Big Cock Boss

Hi everyone, had to re-upload because I found a few annoying mistakes on re-reading. Not my usual futa-related stuff but please let me know if you enjoyed it! -- TSG123

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'A night out with his boss. Should have been a piece of cake right?'

He bounced up and down on his boss's dick, squealing like a pig.

'What a chance, an opportunity to get on his good side!'

The cock throbbed inside him, making Sam go cross-eyed as Alex bounced him roughly against his lap. The fact that his boss was a crossdresser didn't change the fact that a fifty-year-old man was pounding him like a two-dollar whore.

The evening had started simply:

Sam was a young board member, amazed that he had managed to even make it this far after just a few years working as a junior manager. A work night had been planned with a few of the senior board members, and the CEO, Alex; tall, effeminate, with thinning brown hair and large lips for a man. He had invited Alex specifically to join them.

Almost everyone turned up wearing expensive, razor sharp suits. Alex was wearing a black cocktail dress.

Sam stared for what seemed like an age. Was that really his CEO with a figure-hugging dress clamped around his ass? He surprisingly had the figure for it, albeit with no breasts although he was sure he could spot subtle moulds pushing the chest out slightly. His hair was covered by a wig matched to his natural brown and his lashes were large and curled, lips now moist and glistening.

He didn't have time to stare as they didn't waste a second, getting in a limousine and heading straight for a strip club. Soon Sam was relaxing as a bevy of scantily clad ladies were bought to them in a private room.

"Come here, sit with me," commanded Alex, and Sam obediently sat next to him, drinking in the long black lashes fluttering and the pink barbie-doll lips which seemed nearly as kissable as the ones being flaunted by the strippers.

He recoiled for a moment.

'You're not getting the hots for your weird boss in a dress,' he chastised himself.

Sam tried to ignore Alex as best he could and enjoy the woman straddling his lap, watching her gyrate and squeeze her huge melons as other women began to ride their respective guests.

"Nice to see ya again Lexy," smiled the girl on Sam's lap, looking over at Alex.

"You too Candy," he said, his voice deep and not at all girly.

Clearly they knew each other.

Candy, Alex and the stripper who was supposed to be dancing on Alex started having a long conversation about their favourite tv shows, makeup and fashion. It was as if Sam wasn't even in the room, simply a task that needed to be fulfilled.

"Hey, I'm right here honey," said Sam, a little tetchy.

Candy rolled her eyes and went back to grinding with far less enthusiasm.

Alex laughed, and Sam felt his balls shrivel as Candy seemed to be doing her best to be as undesirable as possible.

He felt a hand grab his thigh and squeeze.

He looked down and it was Alex's hand, which made his heart beat a little quicker.

"You need to know how to treat a lady Sam," he said with a knowing smirk.

"Let me guess, you're gonna give me the 'treat em mean, keep 'em keen' talk right?" he said, trying to banter with the wierdo who would hopefully give him a raise if he played his cards right.

"Not quite, here, let me show you," he said gesturing to his lap.

"Uh, what do you mean boss?" he said, still aware that Alex's hand hadn't left his thigh. It was a large hand.

"Come here, and let me show you how to treat a woman."

"No thanks," he uttered sharply.

"Hmmm, I thought you were better management material than that," said Alex idly, taking his hand away.

'Shit.'

"Wait!" said Sam quickly.

He pushed Candy unceremoniously away from him, took Alex's hand and stood up, placing himself on his lap, facing away. Candy seemed quite relieved not to be straddling Sam any more.

"Go on then," he said in a challenging tone, "let's see it boss!"

Alex without further ado pulled Sam in by his waist, and lodged him firmly against his crotch, and the monster that pressed between Sam's butt cheeks made his jaw drop.

Candy sneered; she must have known exactly what had just lodged in between his cheeks.

"JESUS," he cried out as Alex began to hump him, gyrating his hips so that Sam was being bucked by the bigger man.

"OKAY, I-I G-GET IT, Ugh, A-Alex, Alex, B...Boss, UGH...."

Candy took this moment to come back, waving her tits close to his face with renewed enthusiasm, jiggling them. They looked so good that they distracted him completely from the pork-sword being shoved into his buns, and he tried to reach out and touch them, but Alex pulled him back.

"Relax," said Alex into his ear, and Sam groaned as he let the man push against his pants, almost giving him a wedgy with what felt like an 11-inch cock under the dress.

Then Alex's huge hand snaked round and grabbed the front of his pants, and clamped down on Sam's throbbing erection.

