The Boifriend: Ch. 3

[pre-story]In honor of Pride month, I wrote some more gay stuff! Enjoy!
Y'all know the deal by now, there's some very gay stuff in here, so if that's not your thing, feel free to ignore this one. 
If you DO like it, or you at least like my other stuff, [redacted][/pre-story]

The Boifriend: Chapter 3  

Ben winced slightly, the corners of his mouth straining as his turquoise-painted lips stretched around Leo’s almost fist-sized cockhead. The mature, muscular, dark-skinned man loomed over him like a god as Ben knelt before him, his knees starting to hurt a little as they sank into the carpet below. Ben’s hands rested lightly on Leo’s powerful thighs, his head was held firmly in place by both of Leo’s hands, and his heart was pounding with both anticipation and nervousness… but in that moment, Ben had never felt more... right. This was where he belonged, this was his purpose, he was born to be used by a big, strong man, to be made into the pesonal fucktoy of a superior male, a man like Leo…



Leo’s cockhead throbbed as it slowly continued to push forward, stretching Ben’s plump, painted lips a little further, and the boy winced, his eyes watering slightly. Ben felt the pressure ease off for a moment, Leo’s hips backing off just a little, out of concern, but Ben didn’t want the moment to slip away. He pushed his head forward, and Leo’s grip faltered for a moment, intended more to keep the boy from pulling away than from moving forward, and Ben’s lips strained once more as they stretched a little further around Leo’s blunt cockhead, the blue-haired boy eagerly throwing himself onto the fearsome weapon.

Leo let out a groan of lust, his cock throbbing against Ben’s stretched lips. “You really want it that bad, huh?” Leo asked, his voice taking on an edge as his hands once more gripped the younger boy’s head, more securely, this time. “Then fucking TAKE it, you slut!” He half-growled, his body tightening as he drove his hips forward remorselessly.

Ben let out a muffled moan as the alpha male’s cockhead stretched his lips to the limit, his once-plump, painted lips stretched into a thin aqua-blue band around its girth, it felt like the corners of his mouth might tear, like his jaw might break… and then, it was through. Ben’s eyelids fluttered as Leo’s throbbing cockhead filled his mouth entirely, hot and hard and huge and salty, its sheer girth pinning his pierced tongue against his bottom jaw and filling out his cheeks. That didn’t stop Ben from writhing the little pink muscle against that sensitive crown, doing his best to please Leo, and it didn’t stop him from tightening his already-stretched lips and starting to suck hungrily at his shaft. Leo was just so strong, so HUGE... he deserved this treatment, and Ben was just lucky to be the one who got to give it to him.

Leo groaned again as the boy continued to surprise him with his slavish dedication to becoming his personal fucktoy. But taking the head and the first few inches wasn’t going to be enough to satisfy him. He needed more, and if the little slut wanted it so bad, he’d have to take more. His his pushed forward, and Ben’s eyes widened as he felt the fat head of Leo’s cock press against the entrance to his throat. Immediately, Ben’s throat tried to spasm violently in an effort to repel the intruder, but the blue-haired boy squeezed his eyes shut, forcing himself to ignore the reflex as Leo’s cockhead probed at the entrance to his tight throat, stretching the first ring of muscle around its girth.

Leo could feel Ben’s throat struggling to relax around his helmet-shaped cockhead, and part of him sympathized with how that must feel for the boy, but he couldn’t deny it felt absolutely incredible on his shaft. That is, until Ben suddenly started gagging and choking around his shaft. Leo yanked his hips back instinctively, his cockhead pulled from the boy’s lips with a wet slurp and a pop, followed by a few moments of ragged coughing.

Before Leo could even ask if he was alright, though, Ben was looking up at him, his once-perfect, sparkly blue makeup ruined, turquoise eye shadow now starting running down his cheeks in streaks, his lipstick smudged, a good portion of it left behind on Leo’s cock in smears, kiss-marks, and rings, marks of his devotion to that glorious manhood. “Guh… I- I’m sorry, Sir, please, let me try harder, I’ll be a good slut for you, I promise. Just don’t stop pushing, force it in, even if I start choking, just turn my mouth into a pussy and fuck my face. I want to take the whole thing, no matter what.” He pleaded, opening his mouth once more and letting his tongue loll out invitingly, silver barbells gleaming in the middle of it.

Leo groaned. “Fuck… You’re one crazy little white boy.” Leo muttered, shaking his head as his hips came forward again until his cockhead rested on Ben’s outstretched tongue.

