The Side Hustle – Chapter 2
Levi Holland

Chapter 2

“We won! We won! We won!”

A sea of cheering students spilled from the bleachers as they marched toward the parking lot. Ignoring the passing brigade as he leaned against the back of the rear bleachers was Sam Summers. In his hands, he fanned through the wad of cash collected for the evening one last time, adding up the total.

As he rifled through the mismatched money, a tall, gangly-framed eighth grader named Oliver popped up from the bleachers beside him. As Oliver brushed off the grit from his hands and jeans, Sam couldn’t figure out where they had met before. Some theater play or chorus show he’d attended, maybe. Oliver gave Sam a nod, blew some warmth into his hands, and adjusted his hoodie before strolling off with a lopsided smile on his face. Another satisfied customer.

Not long after, Molly Sinclair poked her head out from beneath the inky black of the bleachers. After making sure the coast was clear, she stood and swiped the back of her hand across her mouth.

“Nobody ever tells you how different each guy can taste,” she said, blanching a bit. “Never pegged Oliver’s cum to taste so bitter.”

“Sorry,” Sam said, trying to ignore the blush spreading over his cheeks. He returned his attention to the stack of money in his hands and sorted through half before handing the cash over to Molly, who stuffed the money near her breasts inside her top. Her very pronounced breasts. “Ahem,” she said. “Don’t be a perv, Sam.”

Stammering as he tried to tear his gaze away, Sam made it a point to look anywhere else. “I wasn’t staring. It’s just…why there of all places?”

“Why not? Who’s going to question it if they happen to notice a stray dollar or two. Besides, maybe I like teasing you.”

Sam’s face was burning, but he was thankfully saved by the arrival of his two friends Riley and Caleb as they fought their way against the crowd, a paper Pepsi cup in each of their hands.

“Dude, that last touchdown was insane!” Riley shouted. “I’m sorry you had to miss it.”

“Yeah, sure sounds like it,” Sam grumbled.

“How’d everything go here?” Caleb asked, flicking his gaze between Molly and Sam. Sam, in turn, looked to Molly.

She was the key to their success after all. The plan had gone swimmingly in Sam’s mind. Several weeks had passed since that fateful afternoon at Molly Sinclair’s house when Sam, Riley, and Caleb took turns blowing each other in order to convince Molly to join their operation. She’d been true to her word, too, helping to service any of the boys that showed up looking to get their rocks off in someone else’s mouth. No strings attached. Just pure pleasure. For the right price, anyway.

“As long as the money keeps flowing, things will keep going well,” Molly said. “I’ll catch you boys later. My ride’s waiting for me.”

“Yeah, we gotta go too,” Riley said, showing his phone to the group. “Mom just messaged me.”

Entering the parking lot, the three boys piled into Mrs. Walter’s minivan before being driven home. On the way back, Sam was left to muse over their first few weeks. Things had almost fallen apart before they even began. The real trick to everything had been finding the perfect boy as their first customer—someone who wouldn’t blab to everyone he knew like an idiot and ruin the whole thing. Right away that cut a quarter of the boys in the middle school.

It was Caleb who had the idea to bring along a 7th grader named Dylan Whedon from his Science class. A jock on the track team, but not the boisterous type—quietly popular, Sam liked to call it. He was a good choice. The first thing they had to do was convince Dylan they weren’t bullshitting him and trying to take his money. When Dylan disappeared under the dark space of the bleachers, it was an embarrassingly brief three minutes later when he returned. His track pants ballooned where his penis pushed against them, and Sam spotted two telltale white stains on top of Dylan’s knee. The kid practically forked over the cash in his wallet.

Dylan had been the spark to ignite the fire. Not so big a blaze that Sam and his friends would need to bail out on the whole plan, but enough to start a steady stream of customers from the prepubescent to the adolescent. The way he figured things were going, they’d have enough money to buy a PS5 in no time, and likely plenty of leftover cash for other things, even despite Molly’s large cut she took each week.

The only potential hiccup in their plans would be the coming holiday weekend. There was already talk of a lot of families traveling, which meant a pretty big dip in the amount of money they could make. It wouldn’t be the end of the world since they still had plenty of games left in the season, but Sam was eager to keep the interest high in the side hustle he had going.

It was the following Tuesday at school, and Sam was fishing through his locker to grab the journals for his next class when a familiar set of legs appeared below his locker door.

“Knock, knock.”

Sam poked his head around the locker door to see Molly scrolling through her iPhone while she sucked on a red lollipop.

“Can I help you?” Sam asked. He wasn’t trying to be intentionally rude, but it was Molly’s idea that everyone avoid each other during the school day so no one would suspect who the Bleacher Blower might be.

“So, listen,” she said, slurping the end of her sucker before jabbing it his way. “I’m gonna be gone this weekend. Stupid parents trip. I don’t really get a choice, so you three are on your own this time.”

