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  • 2 weeks later...

One of the more imaginative stories on here, really hot! (and I would love to go to one of these parties, assuming that the older men each kick in a bit for the pot, they don't have to kick in much for a $1,000 pot.... just in case anyone in Boston wants to organize something like this I am in)

in the meantime, I eagerly look forward to the 3rd installment

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I reported my new card – and the total, twelve – to the dealer.

“You are not in the lead,” he said, and I couldn’t help but offer up a bit of a smirk in return.

“I’m not surprised.”

He nodded, and said, “Continuing?” and I nodded back, then moved off to the side to get another glass of the bubbly water. My dick was still hard in my little diamond-marked briefs, and I noticed my hand was shaking as I took a sip.  One thousand dollars. I took some deep breaths, drank some more water, and waited.

The last two of the five other diamonds returned, and walked up to the dealer, one of them looking chagrined, the other pleased. Behind them, the two men in clubs spoke to each other, and then laughed.

“And?” the host asked, a moment later, his voice loud across the room. I looked at him again, unable to help myself from noticing the dark hair across his wide chest, and the short athletic lace-ups that left nothing to the imagination definitely showed a full pouch in front.  The man dressed as the dealer read from his little clipboard.
“We have one player who have bust" and with that there was a rumble of laughter, snickering, and even a couple of cheers from among the men, and I saw the chagrined looking young diamond blush and look at the ground and bite his lip.

Once the noise calmed down, the dealer continued, “and two more who are holding.” He looked at his clipboard again, being unnecessarily dramatic, I could tell, as my stomach tightened. “But no black-jacks.”

I exhaled. Okay. There was me and one other diamond still here to play, and no one had broken twenty-one, which meant we all still had a chance to take home the pot. I only had twelve, but I also had a second hand.
I tried not to consider how many men that meant I would be with before I finished that second hand, and finished the rest of my drink.  The dealer gave the wheel a spin, but before it even stopped, he spoke again. “If the player who has bust and those who are holding will follow me,” he dealer said, “I will set you all up the waiting areas.” The three diamonds followed him – it struck me that the red-haired fellow who had held after his first card was already gone. There were only two of us diamonds remaining – me, and a tall and slim blond who was very handsome and didn’t seem to be remotely nervous.  They left. The wheel clicked around slower and slower, then stopped on the hearts.

“Okay,” the host said, in his deep voice. “Those of you in hearts who already were chosen by players in the first round, hang back.” This meant four of the men in the long cotton pants moved to stand beside the host.
The host tapped the first heart on the shoulder – a short fire-plug of a man who was wide and bore some faded tattoos on his left arm, and he walked straight up to the blond, and leaned in to make his offer. The blond nodded once, and they didn’t even pause – they just left the room through the arch.  I took a deep breath as the host tapped the next man and he approached me. He was fit and vascular – veins stood out on his forearms and I could tell he had strong legs given how tight the cotton pants were riding his thighs. As he got to my side, I realized he was probably older than he seemed – even behind his mask, I noticed the lines beside his eyes and the corner of his mouth. They weren’t obvious at first, but they were there – and there was a ghost of the presence of grey hair on his otherwise shaved head. He was a very well-preserved fifty-something, I figured.
I held my breath as he leaned in to talk in my ear.

“I like to eat a boy’s ass before I bugger it,” he said. “And after. And I like a boy to be very vocal about what I’m doing.”

I swallowed. “You play safe?” I asked, also whispering.

He regarded me, and the creases around his eyes deepened when he smiled. “I’ll add fifty to your pot if I don’t have to. You don’t need to worry about me,” he said, then added, moving closer to my ear until his breath tickled. “All you’re going to get from me is a well-buggered hole.”

Fifty to my pot?  I nodded. “Okay.”  He led me through the arch.

In our room, the older man closed the door – I felt a bit of relief at that, I had to admit, given how all the eyes of the remaining men had followed us through the arch. He crossed his veined arms over his chest, and smiled at me, asking “Does boy want to get naked for me?”

Right. He liked boys who were verbal.

“Yes, sir,” I said. “I want to be naked for you.” I pulled down my briefs, and my dick – it had never really completely softened – was once again on display. “Would you like me to turn around for you?” I asked, aiming for a shy and timid voice, which I hoped would be what he wanted.