“Ahh… Yes, Sir. I’m a sissy white boi bitch, just for you. Please fuck my tight virgin throat with your big black cock, Sir! Make me- mmm!” Ben began to plead, only to be silenced as Leo’s his drove forward, stretching the boy’s lips once more as his cock once again filled his mouth.

Leo was harder than he’d ever been in his life, and he wasted no time in pushing his blunt cockhead against the entrance to Ben’s throat. The blue-haired boy let out a muffled moan as he squeezed his eyes shut, bracing himself as the Leo’s monstrous member pushed harder against the rings of muscle of his throat. Bit by bit they stretched and strained, tears of effort beading in the corners of Ben’s eyes as he fought against his body’s natural reflexes. “Fucking TAKE IT, slut!” Leo growled, his voice deep and animalistic as he stopped holding Ben’s head still and started pulling it down onto his member. Ben’s throat could not resist Leo’s full strength for long, and one by one the rings of muscle gave way as that fat, helmet-shaped head pushed into his tight throat.

Ben could feel inch after inch of Leo’s fat, veiny shaft pushing past his stretched lips as the fat, throbbing cockhead drove deeper and deeper into his throat. He would have moaned if his throat wasn’t currently being stretched wide around his master’s thick shaft. He could feel his neck bulge for the monster’s sheer girth, feel his body being stretched, reshaped around Leo’s glorious manhood, it hurt, but it was so worth it to feel Leo conquering his virgin throat, turning it into his own personal cocksleeve.

Leo was about halfway into Ben’s tight little throat when the boy couldn’t hold it back any longer, his body spasming as he let out a strangled ‘glurk’ sound around Leo’s shaft. Again, Leo’s first instinct was to pull back, but this time, he ignored it, pushing deeper as the boy gagged again. He paused, this time, only to feel Ben’s painted nails dig into his hips, the pale boy’s slender arms struggling to pull the muscular male’s hips forward, to pull him deeper into his spasming throat.

That was all the encouragement Leo needed to slam his hips forward, plowing through what little resistance Ben’s throat still offered as the boy choked on his cock, driving his shaft deeper until his apple-sized balls bounced off Ben’s chin, his hip bone grinding against the boy’s nose. More than a foot of Leo’s steel-hard cock throbbed inside the teenage boy’s overstuffed throat as it spasmed rhythmically around him, milking his length each time Ben gagged. Leo let out a deep, throaty groan of satisfaction as he held himself there for a moment, the incredible sensations on his shaft only enhanced by the way the boy clung to his hips to try and hold him in. There was a rush of power that came with knowing that the sissy bitch boi with tears of strain streaming down his face as he gagged on his cock was loving every second of it.

After a few long moments of savoring the sensations, Leo slowly pulled his hips back, pulling back from Ben’s throat inch by inch. Ben’s lips refused to let go so easily, clinging to every vein-marbled inch of Leo’s shaft, the vacuum seal they formed producing a long, wet, nasty slurping sound as he withdrew. It seemed to just keep coming, but eventually the fat, fist-sized head of Leo’s monstrous shaft slipped from Ben’s lips with a wet pop, and the boy immediately began coughing and gasping for air. Leo’s cockwas soaked with spit and marked by rings of aqua-blue lipstick all the way down to the very base, glistening strands of saliva hanging from the beastly shaft, some dripping to the carpet below, others linking the monstrous member to the teenager’s thoroughly-stretched lips. The boy’s makeup was a total wreck at this point, smeared and smudged into messy streaks all down his cheeks, his eyes still glistening with tears as they stared at the monstrous cock before him with awe.

“Oh fuck…” Ben moaned with his first breath of fresh air. “It- It went all the way in. I can’t believe I took the whole thing! I could feel it stretching out my throat… Fuck, that was so hot…” He moaned, eyes flicking up to Leo’s face, his expression a mix of awe and gratitude. “You did it. You turned my throat into a pussy. Now… Use it. Fuck my face until my throat is raw. Fuck my sissy brains out until those big fat balls are empty! You can cum straight down my throat, or drown my tongue in your spunk and make me taste it before I swallow it, or just pull out and cover my face with your hot cum and mark me as your personal fucktoy…” Ben pleaded.

Leo silenced the blue-haired teen by sliding his fat, pulsing cockhead between his painted lips once more, filling the boy’s mouth and lingering there a moment. “Take a deep breath.” Leo ordered, his voice deep and rumbling, and Ben shuddered at the powerful, commanding voice, doing as he was told, drawing in a big lungful of air through his nose and bracing himself for what was to come. This time, there was no long, slow penetration, Leo didn’t feed his shaft past the boy’s lips inch by inch, no, he gripped the boy’s head and slammed his hips forward in a single, brutal thrust, once more claiming every inch of his fucktoy’s tight throat for his own personal use.