"WAIT-! Huuuunnnnnnn," groaned Sam, as his crotch was assaulted by Alex's meaty fist, panting as the other hand began undoing his belt.

"Alex, ALEX MPHNn-!

Candy shut him up by shoving her tits into his face, nipples rubbing invitingly against his lips. He couldn't deny them and began to suckle on her like a baby as Alex groped him.

The hand that was rubbing his pants had snaked inside and was now fully wanking him, spanking his cock so hard that he was moaning, unable to contain the pleasure that the combination of Candy and Alex's ministrations were giving.

"Mnnnnnn.... MMMMMMMMMnnnNNNNNh!"

The girl drew back as Sam was bobbed up and down on the older man's lap, writhing as his body betrayed him.

"Wait," he begged.

"Lube Lexy?" Candy asked Alex in a business-like manner, ignoring Sam completely.

"Thanks hun," he responded.

She flashed Alex a smile as Sam whined.

"Lube, why do we need lu-?! MMmmmmnnnnnn-!"

Alex shoved his fingers into Sam's mouth, and now Sam was smelling those huge fingers, and tasting something... something tangy.

He screamed as he realised it had been the same hand that had wanked his cock, and he tried to spit out the taste of his own cum, but Alex became aggressive and shoved his hand almost to the point of going down Sam's throat.

Sam gagged and after a few seconds Alex pulled his hand away, leaving Sam gasping for air as the hand, which was now wet with saliva, slid down to his ass, whilst the other hand finished removing his belt.

"Sir, boss... let's stop, maybe that's enough...." he gasped, trying to pull away as the wet hand slid fully down his butt crack.

"I don't think so," Alex grunted in his ear.

Candy jogged back, heels clacking, and gave him a deep, tongue-filled kiss which made his head spin.

"sto....Mnnnnnnn, MMnnnnn."

He didn't see the lube she passed Alex surreptitiously with her left hand as her right began to undo the buttons of his shirt, too busy revelling in the warm taste of her mouth.

The sound of the bottle slathering something underneath the black dress was drowned out by the pounding music, Sam moaning as he and Candy wrestled their tongues back and forth.

Then a fleshy object pressed against his ass, and his whole world came undone as Candy and Alex clamped down on his body and forced Sam's ass onto a meaty skewer.

"AGGHHHH!" squealed Sam, as he felt Alex's slick cock penetrate straight into his anal ring.

His blubbering was muffled by Candy shoving her tits back into his face, and he clung to her and then moaned in pain as she pushed him further down the steel shaft.

"Stopmmhpp," he tried to whimper into her chest, but no-one heeded him as fully half of his boss slid inside him, wet, hot and pulsing as it stimulated everything in his abdomen.

"Huhhhhhhnn!"

He managed to push Candy away, but Alex hugged him so that he was now glued to the man's chest. The satin dress was soft, and a proportionally massive tongue slid across the side of Sam's face.

"Fuck, Alex, just wait.. you can't....," he begged as Alex's hand began pumping his hard-on with a vengeance, his six-inch cock saluting proudly between Alex's fist bobbing up and down it.

Candy dived back on top of him and ripped Sam's shirt off his body, a sneer on her face as she stepped back with rags in her hands.

Sam looked up at her, and then down at his naked, cock which was spurting pre-cum all down its sides like a chocolate fountain.

"I'm right here," said Alex, and Sam turned his head to look back, straight into a world-ending kiss. His boss clamped those huge lips around his mouth and sucked his face so hard that Sam thought he might swallow his head whole, a beast of a tongue then entered his mouth and forced his own around for fun before slithering to his throat and back again.

Sam squealed into the kiss. It was unbelievable. He couldn't think, there was no respite as Alex pulled him a few inches further down the shaft that was rearranging his insides. The older man was utterly dominant, in complete control as Sam tried to pull Alex's hands away from his erection, but this only made the man tighten his grip and pump faster, and Sam had to concentrate not to cum, thankfully helped by the fact his insides were then plundered by a further few inches of cock sliding inside him.

Sam was spasming, and finally managed to rip Alex's grip from his cock before he released his eager sperm into the man's hand.

"Look, just stop, s-stop...." he snivelled, given a few seconds to get his bearings. He made to sit off of Alex's lap and moaned. He tried again, and moaned.

He looked down and realised that the massive cock had completely disappeared, replaced only by a huge pair of balls which his own smaller ones were resting happily on.

'Where is it?'

This was answered by Alex gyrating his lap, and Sam felt a HUGE spear churning his guts.

"FUCK ME!" he blurted as ripples of ecstasy speared through him.

