The Band: Breaking Riley In

by Milton Yearly

8 Apr 2019 3587 readers Score 9.2 (57 votes) PDF Mobi ePub Txt


The following is a story within the larger Hancock Erotica arc called "The Band," which follows the sexcapades of The Steeds, a band of high school boys from the small town of Colton, Hancock. Read more at MiltonYearly.com.


"Guys, very tight!" Pierce Goldman grinned and thrusted his crotch into his guitar a few times.

"Maybe we should always practice in our underwear..."

Pierce's attic was always too hot. But the heat wave had made the past week of band practice nearly unbearable. Not for Pierce, of course. Ever confident, he had no problem stripping right down to his briefs to play, and he paid no mind when his bandmates stared at his firm body and long, bare limbs during practice. Well--almost no mind. He liked to pay just enough mind to notice their stares, and to grind his hips a bit harder into his guitar until one of the guys started blushing.

And today the heat had finally gotten to the others. One by one the boys all followed Pierce's example: sweating through their shirts and pants, then peeling them off to keep playing in nothing but their underwear.

Right beside Pierce was Alden Link singing in rocket-red boxer-briefs that clung to his butt and his package. On Alden's other side was Ryan Timbers on backup guitar, cut muscle in plain tighty-whities, the wet ends of his thick, dark mane sticking to his collarbone and the nape of his neck. Behind them was Hayden Cairns on bass, steady and cool in little fruit-covered undies, and Clark Garner drumming like a dog, dripping enough sweat to soak through his sky blue briefs. And on the sides there was mild Riley Woodrich, flaring up on trumpet or mandolin or violin depending on the song, and more gangly than ever in dark plaid boxers, sweat drops streaking down his long thighs. And of course, shy little Artie Bell at the keyboard. His cheeks burned rosy; he was in nothing but the jockstrap he'd worn for baseball practice earlier. Artie had been the last to strip down over the sweltering rehearsal's course, and Pierce had cheered him on when he finally started peeling off his clothes. When Artie's round buttcheeks bounced free, the band paused in surprise, then spattered a round of applause for him.

And Pierce’s dick swelled up in his briefs--just a semi. Hopefully no one noticed.

"You're right, that was definitely the best sound yet," said Riley. "...But I could do a few more takes. Can't be too careful."

Riley was as practical as his boxers, with a single button on his fly to be sure. But awkward, too. The button didn't quite fit its hole, so every now and then Riley had to fiddle his fly shut again.

"Umm--no," said Hayden. "I think we've done plenty today. And my hands are too sweaty for these strings."

"I gotta side with ol' Hayden," said Pierce. "We should just tap out and drink all my booze instead."

So the boys set down their instruments and trudged over to what Pierce called his "casbah": a curtained off section of the attic with a sofa, some armchairs, and a cooler full of alcohol and soda.

After setting everyone up with beers and a bottle of whiskey to pass around, Pierce settled into his spot on the sofa--the middle, where he could stretch his arms out along the sofa's back and over the shoulders of whoever sat beside him. Today, and on most days, it was Artie and Alden. Neither of them minded how Pierce's fingers stroked at their shoulders when he drank--they'd both let him do that and more at plenty of parties over the years.

Since they'd started playing together as freshmen, most of the boys had found themselves fooling around with one or another of their bandmates at least a few times. Alden and Hayden seemed to fuck once or twice a week, and Pierce had wound up joining them on more than one occasion. Clark was known to trade a blowjob or two backstage, and once Pierce had even seen stone-faced Ryan sneaking away from a firepit with Alden, his hand on the small of Alden's back. And only a couple weeks ago, instead of giving Artie a ride home from rehearsal, Pierce suggested he stay the night. In his room they drank and laughed, and Artie showed Pierce his YouPorn profile, and Pierce loomed over little Artie and fucked him good, raw.

But Riley--well, he was a wild musician, but Pierce hadn't seen him get any wilder. Whenever the boys got carnal together, whether a tap on the ass or a backstage BJ, Riley always excused himself, heading home early or distracting himself with homework until his bandmates' hardons died down. No one minded; they all wanted to respect Riley's boundaries. But Pierce also wanted to see Riley's dick. He was the tallest, lankiest boy in the band, and Pierce had always suspected his unassuming khakis were hiding a long, wild fuckrod. And now that fuckrod was right across the room from Pierce, resting under the creased plaid of Riley's thin boxers. Pierce wanted to see it pop up through the crotch slit in Riley's boxers, stiff and aching--he wanted to see Riley handle it, wrap his hands around it and milk himself for his all bandmates.