The savage thrust made Ben start to gag and choke again, his entire body lurching as his throat spasmed around Leo’s shaft, a series of wet, muffled ‘glurk’ sounds escaping from his lips even as they stretched around the base of Leo’s cock. Leo didn’t even seem to notice as his hips began to pull back again, his flared head tugging at the well-stretched walls of Ben’s throat as it went, drawing back until it threatened to slip out of Ben’s throat entirely. Leo shifted his stance, re-planting his feet and pulling Ben’s head down and forward a little to get a better angle before slamming his hips forward again, once more plunging more than a foot of red-hot alpha male megacock into the teenaged sissy’s throat in a single savage thrust. But this time, Ben didn’t gag. The new angle meant Leo’s cock plunged straight down his throat, instead of scraping along the back of it, and Ben found it much easier to suppress his gag reflex this way. Which was fortunate, since now that Leo had found the right angle, he could REALLY get to work.

Ben got his wish. Leo’s hips started to pump, pistoning his monstrous member back and forth, in and out, slow and steady at first, but accelerating with each balls-deep thrust into the boy’s eager throat. Soon he was fucking Ben’s face like it was a pussy, no, a cocksleeve, and Ben had never been happier. Each time Leo’s churning, cum-filled balls smacked against his chin, his eyelids fluttered, silently chanting in his mind ‘I love this cock, I love this cock, I love this cock…’ over and over, and each time Leo pulled back, Ben’s lips clung to its length, giving it that intense vacuum suction and producing a chorus of wet, nasty slurping sounds. He’d jerked off to fantasies of getting his throat fucked by Leo’s glorious shaft for months, but the reality put anything he’d ever imagined to shame, the taste, the smell, the feeling of its heat, the way it stretched his throat as it pistoned in and out, the way it throbbed each time it bottomed out… he wondered if it was possible for a boy to cum just from sucking cock, because he’d never been more turned on in his entire life.

Leo growled with lust as he slammed his hips against Ben’s lips over and over again. He would never have imagined himself in this situation, he’d never even really looked at other men before, sexually, but as he looked down at Ben, the blue-haired teenager’s face smeared with ruined makeup and spit, his painted lips stretched around Leo’s own fat cock… the boy didn’t look much like a man. He looked like a girly little sissy. It also didn’t hurt that he was also giving possibly the best head Leo had ever gotten. How the fuck did his daughter’s boyfriend get so fucking good at sucking cock? The whole scenario was just so perverse, the sensations so intense, it had been so long... Leo knew he couldn’t hold out for much longer.

Ben’s lungs were starting to burn and his head was swimming, but he could feel Leo’s cock throbbing faster and faster in his throat. It felt like that glorious cock was about to explode any second now, and Ben wasn’t going to give up, not when he was this close to his prize, the oceans of thick, pearly cum churning in the alpha male’s heavy, overstuffed balls. When Leo’s grip on his head tightened and his pace shifted from rhythmic pounding to wild, frenzied thrusts, Ben knew the moment was drawing close.

Leo wasn’t in control of his hips anymore, raw instinct set their pace now, bucking and thrusting wildly, plunging his shaft into Ben’s throat over and over with all the gentleness of an animal in heat. The warm, wet walls squeezed around his shaft over and over, milking his monstrous cock, hungry for his seed. As his swinging balls began to tighten against the base of his shaft, Leo felt a familiar tension building in his core, a raging sea or raw sensation that surged higher and higher as the waves crashed against the dam containing it. He grit his teeth, trying to hold out against the tide a moment longer, but there was no stopping it. He could only prepare. Summoning the last of his strength, he yanked his hips back, pulling his member from Ben’s throat until only the head remained between the boy’s painted lips. Without a moment’s hesitation, Ben’s hands came up to grip the shaft, fervently pistoning up and down the spit-slick length beyond his lips, his big blue eyes staring up at Leo worshipfully. As the dam began to buckle, Leo’s neck rolled back, his eyes squeezed shut, and he let out a deep, powerful groan to the heavens.