He looked up and realised Candy was smiling cruelly as she gave him one last glance before leaving the room. The other board members smirked at him, still with strippers on their laps.

"Wait, HOHHHHH GOD!"

The men laughed as Sam groaned, his hips following Alex's as he gyrated in circles, stimulating waves of electricity throughout Sam's body. Sam and Alex's strippers were gone, Sam glued to Alex's lap and moaning like a whore.

He was the entertainment now.

"Jesus Alex," he moaned as Alex speared him.

"You can call me Lexy if you like," Alex giggled into his ear, nipping at it as the young man quaking on his lap.

"No," he moaned, even as that cock made his lips tremble.

"You're hotter than any stripper, you sexy boy," he grunted, that deep voice vibrating in Sam's ear and making him spasm in fear and pleasure.

"Stop, stop Alex, I'm not gay, I'm not OH FUCK, OHHHHHHHh!!!"

Alex had slid him up and down, giving him the full tour of his penis. Sam's asshole was being ruined, quivering at the base of its brutal invader. Sam knew if he did not get off soon, he was going to fall in love with how good this felt.

"Jesus, jesus..." muttered Sam, terrified of speaking again in case Alex did something that made his insides feel that good again.

"We can just wait here if you don't want me to move," said Alex kindly.

"Yes," Sam begged, "Thank you A-Alex... let's not move."

"Okay," Alex said, and he began to tease Sam's mouth with those pink, tantalising lips.

Sam tried not to be sucked into a kiss, but every movement he made, even taking a breath, was moving that THING inside him....

'It's pulsing, I can feel my bosses' heartbeat, oh God that's so GROSS, He's SO TURNED ON BY BEING INSIDE ME!!!!!'

Sam moaned with real need as that bastard Alex flexed his cock inside him, sending an arc of high voltage orgasmic pleasure ripping up his spine, and the open 'O' shape of his lips didn't survive for long as Alex's tongue found its home safe in the depths of Sam's mouth. Sam melted into the kiss, and this time he was forced to kiss back, melting into the embrace of his big, strong, sexy boss.

Sam's inner walls were collapsing, his body reacting in ways he couldn't control. Alex's violent hip movements were beginning to bring tears to his eye as he tormented what must have been his prostate, or G spot?... he didn't know, but whenever Alex hit that particular place, Sam's whole world lit up, night turning to day, and for a flash he would forget what he was doing, or who was inside him, or why he even cared... as long as he kept giving it to him.

Sam moaned so hard into Alex's mouth that some of the board members struggled to contain their laughter as Sam began to take his boss's dick with much less restraint. He found popping his hips in circular motions made the huge organ rub against the sides of anal wall, stimulating different, incredible bits of his body. He didn't even notice he had started gyrating harder and dirtier than many of the working ladies in the room. Most of the strippers had begun to watch what was going on and were laughing whilst prostrating themselves across their suited men, enjoying the look of pure ecstasy on Sam's face.

It wasn't often they got to see men being emasculated, and what made it even better was knowing that they were getting paid thousands whilst this freak was riding his boss's cock in front of everyone for nothing.

Sam was sweating. He was naked, in a room full of people, and he looked away from the incredible man whose dick he was riding to see Stanley, one of the top lawyers, eyebrows raised with a beautiful woman on his lap also watching. Unlike Stanley she was openly laughing.

He felt a savage humiliation burn his chest, not helped by Alex choosing that exact moment to pump his hips so hard that he forced Sam to go cross-eyed with pleasure.

The girl's lips spelt out 'OH MY GOD,' and she doubled up because she was laughing so hard, forgetting the man she was on top of as she clutched her sides. Stanley too had a look that seemed to say 'oof, tough luck kid,' unable to hide his mirth at Sam's demeaning position.

Sam screamed, he screamed out of frustration that he was actually going to give in to this fucking pervert in a dress, that he wasn't man enough to say no to Alex's dick, and that Lexy's cock was so good.

Then Alex turned him, a freakish sensation as the man's cock rubbed him 180 degrees inside his anal tract

"Unnnnnnnn, Alex... haha, just uh...that was pretty nice.. UGH-!"

Alex grabbed his hips and began to machine-gun pump his ass, and any last doubts flew away, replaced by the dick inside him, roughing up his internal organs in the most gorgeous way. Getting taken isn't something that can be truly explained, but once Sam had managed to breathe through the pain, the pleasure of sitting on someone so strong, so superior, and getting swept up in it, was the most moving sensation he had ever felt (in more ways then one as his ass cheeks slapped loudly against the man's lap.)