Sam slammed his locker door harder than he meant. “What? What’re we supposed to do?”

“I don’t know, but it’s not going to involve me.”

“We can’t do it without you.”

“Sure you can,” Molly said. “Why don’t you just take my place?”

“I cannot do that.”

“Oh, but I can?”

“You know that’s not what I mean.”

“I can’t see how it’s much different than when you and your friends…” She steadily drew the sucker back and forth in her mouth, and Sam suddenly felt like the whole school must be listening to their conversation. Thankfully the bell rang and gave Sam the out he needed.

“Would you stop?”

“Sure, sure. Don’t get your panties in a wad, Sammy. Tell you what: maybe I can find a way to make it worth your while if you take my place this weekend. Meet me in the 700 hallway during 6th period. Alone, obviously.”


“Just do it,” she said before spinning on her heels and swaying her hips as she meandered into her homeroom class.

As the day droned on, Sam had forgotten about Molly’s request to join her in the 700 hallway until his phone buzzed midway through 6th period. After sneaking his phone from his pocket he found a text from her that read, You coming or what?

This girl would be the death of him. He stuck his hand in the air. “Mr. Hinson, I tried waiting until the end of class, but it’s an emergency.”

His math teacher sighed as he waved dismissively. “Fine, go.”

Sam grabbed the plastic red door hanger used for hall passes and slipped out from his boring algebra lesson. Having been through the 700 hallway countless times for gym class, Sam couldn’t imagine why Molly would want to meet there of all places. As he stepped into the empty corridor, Sam was struck by how quiet everything was at this time of day; no squeaky shoes or thumping basketballs to be heard. Hell, this whole side of the school seemed abandoned.

“Psst, over here. Quickly.”

Sam jerked his head toward the girls’ locker room door where Molly’s head stuck out from. He rolled his eyes and walked closer.

“Molly, what’re we doing here?”

She disappeared inside without a word, and Sam knew he would never get to the bottom of things unless he gave in and played whatever little game she was up to. The girls’ locker room was less impressive than he thought it would be as he stepped inside. They had everything the boys did. Same lockers painted in the school’s burgundy colors and an identical set of shower stalls, although the thought of several dozen girls rinsing the sweat from their naked bodies caused a twinge in his shorts.

Sam coughed. “So, what exactly is this?”

Molly ran a hand across the lockers as if admiring them as she paced slowly through the room. “I found out last year that the coaches help with dismissal each day. Nobody’s ever down here on this side of the school.”

“That’s great, but I’m not looking for a way to ditch 6th period.”

“That’s not what I wanted you here for.”

“Then what’s the reason?”

She paused at the end of the locker row and turned to stare back at him. “I really am sorry I can’t help you all this weekend. I’d change it if I could, but I thought maybe instead I could come up with a way to convince you to take my spot.”

“By showing me your secret hideout?”

“By letting you fuck me.”

Sam felt the breath rush from his lungs.

“You…I…what? Sorry, I must have had a stroke just now.”

“You’re still a virgin, right?”

Sam’s mouth dried up as he tried to say yes, but in the end, all he could do was nod. Was Molly Sinclair really suggesting the two of them have sex? Was he really about to lose his virginity at just twelve years old? Surely this was all just some big prank. Any moment people would burst from their hiding spots and taunt him. But as Molly sat down on one of the wooden benches and began removing her clothes, it certainly didn’t feel like a joke.

“Well? You interested or what?”

Sam thought he must be in shock. He saw his hands moving to unsnap the button of his jeans, but he didn’t feel the denim against his fingertips. Nor the grip of the zipper as he pulled it down. It was only when he was shimmying out of his jeans and the coolness of the air nipped against his bare legs that he started to come to his senses.

He kicked off his sneakers and fished himself from his pant leg. Beside him, Molly had undressed to her panties and reached back to unclasp her bra. Now on full display, Sam couldn’t take his eyes from the way Molly’s breasts swayed as she reached down for the last of her clothing, winning the war against gravity as they stood straight out, nipples wide and pert.

Sam’s erection strained against his boxers as the tip brushed uncomfortably against the fabric. He removed the last of his clothes, guarding himself with his hands. This was the second time they had seen each other naked, and yet Sam shook with nerves. Last time he had been with his two closest friends, and now, he was all alone.

“Come here,” Molly said, raising a finger to draw Sam over.

She sat on the gym floor and spread her legs, revealing her pussy in all its glory. His eyes were drawn like magnets to the silky brown hairs on either side of her moist, puffy lips. Sam’s heart fluttered at the sight as he dropped to his knees.

“You can take your hands away, you know,” Molly said. “Really, your penis looks good.”

Despite his nerves, Sam felt himself chuckle. “I bet you say that to all the guys, huh.”

Molly kicked him in the thigh.

“Oww, sorry. Bad joke.”

