Cry About It

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A college asshole gets fucked until he likes it.
5.8k words
4.64
73.6k
156

Part 1 of the 3 part series

Updated 08/26/2023
Created 05/11/2023
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ZenosSays
ZenosSays
64 Followers

All characters are 18 or older. Any likenesses interpreted by the reader are coincidental.

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"Brandon!" Kelly shouted through gritted teeth, followed by a yelp of pain. "That's - URGH! - that's the wrong hole!"

Brandon shoved in again, smirking behind his wide framed glasses as Kelly gasped and tried to pull away. His grip around her wrist tightened as he jolted her back inward, her curly brown hair bouncing so beautifully he just had to grab it.

"Ow, stop!" Kelly pleaded. "It hurts, take it out!"

"Fuck you, this feels great," Brandon panted, picking up the pace in spite of Kelly's cries.

Kelly grunted, but she didn't move. She let Brandon finish before kicking him off and wrapping herself up in her discarded clothes.

"Fuck you, Brandon," she cried, her mascara running. She clumsily tried to put her panties back on while Brandon leaned back on his bed, basking in the post-coitus afterglow. He had a smug look on his face as he watched through the dim light a small sliver of his cum trail its way down Kelly's inner thigh.

"You're lucky you've got a small dick, you gremlin," Kelly spat out as she opened his dorm room door.

"Oh it wasn't that bad, bitch," Brandon barked. "You liked it!"

"Asshole!" Kelly yelled, slamming the door.

"Go cry about it!" Brandon shouted after her.

He let the quiet calm him before going to the bathroom. Brandon looked himself over, grimacing at Kelly's comments.

"Gremlin..." he repeated, pushing up his thick brimmed glasses. Standing naked in front of the mirror, Brandon sighed. She was right...

Brandon was only 4'9" with brown eyes, olive skin, and dark black hair. Dark black curly hair that covered his entire short body. His arms, his chest, his legs, all the way up to his round rump. Brandon gave himself a slap on the ass, watched it ripple. Like a girl's ass, he thought.

Worst of all... small dick. 3" flaccid, 3" hard, with two grape-sized testicles. Brandon shook his head, trying to shake away the images.

He took a long shower and decided that in spite of everything, today had been a pretty good day.

The next evening, there was a timid knock on Brandon's door. So timid, he first thought he may have been hearing things. He pulled his earbuds out, listening closely. Sure enough, there was another soft knock at his door, and Brandon beamed.

He bolted up off his bed and strode confidently towards the door. "So!" he started, raising his voice to be heard. "Back for more, are ya, sweetcheeks?"

Brandon opened the door, and his smile waned. At first, he didn't really register what he was looking at. But being short all his life, he quickly gathered that he was staring at the torso of somebody much, much taller than him.

"You bet, Branny Boy," a deep, masculine voice replied.

With a gulp, Brandon craned his neck upward. The guy standing before him must have been at least 6'11" with thick muscle covering his frame. He had ruddy, reddish-brown hair, piercing green eyes, and a healthy amount of stubble on his chin. He was smiling deeply, showing off an impressive pair of dimples.

Instinctively Brandon took a step backward, and the giant took this as an invitation to step inside. He nearly had to duck to get into the doorframe, but once he did he reached back and shut the door behind him. Brandon was now alone in his dark dorm room with this titanic stranger.

"Name's JD," he said, leaning down ever so slightly to extend his hand out to Brandon's. They shook, and Brandon noticed the guy was taking care to not squeeze his hand too tightly. Even so, Brandon's hand looked like a toddler's cupped within his grasp. Brandon started to sweat.

"I live just down the hall," JD explained, looking around Brandon's room, poking his odds and ends with his long fingers. "Couldn't help but hear you absolutely railing that girl last night. Congrats, dude!"

"Hey, yeah," Brandon nodded, his voice cracking. He cleared his throat to help compose himself. He then puffed up his chest. "She was a uh... a wild one. Couldn't get enough, the bitch... ya know?"

Brandon was trying to act cool, but he was failing miserably in front of JD. And the look on JD's face proved it. He was solemn and no longer smiling. "Thing is... she didn't sound like she was enjoying it."

Brandon laughed nervously, scratching the back of his head and looking away. Anything to avoid that critical gaze JD was glaring at him. "You know how bitches are," Brandon pleaded, trying to nudge JD with his elbow.

"Uh huh," JD frowned, unconvinced. He paused a moment, then sniffed before letting out a short sigh.

"Listen, that bitch?...My cousin."

A dark cloud seemed to pass over Brandon, and his face fell.

"She talked to me this morning, and imagine my surprise when I learned this girl I heard screaming and crying down the hall... was my cousin all along."