Sam's arms fell around Alex. His nose found the man's neck and breathed in the sultry perfume enveloping him, found comfort in the warmth of the man's back, his embrace, still bouncing Sam brutally on his lap in a perverse fuck-hug. He knew his partner wouldn't let up, and that was part of the reason his cock was so awfully hard and still dribbling like a slow-burning volcano, seeping lava down its sides as everything in his body turned white again, and Sam bit into Alex's neck because he needed him to know how deeply he was being ravaged, wilting in the sun of this man's presence.

"All.....Lex....Lex......"

"Lexy," Alex grunted, driving another thrust into Sam's anus which had him seeing stars.

Sam sobbed. He was going insane, whimpering and gasping into Alex's neck, unable to pull away from the lie of comfort in the man's arms because he was fucking Sam so hard that he didn't think he would ever be able to look a woman in the eye again. As the cock sawed in and out he moaned, and Alex grunted into his ear, so loud and wet. It was soul-destroying how much he was enjoying his boss's dick.

"Lexy," Sam whined as Alex pummelled away at his backside, balls rebounding against his buttocks with loud slaps, which indicated just how hard Alex was pumping his cock into the poor, broken boy willingly flinging himself down to be hilted to the base of Alex's prestigious manhood.

"It's.... Oh Lexy," he gasped, and Alex groaned, because there were tears in the eye of the young man straddling him as he came, cock flexing upwards as white ropes of love flew up Alex's chest and face and onto the wall behind them. The smell of cum was thick in the air as Sam's balls released his stomach-churning joy to the world, the awful secret that he had never even had a chance to keep, coerced into open sodomy in front of his peers.

He looked over at one of the beautiful women staring at him, hot, wet tears running down his cheeks, seeing her incredulous expression as his sexuality was gut-wrenchingly re-aligned by the misuse of his body.

'No, stop, I like women....'

He was so strong.

'I... I like wome....'

Alex's cock was rubbing him to perfection.

He surprised Sam by whispering in his ear.

"Wait."

He slowed to a stop, and Sam had a brief moment to get his bearings through the haze of pleasure, but Alex began pulling him up slowly so that he was kneeling, anus just sitting on the head of his penis.

Sam felt empty. Incomplete. He was kneeling above a horsecock, just waiting for the next sheathing to happen.

"Ride me."

Sam bit his lip, looking into Alex's smug expression, his rosy cheeks curled into a grin.

When in Rome.

He reached forward and pressed his lips against those large, tantalising cherry bites sitting on Alex's face, and Alex moaned in surprise as Sam slid his tongue into his mouth. The two men engaged in a violent mouth wrestle, oblivious to the other board members almost crying with laughter at the previously cocksure young buck now swallowing his boss's tongue.

"Sit down boy," Alex grunted, after breaking the kiss grudgingly.

"No, sir" teased Sam, moving his hips just enough to tease the end of his tight rod, flicking his asshole over the tip and making the man swoon and gasp in frustration and desire.

Of course he would have that cock back inside him... but it was so sexy seeing his boss gagging to destroy his ass that he knew he could bear to wait a little longer just to see the man's need writ large across his hooker-like lashes and lips. .

"Oh I've changed my mind about you boy, you're getting promoted..... to my personal assistant," he grunted, sliding the lubed up head across Sam's sensitive asshole. It felt like being rubbed by a large, slippery mushroom, and he pumped his hips, turgid cock bobbing up and down near Alex's face.

"Only if you promise to keep fucking me."

"I promise," Alex uttered.

"Thank you," said Sam, strangely formal which made Lexy chuckle.

"Stop teasing now boy and get it back in you."

"Yes sir!"

Sam slid back down and moaned, because it's never simple to slide back down on a cock that's as wide and as long as your own forearm.

"GOODNESS.....oohhhhh."

He tried to go slow, but Alex's dong was so slippery, and his legs shaking so much, that he almost fell to the base of it, squealing like a stuck pig as he did so.

"UHN! I, sorry... OHHHHHH!."

Alex grabbed his ass and began to kneed his cheeks, and Sam briefly felt like a stripper, being fondled and molested whilst enjoying the pure molten bliss radiating from his belly up to his chest. He closed his eyes. There was no escaping how good it felt sitting on Alex's cock, and a smile flickered onto his face as his body aligned itself with the slight upwards curve of the cock, which allowed it to sit perfectly inside his body like the final part of a jigsaw puzzle with a prize of being intensely pleasurable as well as satisfyingly neat.