“Yes, I would,” he answered.

 

I turned in a slow circle, maintaining my innocent pose and shy glance, and kept talking. “I hope you like me.”

 

“I do, boy. I do.”

 

“What would you like me to do now?” I asked.

 

“I think you should come over here and help me get undressed, too.”

 

I walked over to him, and my fingers shook a bit undoing the knot on his long cotton pants. When I pulled them down, I didn’t have to fake my chatter. “You have really strong legs,” I said, running my hands up and down his thick thighs. “And you’re... big.” He’d shaved his pubic hair and balls – again, I could see that the hair would be grey if he let it grow back from the ghost of stubble that remained – but the man had a large cock that was already mostly hard, and was already caught in a silver studded black leather cock ring.

 

“Do you like big dicks?” he asked, his voice in a deeper, more intense tones.

 

I nodded, then remembered he liked things verbal. “Yes. I like big dicks. And I like to suck dick a lot.”

He made a little noise, and his fat dick shifted as he asked “Do you like having your ass eaten?”

I bit my lip for just a second. “I do.”

“You hesitated. Why?” The tone brooked no argument. It was obvious he assumed I’d answer, and honestly.

“It makes me really horny,” I said, feeling my face heat up. It was true. Having someone eat my butt was pretty much the fastest way to get me going – maybe second to sucking dick, but sucking dick made me want to jerk off and get the guy off, so I could swallow it. Having a tongue inside me made me crazy for having a dick inside me.  I looked again at the man’s fat cock, and swallowed.

“Horny?” he asked, and again, his tone was clear: he wanted to hear more.

“It makes me crazy for getting fucked,” I said. It came out in a rush, my voice trembling. Why was I admitting all this?  One thousand dollars.

“Get on the bed,” he said. “On your back.”

I did as he ordered, feeling my stomach clench and unclench as I lay down. He got onto the bed, between my legs, and slid forward until his knees were pressing against my widely spread thighs. His hands were rough as he slid them under my legs, then he paused, and asked “You want me to eat your ass, boy?”

“Yes, please,” I said, his even gaze making me extremely polite in some bizarre way. He raised one eyebrow, so I repeated my request “Please, eat my ass.”

 

 He lifted me, rocking me higher onto my back, and I reached out to grab the bed to keep myself from tipping to the right. He hoisted my legs high, and then leaned forward and took in a deep breath through his nose, barely an inch from my ass, now up near his face. I trembled.

“You’ve been fucked already tonight, haven’t you, boy?”

“Yes,” I said, shaking still.

“What card did the guy who fucked you give you?”

“Uh... Eight. Eight of clubs.”

The man smiled. Once again, it struck me that behind his mask he could be fifty or more, but his fit, vascular body was definitely up to the task of holding my ass up in the air. Then thinking took a detour as he leaned forward and his tongue darted into my raised pucker.

“Oh god!” I gasped, and then the noises I made after that were more or less just moans and groaning. He had a thick and hot tongue, and he knew how to bury it just right in my ass. His hands held my legs up, and the angle was perfect for him to slobber and lick and suck and even nibble at my pucker. I twisted, writhed, and continued to let out little whimpers and moans as my once-fucked ass was quite overwhelmed by the older man’s powerful tongue.  He paused, and I lay there, panting for a second.

“Speak up, boy,” he reminded me, and then he continued his tonguing.

I could barely formulate complete thoughts, let alone words. What came out of my mouth was nearly a stream of consciousness. “Oh yes! Oh god, yes! I love that, oh that! You’re so good... oh my god I love it! Please! Oh god that feels good – that feels so fucking good! Please! Oh! Fuck!” I went on and on, barely registering what I was saying, looking up at the masked man’s face – his forehead visible above my balls and my cock – which was rock hard now and dripping onto my stomach from the awkward angle I was perched. His grip on my legs grew tighter as he buried his face deeper between my cheeks, and his tongue flicked maddeningly inside me, sometimes slurping, sometimes drilling.  “Please! Please fuck me! Oh god oh god I need to be fucked! God, please!”