Sam took a deep breath before dropping his hands. Standing at full mast, his penis throbbed with the beat of his heart, and a long strand of precum broke off toward the gym floor. He gasped as Molly reached out and took hold of him, giving a few small strokes as pleasure ignited through his body.

“Molly—wait. I don’t wanna cum just yet. I go really quickly.”

She smirked and released him. “I’m not worried. Most cum fast the first time.”

“Do you want me to pull out when it’s time, or…”

She shook her head. “You can shoot it in me.”

Molly got on her knees and leaned forward, pressing her lips against Sam’s. She pushed on his chest until he tumbled backwards, and soon his back was against the cold, tile floor while Molly followed him down, leaning her weight gently on top of him. The heat from her crotch spread to his own while her breasts squeezed against his chest. It was a totally surreal experience.

“You ready?”

“I guess,” he whispered.

Grabbing his penis once again, Molly leaned back and straddled his hips. Sam didn’t have a massive penis, he knew that much. But looking at her vagina before him, it was difficult to imagine how even his tame four inches would fit inside of her. He couldn’t even see the right hole from his angle. Molly seemed pretty sure of herself, however. With a quick adjustment, she raised her hips, pointed Sam’s penis at her entrance, and engulfed him in one single swoop.

It. Was. Incredible.

The first time Sam had been jerked off, he knew it was special. Then he’d been quickly introduced to blowjobs by his cousin, and that had been the new pinnacle of pleasure. But now? This was off the charts. His penis was being gripped by a thousand warm, velvety-slick hands massaging him from all angles at once, while somehow sucking him deeper and deeper. And holy shit was it tight.

He released the breath he’d been holding in a shuddering gasp as his eyes squeezed shut. He was already seconds from cumming as his balls tightened up in their sack.

“How is it?” Molly asked, and Sam peeked an eye open to see her grinning down at him. “Pretty awesome, right?”

When he saw the way his penis was slickly disappearing in and out of her tight entrance, the stimulation tipped him over the edge.


Sam couldn’t hold back his orgasm any more, gasping as he rammed his hips upward, his meager pubic hair mixing with hers as he slammed home. It was unlikely he was making any more semen than normal, but it sure felt like he was blasting Molly’s inner walls with his cum. When he finally felt himself stop twitching, he fell back exhausted to the tile floor, his sweat cooling against his body. Molly’s vagina rhythmically clutched around his twitching erection, keeping him stone hard inside of her.

“How was that?” she asked when he had a chance to catch his breath.

Sam closed his eyes and sighed in contentment before saying, “I think I’ve died and gone to heaven.”

Molly rode him for a few moments more before pausing to glance at the clock. “Shit. We’re gonna run out of time or I’d offer to give you another round. Time’s up, lover boy.”

Sam’s penis was slick with their juices as Molly raised herself up. A bit of his cum trickled from her pussy and plopped to the floor between his legs. He always figured the cum stayed in the girl somehow, but it made sense to him now that some would leak out. His penis gave another twitch as he smiled contentedly. He was no longer a virgin…It had really happened.

Laying there resting on his elbows, Sam gazed at Molly with a new appreciation as she quickly dressed herself.

“Hey, Molly…” he started, and he felt like he had so many things he had to share with her; that she would only understand how he felt if he could somehow get out all the pent up words he had. But those words failed him, and all he could say were two simple words he hoped would somehow convey everything he meant: “Thank you.”

“Hope you had a good first time, cutie. I’ve wanted to do that with you for a while, but wasn’t sure if it would be weird being Rachel’s brother and all.”

“Uggh, please do not mention my sister while we’re naked.”

“Correction: you’re naked. I’m almost dressed. Might want to hurry in case someone comes along.”

Sam scurried to grab his clothes and slipped them on. They made their way to the locker room doors together, but before leaving, Sam reached out and took Molly’s hand in his.

“About this Friday…” he said. “I’m in. I’ll help out however I can.”

“I was hoping you’d say that,” she said, and with a last kiss on his cheek, Molly exited the locker room.

When Sam returned to his classroom, he was buzzing. His whole body was electric. He’d just had sex. Real life sex! Riley was going to be totally jealous Sam had been the first to lose his virginity. He wondered what Caleb would say when he found out. Things had been a little weird between them all ever since that fateful day at Molly’s house. In any case, he hoped his friends would be proud of him. That could all come later though. Right now he had to plan for how best to go undercover for this Friday’s game…

End of Part 2

Copyright 2023 – Levi Holland
All rights reserved

So, Molly has convinced old Sammy boy to take her place in the Side Hustle. Will he tell his friends the plan or will he try and snooker them and keep Molly’s absence a secret? Surely nothing could go wrong! If you’re enjoying the story, feel free to send me comments at the email below!

P.S. This chapter was actually my second write through of these events. Present Levi is still pissed at Past Levi for accidentally overwriting the file with Part 3, but at least it went quicker the second time around. Oh well…