The Side Hustle

By

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?”

“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 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.

“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, 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.”

“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 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.

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.”

“Why?”

“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.

“I’m...ahh…..aaaaaahhh!”

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...

Chapter 3

Sam Summers had lost his virginity, and it was the most spectacular thing in his twelve years. Never could he have imagined losing it before becoming a teenager. That same night, he brought himself to three separate orgasms in as little as ten minutes as he relived the afternoon. By the time he finished cumming the third time, he was firing blanks. Now, staring down at the specks of semen on his torso, he realized he would soon be taking Molly’s place when it came to their blowjob delivery service. He was distantly hopeful he could get away with a few handjobs instead, but Sam was only fooling himself. No one asked for a handjob when there was the option to have someone suck your dick.

Dipping a finger into the cooling droplets of sperm on his stomach, Sam swirled the slick juice around before lifting a finger to his lips and gently licking off his cum. It was like it always was...slightly salty and slimy, not so terrible, just unusual. He remembered what Molly said last week about how all guys tasted different. He wondered how he would fare when it came time to swallow. Hopefully the taste wouldn’t be horrendous, but Sam wasn’t looking forward to getting cum blasted by whoever showed up.

On Wednesday, Sam sat down for lunch with Riley and Caleb and thought about how best to broach the topic of Friday.

“So I was thinking about it the other night, but we’re probably only a few weeks out from having enough for the Playstation.”

“Oh yeah?” Caleb asked. “Sweet! We gotta talk about whose place we’re gonna set it up in.”

“Mine, obviously,” Riley said, which of course started a mini world war between the three boys.

Finally, it was Sam who took charge of the conversation. “It should rotate between our houses. We’re always at each others’ places anyway, so what does it matter?”

“Yeah, I guess I’m fine with that,” Riley said, ripping a bite from his sandwich.

“You really think we’re that close?” Caleb asked.

“I think so. Obviously we lose a pretty good chunk of cash to Molly each week, but she does most of the work.”

“Meh,” Riley said, “I don’t care as long as we get it in the end.”

Sam steeled himself to ask the question he’d been meaning to. It was now or never.

“Would...would you guys ever take Molly’s place if it meant we were able to finish sooner?”

Caleb paused to give the question consideration, but Riley was quick to blurt out, “No fucking way! Some dude blasting his jizz down my throat? That’d be totally gay. Now Caleb here…”

“You’re such an asshole, Riley!”

Sam tried to laugh away the sting in his chest. Despite taking turns blowing each other to help bring Molly aboard, Riley had always been the most homophobic of their trio. Sam suspected a lot of it was just for show, something middle school boys did to protect their rep. But what would he find if he really got the chance to pick Riley’s brain, Sam wondered.

On the day of the game, Sam’s nerves grew even more. Ever since Wednesday’s lunch, he chose to keep his substitution for Molly a secret from his friends. It also meant he had to keep secret losing his virginity. But how best to throw his friends off the scent? The last thing he wanted to do was get busted with some guy’s bologna in his mouth. After wracking his brain for ideas, Sam snuck off to the bathroom during class to text Molly in private. If anyone could help him out, it was her.

The rest of the day flew by in a flash, and before he knew it, Sam was loading into the van with Riley and Caleb, on their way to the school for the game. He texted Molly, letting her know they were on the way. It was time to see if his plan would come together. A few minutes later, all three boys’ phones chirped and buzzed, and they looked down to see a message from Molly that read, ‘Already in place for the evening. Go ahead and start sending people my way once you guys get there.’

“Damn, she is after it tonight,” Riley said quietly in the back. “Maybe I’ll need to pop under there, too.”

Sam gave a nervous chuckle and stared out the window as the remaining sunlight faded from the sky. When they arrived at the school and paid the entrance fee for the game, they walked over to their coveted bleacher section that housed the loose panels of cardboard. By then it was dark enough that no one could see the inner panels unless they were right beside them.

