Black-jack

[Barratboy]

It was promise of 'prize money' that brought me here, although I knew damned well what I was doing would qualify me as a whore, but college didn’t come cheap, and neither did anything else: my crappy apartment, gas, you name it. Frankly, everything was starting to look more and more desperate, so I agreed to put my looks to use with some shady Craigslist 'photo model' request stuff. Although one of the four times had been a guy outright looking for a hook-up for cash, one of the other three had led to this.

The photographer had taken some pretty racy photographs of me, bent over and naked, blindfolded, that sort of stuff, but he had kept my face from being recognizable in any of the shots, just as I had asked. The money had been decent, not great, but decent. The photographer was an older guy, maybe in his forties, but he was in good shape. And, although I’d definitely gotten the gay vibe from him, as he apparently loved looking at my ass, he hadn’t made an overt move. So long story: for the first time in ages I was able to pay the rent as well as put some food in the fridge and still have a little bit of cash left over.

A few weeks later I received a message from the photographer inviting me to a 'blackjack night'. At first I almost dismissed the message at face value as the last thing I wanted to do was gamble away what little cash I had, but then I’d read on and saw that it wasn’t what it sounded like. In fact it was way more than that.

“I’ve shown your photos to a friend who hosts play parties at his home. Handsome young men like you willing to take a risk or two can win big cash at his ‘blackjack nights,’ up to $1,000 for the first prize. It’s consensual. It’s absolutely R-rated and involves what you’d imagine. Don’t worry, though, if you choose to come, you’ll be able to stop at any time.”

I let the e-mail sit for quite a while, but a thousand bucks is a lot to a guy like me, so finally, I replied, and asked for more details. Annoyingly, there weren’t many.

“I can’t tell you much more,” the reply came from the photographer, who added “I’ll be there, and I’ve been to them before. You’ll need a rudimentary understanding of blackjack, and there are usually three or more cash prizes, as well as various other gifts given to some participants. You’ll be popular, if you decide to go, I’ll tell you that. Up to you.”

I replied and said I’d go.

The 'home' the host lived in was large and far enough out of town that I was a bit worried as I drove there in my clunker, but once I arrived I parked in the large curved driveway that led to the place and went for the door, invitation in hand. I had a good body, I liked sex, and I could use a grand. I had no real illusions about the night beyond that, and that was fine by me. At the door, I was greeted by a guy in a nice suit, who took me to a small side-room, where he took my coat, keys and my invitation number, and then traded my printed invitation for a small white envelope with the same number on it. He led me to a door and knocked once before opening it and looking inside, then nodded to me saying “You can go inside to change. The envelope will show you which bag to use.”

I frowned, but he left, so I went into the room as he’d said. There were about two dozen bags lying around, each with a single card attached to them from a deck of cards. A few were mostly empty, though most had piles of regular clothes inside them. I opened my envelope, and pulled out a four of hearts, and a small slip of paper in which were printed these directions: “Dress in the items in the bag matching your card, and then put your clothes into the bag. They will be returned to you afterwards. Then move through the door opposite that through which you entered this room.”

I stripped down, found the bag marked with the four of diamonds, and found that inside, there was only a pair of white briefs with a red diamond printed where my left butt cheek would be. I exhaled. I’d known this was basically going to be that sort of evening, but the reality of holding very little cloth in my hand made it pretty obvious. There was also a small card-holder on a Velcro strap, just the right size for the four of diamonds that had come in my invitation. Inside of the card-holder were instructions that told me to secure the card-holder to my arm with the strap, and to keep my card inside. I did so.

Wearing only the briefs, which, by the way, were very snug and left nothing to the imagination, I took deep breath and pushed through the door.