"Hey," Pierce raised his voice over the band's soft chatter. "Who's got that whiskey? Ryan? Pass it to Riley, he's parched over there."

Ryan, kicked back in the bean bag chair next to Riley, had been nursing the handle while he stared at the ceiling or into a corner, off in his own head with the usual severe look on his face. He nodded his acknowledgment to Pierce and turned to Riley, swinging the bottle toward him in a theatric arc. Ryan had always been pretty quiet and brooding, but he was a goof at heart. And he could surprise you, burst out in flares of physicality, lean muscle, attitude.

"Here Riley," said Ryan. "Please, run free with us."

Pierce let himself stare at Ryan's legs--coarse, dark hairs, thick, angular calf muscles, thighs spread wide--and trace them right up to his tighty-whities. They were awfully tight. From across the room, Ryan's package was a softball between his legs, white and round and thick--Pierce had never seen Ryan's cock out in the open before. He could feel his own bulge starting to grow, heat welling up into his crotch. So he raised his arms and let them settle over the sofa back--then slowly over Alden's shoulders, and slowly over Artie's.

"What're you thinking about over there, Ryan?" said Pierce.

"Who, me?" said Ryan. He smirked over at Pierce, then let his gaze drift back toward the ceiling. "Nothing, buddy, nothing…”

Without the whiskey to clutch, Ryan's hands roamed his body. One rubbed at his pecs and trailed down to his abs, the other palmed his package, kneaded slowly at the firm mound.

“That's not what nothing looks like to me,” said Pierce. He squeezed Artie's and Alden’s shoulders, nodding toward Ryan's bulging crotch. He threw a wily grin around the room, making sure all the guys were listening. “Come on—give us a hint at least. I wanna know what makes your dick tick!”

“Is that so?” said Ryan. “Well… remember the host at that open mic in Buckturn last week? The tall guy?”

“Tall Paul!” said Alden. “He's great—I hang with him at my cousin's a lot, actually.”

“Oh yeah?” said Ryan. “Well he came up to me after our set. Said he liked my drumming. And invited me to suck his dick.”

Hoots and murmurs of approval sprang around the room.

“Nice! I thought he was really hot,” said Artie. He pulled his legs up into the cushion and shifted under Pierce's arm, resting his head on his knees on Pierce thigh. “Did you do it?”

“Nope,” said Ryan. “Told him I’d meet him in the bathroom after the show but I bailed… Think I should go back to that open mic this week?”

“Why? You don't even like sucking dick,” said Alden. “And his is super long, you'd choke to death.”

“You've seen it?” Ryan perked up, looked eagerly at Alden; his grip on his crotch tightened.

“Yeah,” said Alden, “and way more. I've told y'all what it's like at my cousin's place, right? Paul’s there all the time—and he can really fuck.”

“Shit…” murmured Ryan, his eyes growing distant. Under his clamping fingers, his bulge twitched, straining for freedom and attention. “Well that's what I wanted. Would much rather take super long dick in the ass than my mouth.”

“You wanted him to fuck you?” said Pierce. “Hot—I didn't know you bottom.”

“Every now and then I do, yeah…” said Ryan. “Why, got plans or something?”

“Hey man, you're not my type,” said Pierce.

“Too strong, I know,” said Ryan, leering across the circle at Pierce. “Way easier to top little Artie here.”

“Hey, I'm stronger than I look…” said Artie. “And you wouldn't know anyway.”

Pierce had drifted into a brief fantasy—Ryan on the floor a dim tavern bathroom, naked on his back and presenting his hairy hole to a towering, horse hung redneck in flannel and work boots. Pierce pictured Ryan’s pecs bouncing to the rhythm of sledgehammer thrusts, his long hair splaying out over the tiles, his thick lips pouting, becoming an ecstatic “O.” It was true enough that Pierce mostly fucked twinky pussyboys like Artie or slender beauties like Alden and Hayden—but he had pleased a few gruff, scruffy guys like Ryan before. 

“Why not give me a try then, Artie?” said Ryan. He cupped his package with both hands and humped the air slowly, once, again, again. “Don't tell me I'm not your type, either.”

