The Gambler

It was 8th—4 days before Ryan had to give Rico his answer, not that there was any question what that answer had to be. Tonight, Melissa had him strip naked and lay on his back on the bed, his legs spread wide and his ankles tied to the bed supports to keep him that way. She was standing between his legs with the strap-on in position, and hit "go" on the VCR so they could watch the last deflowering.

Mike, a short, skinny redhead, looked barely 18 and completely terrified. Yet even before he was strapped down to the table as the final sacrifice of the evening, his cock had already stiffened. It was surprisingly long and thick for such a little guy. You just never knew what a guy was packing, thought Ryan, as Melissa's strap-on invaded his tight asshole again, shoving all the way in.

Mike's fair skin flushed pink all over as the invading cock found its mark and plunged into his ass. His large erection wobbled with each thrust, but the man deflowering him didn't make a move to touch it. And maybe Mike had seemed terrified before, but the look on his face now looked much closer akin to pleasure, as he tossed his head from side to side and moaned at his anal invasion. The man plowing his virgin rectum took long, slow, deep thrusts. And the crowd went wild when Mike's big cock twitched and he came all over his own chest, just from the stimulation of his ass.

Ryan wasn't quite that lucky. Melissa was plowing him, but his own cock was rigid and nearly purple, and not getting anywhere without a helping hand. She took pity on him and stroked his aching heat with her small, cool hand while she fucked him. With a loud groan, he came on his own belly.

D-Day Even with all the practice, Ryan still never quite saw himself here, in the landscape of the video he'd seen, getting ready to take the stage. But here he was backstage, his heart racing, as he waited for his turn in the lights. He was having a hard time imagining anything more humiliating than giving up his anal cherry in front of a cheering audience, but knew his own actions had led him to this pass. The guy ahead of him was coming back through the curtain now, walking slowly, as if his ass hurt. It probably did! The stagehand motioned to Ryan, and he gulped and followed.

... "And here comes our last virgin of the night: Ryan!" The announcer's voice rang out to the crowd, and Ryan found himself onstage.

"Do you, Ryan, certify that you are here with us tonight voluntarily, of your own free will, and that no-one coerced you to be here?"

"Um, yes. Yes," he replied, finding his voice.

"And do you solemnly swear that you have never engaged in any sex act with another man?"

"No, I've never done anything sexually with another man," Ryan answered truthfully.

"Right, then! Ryan, it's time for you to show our audience what you're packing. Strip for us now."

He'd seen the videos over and over, thanks to Melissa, and knew this was coming. But somehow actually standing in front of a small sea of leering male faces was still different than being in front of the open window, imagining that someone might be looking. He heard hoots and whistles as he unbuttoned his shirt, tugged it out of his pants, and shrugged it off. He pulled off his t-shirt, and someone cheered, loudly. The clapping started after he'd pulled off his shoes and socks and reached for his belt buckle. With a gulp, he proceeded, unbuttoning his jeans, lowering the zipper, and pushing the unfastened pants down his hips. Finally, to shouts of "Take it off! We wanna see your dick!" he let his shorts fall to his ankles and he was naked.

"Nice, Ryan. Now turn around so our bidders can see what we want them to pay for."

Flushing pink, Ryan forced himself not to cover his package as he slowly spun, letting the audience see his lean, taut thighs, his smooth round ass, broad shoulders, muscled calves. He was the tallest and best looking of that evening's entertainment, and as embarrassing as this was, at least he'd be leaving his debt behind him and getting a fresh start. He comforted himself with that thought as the bidding started, fast and furious. Who would be sticking his cock in his virgin ass, he wondered? Would it be long and thin? Short and thick? Would the guy take his time, or pound him hard? He hoped he'd use a lot of lube.

... "$56,000—a new record, gentlemen!" the emcee announced, gleefully. "And, we have an unprecedented special offer. This is new, folks, it's never been done before. So, Ryan, here's the deal. Our winner is willing to deflower you himself. Or—and there's a $10,000 bonus in it if you say yes—Marcus Big will do it!"

The crowd went crazy, cheering so loud that Ryan's ears rang. Marcus Big? Who the hell...oh! That dwarf! The one he'd seen in the video with the monster cock. Oh, shit, he thought. An extra $10 G's—if I let the biggest cock I've ever seen into my ass. What a choice. He silently thanked Melissa for the preparation she's insisted on, swallowed hard, and replied, "Yes."

"Good choice, Ryan," the emcee enthused. "In fact, to thank you for the increased entertainment value, we'll even get an audience volunteer to suck your cock while Marcus takes your cherry. Would you like that?"

"Yeah," Ryan agreed. "I think I would."

In her seat, Melissa was glad she'd worn a skirt. Figuring—correctly—that she'd be the only woman in the club, and no-one would even look at her, she skipped panties when she got dressed that evening. Her denim mini skirt was soaked with her juices even before Ryan came on stage and stripped, from her excitement at watching the first two virgins and imagining her gorgeous boyfriend getting fucked by a man. Her clit was rigid, but she held off on rubbing it until now, when the thought of Marcus Big's huge cock sliding up Ryan's rear passage was too much to take. She reached under her skirt and started to tease herself slowly with feather light strokes as she watched the preparations on stage.

"How do you want him prepared, Marcus?" the emcee asked the little man.

"Truss him," the dwarf replied.

