The Side Hustle – Chapter 1
Levi Holland

Chapter 1

“For the land of the free…and the home of the brave!”

The bleachers rumbled with the pounding of a thousand footsteps after the singing of the national anthem. It was official—Friday night football was underway.

Sam Summers couldn’t get enough of the Friday night lights.

For one, the middle school had garnered a new sponsor in Chic-Fil-A, with fresh sandwiches and fries 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?

Two, the games were always a great chance to see his friends from previous years who never seemed to end up in his 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 had started with his two closest buddies, Riley and Caleb.

You see, the start of sixth grade had been an eye-opening experience. No longer did teachers escort them around and hold their hands 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 were ripe with possibility. As the year went on, basketball was cool but at a certain point, everyone got on their phones instead of actually watching the game, and baseball was frankly too hot. Nothing held a candle to the energy created during the football matches.

At the start of 7th grade, they wanted to do something different, something to add even more intrigue to the games on Friday nights. 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. It practically swallowed him up as he stared up at the other two.

“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. “I’m not trying to go to jail or anything.”

“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. “Man, drug dealers and pimps make all the serious cash. I just want a PS5.”

Sam perked his head and snapped his fingers. “Maybe that’s not such 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?”



“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 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 for a new console 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 lockers in the 7th grade hallway. Although they weren’t personally close, Sam had known Molly for years thanks to his older sister Rachel’s time in dance class. 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 against 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 chicken sandwiches, the three boys scoped out the best place to enact their plan. With all the football games at night, they found the set of bleachers farthest from the industrial lights beaming down on the field. It was the perfect cover for their operation—or at least it would be once they snuck over a few of the loose cardboard boxes near the concessions stands.

By the end of the night, Sam, Riley, and Caleb were satisfied with their handiwork. After wedging the dismantled cardboard boxes in the gaps between bleacher bars, they spent the entire 4th quarter under the bleachers while they chowed down together on a pizza.

Even Molly gave her approval after Sam convinced her to step inside.

“It could work,” she reasoned.

“Glad you approve,” Sam said dryly. “So, what’re your conditions?”

“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. 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 carpeted 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.

Sam scribbled down the rules as Molly rattled them out.

“Rule #1: Everything Stays Anonymous. 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.

“Lastly, no conversations, and 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 writing down the most recent rule before looking to Molly.

“That’s it for everyone else,” she said. “Now let’s talk about you three. What’re you charging, and what’s my cut?”

They had talked it over the night before. The problem was that middle schoolers weren’t strapped for cash. Most of the money being brought to the games was from their parents, and while Misty Pines was well-off economically, 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. It wasn’t just the console, after all. They wanted controllers, games, and maybe even a nice TV to play on.

Sam gave an exasperated sigh. “Okay, deal. Fine. Anything else?”

“Actually, yes.”

Molly walked over to the plush recliner sitting in the corner of the living room 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 shook their heads.

“No,” Caleb said.

“Nuh-uh,” Riley answered.


“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, clasping and rubbing his hands together. “This day just got a whole lot better!”

“From each other,” she said.

A thunderous ruckus of Eeewww! and No way! and That’s totally gay! spilled from Riley and Caleb on the couch.

“Would you two 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.”


“Guys,” Sam said. “We do it together. We’re in as a team or not at all.”

Riley chewed the inside of his lip before finally relenting. “Fine.”

They stood next to the couch, facing each other as they cupped their fists within 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 foolproof.

Riley and Caleb chose paper.

“Best two out of three?” Sam suggested.

He was practically shoved down to the couch before Riley and Caleb squared off. After two back to back ties, 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 alternated 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 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’re sure your parents are gone for the afternoon?”

Molly nodded as Riley took her place, running his palms over his shorts to wipe the sweat from them.

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 help ease the nerves some.”

“Yeah, right,” Riley shot back. “You first!”

Molly shrugged and removed her top, revealing a flat, toned stomach and a white bra which did little to contain her breasts. She unbuttoned her pants before pulling them down to her ankles and stepping out, leaving her in nothing except her bra and a thin pair of lace panties snugged against her crotch.

The boys’ jaws hit the floor, and soon the room was a flurry of loose clothing.

It was Sam who dropped his boxers first, his cut semi-soft cock rising to its full four inches. He stroked himself a few times while the others undressed.

“You’ve got more hair than me,” Caleb pointed out. “Most of mine’s on my balls.”

Their smallest friend was shorter in length than Sam at closer to three-and-a-half inches, but whereas Sam had a small, contained bush above his penis, Caleb’s pubic region had only a few scraggly blond hairs on either end. His sack, Sam noticed, was covered in fuzzy hairs just as Caleb had said.

“I’ve got you both beat,” Riley said, finally dropping his boxers.