“Well no, I—” Artie squirmed in place for a moment, pink blooming across his face. He locked eyes with Ryan. “You're definitely my type… And hey, you can fuck me whenever you want, you know—I'm always ready to play.”

“…Alright then, Artie,” said Ryan. “I accept. But don't be too surprised if I catch you in the school bathrooms.”

Pierce's cock was nearly bolt-stiff, radiating in his lap and stretching his briefs to the limit. And Alden has noticed—his hand had crawled to rest in Pierce’s inner thigh, fingertips grazing his bare skin and the edge of his briefs. Pierce looked up from Alden’s hand to scan the circle of boys. Ryan was just as hard as Pierce; he and Artie were trading smoky stares, flighty glances up and down each other's bodies. Hayden had a pile of empty beer cans between his feet and was tipping the next back now; he was hard, too, his bulge distorting the cherry, pineapple, and banana print on his crotch. Beside him, Clark stared at Hayden’s boner, a moth to a flame, one hand locked over a firm, growing bulge in his briefs. And Riley—sandwiched between Ryan and Clark, he clutched the whiskey handle and downed compulsive sips, determined gulps. And his boxers—Pierce’s eyes widened. Riley was hard, no question; all that loose fabric had risen into a tall, sturdy tent.

“Well hey…” said Pierce. “How about right now?”

“…Me and Ryan?” said Artie. “Fuck now?”

“Yeah,” said Pierce. “Right here. As far as I can see we're all pretty horny. I know I'd love to watch Ryan pounding you. Why not?”

“You know,” said Ryan, “that makes a whole lotta sense, Pierce. Hell, why don't we all pound Artie if we're so horny?”

“Aw, Ryan—I thought you'd never ask!” Artie said with a giggle. 

“Yeah,” said Pierce, “it's about time for some hardcore group bonding. This is our last year all together as a band! We could make it a pretty incredible year…”

Riley listened to all this helplessly, his mind a blur of lusty scenes and his body running hot, nearly wild with them. There was still a tiny chance that his boner would be unnoticed. If he could just think of something gross, surgical footage or his grandmother’s toes, he could get soft enough to stand up and excuse himself, call his mom for a ride. But he couldn't—he could only think of the band. Of Artie slowly revealing his butt during practice, luminous and pert in his tattered jockstrap—of Ryan on top of him, dark mane lurching and abs clenching, pounding Artie’s pussy like those frenzied frat boys on YouPorn do. Pierce’s bubble butt dimpling in a deep, grinding thrust that sent Alden's toes curling in the air, just how Riley had glimpsed them in the costume room after school last month. Hayden sitting naked by a bonfire, squirming and moaning with Clark’s head buried in his lap. 

Oh yes, Riley knew all about what his bandmates did without him. He'd just never had a taste of it for himself. Whenever the opportunity arose, his nerves pushed him right out the door—but not out of fear of failure. No, something told Riley his body would take to it, unleash its true grace and agility after a long, awkward childhood as a beanpole. But that was the problem—a part of him feared that once unleashed on someone, he would go so utterly wild there'd be no going back. He'd roam the country with a terminal boner, fucking innocent boys to death for the rest of his days. After all, he regularly spun out of control all by his lonesome: for years now, he'd been at the mercy of his cock’s machinations. He required three masturbation breaks during the day, be they in a public bathroom or behind the school dumpsters. He finished most nights with hours of edging to filthier and filthier porn, exploding cum all over his room in the throes of some extreme—by now he'd seen every kink, blown shuddering loads to every taboo. But no one knew that. To the band, to everyone at school, Riley Woodrich was a naïve drama geek at best, a hopeless prude at worst. He wouldn't know how to begin explaining the truth.

“Whoa—guys, look.” Alden pointed across the circle to Riley. “Even Riley’s hard. Shit, Riley, that tent looks huge…”

A flurry of shock, disbelief, and approval spread through the boys. Riley thought he felt his stomach harden and drop, but the only feeling he could be sure of was in his stiff, stubborn shaft, its swollen red head. The pressure was an electric cloud around his cock, volatile and dumb. He felt the cool flat of the button on his fly pressed tight against his urethra’s tender lips, the button shifting and straining with every pulse of blood through his shaft.

“Huh? I, uh—hey now…” Riley mumbled.