Brandon didn't say a word. He could barely hear JD over the sound of his heart beating out of his chest.

"So... to make a long story short," JD continued, positioning himself in front of Brandon. "I just stopped by to, y'know... make sure that you're sorry."

There was silence.

"I'm sorry," Brandon whispered, staring at the floor.

"What was that?"

"I'm sorry!" Brandon still wouldn't meet his gaze.

JD huffed. "As if you'd get off that easy. No." JD took Brandon's face into his palm and lifted his eyes upward. Hoisted up like this, Brandon was nearly standing on tip-toe, and he grabbed both hands onto JD's muscled wrist to keep balance.

"First, you're gonna suck my cock."

More silence. This time Brandon knew better than to look away. He watched JD's green eyes look him over, a bemused grin playing across his face, like a lion playing with a mouse.

"I'm not gay..." Brandon murmured, putting up his last defense.

"Pfft!" JD spat, shoving Brandon down onto his bed. Sitting like that, he was now eye-level with JD's crotch. "Don't you know, dude? It's only gay if our balls touch."

Brandon swallowed, fear gripping his throat closed.

"Well, come on, Branny Boy, I ain't got all night." With that, JD pulled away his gray sweatpants and flung them to one side. Brandon looked straight ahead, saw the bulge bursting at the seams there, and decided he did not want JD's balls anywhere NEAR him. Although, it wasn't looking like he had much of a choice.

Brandon hesitated. "What... what do you want me to do?"

"I want you to prove to me that you can use that mouth to do some good for a change." JD hooked his thumb around the band of his boxers, letting it snap back against his tone, freckled skin. "Do everything I tell you to," JD clarified, snapping his waistband for emphasis. SNAP! "And me and my cousin..." SNAP! "...will forget everything that happened here." SNAP! "Understand?"

Brandon swallowed. Hard. "How do I start?"

The smirk that crossed darkly over JD's lips was haunting, and Brandon had to swallow his courage a second time. JD slowly took Brandon's glasses between his fingers, gingerly folded them up, then placed them on top of the dorm room cabinet - a place Brandon could never reach without standing on a chair.

"Now... take off your clothes."

Brandon didn't hesitate until he reached his underwear. His shorts, his tank top... he even took off his socks before going for his undies. JD waited patiently, his stare never leaving Brandon. When he couldn't stall any longer, Brandon dropped his tighty-whities to reveal his mini-dick.

JD laughed, just like Brandon thought he would.

"What is that?" he scoffed, pointing with one hand and fondling his own cock with the other, feeling it up as if to compare.

Through his laughter, JD wiped away a tear from the corner of his eye, then used the same finger to beckon Brandon closer. When he was within reach, JD reached down and put his index finger on the tip of Brandon's cock. His finger was longer and thicker than Brandon's penis was, and Brandon's penis was raging hard at the moment.

JD applied some pressure, and Brandon winced as his hard dick was pushed down towards his receding balls. He doubled over, following JD's guiding finger until a bit of pre-cum beaded from Brandon's piss slit, and slicked up JD's pointer finger enough for it to slide off.

Like a JD's waistband snapping back into place, Brandon's three-inch cock slapped against his pelvis - SNAP! - then disappeared into his thicket of dark, curly bush. JD took two fingers and pinched the tip of his dicklet until it went purple, and Brandon yelped for mercy. Finally he traced a finger down to Brandon's balls and tried to squeeze them, but found that they were so small he couldn't even grasp one to squeeze.

Having had his fun, JD straightened his back and gave his next order to Brandon.

"Take it out," JD said, ominously quiet.

With shaky fingers, Brandon reached out. Because his vision was so poor, his depth perception was a little off, and his fingertips bumped into JD's flaccid cock sooner than he was ready for. Brandon recoiled back, as if burned by a stove, and looked back up at JD, eyes wide and shimmering in fear.

JD basked in that look, flexing his dick ever so slightly so that it began to chuff up. The motion caught Brandon's eye, and he looked back down, mouth agape. He remembered then what he was supposed to be doing, and began to slowly reach for the boxers again.

JD rolled his eyes and humped his hips forward so that his cock bumped squarely against Brandon's lips. But he didn't stop with a simple bump, JD pushed his olympic-sized legs forward so that Brandon lost his balance on the bed.

Suddenly, JD was straddling over top of Brandon, boxers filling his mouth, getting crushed beneath the weight of JD sitting on his chest.

"No need to be coy," JD sang, pulling his boxers down himself, feeling Brandon struggle beneath him. One of JD's thighs was thicker than Brandon's entire body. "This can't be the first time you've sucked cock."

