The Gambler Ch. 01

Okay, folks this time consider yourselves warned. This is about a GUY losing his anal cherry. If you don't like that kind of thing, don't read it. If you do, please vote!

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"Oh, man, I should have known better. I am so fucking stupid!" Ryan thought to himself as he walked out of a college football game that would have been perfectly ordinary, except that his team lost. And except that he'd had 15 G's riding on the outcome. And except that this was the game that was supposed to bail him out of his previous $15,000 in debt—not double his losses.

"What the hell am I going to do now?" he thought. And wasn't surprised two days later when Enrico, one of Big Louis' boys, showed up at his door wearing a trench coat and carrying a shopping bag holding who knows what. Not exactly inconspicuous, thought Ryan. The goon wasn't happy."

"Look, Rico, I know why you're here. I haven't got the money, but I'll get it," he started, as Enrico pushed past him into his studio apartment.

"Don't waste my time, college boy," said Rico. "Big Louis just wants what's due to him. If you ain't got the dough, you got no business getting in the game. You're a smart kid. Figure it out."

Ryan's gesture swept across his nearly empty apartment. He slept on a mattress on the floor, and used the library computer to do his schoolwork. A beat up armchair and a small combination TV/VCR appeared to be his only indulgence. "Go ahead and help yourself to what I've got, buddy. Of course, it won't add up to much."

"That wasn't quite what I had in mind," was the quick reply.

"What are you gonna do, Rico, break my legs or something? I mean, you gotta do what you gotta do, but it won't get Louis back his money."

"Heh heh heh," laughed the goon. "What do you think this is, 1980? We're a little more creative than that these days."

Something in Rico's tone made Ryan uneasy.

"You see, college boy, you do have something valuable. You just don't know it. Are you straight?"

"What?! Yes, I'm straight. I have a girlfriend. What business is that of yours?"

"It's like this, college boy. Turn around."

With a puzzled expression on his face, Ryan slowly spun around, obediently. At 6'2", with dirty blonde hair, blue eyes, broad shoulders, and long, lean legs, he may not have been smart enough to get himself out of this particular worst case scenario, but he was quite good looking.

"Just what I thought. You got one fine ass on you. And I know some folks who'd be willing to pay for it."

"Whaaaat do you mean pay for it?"

"It's like this. Louis is what you might call...'diversified.' He's got action in a lot of different places, if you know what I mean. One of 'em's a club. A sex club."

"Rico, I can see where you're going with this, but we're talking about 30 G's. I don't see where my ass would bring that kind of dough, even if I was willing to drop out of school and shake it for the ladies full-time!"

"Who said anything about ladies? This club is for very wealthy gay men. They have an auction on the first Thursday of the month. They pay very good money for straight virgin tail. Louis' last boy brought in nearly 40 G's. And he wasn't nearly as good-lookin' as you."

"You can't make me auction off my ass to the highest bidder!"

"No, college boy, we can't make you. The club only takes 'volunteers.' So, I'll tell you what we're gonna do. The first Thursday is 2 weeks off." Rico handed Ryan the shopping bag. "There's a video in here, and, uh...something else. You can watch the auction on the video. And you can, um, practice. Might make things go easier on you."

"I am not doing this, Rico."

"Maybe you are, maybe you're not. Anyways, for right now, I owe you a spankin'."

"What?!!"

"You heard me. Big Louis says 20 smacks on each cheek for being a dumbass college boy. Take off your pants."

"I am not taking off my pants."

"Actually, yes, you are." Rico pulled a gun out his jacket pocket, and watched as Ryan's eyes got bigger, and then, still watching the gun, his hands fumbled with his belt buckle and unbuttoned his jeans.

"Shit," muttered Ryan.

"Off," repeated Rico.

Ryan unzipped, and, still disbelieving his eyes, pushed his jeans down his long, lean thighs and stepped out of them.

"The shorts, too."

In a moment, Ryan was humiliatingly standing half naked in front of the goon, who sat down on Ryan's mattress and said, "Okay, now over my knees."