“That's okay Riles,” said Ryan with a toying smile. “Let your body do the talking.”

He leaned over to shoulder Riley, and as their bare skin connected, warm and sticky, Riley saw it beginning. The little wooden button—it's flimsy hold on his fly was giving. The buttonhole, frayed and warped after years, seemed only to kiss the button’s edges. When Ryan's force jostled Riley into adjusting himself, it happened. The button snagged and slipped itself away; his fly fell away like two breezy veils, and a strange groan rattled out of him—his cock sprang tall into the open air, swaying and pulsing in his lap.

In the silence that followed, Riley glanced between his rigid hardon and his gawking bandmates—the gaping mouths and raised eyebrows, a sudden softness of need in the eyes, a subtle arching of the spine in Artie and Alden, instinctual. 

“So,” said Pierce, “does this mean you're staying for the orgy?”

Pierce laid a few blankets and a pillow on the floor in the middle of the circle, and Artie settled there on his back, the pillow tucked under the base of his spine.

Riley agreed to go first, grave excitement whirling in his eyes, in special “virginity taking,” a kind of ceremony. The other boys would watch while Artie offered himself to Riley. While Artie helped Riley explore, the others could step in for support—fondling Riley’s balls, sucking his ass, face fucking Artie or pinning him down for a thrashing. But no one was allowed to cum until Riley was done with Artie. After that it was a free-for-all, with little Artie’s only request, sincerely, that everyone shoot at least one load inside him.

Riley stood over the makeshift bed and watched his stiff cock bounce over Artie's figure below. Artie smiled up at him, bright eyed in his baseball cap. He had tucked his hands behind his knees and hoisted his legs into the air, showing his hole to the room—a pink kiss in the middle of his round little butt, puckering at Riley gently.

“What do you want to do to me?” asked Artie.

Where to begin? Riley studied Artie’s body, waiting for that strange rush in his cock to lead the way. He had always felt a deep churning near Artie, some smothering drive to loom over and primp him, tie his loose shoelaces, handle him through the hallway a bit. For years they had helped each other as friends do through music and drama classes, chemistry disasters, class trips and school dances, but in Riley’s heart he knew what Artie was to him. He was little. Almost as little as the boys Riley have music lessons after school. Artie’s was a pipsqueak with a soft, sweet voice, and Riley could handle him like a Raggedy Andy, wrap himself around him and say it's time for bed.

“Well… first,” said Riley, “say, ‘Um, excuse me, Riley—please don't be mad, but I can't find my backpack.’ When I move, whimper a little. Like a dog.”

Artie said the magic words with a meek, cautious touch.

“I told you, Artie, now that I'm taking care of you, you call me Mr. Riley—got it?” 

Riley descended over Artie in a heavy, spidery curl until his stiff cock disappeared between them, grooved between Artie’s butt cheeks to pulse bare against his trembling hole. Riley leaned his face in close to Artie’s and breathed hot breath into his open lips as he whimpered.

“And the backpack… Baby boy,” Riley cooed, “I’m not mad. But rules are rules, and I still have to punish you.”

Riley started with two fingers, slathered in spit and jammed knuckle-deep into Artie's hole—wet and tight and soft, it suckled at Riley's fingers as he kneaded them in and out. It was better than Riley could have imagined. Watching Artie’s eyes widen and his lips curl in pleasure, Riley fell into a trance, envisioning his new, free life: He would never hide his boners again. From now on he'd jerk off in the boys room with the stall door open. He'd give the neighborhood boys their guitar and piano and horn lessons in his underwear, and when they hit a wrong note he'd—

“Unnh—Mr. Riley…” moaned Artie. “Please, Mr. Riley, I want to feel your cock inside me—put it in, please…”

“Oh…” Riley let his fingers slip out from Artie's hole. “Only if you're sure you're ready to be punished. Can you be a big boy and push it in yourself?”

“Yes, Mr. Riley…”

Artie's hands darted into the dark crevice between their pelvises, and Riley felt two small, cool hands wrap around his hard cock—his shaft raged with hot, electric pleasure, a pressure he had never felt before. Artie guided the tip of Riley's cock to his hole and pressed it into the tight flesh, and Riley felt himself pop through into warm, wet pussy—he gasped, and he thrusted deep, hard, until he was sure every last millimeter of his pulsing rod was inside Artie.