The room had quite a few men in it already, and I felt my stomach clench a bit when I stepped through the door. Everyone was wearing white – there were already four other guys like me in little white briefs with diamonds on the back of their asses, but there was an obvious division beyond that. Some of the men were wearing white wife beaters and white cotton pants through which it was obvious there was no underwear, and they had the black 'clubs' symbol from a deck of cards on the back of their wife beaters. The 'spades' were all wearing white athletic lace-up shorts with the spade across the right side, and no shirt. The 'hearts' wore similar cotton pants to the 'clubs' but no shirts, with the heart design at the front right where a pocket might otherwise be. Only the diamonds like me didn’t have masks. Everyone else wore a plain white mask that covered his eyes, lending a sense of anonymity. The guys ranged in body types quite broadly, although it was obvious that other than the diamonds, these men were in their forties and fifties. They obviously, however, took care of themselves . And every one of the men wore a Velcro pouch strapped to his arm.

A waiter, full uniform, and mask, slid over to me and offered me a drink. I took one, waiting nervously. One of the clubs walked up to me, and when he spoke, I recognized the voice of the photographer. I had thought he was in good shape, and I’d been right: his chest was wide, he had thick arms, and under the edge of the wife-beater, I could see the start of a dusting of dark hair on his chest. “Glad you could come,” he said.

I smiled. “Thanks.” The door opened a few more times while we chatted about nothing, and finally, one of the men in the Spades outfits, a bit of a musclebear, really, hairy and thick chested and definitely built strong, stepped to the middle of the room and raised his hand. The room fell silent.

“Thank you all for coming,” he said. “As you all know, the game tonight is blackjack, or twenty one. Those of you playing for the prize money, that’s the diamonds in the room, will gather cards from those with whom you choose to...” he paused, smiling behind his short beard, “...interact.” He paused, and looked around. “The only rule, of course, is that no one can tell each other what card he is handing out, though the suit might be obvious.” Again he smiled. “Remember, you are gambling with yourselves, and you may stop at any time. There will be an opportunity for many draws, but don’t forget you will not wish to bust,” he said, smiling again. This time, he pointed at a door. “There is a special room for those who ‘bust’ but would like to deal themselves back into the game.”

A few of the men laughed, and standing next to me, the photographer smiled. I felt somewhat nervous.

“As always, negotiate as you will, and remember, the first place prize is a thousand dollars for the lucky diamond who achieves 21, or closest to that number without going over. Otherwise, all the rules of blackjack apply. We’ll begin with the diamonds making their choices, but after our first round, we’ll move through the suits accordingly. Diamonds – if you could line up, please?”

We did. My stomach clenched and unclenched, and I decided right off that I’d pick the photographer, who was not only hot, but someone I knew. There were five other guys with me in the 'diamond' group, and I saw that there were the same number of hearts, clubs, and spades. I did the math: there were two dozen men in attendance. I swallowed.

Our host continued. “The private rooms are through the archway there and up the stairs. They’re marked with diamonds. Feel free to leave the doors open or not as you wish,” he grinned. “Some do enjoy watching.” I swallowed again.

The host tapped the first diamond on the shoulder – a lanky red-head with a lean body and freckles – who nervously approached a salt-and-pepper daddy type in hearts. As soon as they started to speak, the host tapped the next diamond, who was beside me, and he went to talk to one of the clubs, a larger black man with very thick arms. Then it was my turn. I went to the photographer, the only one I knew, and he smiled at me. “I’d hoped familiarity would be a good thing,” he said.

I smiled at him, feeling myself blush a little. “Yeah.”

Once all six diamonds had chosen, the host said, “Okay, gentlemen. You may now let your diamond know what you intend, and he may accept or make another choice.”

I looked at the masked man who I actually did kinda-sorta know, and he smiled at me. “I intend to fuck that pretty face of yours and make you swallow every drop,” he said, leaning in. I felt my dick harden in my briefs. I loved to suck dick, and as far as whoring myself out, sucking cock seemed a pretty small price to pay. I nodded.

Four of the six diamonds seemed to like what they heard, since we all left for the archway and the four rooms. Two stayed behind, to make a new choice, I assumed. I led the older man into the first room with a diamond on the door. The room was richly dressed, with a bed decked out with fresh white sheets and pillows, as well as a small chest at the base of it labeled, helpfully, 'Toys'. When I went to close the door, the photographer took my wrist saying “I don’t mind an audience,” as he undid his cotton pants. He was facing the door, and he pulled one of the pillows and tossed it onto the floor at his feet. “Kneel there,” he said.

