurate) more sex.
And that is exactly what Brittany was thinking as she turned onto Justin's street. It was going to continue to be an interesting week.