I’d moved on from telling him how good it felt and was now begging him to fuck me. I wasn’t sure when I’d done so, but I realized I was asking for it over and over when he pulled away from my pucker with what was almost a sneer on his face.

“Yeah, boy?” he asked. “You need to get fucked, do you? You want my fat dick, do you?” He leaned back down and licked hard at my pucker.

“Yes!” I gasped. “Please! I need you to fuck me! I need your dick! Oh fuck god yes please!”

He grunted, and with three large swipes of his tongue, he deposited a mouthful of saliva into my pucker. I could feel his spit leaking around my balls and onto my stomach, as well as down between my ass cheeks, and writhed as that tongue teased my hole once more. Then he shifted my legs lower and wider, letting my back drop enough that the next thing I felt between my parted ass cheeks was his hard fat cock.  He pressed just the head of his dick against my opening, and leaned ahead until it pushed into me. I groaned, biting my lip, and he paused.

“Tell me, boy,” he ordered, his voice sounding like gravel.

“I.. Oh.. I like that,” I gasped. “It’s big... it hurts, but... oh! Yes, please!”

“You want more?” he leaned forward just a little, and perhaps an inch of his cock moved inside me, his head slipping in, and my ass opening to take it with a welcome heat.

“Oh! Fuck yes! More! I want your dick inside me!” I was begging again, and writhed to try and pull him into me, but his grip was firm on my legs.

He leaned over, and slowly entered me – every inch was tease, every few moments he made me beg for more, and every time he did, I did so willingly. He might have had the fattest dick I’d ever had inside me, and with nothing but his ample saliva (and the leftover lube and spunk from the man before him) the friction was incredible. When I felt him pressing skin-to-skin, and knew that entire dick was inside me, I gasped, and managed to say “Fuck! Oh! Fuck!”

“Yes, boy,” he said, and he began to fuck me. His thighs were as strong as they looked, and his grip never loosened as he started to pump his cock up my ass. His thrusts were steady, measured, and he never had less than half of that fat dick inside me. I continued to babble to him, telling him I loved it, I wanted it, that I loved being fucked that I loved his dick – I wasn’t sure what else I was saying, right up until he leaned over me and gave me a series of three deep thrusts in rapid succession, and I gasped out loud at the way his dick was rubbing inside me.

“Oh, fuck, yes! That! That!”

“You ready for my load, boy?”

“Yes, please! Fuck yes please!”

He gave me another series of those deep quick thrusts and then grunted loud into my ear and said, “Here it fucking comes, boy,” as I felt his load blow deep inside me. I wrapped my legs around his back and pulled him into me, grinding myself against him. My hands tried to get to my dick – I was desperate to jerk off – but he pressed down hard on me, preventing my grip.

“Did I say you could touch yourself?” he asked.

I whined. “No.”

“I’ll make it seventy five if you don’t touch yourself,” he said.

I whimpered, but nodded.

He laughed, grinding himself again, then raising himself. He left his dick inside me as he positioned his arms back under my legs, and was careful how he lifted me. When his fat cock slipped free, his mouth was almost immediately on my ass, and I nearly convulsed with the sensation of him slurping, licking, and swallowing his own load from my hole.

“Oh my god that’s so fucking hot!” I was babbling. My hands twisted in the sheets. I was desperate to jerk myself off, but didn’t. Seventy five extra bucks. I could wait.

He ate my ass clean, licking every last drop from my hole and leaving me heaving and shaking on the bed when he finally let go. I sank back onto my back, and he smiled down at me, obviously pleased with himself.
“Lick my dick clean while I get out your card,” he said.

I was happy to oblige. Even softening, it wasn’t an easy task, but I do love sucking a dick. The taste of his spunk was incredible. When I finally let go, he smiled, and handed me the card from his small leather arm pouch.  It was the jack of hearts.  Oh shit.  Twenty two.  Bust.

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The paddle slapped my right ass cheek with just enough force that I closed my eyes for a second.

“Twenty-two,” I said.

I was bent over and holding the back of a large leather chair, the little diamond briefs down by my ankles, and paying for going “bust” in the manner that all the players did when it happened. I wasn’t the only one – when I’d walked in, after telling my total to the dealer, he’d brought another guy here with him, too. He’d taken up the same position on the next wing-backed leather chair to the other side of the small table, and a moment after the paddle landed on my butt, I heard the other guy in the diamond briefs take a similar hit, and he said, “twenty-five.”

