The Side Hustle
Disclaimer: This story depicts sexual acts between minors. Some of the chapters feature boy/boy, others boy/girl.
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Author’s Note: I’m still pretty new to erotica stories, and I’m definitely trying some ideas out as I go, but I would love to hear how the stories might connect with you! Feel free to shoot me a message at LeviHolland@protonmail.com
Also, like exploring the idea of some first-time stories, so if any of you have an idea or personal examples to share that you might want to see turned into a story, feel free to shoot them my way, too!
Synopsis: A group of preteen boys think they’ve discovered the perfect way to score some extra cash for themselves under the cover of the middle school football matches. Before they can get started however, they’ll have to learn to pay it forward.
The Side Hustle
- Chapter 1 -
“For the land of the free...and the home of the brave!”
The bleachers rumbled with a thousand footsteps after the singing of the national anthem. It was official; Friday night football was underway.
Sam couldn’t get enough of the Friday night lights.
For one, the middle school had gotten a new sponsor in Chic-Fil-A, with fresh sandwiches coming from the concession stand every game. That combined with the aroma of Domino’s Pizza was pure Nirvana to his twelve-year-old nostrils. What more could anyone possibly need to live off?
Two, the games were always a great chance to see some of his friends from previous years that never seemed to end up in his same classes. Seriously, it was like the teachers all had a secret pact about who shouldn’t be with who when the class rosters were made.
But the main reason Sam loved the games was because of the side hustle he began with his two closest buddies, Riley and Caleb.
You see, the start of middle school had been an eye-opening experience. No longer did teachers escort them around the school like a bunch of babies. In the magical land of middle school, they were given actual freedom. This was the freakin’ U. S. of A. for cryin’ out out loud! They deserved to be given a loose leash! And what a freedom it was. Lunch with whoever you wanted, pep rallies where they could go nuts, and the sports. So many different games to see, and for the trio of friends, football was where it was at.
Not to play, of course. They didn’t have the bulk for that. No, for them it started as a fun way to cut up at the end of the week. The snacks were delicious, the games were exciting, and it was one of those intangible moments in life that seemed ripe with possibility. As the year went on, basketball was cool but didn’t have the same life to it. Baseball was frankly too hot. Nothing seemed to hold a candle to the energy created during the football matches.
For the start of 7th grade, they wanted to do something a bit different. And so it was that the trio united in Sam’s bedroom, a week out from the first game of the season.
“What if we ran a gambling ring?” Riley suggested. He was picking at one of his toenails. “You know, like we take bets on how many points people think Misty Pines will win or lose by?”
“Dude, dig out your toenail funk somewhere else!” Sam shouted. “That’s my bed!”
“Isn’t gambling illegal?” Caleb asked from the yellow beanbag chair on the floor. He’d always been the smallest and shyest of the three boys ever since the 4th grade, scared to take chances where Sam and Riley were the more daring.
“Isn’t gambling illegal?” Riley mocked. “Who cares? Money is money!”’
“I was just saying,” Caleb replied, hanging his head as his sandy blonde hair fell in front of his face.
“No, Caleb’s right,” Sam said. “Too much risk of someone being a little bitch and snitching on us.”
Caleb laughed at Sam’s swearing. “Oooh, Sam’s cussing. I’m telling.”
Sam leaned over and shoved Caleb on the shoulder. “What’re you, ten? We’re big kids now. We can say shit like that.”
“You can, maybe,” Caleb said. “My mom would kill me.”
“Well, duh, doofus,” Sam shot back. “Just don’t let her hear you.”
Riley stopped messing with his toes and fell back against Sam’s mattress. “It’s too bad we can’t get away with something crazy. I feel like drug dealers and pimps make all the serious cash. I just want enough to buy a PS5.”
There was a silence in the room until Sam raised his head. “Maybe that’s not a terrible idea.”
“Uhh, what?”
The two friends swapped glances before turning back to their de facto leader.
“No, really. Think about it. What does every middle school student have on their mind half the time?”
“Fortnite?”
“Snacks?”