Leo’s cock bucked in Ben’s grasp like a wild animal trying to escape, the fat head swelling even larger inside the boy’s mouth, pinning down his studded tongue. Cum coursed along the length of his shaft, his steaming-hot seed surging up from deep inside his body like an erupting geyser, the sheer volume of it making his cum-channel bulge as it went. When the surge of cum finally reached the tip, his cock bucked again, firing a finger-thick blast of pearly white cum straight into Ben’s eagerly-waiting mouth with all the force of a fire hose. The first volley struck the teenager’s tongue and splattered in all directions, instantly coating every surface of his mouth in a thick glaze of thick, creamy spunk. The taste exploded across Ben’s tongue, clinging to his taste buds, salty and musky and just a little bit sweet, the heady, intoxicating flavor made only the more potent by the knowledge that it was the taste of his master’s seed. Ben let out a muffled moan, eyelids fluttering, too lost in the taste and the sensations to realize that wasn’t the end of it.

The second shot caught the boy off-guard, flooding his mouth until his tongue was completely drowned in creamy spunk, silencing his moan. Ben’s eyes widened as he realized what was still in store for him, and hurriedly began to swallow, audibly gulping down one mouthful of his master’s thick, potent ball-batter after another, but even swallowing as fast as he could, there seemed to be no end to Leo’s cum, each surge of seed filling Ben’s mouth a little fuller than the last, until his cheeks were ballooning as he struggled to keep it all contained. Soon it was just too much, and the next shot forced itself up and out the boy’s nose, forcing Ben to pull back until the fat head slipped from his lips with a pop.

The endless waves of cum didn’t stop as ben struggled to swallow his oversized mouthful, another thick rope of potent seed firing from the tip, arching through the air before landing with a heavy splat on Ben’s upturned face, painting a pearly white stripe across his pale features, covering his ruined makeup. Ben’s hands continued to stroke and milk that glorious shaft, now aiming the fearsome weapon squarely at his own face as stream after stream of steaming hot spunk fired from the tip, each finger-thick rope painting another stripe across his features until he could barely be seen beneath it.

It may have seemed to be endless, but all good things must end eventually, and slowly, the blasts of cum grew weaker and weaker, coming slower and slower, until it was little more than a slow, steady trickle that dripped from the tip. The raw pleasure of orgasm gave way to the warm, gentle bliss of afterglow and Leo’s mind slowly returned. Ben still kneeled before him, kissing and licking worshipfully at the enormous head of his still-hard cock, one hand wiping at the layer of cum that coated his face, bringing each fingerful to his mouth and sucking the digit clean, almost in a trance. When the task was done and his face was clean again, he seemed to come back to his senses, looking up at Leo with pure adoration on his face.

“Oh, Sir, thank you, thank you so much, that was incredible, it was everything I dreamed and then some, I’m so glad you let me be your little sissy slut~... I nearly passed out when you were fucking my throat, I never wanted it to end, but then you CAME, and it was… ohh, Sir, there was just soooo much…” Ben moaned, excictedly recounting the moment. “It was so delicious, I tried so hard to swallow it all, Sir, but there was just too much, you just kept cumming and cumming… I’ll try harder next time, Sir, I promise, I’ll be a good bitch boi and I won’t spill a drop. But then, it felt so incredible on my face, too... The smell, the feeling on my skin, they’re burned into my brain now, I’ll never be able to forget it… I’m marked, now, I’m your bitch, Sir, your personal sisssy fucktoy~! I’m so glad you decided to use me...”

A smirk spread across Leo’s lips as he stared down at Ben, still kneeling before him, taking note of an obvious wet spot on the front of the boy’s lacy lingerie panties. His hands released their grip on Ben’s head, though one lingered there, slowly stroking through the boy’s soft blue hair. He said nothing for a long moment, then suddenly, his hand tightened into a fist, gripping a handful of Ben’s hair, his expression darkening. “...Did I say you were done, slut? You sound like you think you’re done. It’s gonna take more than one load to satisfy me. A LOT more.” He half-growled. “Still think you got what it takes to be my bitch?” He demanded.

Ben’s eyes went wide with surprise at the sudden roughness, but as Leo spoke, his expression turned to one of nervous excitement, his teeth sinking into his plump, painted lower lip. “I’m sorry, Sir, I’m just a dumb little sissy, of course you wouldn’t be finished so soon. Please, Sir, punish your worthless little sissy bitch and then use me however you want, for however long you want!” He pleaded, squirming on his knees with anticipation.

Leo’s wicked expression split with an equally wicked grin, and he released his grip on Ben’s hair. “Go fix your makeup.” He commanded, simply. Ben blinked, surprised, then nodded and pushed himself to his feet, turning for the door. “And grab some lotion on your way back.” Leo added just before Ben reached the door.


Ben looked a little surprised, then smiled. “Yes, Sir!”