The Gambler Ch. 01

Once Evan's dick was fully hard, the man continued to stroke it with one hand, while he slid the other hand between Evan's legs, first bobbling and gently teasing his balls, then spreading his cheeks apart and finding his sensitive anus and stroking it with a fingertip. Melissa wondered if Evan "practiced" on his own, like Ryan had been doing.

The man in the suit unbuckled his belt and dropped his pants and shorts, revealing a surprisingly thick, dark red, fully erect penis. Laying on his back, completely bound, with his legs humiliatingly spread wide, Melissa was sure that Evan could see the sizable instrument of his own deflowering quite clearly. The man between his legs rolled on a condom and helped himself to a generous dab of lube, dribbling some of it onto Evan's still-hard cock and continuing to stroke it slowly so he wouldn't lose his erection. He placed the nozzle of the lube bottle against Evan's anus and squeezed, and Melissa could see him jump, as if it was very cold. Then the man positioned his big cock against Evan's tiny pink hole, and the camera closed in on the action: the large, rounded head pushing insistently until it slipped inside, then the slow shove of the full bulk of the invading cock into Evan's virgin ass, as he arched his back against the alien intrusion and the crowd roared its approval. He must not have practiced enough, thought Melissa.

She watched the man's slow thrusts—he'd paid a lot of money for this and planned to take his time and completely enjoy it, she bet. His slick, shiny cock pulled almost all the way out, then sunk all the way back in to the hilt, over and over and over again. One time he pulled out completely and had to repeat the initial penetration, although with Evan loosened up, it went in more easily the second time. With one hand, the man slowly stroked Evan's cock, going faster and faster as he himself got closer and closer. Finally, with a groan, he pulled out his cock, pulled off the condom, and came in spurts on Evan's belly, to great cheers. Then he covered Evan's aching dick with his mouth and finished him off, swallowing every drop of his cum.

She stopped the tape, rewound and ejected it, and dropped it into her purse. Glancing at her watch, she couldn't believe only half an hour had gone by. She still had shopping to do!

At the local erotica store, Melissa was sure she could find what she was looking for, and she wasn't disappointed. The public deflowering of poor Evan and the wild selection of magazines, videos, and sex toys aroused her, even after she'd taken the edge off earlier. With her purchases discreetly wrapped, she headed back to Ryan's to teach him his next lesson. She wasn't pleased to find him laying on his back, when she'd left him on his stomach. But the dildo was still buzzing, and his cock was rigid—since, with his hands behind his back, he couldn't reach it to get any relief.

"I'm sorry, baby," he said, "I had to turn over. I got hard and was afraid I was going to hurt something."

Melissa had already used her pantyhose earlier, and she'd left off her panties when she stopped at the store. Without saying a word, she pulled off her skirt and straddled Ryan's face. Ever the dutiful boyfriend, he obligingly lapped and licked and teased her swollen clit, moving first in slow circles with just the tip of his tongue, then used broad, soft strokes, and then moved his tongue more rapidly back and forth, stopping occasionally to softly suck her clit between his lips and lap up her flowing juices. Aroused even further by his forced task, his cock was strained past the point of pleasure when she finally came, arching her back and thrusting her hips rhythmically against his mouth.

"That's a little better," she said, climbing off him.

"Good," he said. "Can you take this thing out of my ass, then?"

"Sure thing!" Melissa replied, slowly withdrawing the buzzing dildo. "Stand up. I want you over here behind the chair." Ryan moved into position, his arms still behind his back and his aching cock rubbing against the back of the chair, which faced the TV. Melissa pulled a length of rope out of her bag, tied one end of it over his already-bound wrists, and tossed the other over a plant hook in the ceiling that must have been left by a previous tenant. She pulled the rope end until he was doubled over the back of the armchair, his ass completely exposed, and tied the other end to hold him in place. Then she took out two silk scarves and tied his ankles to the chair legs to keep his legs apart. He couldn't move a muscle. Melissa popped the tape into his VCR, then stood up in front of him and withdrew a black leather harness from a bag he hadn't noticed her come in with.

"What's that?!" he said, alarmed, as she began to strap it around her middle, then realized, with a sinking feeling, what it was, when she withdrew an even larger dildo than the one she'd just removed from him, and fastened it into the center. It was very strange to see his own girlfriend with an "erection," and even stranger to know that she was almost certainly going to shove her "cock" up his ass—and that, tied securely, he couldn't do a thing to stop her.

Melissa turned on the TV and started the tape, noting, with satisfaction, the horrified expression on Ryan's face as he watched Marcus Big become fully erect on stage. She moved around behind him and began to gently play with his thighs and his ass as Evan took off his clothes, and caressed his balls and his asshole when the guards strapped the young man down.

"Why are you doing this?" asked Ryan.

"Because you don't have much choice about this, Ryan. You need to get out of debt, and they just threw you a lifeline. But we can make it less awful for you if we practice."

"I was practicing."

"Sticking something up your own ass is not the same thing at all as having someone else doing it to you."

She had a point, he thought. But Ryan flinched at the sight of the man's hands running freely over Evan's bound body, and cringed when the man took Evan's cock into his mouth and sucked it until it was hard. On the video, the bidder was now dropping trou and revealing his own red, pulsing erection, and Ryan's eyes bugged out at the sight of it. "Holy shit, that guy's big!"

"I'm bigger," teased Melissa, and at the same time that the man on TV pushed his big cock into Evan's virgin ass, she stood behind Ryan, probed her own lubricated "cock" against his unprotected asshole and pushed it all the way inside. He grunted. It felt very full, but didn't really hurt. Even though the new cock was thicker, it went in pretty easily, since he'd already been opened up by the dildo and she used lots of lube. She thrust in time with the bidder on the screen, slowly and deeply, stopping when the man on TV came.

"You have to let me come!" begged Ryan.

"Do I?" asked Melissa. "I suppose I should. We wouldn't want to damage the hardware." She untied his hands. It only took him about five quick strokes to explode. "Now, when is this auction?"

"The 14th. Rico's going to ask me about it on the 12th."

"You're going to say yes. I'm going to come along in the audience and watch you getting fucked. And we're going to practice every day between now and then. That's what you need to do to get rid of this debt and to keep me. Got it?"

Ryan's ass was buzzing from all the attention, even without the vibrator, but he knew when he was beaten. "Got it," he said, reluctantly.