“Sex, you dumbasses!” Sam shouted and winced, realizing how loud he’d just yelled in his house.
When there was no commotion, and his parents didn’t come barging up the steps to his room, Sam continued.
“I’m not talking like full-on sex or anything, but you can’t tell me people wouldn’t kill for a little hand action or a blowie?”
Caleb laughed again from the beanbag chair.
“I’m serious, dudes! We could charge like $20 per person and have enough cash in no time!”
Riley sat up from the bed, doing a different kind of math in his head. “Alright, genius. And just where do you plan on finding someone who’d be willing to do that?”
“And how would we even pull that off?” Caleb asked.
“Leave that part to me. I think I know just the person.”
“Absolutely not.”
Sam stood with the infamous Molly Sinclair outside the row of lockers in the 7th grade hallway. Although they weren’t personally close, Sam had known Molly for years thanks to his older sister, Rachel. Rachel and Molly were best friends from dance class, and over the past year, Sam had caught more than a whisper or two about some of the extracurricular activities that Molly got up to. It wouldn’t surprise Sam if Molly Sinclair was Misty Pines Middle’s worst kept secret.
“Oh, come on. Think about it. It could be a great way to earn a little money. It’s not like you wouldn’t do it either way.”
It was like someone shot a pistol in Sam’s chest with how quickly Molly jabbed a finger at him.
“You’re lucky you’re Rachel’s little brother or this would be a very different conversation right now.”
“You’re right, sorry,” Sam apologized. “At least think about it. We’d find a way to keep it completely anonymous. No one would ever know. Just me. And Riley and Caleb. But that’s all, I swear!”
Molly rolled her eyes in disgust and stormed down the hall into her first period class.
It was a week later, and Sam had all but given up on the idea ever taking off, but on his way home from the bus that Friday afternoon, he opened Snapchat to find a message from Molly.
I’m in, but I have a few conditions.
Cruising around with their Chic-Fil-A sandwiches, they scoped out the perfect place to enact their plan. All the football games were at night, and even with the industrial lights beaming down on the field, the far set of bleachers offered the perfect cover of darkness. Or it would once they snuck in a few of the loose cardboard boxes they always found near concessions.
The three boys were spotted lugging around the cardboard by a few of their friends, but in the grand scheme of things, they’d gone unnoticed. It was a perfect spot that would give them plenty of warning should a curious teacher or, god forbid, one of their principals start moseying their way.
Sam, Riley, and Caleb all felt pretty satisfied with their handiwork by the end of the night. They spent the entire 4th quarter beneath the bleachers splitting a pizza, and during that whole time, their eyes never adjusted well enough to the inky blackness.
Even Molly gave her approval after Sam convinced her to step inside.
“It could work,” she reasoned.
“So, what’re your conditions?” Sam asked.
“Not here. My place, tomorrow afternoon.”
All in all it was a good night, with Misty Pines winning over their rival 28-10.
It was just after lunch on Saturday when the three boys biked over to Molly Sinclair’s place. She met them at the front door and told them to bring their bikes around to the back. Her parents were gone for the afternoon, and they would have the house to themselves.
Once inside, she brought them into the living room where the three boys sat shoulder to shoulder on the sofa. Molly fished out a black marker and a spiral notebook from her backpack, tearing out an empty page before handing it over to Sam.
Rule #1: Anonymity is Key
Sam was busy scribbling down the rules as Molly rattled them out.
“I swear to god, Sam, if anyone ever finds out about this, I’m kicking your ass inside out.”
Sam raised his hands in surrender. “Got it. We won’t say a word, right guys?”
Caleb made a zipped lips sign with his fingers and Riley shrugged. “Who would I tell? We’d catch just as much shit.”
Rule #2: No Phones
“You take them before letting anyone through. Pat them down for all I care. First person I see with a flash, I’m biting their dick off.”
“Jesus!” Riley exclaimed, cupping both hands over his groin.
Rule #3: No Conversations
Rule #4: No Touching
“We don’t want people figuring out who’s on the other side. Take it from me, it’s best for everyone involved.”