I’d have my back to the door. I knelt, and he tugged down the pants to reveal a thick cut cock already growing hard. He took my head in both hands, and pushed my face into his crotch. I licked and rubbed my face against his hardening dick, and he chuckled. “I knew you were a cock sucker the moment I took that first picture. Lips like yours?” he laughed again. “Cocksucker lips.”

Frankly, I agreed, and set to work whole-heartedly. His cock was salty with sweat and I loved the taste of pre-cum that drooling from his cock head almost the moment I swallowed his length. He hardened quickly in my mouth, and his grip on my head was strong without being too harsh. He fucked my face, short thrusts in and out of my mouth, without letting his dick come free. I gripped his thighs after a time, realizing quickly that he was the one in charge here, and wanted to enjoy knowing that fact. As his dick hardened, he grew a bit more forceful, but it wasn’t the longest dick I’d sucked, even if it was one of the thickest, and the reality was I was enjoying myself. My own cock was hard, proof that I loved to suck dick, and doing so was a quick way to get my own dick hard, and I let one hand go to reach down and tug my own dick free from my briefs.

“You can pull it out,” he said, in a low voice, “but you don’t get to jerk it. Hands back on my legs.”

I obeyed with a little grunt as he pushed his dick into my mouth, freeing my cock but not being able to tug on it. I decided to go balls deep on him, and surprised him by swallowing his full length and pressing my face into his pubes for a long moment. “Oh, fuck yeah,” he groaned.

Behind us, someone added, “Nice!”

I shivered, but pinned on the man’s cock, it wasn’t like I could turn around and see which men, or how many men, were watching. I moaned though, aroused despite myself.

“Fuck.. Fuck..” the older man said, and gripped all the tighter for a moment. “Swallow it all, boy! Swallow... it... all!” he grunted, and my mouth filled with his spunk in three sudden spurts. I swallowed spasmodically, narrowly avoiding choking as the thick liquid hit the back of my throat, and managing to get the rest down in two more swallows. I slurped at his dick, tonguing the head of his dick and then bobbing again up and down the full length of him. He let go, and I took a few more moments to lick and suck at his balls, making sure to get him spit-clean. “Damn,” he said, once I leaned back on my heels. “That’s good service.”

I smiled up at him, my lips feeling a little raw. He tugged me up, and we turned, our backs to the door, although I glanced and saw there were three men watching. Then he undid his pouch, pulled out a card, handing it to me. I looked at it. Four of clubs. That made eight. That sure wasn’t going to win. Still, I smiled at him, and put it into my own little Velcro carrier as he pulled his pants back up and I tucked myself back in, and then he led me back to the main room. There was a new man there now, in a 'dealer’s' outfit like at a casino, and he walked up to me as we arrived. “Your cards?” he asked me. I pulled them out of the Velcro case, and he pulled out a small pad, asking “Do you want to double-down?”

Oh shit! I’d read up about blackjack, but I’d forgotten this rule when I’d gotten the second four. If you get dealt the same card that you already have, you have the option to split it into two hands. I’d basically be starting over again with two hands of four. If I wasn’t mistaken, everything I’d read said it was the smart thing to do. “How does that work?” I asked.

The dealer didn’t seem phased by the question. “You’ll build one hand until you hold or bust, then the other. It will make for a longer night,” he said, without a hint of a smile, though I could have sworn I heard some amusement in his voice.

I took a deep breath. “I’ll double down."

He nodded. And we waited for the rest of the diamonds to return.

Edited May 28, 2014 by Hotload84

[subbttm]

Great story. It sounds like a lot of fun. I can't wait to hear more.

[baretop4yng]

Great start! It's a split and not a double down though.

[cublad]

gggrrrreat start as always Barrat

[Guest JizzDumpWI]

Nice, More?

[haireebear]

Great start to the story!!! Can't wait to read more!

[rawemobttm]

awesome story =)

[wroxguy]

I agree - great story :::::

[bearbandit]

I love the way you make a simple game of cards into a "pervertible". Excellent stuff - very much looking forward to reading more!