It was another chilly evening, but the weather couldn’t stop kids from flooding inside the school’s football stands. Plenty of people were already equipped with popcorn and soda as they picked out their seats. Sam was pleasantly surprised to see that the holiday weekend wasn’t having too much of an impact on the game’s attendance. On the other hand, that probably meant they would have about the same number of students under the bleachers looking to be serviced.

“You guys ready?” Sam asked Riley and Caleb.

Each week the three boys took turns on who would man the front of the bleachers. That person would collect the cash and send people inside. The other two would try to seek out potential prospects while watching the game, sending them toward the bleachers if there was enough interest. Over the past couple of weeks, some students started to seek them out rather than the other way around. Tonight it was Caleb’s turn to man the bleacher opening.

As the three boys split their separate ways, Sam waited until he was out of Caleb’s sight before doubling back toward the bleachers. Peeking his head around the corner to make sure his friend wasn’t looking, Sam scurried to the edge of the bleachers, ducked down, and crawled inside until he brushed up against the cardboard paneling used to shield Molly. It was easy to peel the cardboard away, and once Sam was safely inside, he secured the cardboard back in place.

Other than the residual glow toward the opening in the back, the inside of the bleachers was nearly pitch-black. Along with the low visibility came the cheers and thundering footsteps of fans. No one would be able to pick up on the noises happening beneath their feet.

Sam adjusted his beanie and tried to blow some warmth into his hands while he waited for the first customer. To keep up appearances, he sent a text in their group chat after ten minutes.

Sam: No one yet. Still looking for a good target.

Caleb returned a thumbs up emoji, and another fifteen minutes later, Riley answered back.

Riley: Do we offer birthday discounts?

Caleb: What? Whose birthday?

Riley: Ryan Dorsey’s younger brother apparently. Anyone know him?

Caleb: Ryan or his younger brother?

Riley: Either

Caleb: Had class with Ryan back in 5th. Think I remember hearing about a brother maybe? Ryan’s cool.

Riley: Well a discount means less $$$, so idk how I feel about it.

Caleb: Sam? What do you think?

Caleb: Hello? Sam???

Sam stared at his phone, his thumb hovering over the send button as he warred with himself. Maybe starting off with someone younger was the way to go. It would be easier to get his bearings steadily rather than immediately having to choke down someone larger.

Sam: It’s fine. Just don’t make it a habit. We want money.

Riley: K.

Riley: They’re both on the way.

Riley: Charge them for time and a half.

Caleb: Sounds good. Think I see them now.

As he waited for Caleb to explain the rules to the Dorsey brothers, Sam couldn’t keep his knees from bouncing as he looked to see which of the two would slip inside first. He still couldn’t see very well, but his eyes had begun adjusting to the silhouettes of the bleacher bars. Sam figured he’d at least be able to spot which of the two brothers entered first.

A shadowy figure blocked the dim lighting, and Sam heard the shuffling sound of sneakers on concrete as someone slipped inside. The boy had a short, thin frame, but it was impossible to see any distinguishing features. It was finally time, Sam thought.

Carefully scooting himself over to the boy, Sam lay his hand against the boy’s thigh. The boy jerked at his touch and gave a soft yelp. Definitely the younger brother, Sam decided.

“Sorry,” the voice said. “Just nervous. I’ve never done this.”

The kid was already breaking one of the main rules: No talking once you’re inside.

Instead, Sam reached out again, and this time, the boy didn’t shy away. Sam took this as an encouraging sign and gave the boy’s soft hand a gentle squeeze. They were cool to the touch thanks to the chilly night air, but Sam thought it was cute when the hand grabbed his back in return. Moving his way to the front of the boy’s jeans, Sam wrestled a bit with the front button before the younger Dorsey caught on and helped him out. He watched the kid wiggle his hips as he dropped his jeans.

Sam grabbed the waistband of the boy’s briefs and gently hooked his fingers inside before lowering them past the boy’s ass. Sam was shaking as much as the boy and took a deep breath to steady himself. It was no big deal, he tried to tell himself. It was just like with Riley and Caleb. No big deal.