Sam finished scribbling down the most recent rule before looking up to Molly for more.
“That’s it for everyone else,” she said. “Now let’s talk about you three. What’re you charging; what’s my cut?”
It was a conversation they had on the way over. The problem with their plan was that they knew they could charge so much more than what they’d settled on, but it was other middle schoolers they were dealing with. They weren’t strapped for cash. Most of the money being brought to the games was from their parents, and while Misty Pines was a pretty well-off place, the money trickling down into kids’ hands wasn’t endless.
“Twenty for jacking someone off, and forty for a blowjob,” Riley said.
“We split it four ways,” Caleb added. “Five and Ten each.”
“No way,” Molly said.
“Why? What’s wrong with that?” Sam asked. “It’s an even split.”
“Remember who’s doing most of the work. Without me, your little plan doesn’t go anywhere at all. I want half.”
“Half!? Are you crazy!?”
“Half, or I walk. Unless you boys plan on getting in on the action yourselves.”
There was an uncomfortable silence in the room as they traded glances with each other. Half was a lot to give away, and that meant they’d have to split the remaining half for themselves into thirds. It would take them ages to make enough money to buy anything worthwhile.
Sam gave an exasperated sigh. “Okay, deal. Fine. Anything else?”
“Actually, yes.”
The three boys watched as Molly walked over to the recliner and plopped down before making eye contact with each of them.
“I think you all need to be fully aware of what you’re asking me to do. Have any of you ever gotten a blowjob before?”
Sam blushed but the other two just shook their heads.
“No,” Caleb said.
“Nuh-uh,” Riley answered.
“Sam?”
“Just once,” their leader admitted as his blush continued to spread.
“You did!?” Riley shouted.
“Why didn’t you tell us?” Caleb asked.
“Boys,” Molly said, drawing their attention back to her. “My last condition is that each of you have to get a blowjob, including you, Sam.”
“Cool!” Caleb shouted.
“Oh, baby!” Riley said, clapping and rubbing his hands together. “This day just got a whole lot better!”
“From each other,” she said.
There was a tremendous ruckus and shouts of Eeewww! and No way! and That’s totally gay! from Riley and Caleb on the couch.
“Would you shut up already?” Sam shouted, silencing his two friends who stared at him in bewilderment. He looked back at Molly. “Just this once?”
“Just this once,” she said. “If you’re going to ask me to do it with whoever shows up and still take half the pay for yourselves, then it’s only fair.”
“How would it work?” Sam asked.
Molly shrugged. “Each of you does it for the next person. I don’t care what order.”
“Are we really considering sucking each others’ dicks?” Riley complained.
Caleb surprised them all by interjecting first. “It’s the only way. Besides, it’s just us. Molly’s not going to say anything. Rule #1: Anonymity is Key!”
“You’ve gotta be kidding me,” Riley said.
“We do Rock, Paper, Scissors,” Sam said. “Winner gets one first. They can decide who.”
“This is so stupid,” Riley said.
“I’m in. I want to know what it feels like,” Caleb said.
“Of course you do, homo.”
“Hey!”
“Guys,” Sam said. “We do it together. We’re in as a team or not at all.”
Riley chewed the inside of his lip a few seconds before finally relenting. “Fine.”
They stood from the couch facing each other as they held their fists in their palms.
“On shoot. Rock, Paper, Scissors, shoot!”
Sam always went rock. It was a system that never failed him. Most people, he realized, over-analyzed with Rock, Paper, Scissors and wound up in their own head. Going rock never let him down. It was a foolproof tactic.
Both Riley and Caleb chose paper.
“Best two out of three?” Sam suggested.
But it was no good. Riley and Caleb squared off. After two ties with each other, it was Riley who came out on top, besting their smallest friend with Scissors over Paper.
Molly gave a light round of applause from the recliner. “Riley, you’re up first. You can decide who you get it from.”
Riley bounced back and forth between his two closest friends; all in all, there was one person to blame for why they were in this mess together.
“I think it should be Sam. You’re the only one of us who’s gotten one before, so it’s only fair.”
