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.