His fingers bumped against the smooth velvety texture of a growing erection, and Sam continued his exploration, not surprised to feel the bare smoothness of the kid’s groin against his fingertips. Within a year, maybe two, the kid would have plenty of hair. Letting his hands explore further, he moved them around to the boy’s backside, taking one of his cheeks in each hand before gently tugging the boy towards him. Despite the darkness, Sam closed his eyes until the boy’s boner prodded against his upper lip.

Steeling himself one last time, Sam opened his lips and allowed himself to slide over the penis. Immediately the boy gasped above him and shoved himself forward without giving Sam time to adjust. There wasn’t a whole lot of length to it, and his penis was pretty thin overall, but still Sam was shocked at how much of his mouth the younger brother’s penis filled. He tried relaxing his jaw as he ran his tongue over the parts he knew would feel best.

“Oh, that’s so good,” the boy groaned out, shaking in place as Sam continued to lather the kid’s dick with his spit. Sam figured he might as well make the kid’s birthday one to remember, although Sam figured the blowjob could totally suck, and the kid would probably still be appreciative. The more he ran his tongue over the sensitive frenulum, the more the boy shuddered, and it wasn’t long before his hips gyrated back and forth and his butt muscles clenched in time.

His jaw was getting tired, and he considered pulling back and finishing the boy off by hand, but before he could, the kid began to gasp.

“Hey, hey stop,” he whined. “I’m about to pee!”

Wait, what? Sam couldn’t believe his ears. Did this kid not know anything about having an orgasm? He figured anyone coming to the bleachers had to know what the endgame was all about. And what kind of brother was Ryan Dorsey that he didn’t teach his younger brother about the wonders his dick could bring?

Instead of relenting, Sam redoubled his efforts, frantically running his tongue back and forth over the boy’s smooth, velvety skin as he bobbed up and down in time with the kid’s thrusts. With a high-pitched squeal and tensing of his entire body, the boy finally came with a guttural moan, and Sam felt a dozen twitches in quick succession inside his mouth as he continued to work the boy’s cock with his tongue. The boy’s hands clamped themselves around the back of his head over his beanie, but Sam figured the boy was too far lost in pleasure to realize it wasn’t a girl’s head he was holding. As the boy’s first ever orgasm finished, Sam was grateful to find there was no splash of cum in his mouth of any kind. He was certain Ryan’s would be different, and he was glad to be able to work his way up.

The kid’s quivering penis was still just as hard as Sam slid his lips from the tip. His own penis was steel inside his jeans as Sam reached down to adjust himself to a more comfortable position.

The younger boy pulled up his underwear and buttoned himself back up. “That was a great birthday present!” the boy chirped. “I don’t know who you are, but thanks! Ryan’s going to love this!”

Sam knew he had only a few moments before the boy’s older brother would enter, and he truly didn’t know what to expect. Just from working on the prepubescent boy whose dick couldn’t have been longer than maybe three inches hard, his jaw had gotten pretty sore. How was he supposed to keep this up all night? How did Molly manage to do it?

When the next sound of shuffling sneakers caught his attention, Sam turned his gaze to see the shadow of a new boy coming through, presumably Ryan. As he entered and stood to his full height, Sam could see that Ryan wasn’t much taller than his brother. Maybe a bit more broad-shouldered, but that could have had as much to do with the jacket he wore.

Here goes round two, Sam thought as he slid over to meet Ryan at the entrance. Unlike his younger brother, Ryan knew what he was after and didn’t hesitate to drop his pants. They flopped to the base of his feet all at once, and with a quick tug, Ryan dropped his boxers as well before lifting his hands to grab the crossbar above him for support.

“I’m ready when you are,” a slightly husky voice said.

Ryan’s dick had more girth as Sam wrapped his hand around it. The length didn’t feel too different from his brother’s as he stroked his hand back and forth, maybe upwards of four inches, but it was definitely fatter. What’s more, Ryan already had a pretty dense bush despite his mostly unbroken voice. Sam figured that meant Ryan was making plenty of cum.