“Sure, that makes sense,” he said.
“So, uhh...where do we do this?”
“Here’s good,” Molly suggested, lifting from the recliner and patting the cushion.
“And you sure your parents are gone for the afternoon?”
Molly gave a nod, and Riley took her place, running his palms over his shorts to wipe the sweat from them. He couldn’t say why he was so nervous. If anything, he figured he would have something incredible to look forward to. He was no stranger to jacking off, and from the few porn videos he’d seen, getting blown was supposed to take it to the next level.
Sam walked up and pointed to Riley’s shorts. “You gonna lose ‘em or what?”
“You want me to take off my shorts?”
“Duh, man. Do you want it to be a good one or not?”
“Why don’t we all strip down?” Molly suggested. “It’s warm today anyway, and besides, it might stop you all from feeling so nervous.”
“Yeah, right,” Riley shot back. “You first!”
Molly shrugged and removed her top, showing her flat stomach and bra which did little to contain her breasts. She unbuttoned her pants before pulling them down to her ankles and stepping out. She was in nothing but a white bra and a thin pair of lace panties which hugged her crotch.
The boys’ jaws hit the floor, and soon it was a flurry of clothes tossed wherever they could get them.
It was Sam who dropped his boxers first, revealing his semi-soft cock that was currently rising to its full four inches. He stroked himself a few times while the others undressed.
“You’ve got way more hair than me,” Caleb pointed out. “I’ve got most of mine on my balls.”
Their smallest friend was decently equipped for his size, maybe a tad shorter in length than Sam at closer to three-and-a-half inches, but whereas Sam had a small, but nicely contained bush above his penis, Caleb’s pubic region had only a few blond scraggly hairs on either end. He wasn’t wrong about his sack, Sam noticed. They looked like they had a fuzzy coating to them.
“I’ve got you both beat,” Riley said, finally dropping his boxers.
Riley’s dick was thicker than either of his friends’, rising to an impressive five inches with a much denser bush of black hair. He also seemed to have a bit of short leg hair coming in on each of his lower legs.
“Jesus, your dick is so big!” Caleb shouted. “Try not to choke, Sam.”
“Gee, thanks,” Sam said, rolling his eyes before dropping down to his knees.
Molly removed her bra and panties, leaving herself fully exposed for each boy to ogle. It was no secret Molly wasn’t one of those girls with tiny breasts. You could tell even fully dressed. Sam wondered how it was possible for someone in the 8th grade could have such enormous breasts. He doubted he could even cup them fully in one hand. Her vulva was pronounced with a very clear slit surrounded by shaved light brown hairs on either side. Puberty had chosen Molly to herald the way for all the other girls in their school.
If it was possible at all, Sam thought Riley’s penis had gotten even harder as his friend was enraptured by the middle school’s most infamous girl.
Riley’s cock likewise seemed like an impossibility. Sam knew enough about penises to know Riley still had a bit of growing to do, but already it seemed so huge on his friend. He hoped his own would continue to grow thicker over the next few years.
“Alright, Mr. Expert,” Riley said, reaching down to lift his scrotum and spread his legs. “Let’s see what you’ve got.”
Sam glared at Riley. “You better make sure you give as good as you get.”
Sam reached a hand around Riley’s penis and was thankful to get it all in one grip. He didn’t need his jaw split open trying to do this.
“Well,” he said, giving one last look at the head of Riley’s penis, “bottom’s up, I guess.”
He leaned over and gave a soft lick against the underside of Riley’s head, earning him a low hiss from his friend before he swooped down and tried to take in the first few inches. It was a strange texture in his mouth, almost like bendable rubber. The combination of firm and soft was an unusual sensation against his tongue as he tried to map out parts of Riley’s dick. There was no way Sam could take it all in without gagging, but at least he could give Riley a good time.
What Sam had failed to mention earlier was that while he was the only one of his friends to receive a blowjob, he was probably the only one to give one as well. It was a separate story involving his cousin where he was coincidentally taught about masturbation.
“Oh, shit.” Riley gave a husky groan above him.