"You have got to be kidding," thought Ryan, as he assumed the position. His penis was rubbing against the rough wool of Rico's pant legs, and his balls were uncomfortably compressed between the goon's legs. He felt like a naughty 4-year old, especially when the first sharp smack of Rico's hand hit his bare ass. Smack! Smack! Smack! Rico's stinging slaps hurt more than Ryan had expected them to. He established a rhythm, and with each blow, the friction against Ryan's trapped cock was greater. Against his will, he felt himself start to harden, and knew that Rico must be able to feel his stiffening rod between his thighs. Oh, God, Rico was taking a break, gently rubbing his ass cheeks, now. He must know.

Rico smacked him some more. "35, 36, 37, 38, 39, 40!" he counted out loud. Then, done with the spanking, he rubbed Ryan's ass again, this time teasing a forefinger between Ryan's cheeks and brushing lightly against his anus for an instant. Ryan's balls tightened, and his heart pounded. Was Rico going to insist on raping him right here? His own erection might betray him and give the goon the idea that he was interested! But no, Rico was telling him to get up. He stood, covering his hard on with both hands—as if Rico hadn't noticed it already.

"I'll come by for your answer on the 12th. By the way, if you bring in anything beyond the 30 G's you owe Louis, you keep 80%. Maybe you could buy yourself some furniture. Get a new start. I suggest you seriously think about quitting gambling, kid. You ain't very good at it."

With the door shut safely behind Rico's exit, Ryan flopped onto his mattress, his cock still hard, shopping bag in hand. He withdrew the video carefully, with two fingers, holding it away from himself. Beneath the video was a layer of tissue paper. And beneath that, an 8 oz. bottle of extra-slippery lube and a box. Ryan forced himself to open the box and look at it: it was an anatomically correct dildo, about 7 inches long, made of flaming pink silicone. He withdrew it gingerly and gave it a shake. The tip wobbled like Jell-O. It looked like a pretty good size, with a large head and a good heft in his hand, and despite himself, Ryan wondered how he measured up to the sex toy.

He held the dildo up against himself. Not too bad. It was a bit longer and a little thicker, but he was pretty respectable. He added a dab of lube to his palm and enjoyed the smooth feel of it along his shaft.

Ryan was straight. No question. But like most guys, he had a healthy interest in the full range of sexual experience. He'd done the circle jerk thing with a couple of friends in middle school at sleepovers, enjoying the feel of someone else's hand on his raging dick. Once he'd even stuck a pencil very gingerly up his butt, pretending it was a thermometer at the doctor's office. It felt good. Kind of dirty. So, thinking with his cock now, rather than his head, he lay down on his mattress and generously lubed the tip of the dildo. Shivering a bit even though the room was warm, he spread his legs wide and held his butt cheeks apart with two fingers, then gently touched the slick, pink head of the fake penis against his sensitive asshole and moved it in small circles. His cock jumped at the sensation.

My old girlfriend Sherry used to do something like this, he thought, teasing himself with the silicone glans. She would tickle her finger against my hole sometimes while we were doing it. Thinking about this, he started to exert a little careful pressure against his anus, slowly wiggling the rounded tip of the dildo to open himself up. The stretching sensation felt good, so he continued, stopping once to add more lube, and stroking his aching dick with his other hand. After a few minutes of this, with ongoing gentle pressure, the bulbous tip slipped inside his anal ring.

Oooh! The pressure and fullness were an incredible turn-on. In a few moments, he'd worked almost half of the silicone dick into his own ass, and was holding the "balls" of the base, slowly pushing the shaft in and out of his ass with one hand, while the other caressed his slippery cock, which was leaking clear fluid. It felt amazing. He was so close to the brink that he was panting, his heart pounding so hard he could feel it: Thud! Thud! Thud! He was too far along to react when he heard Melisssa's key in the door.

Oh, shit, he thought. Could this day get any worse? Here he was: butt-naked, spread-eagled, impaling his own ass on a large hot pink fake cock, and so close to the edge that he came in spurts as she walked through the door and took in the scene.

Melissa's Revenge

Melissa did a double-take as she took in the sight of Ryan, who'd apparently started without her. When she realized exactly what she was seeing, she went immediately into full freak.

"Ryan, what the hell is going on? What on earth are you doing? Are you gay or something?!"

No, baby, I'm not gay," he answered, while trying to unobtrusively remove the dildo. "I can explain!" Too late. She'd seen it. In three steps she'd crossed the tiny apartment and was picking up the pink jelly toy by the balls with two careful fingers.