Sam leaned forward like before and pressed the tip of Ryan’s cock against his lips. He was immediately met with a gooey sensation as the boy’s precum smeared over his lips. When he ran his tongue over the tip to sample the flavor, he was only slightly put off by the hint of saltiness to it. What Sam really noticed was the waft of musk that struck his nostrils, an interesting scent mixed with a bit of heat.

“Oh shit,” Ryan shuddered as Sam slowly descended, running his tongue over the fat mushroom head. The real strain would be its width, and Sam knew he wouldn’t be able to manage the thickness for long. It didn’t end up mattering though. Nearly thirty seconds in to the dedicated sucking, Ryan started to convulse and fire off in Sam’s mouth with a loud groan. The first thick blast caught him by surprise, and Sam had just enough time to recognize the hot and slimy texture before shot number two came, forcing him to swallow. By the time Ryan finished cumming, Sam had swallowed a total of three times. Granted, three quarters of his mouth was stuffed with the equivalent of German sausage, but he was left bewildered by how a boy Ryan’s age could cum so damn much.

His nostrils were filled with a musty, bleachy smell as Ryan began to raise his underwear, seemingly unbothered by the fact that he’d cum in less than a minute. Before leaving, he at least had the decency to thank Sam for taking care of his brother before ducking back down and crawling out from behind the bleachers.

With the brother duo taken care of, Sam rested against one of the bleacher poles to catch his breath. He really wished he had thought to sneak himself a soda to help wash down the taste and smell of cum from his mouth. He knew from his own personal experience that semen had such a distinct odor to it—surely people were going to recognize it on him.

He fished out his phone to text Molly.

Sam: Hope your night is going better than mine. Not sure how you do this.

Sam: Also, can you text Caleb to bring “you” a drink?

A few minutes later he got a reply.

Molly: See, not so easy is it? How many so far? And done.

Sam: Thanks. Two brothers. The Dorseys.

Molly: Kinky. Also, just two? Suck it up, buttercup.

Molly: Gotta go. Good luck. Try to relax your jaw.

Sam received a new message from Riley announcing he would have the next person on the way soon.

During the evening, Sam tried his best to act like he was struggling to find potential takers. It was Riley who had done all the work in finding customers. At one point, Sam faked an upset stomach and pretended he was in the outside bathrooms for a solid twenty minutes. He considered even dipping out from the bleachers and making an appearance, but it would have been tricky if someone were to come by for a blowjob while he was out wandering.

By the time fourth quarter rolled around, Sam had thankfully only gone through two other boys. The first of the dicks had been the worst, with Sam struggling to get half of the eighth-grader’s seven inches down. Sam had thought porn-sized dicks only existed on adult men, but apparently that wasn’t the case. A couple times his teeth scraped against the large cock, much to the aggravation of the older boy, but Sam was doing his best to avoid dying from asphyxiation. When the boy finally cummed ten grueling minutes later, he didn’t thank Sam or anything. Sam never got his name, and honestly, he was glad it was anonymous. He might have taken some kind of revenge if he knew who the jerk was.

Thankfully the other customer was at least bearable. After the Unholy Python, he had a good forty minutes in between, which gave him time to cool off mentally while he sipped his Pepsi. The second boy was short, lean, and just into puberty based on his minimal strands of pubic hair. While blowing him, the boy spread his legs and asked for a finger to be rubbed against the outside of his taint, which Sam thought pretty strange. He must have loved it though, because not long after pressing against the kid’s perineum, a couple sprays of watery jizz peppered the inside of Sam’s mouth.

Sam thought he might have been done for the night when the sound of shoes and clothing against concrete caught his attention. He set his phone down beside him before getting on his knees. By this point, he had been in the darkness so long that his eyes had fully adjusted, and while he couldn’t exactly tell who was coming inside, the shape was familiar. Oh well, Sam thought. It really didn’t matter to him if he knew the person or not. He knew the football game was nearly finished, so this was likely his last person for the night. Plus it sounded like Misty Pines was losing. Maybe people would clear out sooner, and he could be done earlier.