“What’s it feel like?” Caleb asked.
“Pretty fucking unbelievable,” Riley said, his eyes closing as he leaned his head back. “I mean, for it being a guy and all.”
“I can’t wait to try it,” Caleb said, reaching down to fiddle with his own boner as Sam began a steady up and down motion.
“Some guys like their balls played with,” Molly said, a few fingers spread around her clit. “I don’t really get why, but sometimes it makes them cum faster.”
Sam nodded and reached a hand forward, curling his fingers to lift up Riley’s nuts. He knew how sensitive they could be and was careful to just tease them a bit as they began to raise on their own accord. It had the right response, and Riley spread his legs as wide as he could on the recliner.
Sam was just as hard as he bobbed up and down on one of his best friend’s penises. He reached down to give himself a tug or two but was careful not to take things too far. He was guilty of having a short fuse. He wasn’t sure whether his dick nerves were super sensitive or if he hadn’t built enough stamina yet, but it always seemed like he cummed in under a minute once he got going.
If he was honest with himself, he didn’t hate the feeling of a penis in his mouth. It was kind of neat feeling it pulse as he pushed it around with his tongue and created pressure with his lips. Riley seemed to be loving it, anyway.
It surprised Sam to feel Riley’s hand on the back of his head, and soon Riley was thrusting forward each time Sam moved down. It made the tip of Riley’s dick tickle the back of his throat.
“I’m gonna blow,” Riley panted.
Sam tried to lift off before Riley’s orgasm hit, but his penis kicked sharply in his mouth, and the first stream of semen caught his tongue on the way out. Riley groaned as his dick pulsed on its own, spewing out three thick blasts of semen that landed on his lower stomach and pubes.
“Oh wow,” Caleb said. “That was awesome! Your jizz is like white too.”
“Molly, can I get a Coke or something?” Sam said, trying to rub the taste of Riley’s semen off his tongue with the roof of his mouth. It was a hotly bitter kind of taste, not at all like he remembered from the last time he tried it.
Molly returned with a soda for each of them, and Sam downed his, trying to let the fizz and dark caramel flavor rinse over his tongue. He gave his dick a quick pull and wasn’t surprised when a string of precum dripped down to the carpet. Even if the taste of Riley’s cum was a bit unappealing, there was no doubt that the whole situation was making him incredibly horny.
“One down, two to go. Caleb, you’re up next. Since Sam just went, Riley’s gonna help you out.”
Grabbing a tissue from the Kleenex box, Riley was wiping the remnants of cum as best as he could from his pubes. He tossed the wadded up tissues on the floor and traded places with Caleb.
The recliner seemed to swallow Caleb up with how little he was compared to Riley. Caleb seemed pretty excited though, wearing a goofy grin as he teased a few of his ball hairs. His penis hadn’t faltered once since they’d stripped as far as Sam could tell.
“When did you start growing hair, Caleb?” Sam asked.
“Just like four or five months ago maybe. I love the way they feel.”
Riley grimaced in front of Caleb’s groin, no doubt in the same post-orgasmic funk Sam sometimes found himself in. When he came, sexy things just didn’t seem so sexy anymore.
“It’s okay, you’ve got this,” Sam said, trying to encourage his friend.
“Yeah, whatever,” Riley said, and squeezed his eyes shut as he stuck out his tongue. He leaned forward until he made contact with Caleb’s penis.
“Oooh,” their friend squeaked.
Riley took a few more hesitant licks and blinked in surprise. “Doesn’t taste like anything at all. Skin, I guess.”
“Well, keep tasting then,” Caleb said. “I’m dying here.”
Riley dove back in and this time wrapped his lips around Caleb’s thin penis. Unlike Sam before, Riley was able to slide down until his nose tickled the few pubes above Caleb’s dick. On the recliner, their smallest friend was squirming in pleasure.
“Oh man, that feels so strange,” he said, laughing and groaning at the same time.
Sam wasn’t surprised to see Riley sliding back and forth quickly on Caleb’s dick. No doubt he wanted the blowjob over as quick as possible, and while it may not have been the world’s best, it was certainly getting the job done.