[Piginhtx]

Can't wait to see where this goes. Great story!

[cum2me]

we know he is going to be knocked up......

the question is...... WHEN ?

please.... time for the sequel.

great story.

[mike43]

very hot story and a great idea cant wait for the rest

[pisces bearcub]

Definitely can't wait for more.

[Barratboy]

Waiting for the rest the guys wearing the diamonds briefs to return, I looked around the well appointed room and at the men gathered. Again, I was struck by the casual air of the evening. No one seemed at all phased by the half-naked guests, the masks, or the reality of the sexual play happening through the archway. I picked up a glass of water and drank deeply. It was bubbly, like Perrier or something. I shook my head, a little overwhelmed at just how strange this all was, but still reminding myself 'A thousand dollars,' - even if building on two fours wasn't the strongest start.

The burly host raised his hand once the last couple, a sandy haired young man in diamond briefs and the stocky smooth man in spades who had returned with him, came back into the room. The young man showed his cards to the dealer, and the man made a note. The stocky guy who'd returned with him received a card to put into his pouch. The math of the evening gelled. With two dozen of us, there would be enough cards in a deck to replenish those gathered by the diamond boys from the men we had chosen. I looked, and, sure enough, saw the photographer whose cum I'd just swallowed standing among some of the other men. We all fell silent as the host cleared his throat and asked the dealer ""How are we doing?"

"We have one diamond who has chosen to hold," the dealer answered, "and another has doubled down, but no blackjack."

One of the diamonds, the red head I had noticed before, smiled and nodded. I assumed that meant he was the one holding. He'd gotten a good draw right away, maybe a nineteen or a twenty? Either way, that meant first place just got that much further away. The host nodded, and moved over to the side of the archway, where I noticed for the first time a wheel decorated with the four suits. He spun it. It clicked through its orbit a few times, and settled on clubs. The men in the (outfits) murmured. I watched my photographer 'friend' and he smiled widely.

"As discussed gentlemen, line up." They did so. The host, in spades, waited for them for a moment to organize themselves then tapped the first man on his shoulder. He was tall, bald, and barrel-chested, with a walrus mustache. He was definitely built strong, but he had a gut to him as well. He walked right up to the sandy haired young man in the diamonds briefs and whispered into his ear. The young man nodded. "Good," the host said, smiling through his beard. He tapped the next man, a wide, thick-necked man with greying hair buzzed short, an impressive chest and equally impressive arms, who honestly made me think of a bouncer, walked over to me.

I tried really hard not to tense-up when his eyes, also a grey shade of blue, looked me up and down as he leaned over and asked in an even, conversational tone, his voice close to my ear, "You been fucked yet tonight?"

"No."

"Good. I don't mind sharing, but I like to be the first in a boy's ass of the night. I intend to bend you over and fuck you."

I looked at him, feeling an odd flutter in my stomach at the bluntness of his words. He was masculine, solid, and judging by the front of his cotton pants, he was well on his way to aroused. I nodded, not quite trusting myself to speak, and the host repeated "good," before tapping another of the clubs on the shoulder. A thousand dollars, I again thought.

Since one of the diamonds had held his hand, I wondered what would happen to the sixth club, but when a the young Latino guy in diamonds shook his head at whatever the hairy goateed bear in clubs suggested, the host moved on. The bear who didn't get a partner and the Latino was chosen by my photographer friend. We left the room for the hallway of bedrooms.

The man who’d chosen me kept one hand on my shoulder for the duration of the walk, and gave me a little shove when we got to the first unoccupied bedroom, asking “You want lube, or spit?” Again blunt and to the point. adding “Lube, I leave the door open. Spit, I close it.” I glanced at his wide chest, thickly muscled neck, and the obvious tenting in his cotton pants.

“Lube,” I said. He smiled briefly, and left the door open.