The new arrival stepped inside and dropped his pants in the same manner most of the boys had done. He struggled to reach the crossbar, and Sam could see this newcomer was definitely on the shorter side.

When he made his way over to the boy’s waist, Sam prepared himself for whatever he might encounter. There was no telling with the different boys anymore. Molly wasn’t just right about each boy’s cum tasting different. Honestly there was no rhyme or reason to any of their dicks. Longer, shorter, thicker, skinnier, hairy, bare, cum, no cum. Hell, even the way they curved was different. The boy in front of him had a fairly hairy ball sack, but as Sam grabbed the base of the boy’s penis, there were just a few, sparse tufts on either side of his erection.

He slid his lips over the head of the boy’s penis and gave a tentative lick against the squishy tip, drawing a gasp that once again had a familiar tinge to it.

Above him, the boy groaned in pleasure, whispering words Sam couldn’t make out. The crowd was definitely dying down, but most of their noise was still buried from the movement on the bleachers. Though Sam was holding on to his hips, the boy started thrusting his smaller length in and out, almost massaging his penis against Sam’s lips as he ran his tongue along the length. Whoever it was definitely knew what he wanted.

Once or twice, he pulled out too far, leaving the wet warmth of Sam’s lips, but it wasn’t long before he pistoned himself back inside, and as his speed increased, Sam knew the kid had to be close to blowing his load.

Again Sam heard the groans escaping the boy, this time able to make out a little of what he was saying through his hushed tones.

“Yes…so good…”

The boy instinctively spread his legs as he squatted a bit, and Sam took a risk with what he did next. Remembering the boy from earlier in the evening who wanted his taint rubbed, Sam took his opposite hand and slid it behind the boy’s fuzzy sack until he reached the seam connecting his balls with his ass.

Rubbing and pressing gently along that line, the boy began to tense and groan hard.

That’s when their phones went off.

Below him, Sam’s phone screen came on as it vibrated once against the ground. It wasn’t bright enough to light anything in the darkened space, but with a quick glance down, Sam saw it was from their group chat. At that same moment, a phone went off in the pocket of the boy he was sucking.

The boy froze.

Immediately, the kid stopped thrusting and pulled out from Sam’s mouth. Without another word, he zipped up his pants and scurried from beneath the bleachers.

Definitely weird, Sam thought. He didn’t think he had done that terrible of a job. Maybe the kid just got wigged out by the finger near his butt.

Drawing the back of his hand against his mouth to wipe the slobber, Sam bent down to check the new message.

Riley: Yo, where the fuck are you guys? Can’t find either of you.

Sam took another long look at the message before gazing at the entrance of the bleachers. He had thought there was something familiar about the last boy that came through. And now that he was connecting the dots, it all made sense: the familiar silhouette, the fuzzy sack and penis size, and even the groans reminded him of the ones he’d heard the day they all blew each other. It was Caleb.

As the game concluded, Sam exited the same way he came in before taking a very long loop around the many sets of bleachers. He traipsed about as long as he could, not wanting to encounter his two friends.

Did Caleb know it was him who was under the bleachers as well? And if he did, what would he say to Riley?

When he finally mustered up the strength to return, his heart pounded as his friends waited for him, one impatiently, the other avoiding his stare.

“Dude, finally,” Riley whined when he caught sight of him. “Next time drink some milk or something if your stomach hurts. We’ve been waiting forever.”

Caleb only cut him a small, weighing glance before looking away.

“Sorry,” Sam muttered. “Don’t know what it might’ve been.”

“Well, whatever,” Riley said. “I’m ready to get out of here. Game sucked ass.”

It was quiet car ride home with hardly a word mentioned between any of the boys.

When Sam got home, he went straight to his room to brush his teeth and get ready for bed. He swapped a few texts with Molly but didn’t mention anything about Caleb. He didn’t mind blowing his friend. If he was honest with himself, there was a part of him that really enjoyed it. But it left him conflicted. As much as having sex with Molly was amazing, his time under the bleachers had also turned him on quite a bit. Maybe he just liked sex, period. Giving or receiving. And if he did, was there anything wrong with that?