The paddle struck my other ass cheek.

“Twenty-one,” I said.

I’d been told to count down from my score, and the man with the paddle – mine was one of the men wearing hearts, a thick-bodied man in his forties maybe, with a hairy chest and a neatly trimmed moustache and dark hair – had begun his work.

Another hit – and I couldn’t help but notice it was a bit harder.

“Twenty,” I said.

On the other side of the table, I heard the other guy say “Twenty-four,” and I thought the crack of the paddle on his ass that had proceeded it was louder than my own. The guy paddling him was the big hairy bear in clubs I’d seen turned down by the Latino guy in the diamond briefs.

The next hit was harder, and landed right across my ass.

“Nineteen,” I said. I squirmed a bit, shifting my grip on the chair.

It went on. Eighteen was an up-stroke that landed deftly below my right buttock, almost on my thigh – it made me yelp out loud and the mustached man chuckled as the next strike, number seventeen, did the same on the other side.

By the time I was said “Ten” my eyes were watering and my ass was hot. It was obvious the man with the paddle knew what he was doing. From the way the other voice in the room nearly broke when he cried out “Twelve” I figured I was actually having an easier time of it than the other guy, but it was definitely taking a toll.

I huffed in a breath at “Eight” and managed to get to “Five” by breathing evenly and running over the mental tally in my head. Only four more. Only four more.

Another smack, square across my right ass cheek.

“Four!”

Only three more. Only three more.

Another, left ass cheek. “Three!”

The last two were up-strokes again, and they landed hard, one on either side of my butt. After I called out “One!” with nothing shy of total relief, the mustached man had put the paddle back on the little table where three other paddles already sat. I straightened up, and slowly pulled up the diamond briefs over my burning butt. The material felt cold, but it wasn’t soothing. I flinched a little, feeling every spot it touched my skin.

“Two!” the strangled voice cried again, and I turned and watched the burly hairy bear swing at the other diamond boy’s but for the last time. The bear was definitely putting his strength behind the blow, and the sound was a loud crack in the smallish room.

“One!” the boy said.

The bear tossed the paddle on the table, and walked out.

The other guy’s ass was bright red, and he leaned against the chair for a few more seconds than I had, then slowly leaned down to pull up his briefs. He took a deep breath, like he was working up the courage, and I walked out of the room before he was done.

In the hall, the dealer approached me.

“You have a second hand for this round. The others will be resting for a half-hour or so, but you’ll need to finish your second hand – built on the four of clubs – before the second round begins.”

The idea of that second hand – let alone a whole other round – brought tears to my eyes again. I blinked. Okay. I could do this. I needed the money, and hey, I could take a nice long soothing bath when it was all over. For maybe a week.

The dealer led me back into the main room, where, I saw, not all the men had gathered. The diamonds were gone, of course, but I was starting to realize that the deck of cards, split up among the men that had gathered, only meant that most of the men would be able to be picked twice. I was trying to distract myself from the pain in my ass and what I was heading into, but the math of it had just clicked. Six men for each suit – and if you took the diamonds out of it, since there was no way for me to draw a diamond – then those eighteen men could each have two cards each, and one of them would be able to have a third, assuming all the cards were used only the once.

When I looked around the room, it made sense. The first turn, the diamonds had all just chosen a guy we liked – I’d gone for my photographer friend, who was a club. The next round, the clubs had come up on the wheel, and we’d all had a club come talk to us. I’d seen my photographer friend go off with someone – and now he wasn’t in the room. There were five clubs here, and he wasn’t one of them. That meant, if I was right, that another club had gotten the last – the thirteenth – club card, and he’d had his two turns already for the night.

“As you know,” the host said, and I jumped, looking at the man in the spade athletic shorts with a start. “This lucky young man doubled down. So our usual half an hour respite will be his opportunity to play this second hand for the first round.” The men all looked at me from behind their masks, some smiling, some leering. I felt my face grow as warm as my butt.