Vaguely, off in the background, Riley heard Artie’s gasping moan, a chorus of hungry exclamations from the boys. But Riley was in his own world now—pleasure boomed from his cock and through his body, clouding around him, nipping at his skin. This was what his life should be. He began to pump and pump into Artie, ramming his cock into his tight little pussy faster and harder until the room seemed to quake with the force of his thrusts.

Pierce watched all this with wide eyes, hand glued to his own long hardon. He had expected Riley to have a huge dick, but he had never pictured him like this. Riley had little Artie in his grasp like a tarantula—he fucked like a demon, a foreign, wild look on his face, almost a snarl. Pierce could only tell when Riley came by the sound—he didn't slow down, just kept pounding as a strangled, guttural bellow seethed through his bared teeth. Pierce wished Riley had taken off his boxers so the boys could watch his hole and balls tighten up as he shot inside Artie. All around the circle, the boys nurses their swollen cocks, stroking in rigorous bursts until their toes curled and they had to freeze, force their cum to wait. 

By Riley's second roaring orgasm, Artie was a whimpering doll beneath him, clinging to his shoulders desperately as Riley showed no signs of stopping. Pierce watched as across the room, Ryan rose from his bean bag chair, thick boner tugged out the fly of his tighty-whities, bouncing as he approached Riley and Artie in the center. He kneeled behind Riley and tugged his boxers down to expose his pale butt. Ryan latched his fingers into Riley's cheeks as he hammered into Artie, and he dove in, sucking and tonguing Riley's hope hard enough to slow him down until he was reduced to grinding balls deep in Artie, moaning and panting. Ryan's dark mane tossed and swayed as her devoured Riley's hole, and soon Riley was gasping out as if mortally wounded, his limbs shaking with the force of his orgasm. He collapsed over Artie, and Ryan gently tugged him by the hips until his dick finally popped free. Riley's cum was oozing from Artie’s pussy, thick and white.

“Atta boy,” said Ryan. “Ready for a breather?”

“Sure,” panted Riley.

He wobbled uptight and returned to his chair, his dick still hard, red hot, raring to fuck and fuck and fuck.
Now the rest of the band could have Artie. Pierce wanted to go last, watch his bandmates give Artie their loads so he could slosh around in all their cum when he planted his rod inside. He watched Ryan first coddle Artie, rimming his sore pussy slowly, even tickling at his hips and feet. Once he had Artie cooing and blushing, asking for it, he began thoughtfully, slow but deep, and soon he had Artie grinding back against him, milking him with his pussy, his brow furrowed with determination. Ryan shot his load in two heaving thrusts, veins bulging in his neck, his body all taut musculature. Artie swooned beneath him, nuzzled at his thick chest.

Clark staggered up to bat next, one hand pumping his rager while the other wrestled his briefs down to his ankles. He was wincing, already on the verge of shooting; he snatched off Artie's baseball cap and slipped it on his own head, then took his briefs and tugged them over Artie's head, covering his face. Clark blew his load as soon as he popped inside Artie. He gave Artie his cap back, and he left his briefs lying on the floor by Artie's head.

Alden and Hayden went at Artie as a team. First they sat him upright and sandwiched him between themselves so they could make out while trading Artie's hole from cock to cock. When they were ready to cum, each turned Artie around for the other, spreading his doughy cheeks wide. Hayden shit his load like a pistol, pummeling Artie with a spate of sharp thrusts; Alden sank his his load like an anchor, grinding deep down in Artie's pussy for a good minute while his cum spat and roped inside.

When Pierce finally came to loom over Artie, hot excitement jolted through his cock, nearly buckled his knees—finally, his dream had come true. Artie's little pussy couldn't even hold all the band’s cum. It dribbled snow white from his raw hole and globbed on the blankets under him; it coated his butt cheeks, was smeared in handprints on his torso. And Pierce saw a dark spot growing on Artie's tight bulge, creamy white seeping through his jockstrap—the band had fucked little Artie's cum right out of him. Pierce wiped up Artie's load with his finger and smeared it onto his throbbing cock. Smiling down at Artie, he held his thick shaft at the base, aimed at Artie's creamy, winking hole, and lowered himself balls deep into tight, messy pussy, plunging his cock into a bath of his bandmates’ hot cum.


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by Milton Yearly

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