Laying his head against his pillow, Sam was about to close his eyes for the night when a final message came through his phone.

Caleb: Can we talk? My place, tomorrow?

Sam stared at his phone screen, rereading the message from Caleb.

The cryptic nature behind the text was all Sam needed to confirm that Caleb knew it was Sam giving blowjobs in Molly’s place during the football game. The only question was how would his friend react when they met face to face.

Several times he had a reply typed out, but in the end, Sam turned off his phone before setting it on the charger. For the next several hours, he tossed and turned, unable to drop into the restful kind of sleep Friday nights could bring. Having given five different blowjobs throughout the game, one of them to his best friend, Sam was surprised to find how overstimulated his brain felt. He couldn’t even bring himself to get hard and jack off, which might have been a first since being taught how to do it.

When he finally conked out, Sam’s sleep was filled with a series of different nightmares where his friends teased him about sucking other dicks, calling him names and shoving him down. The dream then morphed into people using him for free blowjobs, but it was far from enjoyable. The people shoved their cocks in the back of his throat, gagging him and filling his mouth with their cum before ditching him on the ground. By the end of his nightmare, he had been abandoned by everyone he thought cared about him.

Sam’s eyes snapped open, and it was some time before he moved from bed. Instead he stared at the white popcorn ceiling above him and contemplated faking a sickness so he wouldn’t have to go to Caleb’s. With a sigh, he snagged his phone and took one last look at his friend’s message before sending his reply.

Sam: Sure. I can come by whenever.

During breakfast his mom sensed something was wrong, but Sam brushed it off as tiredness from a long week at school. Even still, she checked his forehead for a fever with the back of her hand as he lazily pushed around the bits of cereal in his bowl. When she was satisfied he wasn’t going to spread the flu around, he got permission to ride his bike to Caleb’s house later that day.

Pedaling down the familiar streets of his neighborhood, Sam wasn’t sure his heart had ever beat faster while riding his bike, especially as his friend’s two-story home loomed over him. The neighborhood was unusually quiet for a Saturday afternoon, as if all the homes were fast asleep. Even the windows of Caleb’s house were darkened. Looking at the abandoned driveway, Sam wondered if Caleb was even home, but then the front door creaked open, and his best friend stood in the doorway, sipping from his Mountain Dew in a t-shirt and sweatpants.

He followed Caleb inside after parking his bike, and suddenly the living room where he’d spent so many nights watching movies in and eating popcorn on the couch with his friends felt stuffy and cramped. On the coffee table in front of them, a stack of unsorted cash lay spread out like a stretched out finger pointed at Sam.

“You want something to drink?” Caleb asked.

“Not really, no.”

“Okay…”

They sat at opposite ends of the living room couch, an uneasy quiet between them. Caleb’s toes dug into the carpet and Sam knew his friend was waiting for the right time to tell him off. The waiting was agonizing, and Sam couldn’t take much more of it. Either Caleb hated him or he didn’t, but either way he just wanted him to speak. He had to know!

“Listen, if you hate me, just go ahead and say it!”

Caleb lifted his head with a look of shock.

“Hate you?” he sputtered. “Why would I hate you? It should be me who’s apologizing.”

Sam didn’t know what to say. He’d come here expecting to get reamed by his friend, and now it was supposed to be the other way around?

“Wait, wait, wait,” he said. “What’re you talking about?”

Caleb’s cheeks flushed, but he continued. “Come on, man. Riley may be an idiot, but you can’t fool me. It was pretty obvious Molly wasn’t there when we never saw her once and you were being so sus the whole night.”

“If you knew then why didn’t you say anything?”

Now Caleb had the decency to look away. And that got Sam thinking. Caleb knew all along he was under the bleachers...and Caleb had chosen to get a blowjob from Molly. From him.

“You wanted one from me?” Sam’s words slipped out in a whisper.

“You weren’t supposed to find out...and I know I should have asked first. Sam, I don’t care that you were in there for Molly. I probably would have too if given the chance, because, you know...”