He was true to his word and attitude – he walked over to me, took my shoulders and turned me around, walking me to the foot of the bed. His hands slid down my arms and he pushed me until I was bent over, and moved my hands up to grip the bedpost. He reached down to my waist once I gripped the wooden pole, and slid his fingers into the edge of my shorts and then tugged them down. My dick was already a little hard, somewhere between having just enjoyed the blow-job I’d given and knowing that I was about to get fucked. I stepped out of my shorts, and his hands gripped the inside of my thighs, pulling my legs a bit further apart, and then making me step a half-step back, stooping and leaning and gripping the pole.

“Mmmmm,” he grunted. Then he walked over to the 'toys' chest and flipped open the lid. I looked over my shoulder and, as he returned, saw there was already a man watching from the doorway. It was the large goateed bear who’d suggested whatever it was to the diamond who’d turned him down. Then the grey haired man returned, a bottle of lube in hand, ordering me "Face front.”

I looked ahead.

The lube was a cool shock with the first squirt, but then the older man started rubbing his finger up and down between my cheeks, and soon I was rubbing back against him. He dipped just a fingertip against my pucker, and I let out a little breath. I could hear his breathing behind me, growing a little faster with every stroke and tap of his slick finger, and he added more lube, and another finger, and I was soon pushing back against him. “Nothing but a whore, aren’t you?” he said, his voice pitched very low, continuing with "a chance at some money and you’re bent over and waiting for it, aren’t you?”

I bit my lip, and he gave my pucker a little push with his fingers. “Aren’t you?”

“Yes,” I said, feeling my face burning. Hell, it was true.

“Alright then, whore... here you go.” He shifted behind me, and a moment later the unmistakable feel of a cock was pressing against my hole. For just a second I was too scared to move, and then the older man’s strong hand gripped my side as he aimed his cock into me and slowly pushed. I couldn’t help but let out a moan, and when his other hand took my other side and he continued to push into my ass, I groaned a bit louder. He had a long cock, that was for sure.

“Love to get ‘em while they’re still tight,” the man said, and then with no further discussion, he started to fuck me, shifting behind me to slowly draw his dick almost all the way out before burying himself back in, this time to the balls, with a long steady stroke that made me groan a third time.

He picked up the tempo quickly, and I gripped the bedpost and pushed back against this thrusts as the older man proved to be as strong as he looked, and possessed of a great sense of rhythm. His dick seemed to hit me just-right, and if it had been a while since I’d been dicked this deep, it was coming back to me why I liked it so much. I began to grunt and gasp as he fucked my ass, and he shifted his grip, sliding his hands up and down my side, and once or twice gripping the back of my head for a series of particularly sharp thrusts that made me curse out loud. My dick was hard again now, no half about it, and I gripped the pole with both hands lest I lost my stance. I wanted to jerk off, but I knew better than to risk my balance.

“Here it comes, boy,” the man said, and it was only as my ass filled with hot thick ropes of heat that I realized he wasn’t wearing a condom. I gasped, and swore again, but his grip held me firm until the last surge of his spunk erupted in my hole. When he pulled out, I turned around to face him, more than a little shocked.

“No condom,” I said, as I felt some of his sperm leak from my ass. My cock, though, was still rock hard.

He regarded me with thinly veiled amusement. “I didn’t say I’d use one. Don’t worry though, you’re safe with me.” He looked down at his dick, still slick with lube and spunk. “You should clean up the mess, boy.” I looked past him at the men outside the door. The goateed bear was there, as were three others, and then slowly I sank to my knees. More of the man’s spunk leaked as I put his dick into my mouth, and savored the taste of spunk for the second time that night.

A thousand dollars, I thought. But it sure as hell wasn’t without risk. I’d have to be smart. Smarter.

I licked and sucked the remnants from his cock, thinking to myself that he really did have a long dick. He nodded once, undoing his little pouch and handing me a card without showing what it was to the men outside. Eight of clubs. That made twelve. I took a deep breath, rising to my feet. The grey-haired man handed me a wet wipe from the chest and I awkwardly wiped at my ass while he pulled his cotton pants back up. By the time I was done, he’d left, and I walked alone back down the hallway and through the arch to report my card to the dealer.

Twelve. It wasn’t enough.

Edited May 29, 2014 by Hotload84

[cublad]

great continuation Barratboy, loving the story again already