The host walked to the wheel. “Given the limitation, I think there’s time for two draws. Let’s settle that first so everyone else can enjoy a break. If you decide to hold after one card, we’ll just move on from there.” Then he spun the wheel. It spun, then stopped on the heart.

“I believe five of you have already had one turn?” the host said. One heart nodded and stepped forward. He had a shaved head, a single silver hoop in one ear, and a smooth wide chest. If it hadn’t been for the mask and the lack of a white t-shirt, he could have been Mr. Clean’s twin.

“I like my first time to be a blow job,” the man said, loud enough for everyone to hear, even though he’d moved closer to me. “Makes my second turn last longer. You like to swallow?”

“Okay,” I said, admittedly relieved.

The wheel spun again. Clubs this time.

“Damn,” the host said. “Clubs are having all the luck tonight.” Most of the men in the room laughed, and I swallowed. There were only five men left in the wife-beaters and cotton pants marked with the club. The big burly bear was one of them, and I flashed back on how much he’d seemed to enjoy beating the other boy’s ass with the paddle.

“You’ve all had a turn, no?” the host said, and the four men nodded. He turned back to me. “Close your eyes,” he said. “I’ll line them up, and you pick a number from one to five.”

I closed my eyes, feeling my stomach clench and twist. I heard the men moving around.

“Okay,” the host said. He sounded very amused.

“Four,” I said, thinking of the card number I’d gotten twice already. When I opened my eyes, the black man with the big arms I’d seen get picked by the diamond before me in the first round was moving toward where I stood waiting with the Mr. Clean lookalike.

“Listen,” he said, smiling. I realized he wasn’t talking to me, but to the man in hearts. “You want his mouth – and I don’t want to end up rushed, so how about I take his ass, and we all go play right off?”

“Sure,” Mr. Clean said.

I swallowed, and looked at the host, not sure what to do.

“That’s fine by me,” the host said, a sly smile firmly in place. “And you can still choose not to draw the second card if you want to hold,” he said to me.

I took a deep breath.

“Okay,” I said.

The two men led the way.

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I’m a born cocksucker and maybe I don’t often admit that, but on my knees in front of two older men in white masks, my hand gripping their cocks, and alternating my mouth from one to the other, I was definitely enjoying myself. The reality that it was part of potentially taking home some part of a thousand dollar prize in an evening loosely based on black-jack – if black-jack also came with masked older men willing to fuck you as part of the game – had definitely made me nervous at first.

One of the men moaned while I swallowed him down to his balls. He was a stocky smooth white guy who, I’d thought, reminded me of Mister Clean – complete with the single hoop earring. I tightened my lips around the last inches of his shaft for a moment, then let his dick slowly slide free from my mouth and turned my attention to the other man, who was taller, black, and had the build of a power-lifter and the arms to match. I wasn’t sure I’d be able to swallow the entirety of this second dick – he had a wicked curve to his cock and the root of his dick was much fatter – but I wanted to try.

I sucked him, and looked up at the two men while I did so. I was hoping to distract the black man if I could, because –

“Okay,” the black man said, as if he was reading my mind. “You’re gonna make me cum if you keep slurping me like that.” He pulled back, and as his thick curved cock slipped out of my mouth, I took in a couple of quick breaths.

We were back in one of the rooms – door closed – and I’d half hoped to spare my ass and give it some time to recover from the paddling I’d received for going bust with my last “hand.” Blowing them both and making them come in the half-hour we had before the second round began could have done it, but the older black man had suggested he and Mr. Clean enjoy me together since Mr. Clean had wanted my mouth, and he wanted my ass and that would give them both more time if they didn’t mind each other’s company.

“Okay,” the Mr. Clean-like daddy said, smiling down at where I kneeled. “On the bed.” He backed away, at the same time stepping out of the cloth pants I’d pulled down to access his dick. He sat on the bed and then scooted up to sit between the pillows, spreading his legs. His dick, hard and wet with my spit, stood up and ready for more attention, his cockhead peeking out from the foreskin.

“Go on,” the black man said with a chuckle.