Caleb was confirming what Sam already suspected. Not so much because Caleb had done anything overtly gay. It was the little things: less than half-hearted comments about the other hot girls in school, the effeminate way he sometimes gestured and caught himself, and the slight judgments here and there against how people in the school dressed that day.

“Yeah, but why one from me?”

Caleb snorted and turned to face him. “Are you kidding? Sam, you’re like crazy hot. When we all gave each other blowjobs at Molly’s last month, that was the best day of my life. The fact that it was one of my best friends just made it even better.”

“You like me?”

“Well, yeah. Who wouldn’t? You always look out for us, you stick up for us, you’re super cool. What’s not to like? Look...I need to apologize for last night. I know you’re probably not into me the same way, but it doesn’t matter. Taking advantage of you wasn’t cool.”

“No, it wasn’t,” Sam agreed, and for a moment the silence that had started their meeting returned. “But I forgive you. Honestly I thought you were gonna be pissed with me for lying to you both.”

“It’s alright. Obviously the money on the table’s yours. I told Riley yesterday that Molly split early.” Caleb took a sip of his drink as Sam fingered through the cash on the table.

“Thanks, man,” he said. “It’s still ours, though. I did it for us.”

Caleb nodded before looking at Sam and wiggling his eyebrows. “So...how was it?”

Sam cut his eyes to his friend and grinned. “Some parts were better than others. I didn’t hate it though.”

“Who was the best, and who was the worst?”

“Well the worst is easy. Some jackass in the eighth grade basically rammed a flagpole down my throat. Dude had a dick made for porn films.”

“Oh, that was Darius from the basketball team. I guess the rumors are true about him.”

“The rumors about him having a big dick?”

“No, the rumors about him being half horse.”

Sam burst out laughing, happy that he and Caleb were back to their old selves. The weight crushing him down since last night was free from his shoulders.

“And how about your favorite?”

Sam thought about it. “Well, if I’m being honest, it’s hard to say, you know? Because I didn’t get to finish with everyone…”

Letting the statement linger, Sam noticed how his friend’s sweatpants began to tent as realization spread across Caleb’s face.

“Well, we could, uhh...go up to my room if you want? My parents won’t be home for a while.”

The two practically dashed upstairs as they raced to Caleb’s bedroom. Sam found himself paying attention to Caleb’s bubble butt and the way his sweatpants molded around his cheeks. When they made it inside, they locked the door shut behind them and faced each other.

“So what did you have in mind?” Caleb asked with a sheepish grin.

“Screw it. Let’s both get naked.”

“Yes, sir!”

As Sam pulled his shirt over his head, he was only slightly surprised to see Caleb wasn’t wearing underwear. His small boner was hidden behind his t-shirt, but that would be coming off soon. When Sam dropped his own jeans, his dick strained against the fabric of his briefs until he slipped those off as well.

“I really like the way you look, Sam,” Caleb said admiringly.

Sam didn’t think his body was that impressive. He didn’t play much in the way of sports, and while he practiced flexing in the mirror like any other boy, there wasn’t much to flex. But he guessed he kind of understood what Caleb was talking about. Even though his friend’s torso was mostly ribs, he liked his small stature and the way his dick was perfectly proportionate to everything else about him. He even liked the way his small tufts of pubes matched the color of his sandy blonde hair. His dick twitched in response as he drank in the sight of his best friend.

“You drip a lot of precum, don’t you?”

Sam put a hand in front of his penis to catch a dripping strand.

“Sorry, I can’t really help it.”

“It’s fine,” Caleb said. “I think it’s cool.”

“Let’s move to your bed. I’ll try not to make a mess.”

Now that there was nothing covering it, Sam was drawn to the way Caleb’s butt swayed with each step he took. His cheeks were pale, but smooth, stretching tight without a lot of extra fat. Butts weren’t really something he’d noticed before on people, but maybe he ought to pay them more attention, he thought.

“Do you want to try doing it to each other at the same time?” Caleb asked.

“What, like 69ing?”

“It has a name?”