Caleb’s eyes had squeezed shut once Riley started going at it, but all of a sudden, his eyes sprang open and glazed over. He shuddered as he grabbed the arms of the recliner in a white-knuckle grip.
Riley made a panicked mmph around Caleb’s penis before immediately pulling off.
“What the fuck, man!? Why didn’t you tell me you were about to cum?”
Caleb giggled. His penis was soaked with spit, but honestly, Sam couldn’t really see any evidence of cum at all. He wondered if Riley had swallowed it by accident.
“Sorry, it happened so fast.” Caleb sighed and flattened himself into the cushiony recliner. “It’s not like I make much anyway.”
“Yeah, well, not cool!” Riley said. He opened his soda before gulping down several huge swigs.
Sam noticed that Riley’s dick had started to raise a bit again. Say what he will, but it seemed like their friend might have enjoyed giving head more than he let on.
“Scoot over, dude. My turn.”
Sam had to practically peel Caleb’s naked form off the recliner before taking his spot. The cushions were warm against his bare ass from the recent bodies.
“You’re all drippy,” Caleb said, taking hold of Sam’s penis. “Does that stuff taste like cum?”
“No,” Sam said immediately. “It doesn’t taste like anything.”
“I don’t mind,” Caleb said with a mischievous grin. “Both of you tasted it already. You can do it in my mouth when you’re ready.”
Sam felt his penis twitch with his friend’s naughtiness. The three of them were tight, but they had never gone so far with each other as they had today. Of course there was talk about sex and tits and blowjobs, but it was all bullshit between friends until now.
“Do it,” Sam said desperately. “Suck my dick, Caleb.”
What Caleb lacked in technique, he made up in gusto. His friend’s tiny mouth was like a hot pocket of moist warmth, and right away Sam felt a tongue swipe up the precum dribbling down his length. It was unreal, and he realized how much he missed the feeling of another mouth on his dick. There was no doubt in Sam’s mind their plan was going to be a huge hit.
He moved both hands to either sides of his friend’s sandy blonde hair and helped face fuck him as Caleb moved back and forth. Caleb’s teeth grazed him once or twice as he readjusted, but Sam was loving every second of it. He seemed to know exactly where to make Sam go wild as well, the tip of his tongue rubbing with constant pressure against the bundle of nerves beneath his dick head.
His hair trigger was coming on fast.
“If you’re gonna change your mind, now’s the time,” Sam grunted.
Caleb pulled back, but only enough to let the tip of Sam’s penis rest on his tongue. The sliding friction was enough to make him bust, and with a loud groan, Sam fired off several rapid bursts of cum, shuddering as the pleasure washed over him. It was, without a doubt, one of the greatest orgasms of his life.
Caleb’s tongue continued to bathe his dick until it was too sensitive, and Sam pulled out.
His friend’s cheeks were blood red, but he gave another grin as he smacked his lips.
“It’s not bad,” Caleb finally said. “Like a salty snack.”
“What a homo,” Riley said, rolling his eyes, but Sam noticed that their friend’s dick was at full mast as he lightly stroked it.
“Well, well, well,” Molly said. She’d been teasing her moist clit with one hand and fondled a breast with the other. If Sam hadn’t been so turned on by Caleb’s blowjob, he probably would have paid her more attention. Oh well, Sam thought. There would be plenty of chances for more action later. Besides, who was to say they couldn’t use the bleacher spot for themselves?
“I didn’t think you boys had it in you. Consider me in. You’ve got yourselves a deal.”
The three boys turned and grinned before giving each other high fives.
This was it. By the end of the football season, they would be loaded with cash.
The plan was a go.
Let the games begin.
- End of Part 1 -
That’s it for the first of three parts to this story. I decided to take a bit more of a free-form approach with the plot. Each chapter is going to be its own little self-contained arc. The biggest goal was to get a story written in another category for the site and to stretch out the erotica chops with some boy/girl stuff which will be coming up far more heavily in the second chapter. Feel free to send me some feedback or if you enjoyed Chapter 1!