Brandon's head wriggled, desperately trying to say no. All he successfully did was rub his face and nose deeper into the pit of JD's boxers. As JD's flaccid cock slipped free, it wetly slapped against Brandon's forehead before settling down and kissing the bring of his nose, pre-cum oozing down across his face. JD flexed his cock again, having it kiss Brandon's nose over and over, making smooching noises with his lips.

"Muah! Go on, it's rude to not kiss it back."

Brandon felt his stomach churn. Kiss it? Kiss it?! Disgusting! But JD grabbed his dick in a chokehold and squeezed out another dollop of pre. It dripped into Brandon's mouth and he sputtered. JD used this to aim his cock head into Brandon's mouth, rubbing his piss slit along it until he felt it gliding against Brandon's tongue.

"Ooooh yeah," JD bellowed, closing his eyes. He thrust forward gently, but just enough to activate Brandon's gag reflex.

"GRRRGGH!!"

JD pulled out, then hit his hardening cock across Brandon's face a dozen times. "Have you guessed how many inches it is yet?" JD asked as he practically gave Brandon a black eye.

"We're all smart college kids, right?" JD continued to mock him. "If Brandon has three inches, and JD has ten more than that, how many inches does JD have?"

He didn't wait for Brandon to answer, instead using his thumb and forefinger to widen the opening of his piss slit, allowing an obscene glob of pre-cum to spill forth and drizzle across Brandon's tongue.

"Now you gotta introduce yourself to my balls." JD threw away his boxers entirely, freeing himself fully. His gargantuan testicles hovered over Brandon's face, and he could smell the heavy musk falling from them. JD lowered himself, tea-bagging Brandon. "Kiss!" he commanded.

Brandon presented his lips, and JD rested his sack squarely on top of them. Then gave Brandon's face a little rub, dragging his balls back and forth, his scrotum sticking sweatily to Brandon's cheeks. The slapping sound of his balls echoed through Brandon's ears, and they kept sticking to him, JD's testicles resting comfortably atop his eye sockets.

When JD was done, Brandon had several of JD's red pubes clinging to lips.

"Please," Brandon begged, spitting and sniffling. "I've learned my lesson, I swear! Tell Kelly I'm sorry and it'll never happen again! I swear!"

"Oh I know it won't," JD said, menacingly. He smiled darkly, then reached forward and palmed Brandon's face, covering his mouth entirely, muffling him. "But how can I trust you're truly sorry... if you've never felt the same pain she felt?"

Brandon's eyes went wide, and his breath caught in his throat. Somewhere, in the back of his mind, he knew this is what everything was leading up to. But still, he didn't want to believe it. JD's pubic hair in his teeth, his musk filling Brandon's nostrils, his pre-cum's salty, satisfying taste....

"Please don't," Brandon whispered, defeated.

"Is that what Kelly said last night?" JD asked, the bass in his voice rumbling into Brandon's rib cage. He shut up, and shut up quick.

The preparation was like a foggy nightmare. Brandon felt the lube, he realized JD had gotten three fat fingers past his anal ring... somehow. It felt like his life was moving in slow motion. Before he knew it, he was on his stomach, another man behind him, lining up his cock to take his sweet, unmolested cherry.

"You're so fucking small," JD nearly laughed, and Brandon realized he wasn't talking about his three-inch dick. His tight pink hole, surrounded by thick, curly black hair. Never once touched or even experimented with. JD was prying it open with his two thumbs, pre-cum from his throbbing cock dripping inside, running hotly down into Brandon's intestines. He tried to clamp his hole shut, but all that accomplished was to make him itch deep down inside.

"Fucking tight..." JD mumbled. "I might not be able to fit inside you after all."

A wave of relief washed over Brandon, and he looked over his shoulder, a look of hope stupid across his face. JD snorted and laughed, slapping Brandon's bare ass and leaving a stinging red handprint.

"Just kidding, I knew you've been looking forward to this." JD used the dome of his cock to rub circles along Brandon's pulsing ring. "Wouldn't leave you hanging, Branny Boy."

And with that, JD pushed in.

There was resistance at first, of course. But JD knew what he was doing. He was patient, and he also teased Brandon's nipples to trick his body into relaxing. After only a few seconds, the ring began to slip open.

"Nooooooo," Brandon groaned, gripping his small hands into the covers of the bed, trying his very best to clench shut, to not let JD in. "No, no, no, no, nooooooo!"

"Oh yesssss!" JD cried out, feeling the breach give way and sweet, sweet warmth wrap around his cockhead. "That's the stuff right there."

"Take it out!" Brandon shouted, gritting his teeth. "You're too fucking big! Take it out, pleassssse!"

"It's so stretched out," JD commented, looking down at his handiwork and ignoring Brandon completely, pushing in even further. "Look at that! It's fucking clinging to me, dude!"