“Everything with sex has a name.”

“Oh. Then yeah, let’s 69!”

They crawled onto the bed and agreed that Sam should be on the bottom, in part because of his flowing precum, but also because he was the bigger of the two. Caleb crawled over top of him on his hands and knees, and Sam easily slurped in Caleb’s penis down to the hilt. Despite being at a different angle, Sam curled his tongue toward the sensitive parts of Caleb’s penis, using the boy’s groans and shudders as a guide to know when he was on the right track.

Having Caleb’s mouth around his dick reminded him of when they blew each other in front of Molly. Just like then, Caleb moved with a hunger, bathing Sam’s penis with his saliva and tongue. He shivered at the contact, and found himself trying to squirm away, but in the end he could only press back against the mattress. If Caleb kept this up, he’d be shooting in no time.

Thankfully Caleb paused long enough to pull off and groan audibly. If Caleb’s parents were home, they definitely would have heard his moans.

Sam pulled off and chuckled. “Are you always this noisy when you jack off?”

In response, Caleb pressed against Sam’s perineum using his finger, and the pressure sent a sharp jolt of pleasure through him as he yelped.

“Are you always this noisy when people touch your ass?” Caleb teased.

“Whatever, blow me.”

“With pleasure.”

The two went back at it, sliding up and down each other’s dicks, and while it may have been a joke between them, Caleb’s finger against him had felt really good. The boy from last night had asked for the same thing, and now Sam understood why. There must have been even more nerve endings down there he didn’t know about.

“Hey, will you touch that spot again while you suck me?”

“If you’ll do it for me, too.”

Sam didn’t need any further permission. With Caleb above him, the boy’s legs were naturally spread, and Sam brushed his fingers past Caleb’s hanging balls with their peach fuzz all around them and traced the seam up until he ran against his crack. A little nub swelled in the spot right before his hole, and wondering if it was the place, Sam gave a firm nudge with his thumb. The response was immediate as Caleb bucked his hips downward as he groaned around Sam’s dick.

It wasn’t long before Caleb recovered and pushed back against Sam’s own taint. How had he not known this spot could bring him so much pleasure? Caleb continued moving his fingers until one pressed gently against his puckered hole. He was pretty sure he was sweating down there since Caleb’s finger was moist against him. The finger disappeared from his crack the same moment Caleb pulled off his dick, and when Sam peered down, he could see Caleb was wetting his finger.

“What’re you—” he started to ask, but then Caleb found the spot again while resuming his work on Sam’s penis, and with a gentle push, he slipped the tip of his finger inside. That was it for Sam. The combination of his ass squeezing against its new invader, the sensation of Caleb pressing his thumb against his taint, and of course the warm wetness of Caleb’s mouth was too much. He groaned and lifted his knees as he started pumping his cum into Caleb’s mouth, the build up squirting out from him after not cumming the night before. That combined with the mischief of what they were doing had sent him into sensory overload.

On top of him, Caleb’s small body shook as he clenched up, and a sprinkle of cum dotted across Sam’s tongue. It carried a slight sweetness to it, and Sam decided he liked this taste the best. Caleb’s boner twitched a few more times in his mouth before beginning to soften. As he pulled out, Sam stared dreamily up at Caleb’s ceiling before his best friend plopped down beside him.

“Okay, it’s official,” Sam said. “That was the best one.”

Caleb leaned over and pecked a quick kiss on Sam’s cheek, making him blush.

There were things he needed to figure out still, he realized. Sex with Molly had felt really good, but it was over and done, and Molly wasn’t the type to be interested in something long term. With Caleb, sex had been just as amazing, and Sam wondered if that had more to do with their bond as best friends. Maybe it didn’t matter who Sam had sex with as long as the person he shared it with was special. Why did he have to worry about how he was labeled?

It was with that thought that he took Caleb’s hand in his, intertwined their fingers, and gave him a slow kiss back, this time on the lips.

“Oh, hey, I forgot to mention. We have enough money for the Ps5 now.”

The End

Copyright 2023 – Levi Holland
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