The Side Hustle – 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?
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: 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.
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.”
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.”
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.”
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.”
End of Story
Whew, there we have it. Hope you enjoyed the story. Went with more of a free flow form with this one, so while it may not be as narratively tight as it could be, I’m pretty satisfied with the little mini arcs that each chapter of The Side Hustle presented. Like my other stories, the door is always open for more, but for now I feel like there’s been closure enough with these characters.
I’ve got a few other ideas in the works, but honestly there’s an ever-expanding list. Where will I find the time!? If you ended up liking the story, please send a message my way and let me know! It’s the only way I’ll know for sure.