"How, exactly, do you explain this?

In his immediate post-orgasmic glow, Ryan was unfortunately no match for her. He racked his brain for a plausible lie, then settled on the truth. "I've been gambling again, and I owe a lot of money."

"Oh, shit, Ryan, not again. I've already been through this with you. I'm not interested in going through it again. How much do you owe this time?"

"$30,000."

"$30,000! You lost more than money this time around, buddy. You lost me." Melissa tossed her key on his mattress and turned around to leave.

"Melissa, baby, please wait. There's a way I can get out of this. I can pay it all back. And it doesn't involve any gambling. If you stick with me, I swear I'll get help. I'll never gamble again. Not even so much as a lottery ticket. I swear!"

She turned back around to face him. "Keep talking."

"Well, um, that's the reason for the dildo. I mean, you know, the way I pay back the money."

"You pay back $30,000 by sticking a dildo up your ass?"

"No. See, there's this gay club, and they have an auction once a month for straight white guys. They pay a lot of money. A lot of money. If I go along with it. I could bring in more than I owe, and keep most of the difference. It would give us a chance to start fresh."

"Just what are you auctioning, exactly?"

"There's a video." Ryan pointed to it. "I don't know how it goes, I haven't seen it yet. But basically, I'm a virgin that way, and rich gay guys bid on who gets to fuck my ass."

"Let me see if I have this straight. You can pay back the $30,000 you owe, and maybe some extra, by getting naked at a gay club and letting some stranger stick his dick up your ass?"

"Um, yeah, that's about right," muttered a sheepish Ryan.

Melissa was furious. "You owe me, Ryan. If I stay with you this time, you had better do exactly as I say. Got it?"

"Yes, baby, I get it. I'll do anything."

"Good. We're gonna start right now seeing how disciplined you are. Lay down on your stomach."

Ryan, jeans and shorts still puddled around his ankles, quickly obliged. Melissa pulled off her pantyhose and used them to tie Ryan's hands very securely behind his back.

"I'm going out for a bit. Shopping. But you're going to stay right here. And since you like your new little friend so much, I expect it to stay exactly where I put it. Spread your legs apart. Wider."

With that, she squirted a large dab of lube onto the dildo, found the spot, and pushed the fake penis all the way inside of him—much deeper than it had been before. Ryan could feel the thing's balls resting against his own, and realized he now had about 7 inches of plastic lodged in his rectum. With a flick, Melissa switched on a knob he hadn't noticed in his earlier rush, and the silicone cock started to vibrate inside him. Ryan groaned out loud.

"See you later, lover. And I expect to find you right here, and it right there." She snagged the videotape and locked the door behind her.

Home was Melissa's first stop. She had an idea, but first wanted to see the video for herself. Her apartment was 3 blocks away from Ryan's, and she'd started to get aroused as soon as she saw her big hunk of a boyfriend with his legs apart and his cock rigid, working the dildo in and out of his own ass, and her clit was throbbing so hard now that it was distracting. The walk was exquisite torture, especially thinking about how she'd left him—and what she had in mind when she returned.

In her apartment, she loaded the tape into her VCR and settled on her couch with the remote. The first scene was raucous: a club scene with half-naked men with tattoos and nipple rings dancing, loud music, drinking. Some of the men were tongue kissing each other. In a corner, a man was on his knees in front of another man who had his hands in the lower man's hair and an ecstatic expression on his face, no doubt giving him head—right there in the middle of the party. The camera panned around and she could see a stage. This must be it, she thought, and wasn't disappointed.

An emcee with a microphone announced the start of the evening's festivities: the once-a-month virgin auction! "Well, gents and gents, we'll have 3 young ass virgins for your bidding pleasure a this evening, but first, we've got a really special show for you tonight. From sunny Miami, we've got the one and only Marcus Big!"

The room broke into applause as a burly dwarf clambered onto the stage, dancing to a salsa rhythm and taking off his clothes, each discarded garment met by rousing cheers. His hips swiveled, his shoulders swayed, and when he got to the belt of his slacks, the room fell quiet. As he pulled them off and pushed down his shorts, Melissa could see why. The miniature man had a cock like a baseball bat. Already partially erect from his gyrations, it was easily 10 inches long and as thick around as her wrist. He may as well have had an extra limb. She'd never seen anything like it, and wouldn't have even believed it was possible, except that he was so clearly naked, and there was no hiding that the huge thing was part of him. It hung to his ankles. Even more aroused, Melissa pulled up her skirt and slid a finger into her panties, stroking her slippery clit in circles, in rhythm to the music.