Ryan was guided to lie down on the table he'd seen before. His heart raced as the security guard fastened the leather straps around his arms, holding him in place. One strap crossed his belly at his hip bones, keeping his upper body fastened to the table with his ass at the very edge. The observing crowd hushed as the guard raised Ryan's left leg and placed a strap with a large, metal ring around his knee. Ryan flinched at the intimate touch. Then the guard strapped his ankle to his thigh, just below his groin, and repeated the process with Ryan's right leg. Finally, the guard spread Ryan's legs wide, one at a time, and clipped the rings at his knees to the table. The effect was to spread Ryan like a butterfly on a pin, with his genitals fully exposed, and his ass cheeks held tautly apart. Finding his asshole was not going to be a problem, Ryan thought wryly. Somehow, this position seemed even more humiliating than any of the others he'd seen in the videos. He tried to relax as a wooden box was placed at the end of the table for Marcus to stand on.

On the giant screens, Ryan could see his soon-to-be deflowerer shoving his pants down, exposing his already half-hard manhood, which was stiffening in quick jerks as blood pulsed into it. The dwarf stroked his massive tool with both of his small, stubby hands, as the audience howled its approval. The security guard handed him a giant condom, which he slowly unrolled over his throbbing meat.

Ryan, eyes wide, turned his head and searched the crowd for Melissa. She caught his eye and mouthed, "I love you," and he nodded, a little calmed. The announcer directed a large, stocky man with an open shirt and a thickly furred chest to stand at Ryan's side, facing the stage.

"Start 'im up," instructed the dwarf, and the hairy men bent and took Ryan's soft cock entirely into his mouth. In her seat, Melissa applied a bit more pressure to her slippery clit as she watched her boyfriend's cock engulfed in a man's mouth for the first time. Ryan's hips writhed, and he sighed, realizing that a warm, wet mouth was a warm, wet mouth. He closed his eyes and felt his cock thickening and lengthening under the man's expert ministrations. Marcus Big climbed the steps between Ryan's spread thighs, and Ryan startled as the small man trailed his fingertips between his ass cheeks, lightly brushing his asshole. Involuntarily, he opened his eyes and looked at the screen, seeing the head bent over his now fully erect cock, the pink tongue trailing slowly from tip to base—giving him enough stimulation to keep him hard, but not enough to let him cum.

Marcus Big focused his efforts on Ryan's crinkled, pink hole, deliberately tracing each delicate, lubed bump with a stubby finger, moving in slow circles. Ryan, for his part, was more turned on than he thought he'd be. All of the anal stimulation Melissa had been dealing out for the past couple of weeks was making him crave the feeling of being filled, although he was frankly terrified at the thought of Marcus' enormous size. He groaned out loud when he felt Marcus's soft, wet tongue circling his sensitive asshole, then lapping at it insistently, and even forming into a point and poking inside. Watching himself being rimmed on the giant screen multiplied the feeling.

Ryan's volunteer cocksucker was now running his tongue around the head of his swollen glans, and Marcus squirted a generous amount of lube and wriggled one thick fingertip into his tight hole and ran it around in a circle, just inside the tight ring of protesting muscle. The feeling was incredibly erotic—scraping gently against sensitive nerve endings and patiently stretching him for penetration. The small man continued his circling, finally thrusting the thick finger inside, and then adding a second, and finally a third. He twisted his small hand one way and the other to continue widening Ryan's opening. Finally, it was time.

Melissa held her breath, watching the dwarf hold his huge cock in one small hand, generously lubing the condomed tip with the other, and smearing extra lube on Ryan's vulnerable asshole. Ryan watched the enormous, plum-like, bulbous tip approaching his virgin hole and then brushing intimately against his flesh. His own cock was rigid and leaking clear precum, which was lapped up enthusiastically by the man leaning over him. Marcus applied steady pressure, and Ryan bore down to make the entry easier. Melissa teetered on the edge of a violent orgasm, watching the huge, pale shaft start to penetrate her defenseless boyfriend. The crowd gasped, collectively, as the round head popped through the anal ring and into Ryan's ass.

The cocksucker took Ryan's balls into his mouth and sucked on them, one at a time, as Marcus slowly pushed the length of his engorged manhood into Ryan's virgin rectum, an inch at a time. Ryan felt very stretched and increasingly full. The tip of Marcus's phallus was soft and spongy, and even the shaft was a bit rubbery. It slid into him and filled him fuller than he'd ever been, until the little man was balls deep in his ass. The crowd cheered its approval, and a glance at Melissa found her with her head thrown back, in the throes of a powerful orgasm. He smiled at the sight.

Marcus and the volunteer sucking Ryan's cock established a rhythm. With each deep thrust into Ryan's ass, Ryan's cock was fully engulfed in the man's mouth. In and out. In and out. In and out. The audience started to clap to the rhythm the three men established, yelling, "Make him cum! Make him cum! Make him cum!" Each deep thrust rubbed Ryan's prostate, and he felt pressure building for an orgasm that promised to be bigger than anything he'd ever felt before. He groaned out loud and his nipples tightened. With one, final deep thrust, Marcus pulled his cock out, ripped off the condom, and came in long, white jets on Ryan's chest at the same time that the man sucking Ryan's cock pulled his mouth away and Ryan spurted his own seed onto his belly. The applause was deafening, and Ryan's ears rang from the force of his climax. He was drenched in sweat and cum, exhausted, and limp as a noodle. And his ordeal was over.

Backstage, Ryan's arm around Melissa, Rico handed him a check that would cover a new start—and extracted his promise to never gamble again.