I rose and sort of crawled onto the bed. The black man gave my ass a light swat with his hand as I passed him and I yelped – my ass was probably still bright red from the paddling underneath the tiny white briefs with the diamond design on them that made up my only clothes. His laugh was deep and as I put my face between the smooth daddy’s thighs and gave his balls a quick lick, I felt the bed tip behind me as the other man got onto the bed.

I focused on licking and sucking at the uncut cock in front of me as I felt hands work to peel back the shorts that covered my freshly paddled ass. Lying back and enjoying my attention, the stocky daddy rested one hand on my head while I bobbed up and down on his dick, twirling my tongue around his cockhead and in and out of his foreskin. I truly love sucking cock, and even with my ass still burning and a tremble in my stomach over what it was going to feel like to have that curved black cock inside me, I was getting hard.

Behind me, the black man’s hands were rubbing my reddened butt gently, though even that was setting off the heat on my skin. When he ran a finger up between my cheeks, my back arched and I shivered, which made Mr. Clean groan and push on my head a bit – obviously he’d liked the way I’d swallowed him when I’d reacted to the touch.

“Boy’s ass is hot and ready,” the man said behind me, and I felt him let go while he stirred. When his fingers returned slick with cool lube, I nearly moaned with the temporary relief I felt when he ran them between my ass cheeks again, and the result was obviously pleasing for Mr. Clean, who put his other hand on the back of my head and started to thrust up a little with his thighs.

There were more squirting sounds behind me, and then the unmistakeable feel of a dick pressing at my pucker. I groaned again, burying my face down to the bottom of Mr. Clean’s shaft, and held my breath as the black man gripped my waist with one hand, and guided his dick into me with the other.

I felt every inch, and though he went slow, I was soon grunting and twisting between the two men, trying to find a position that didn’t feel like a cock was setting my ass on fire from the inside out. He wasn’t the thickest cock I’d ever taken, or the largest, but after being fucked already this evening – twice – and the battering my butt had taken with a paddle, the sensation was unbelievable.

“Oh fuck yeah,” the black man’s voice was almost a rumble. “This boy’s ass is fucking hot velvet...” He pushed his last thick inch into me with a little jab, and the curve of his cock made my whole body arch between them. I swallowed Mr. Clean’s dick convulsively, breathing in little explosions through my nose while I tried to keep up with his thrusts, which were getting rougher and faster. His hands tightened in my hair.

“Yeah, fuck him,” Mr. Clean said.

Spit-roasted between the two dicks, it was all I could do to keep upright as the two men fucked me at both ends. My ass burned, but soon the heat wasn’t entirely unpleasurable – he wasn’t being rough on my hole, though he was definitely fucking me with the full length of his curved meat. Mr. Clean, on the other hand, was ramming his cock into my mouth with a vengeance, and I was pretty sure he was impressed I was keeping up.

Like I said, I love to suck cock.

It didn’t surprise me that he blew his load first – he grabbed my head and buried his dick in my mouth as his cock erupted. “Swallow it, fuck!” he growled, and I did, happy to oblige. After that, I licked and sucked at his shaft – he didn’t quite soften completely, and got every last drop while behind me the black man continued his slow deep rhythm on my hole. A few minutes more passed like this, and I was sucking on Mr. Clean’s balls and actively pushing back against the other man’s thrusts when he grabbed my waist in both hands, buried himself deep, and came with a long rumbling exhalation of “Yeah...”

The flood of his cum in my ass made me realize he wasn’t wearing a rubber and that we hadn’t even discussed it. My head swam, my mouth still full of the taste of spunk and sweat.

The black man pulled out of my ass and was upright and wiping his dick with a cloth before I even got off the bed.

Mr. Clean nodded to the ensuite that accompanied this room. “Most of the boys take a shower between hands. You’ve probably got time,” he said. He reached up to the pouch on his arm, and pulled out his card. He handed it to me.

Ace of hearts. Along with my four of clubs, that was either a five, or a fifteen. I turned and looked at the black man, feeling some of his cum leak out of my pucker, and winced at the feel of the blankets on my reddened ass.

He pulled out his card and handed it to me. Five of clubs.

I grinned.

Twenty.

“Thanks,” I said, unable to help myself.

Mr. Clean laughed. “Believe me, boy. Our pleasure.”

I got up to take as quick a shower as I could.

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