As Marcus danced and stroked himself in front of the crowd, the giant phallus jerked as blood pumped into it and became fully erect and even larger! The announcer's voice called out, "Okay folks, tonight's lucky numbers are 114, 56, and 83," and three men leaped onto the stage and began helping Marcus to caress his huge cock and large, dangling balls. Four men's hands and mouths touched and licked the huge thing for several minutes until he erupted, to great cheers. A moment later, Melissa came, gasping.

"Well, wasn't that great?!" noted the emcee. But now, it's the time you've all been waiting for: let's introduce our first virgin for tonight!"

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Finally, with visions of permanent damage to his manhood, he decided to chance a quick rock. With his hands behind him, he reached down and found the base of the dildo with one hand. Holding it in place, he carefully rolled onto his side, wriggled until his cock sprang free and up against his belly, then landed on his back. Phew! The dildo was safe—and still buzzing. - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -

Melissa paid close attention to the first attractive young man on display for the evening's festivities. Evan was a short, wiry, intense fellow with dark brown eyes and hair. Dressed in jeans and a button down shirt, he seemed scared, but resigned, which made sense under the circumstances, she thought, eyeing the bulge in his jeans that she suspected she'd see more closely soon enough.

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

"Yes sir," he answered in a low voice.

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

"Yes," came the reply.

"So, you've never sucked a man's cock, then?"

"No sir."

"Never had a man suck your cock?"

"No."

"Never taken a cock up the ass?"

"No!"

"Or given one?"

"No."

"There you have it, people, this boy is genuine cherry! OK, Evan, boy, it's time for you take off your clothes and show us what you've got."

As Melissa watched, the young man reluctantly stripped to the skin, covering his genitals with both hands as soon as he dropped his shorts. On the emcee's instructions, he pirouetted around a full turn in the spotlight, then bent over to show his ass to the crowd, which was met with cheers of approval. The emcee laid his hand on his smooth, white cheeks, and teasingly stroked Evan's asshole, laughing when he visibly flinched. And then the bidding started. Melissa couldn't believe the amounts—it started at $10,000 and quickly reached $41,500 for the final bid. "OK, boy, it's time to assume the position your winning bidder selected. Will it be sunny-side up? Over easy? Or something else. Let's see." He pulled an envelope out of his pocket and opened it: "Ah, sunny-side up it is!"

Two uniformed security guards took the naked Evan by the upper arms, forcing him to reveal his substantial dangling cock and round, pink, dangling balls to the cheering crowd. The guards led him to a table and helped him climb aboard and lay down on his back. "Now," said the emcee, "as you all know, to ensure the complete safety of our winning bidders, the rules require that our virgins be restrained for their very first act of anal penetration for our audience." Evan gulped and nodded, and the security guards fastened leather straps around his upper arms, elbows, and wrists, and around his thighs, knees, and ankles. The emcee pushed a button, and the triangular portion of the table between Evan's legs dropped down. With a push of a second button, the sections of the table under Evan's legs spread wide apart, exposing his unprotected ass to the crowd—and the video camera.

Melissa was spellbound. Evan looked terrified. A portly man in a business suit ascended the stage, apparently the winner of the round of bidding. "Are the preparations of your virgin to your liking?" asked the emcee. "Yes they certainly are!" the man replied in a deep voice. "Hello, Evan." He walked up to the table and stood between Evan's spread legs, evidently admiring the view. He ran his hands gently over Evan's body, stroking his neck, his chest, tweaking his nipples, while Evan, strapped securely to the table, uselessly tried to avoid the questing hands by wriggling and writhing.

The man touched slowly, but surely, down Evan's belly, reaching his inner thighs, then softly caressing his cock. The sight of the fully dressed man in a dark suit touching the helplessly bound naked one was amazingly arousing to Melissa. The winner bent and took Evan's limp cock into his mouth, licking and sucking it vigorously into a reluctant erection. Evan closed his eyes and let go as his cock stiffened under the expert coaxing.