Riley’s dick was thicker than either of his friends, his five-inch cock surrounded by a much denser bush of black hair. Riley was also the only one of the three to have any hairs near the base of his 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 and fully exposed herself for each boy to ogle. Puberty had chosen Molly to herald the way for all other girls in their school. Sam wondered how it was possible for an eighth grader to have such enormous breasts. Or maybe they just looked oversized on her skinny frame, but he doubted he could cup them fully in one hand. Her vulva was pronounced with a very clear slit surrounded by shaved light brown hairs on either side.

Sam’s boner ached as he absorbed the fact that he was surrounded by three naked preteen bodies, two of which belonged to his best friends, and the other who was often the talk of many a boy. Standing like a skyscraper from his groin, Riley’s cock made Sam wary. He knew enough about penises to know his friend 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 as he spread his legs. “Let’s see what you’ve got.”

Sam glared at Riley. “You better give as good as you get.”

Sam reached his hand around Riley’s penis, 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 pink head of Riley’s penis, “bottom’s up, I guess.”

Leaning over, Sam gave a soft lick against the underside of Riley’s tip, earning him a low hiss from his friend before he swooped down to take in the first few inches. It was a strange texture, almost like bendable rubber. The combination of firm and soft was an unusual sensation against his tongue as he tried to map out 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, fiddling with his boner as Sam began a steady up and down motion.

“Some guys like their balls played with,” Molly said as she teased her fingers 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 only tease them as they tightened in their sack. It had the right response, and Riley spread his legs wide on the recliner.

Using his free hand to stroke himself, Sam was careful to only give himself a soft squeeze. He wasn’t sure whether his dick nerves were super sensitive or if he hadn’t built up enough stamina, but he always had a short fuse that led to quick, but fierce orgasms. As he continued bobbing along Riley’s dick, Sam didn’t hate the feeling of a penis in his mouth. It was neat how it flexed against his tongue as he created pressure with his lips. Riley seemed to love it, anyway. When Riley’s hand grabbed the back of Sam’s head, he began to thrust upward, making the tip of his dick tickle the back of Sam’s throat. The hand against his head began to tighten.

“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 asked, trying to rub away the taste of Riley’s semen against the roof of his mouth. It was hot and bitter, not at all like he remembered from the last time he tried his cousin’s cum.

Molly returned with a soda for each of them, and Sam downed his, letting the fizz and dark caramel flavor wash over his tongue. He gave his dick a quick pull and wasn’t surprised when a string of precum dripped onto the carpet. Even if Riley’s cum was a bit unappealing, there was no doubt the whole situation was making Sam incredibly horny. The only reason he hadn’t cum yet was because he wanted to hold out for the blowjob he knew was coming.

“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 wiped away 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 who jumped down on the recliner 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.

“Only like four or five months ago. 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. Whenever he came, sexy things just didn’t seem as 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 tentatively stuck out his tongue until he made contact with Caleb’s penis.

“Oooh,” their friend squeaked.

Riley took a few more hesitant swipes and blinked in surprise. “Doesn’t taste like anything at all. Skin, I guess.”

“Well, whenever you’re ready then,” Caleb said impatiently. “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 squirmed in pleasure as he flexed and wriggled his toes.

“Oh man, that feels so strange,” he said, laughing and groaning at the same time.

Riley sliding back and forth quickly along Caleb’s dick, no doubt wanting the blowjob finished as quick as possible. Maybe it wasn’t the world’s best, but it was certainly getting the job done. Caleb’s eyes had squeezed shut once Riley really started going at it, but all of a sudden, his eyes sprang open and glazed over. He shuddered, holding his breath as he clenched the recliner in a white-knuckle grip.

Riley made a panicked mmmph 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 rigid penis was soaked with spit, but Sam couldn’t see any evidence of cum. 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.

Riley’s dick had started to harden again, despite his protests about giving the blowjobs to begin with.

“Scoot over, dude,” Sam said. “My turn.”

He 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.”

Caleb leaned forward with a mischievous grin as he lowered his voice. “I don’t mind. Both of you tasted it already. You can do it in my mouth when you’re ready.”

Sam’s penis twitched, and another dribble of precum leaked out from the tip. The three of them were tight, but they had never gone so far with each other as they had today. Of course they had talked 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 scoop up the precum running 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 up and down. Caleb’s teeth grazed him once or twice as he readjusted, but Sam was loving every second of it. Caleb 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 and seeing his best friend in such a lewd state was enough to make him bust. With a loud groan, Sam fired off several sharp bursts of cum, shuddering as the pleasure spilled out from him. No question, it was one of the greatest orgasms of his life.

Caleb’s lips closed back around his penis and he continued to bathe his dick with his tongue until he got 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 while rolling his eyes, but his thick dick was once again jutting out from his groin.

“Well, well, well,” Molly said. She’d been teasing her moist pussy with one hand while fondling 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

Copyright 2023 – Levi Holland
All rights reserved

That’s it for the first of three parts to this story. This story has more of a free-form approach with the plot, with each chapter designed to be its own little self-contained arc. The biggest goal with this story was 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 a message if you enjoyed Chapter 1!