"Pull it out! Pull it out!"

JD did begin to pull out, but he swooned and let out a guttural moan.

"Fuuuuuuck! It's sucking me back in, dude. Aw ffffffuck, it's not letting go." JD tried to pull out, but only got about halfway down his dick before Brandon's hole started pulsing and gripping of its own volition. The suction was so great that JD gave up and sank back in, fully sheathing himself once again.

"This isn't happening," Brandon pleaded, tears streaking from his bloodshot eyes. "This can't be happening!"

"Like a dream come true, isn't it?" JD grunted, pounding his hips back and forth. "Suh-weet jeezus! Time somebody opened this pussy up!" JD lost a bit of his composure and used both hands to grab either side of Brandon's hips. Instead of fucking down into Brandon, he started lifting Brandon's body up into his pelvis. He smashed Brandon into him like this several times, each thrust knocking the wind out of Brandon as he struggled to maintain consciousness.

JD let him fall to the mattress, and amazingly JD's dick was still lodged inside of Brandon. JD danced his hips a bit, enjoying all of the unique sounds that came out of Brandon's throat at each different angle he fucked him.

Brandon's prostate - which had before this moment gone his entire life completely untouched - was suddenly being pulverized. That tight bundle of nerves had been turned to mush the instant JD's cock slid past it. And that button inside of Brandon's core flipped a switch somewhere in Brandon's brain. Which JD's cock succinctly broke, never to be switched off again.

Oh yes, JD knew what he was doing. He was a pro at breaking straight boys at this point, and he could tell Brandon was going to break. He was going to break soon.

"This was too fucking easy," JD chuckled to himself, confident that Brandon didn't hear his taunt.

He didn't.

Brandon didn't hear anything except for the rush of blood pounding in his head.

Because something was happening.

Something deep inside Brandon's core.

Muscles he didn't know existed began to come alive and scream out for attention. His abdomen spasmed out of his control, and he could no longer move his arms or legs. Brandon had never been electrocuted before but DAMN - Brandon felt like he was being electrocuted.

Through this great spasm, JD flared his nostrils and plunged his cock as far into Brandon's hole as he could.

All at once, Brandon's body relaxed. He went utterly limp, and for a moment had absolute, heavenly, zen-like clarity. Of his situation. How he got here. Why he deserved it. And in an instant, it all came crashing down as his body was once again seized by the powerful grips of a spasm.

It didn't stop there. His whole body shook, and the ring of muscle clenching around JD's cock chewed hungrily around that rock hard pole. Brandon could feel JD's hot, sweaty balls so very very close to his own. And through the shaking and whimpering, JD had been sure that his balls never touched Brandon's. But just now, as Brandon's cock could no longer hold back its cum, his grape-sized balls rose up ever so slightly.

Just high enough... to tap against JD's heavy, hanging balls. With each spurt of cum that rocketed out of Brandon's cock, his balls would lift up and tap JD's.

...tap...tap...taptaptap...

"Oops," JD laughed, realizing what was happening at the same time as Brandon. "Guess that means it's gay now."

It was only just now that Brandon realized he was having an orgasm. Never before had he experienced... THIS! To compare it to an orgasm was like... was like...

JD dragged his cock slowly from the depths of Brandon's stomach, each veiny inch tickling past Brandon's defeated hole until just the massive dome of JD's dick remained. Then, just as slowly, he sank back in.

And with that thrust, another jettison of cum shot out of Brandon's tiny dick. JD repeated the motion, and another spurt of cum pushed through him. Another thrust, another spurt of cum. Another thrust, another spurt of cum. Oh gawwwwd, Brandon shrieked in his mind, he's fucking the cum out of me! He fucking the cum right out of me!

Brandon's lifeforce was being thrust out of him in THE longest orgasm he could ever have dreamed of. It just... didn't stop!

They must have lay there for only a couple of minutes, Brandon sandwiched between JD and the mattress, his balls aching as they ran dry. But for Brandon, it was a lifetime.

"Congrats on your first anal orgasm," JD huffed, without a hint of insincerity. He peeled himself off of Brandon, but kept his cock firmly lodged inside him. He repositioned his legs for a more comfortable angle, then took a steadying breath before grinning down at Brandon.

"Wanna have another one?"

JD didn't wait for an answer. He simply fucked Brandon, palming the smaller man's ass cheeks and digging his fingers deep into the soft, pliable flesh. He could feel Brandon resisting, trying to keep the on-coming orgasm at bay. Maybe the lil' guy was desperately trying to think of baseball or something. How cute. JD clicked his tongue, then leaned down and wrapped his forearm around Brandon's neck.

ZenosSays
ZenosSays
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