The Gambler Ch. 02

Calculus was a whole new experience with a butt plug, thought Ryan, wishing his erection would subside so he could concentrate at least a little on the subject at hand. Melissa had come over early in the morning to start him on his newest lesson, and there would be hell to pay if he removed the big shaft from his ass—or the cock ring from around his balls—before she got home from work at 5:30. It was 2:30 now, and he'd spent half his day trying to hide his hard-on with a notebook and walk as normally as he could. Twice he'd had to duck into a men's role stall and beat off, which helped a little. The constant stimulation was maddening.

"Hey, what's with you today, Walker?" a fellow student asked him. "You look like you got a stick up your butt!"

You don't know how close you are to the truth, thought Ryan. "I, uh, pulled a muscle," he replied.

"Tough break."

"Yeah."

Finally it was 5:15 and he could head back to his apartment for tonight's "entertainment." Melissa had made him watch Evan's deflowering over and over until he could view all of it without cringing, and maybe even the tiniest flicker of desire. She made him practice taking off his clothes in front of her while standing on top of his mattress, as if she were the audience and he was on stage. Last night she started to leave the window shades open so he could get a feel for what it would be like to know that people might be watching him naked. Tonight, they were moving on to the next segment of the tape, with 8 nights left to go. The second virgin.

"So, Bud, tell us a little something about yourself," asked the emcee to the tall, broad-shouldered young man on stage.

"I'm, um, studying engineering. At UCLA," replied Bud.

"Yeah, and how to lose a ton of money," added Melissa. Bud had big brown eyes and was a milk chocolate color that she liked a lot. She couldn't wait to see him naked.

Ryan was already naked. She'd handcuffed him and hooked his hands above his head to the plant hook, which someone must have thoughtfully screwed into a beam, since it held so well. His ankles were tied to the chair legs, because she liked them apart like that. It made it easier to play with his body when he couldn't do anything to stop her. She tweaked his nipples playfully and ran her hand down his belly, tickling him where she knew he was sensitive and watching him wriggle. With the window shades open, who knew who might be watching.

"Do you have a girlfriend?" asked the emcee.

"Yeah," replied Bud.

"So, why are you here with us tonight, Bud?"

"I needed the money."

"But you're here of your own free will?"

"Yeah."

"Ever been with a man?"

"No!"

"Now, son, you watched in the back room when it was Evan's turn and you saw it on the closed-circuit TV. What did you think of that?"

"I thought that fellow had a mighty fat dick!" The crowd laughed.

"I thought so too, Bud. You never know who you'll get, of course. I'll just promise you that our bidders always wear a condom and use lots of lube." The crowd laughed again. Marcus looked a little bit relieved. "So, go ahead, Bud, show us what you've got!"

Naked, Bud was even more impressive than he was clothed. He looked like he might be a football player, or at least a weightlifter. He had huge arms, a solid chest, powerful thighs, and a long, thick cock which was still limp. Very nice, thought Melissa. She wasn't surprised this time when the bidding stopped at almost $49,000, and wondered how much Bud owed to Big Louis.

However much it was, he was paying for it now. The guards strapped Bud into something that looked a lot like a medieval stocks. He was bent over at the waist, with his arms and head locked into slots in a board, and his ankles attached to rings in the floor that were at least 3 feet apart. The net effect was to present his ass like a gift to his bidder, who stood behind him now and fondled it very gently, then went around to Bud's face and unzipped his pants, presenting him with a limp penis. "Suck it hard," insisted the man, rubbing it against Bud's cheeks and lips.

"Suck it hard," repeated Melissa, and Ryan licked and sucked her plastic phallus. Bud opened his mouth, reluctantly and let the tip of his tongue touch the head of the penis, then closed his mouth around it and began to lick and suck. The crowd murmered as the winner's cock lengthened and thickened into a sizeable erection, slick from Bud's saliva.

Once hard, the man wasn't especially patient. He walked around to Bud's rear, squeezed and stroked it for a minute, then pulled on a condom and gave himself a good squirt of lube. He inserted the tube into Bud's anus and gave him a squirt as well, Bud startling at the cool intrusion.

Melissa, who had watched the film before, was ready with some cool lube for Ryan as well.

On screen, the man took his stiff prick in one hand, rubbed against the spot, and thrust steadily until he penetrated deep into Bud's belly. From the side, the camera easily caught the man's long thrusts—he pulled almost all the way out with each one, then penetrated again and again for maximum friction. Bud let out a rhythmic "unh, unh, unh" with each stroke.

Melissa lubed up her fake cock and shoved it abruptly into Ryan's ass, mimicking the man's technique.

"This is like feel-o-vision," thought Ryan, watching the screen while he was ritually butt fucked by his girlfriend—with the curtains open so the neighbors could see it all. He imagined them at their windows with binoculars in one hand and their genitals in the other, masturbating furiously to his violation.

After several long minutes, the man pulled out all the way, tore off the condom, and came in spurts on Bud's naked ass, rubbing his cream into Bud's milk chocolate skin. Melissa couldn't accomplish the same, but she pulled out and untied Ryan. Unlike Bud, Ryan had a massive erection and wasn't making any money off of this particular transaction. And unlike Bud, Ryan had a bone to pick with his girlfriend. And turnabout was fair play. Still naked, he rubbed his wrists where the handcuffs had been, musing out loud, "Hmm. So, how do these work?"

Melissa walked right into the trap, handing him the cuffs to examine. Ryan played with them innocently for a minute, then snapped one onto her wrist.

"What are you doing?" she asked, but he'd already gotten her other arm behind her back and locked the cuffs shut.

"You've had enough fun with me, baby. It's my turn now."

Ryan used the ropes she'd left in place to secure Melissa in the position he'd just used: bent over the chair with her arms behind her. He tied her ankles to keep her legs apart, then unsnapped and removed the harness and surveyed his helpless victim. Her ass was smooth and pink, her thighs long and lean and shapely, and he lifted up her tank top to expose her breasts, squeezing them gently to let her know who was boss now. Melissa knew she was overpowered, and felt her excitement rising as she wondered what her pushed-to-the-limit boyfriend would do. Glancing over to the window, she saw a man silhouetted. Naked. Watching them with one arm curved around to his center. She had a pretty good idea that she knew what he was doing.

Ryan picked up a belt from his jeans and used it to smack Melissa's helpless ass. Not too hard, but enough to sting. After he'd made sure that it was a uniform shade of rose, he knelt between her legs and found her erect clit with his questing tongue, caressing it until she was moaning and his face was slick with her juices. Then he pulled on a condom and entered her from behind, finding a slow rhythm. After several thrusts, he withdrew and stopped.

"Why are you stopping?" gasped Melissa. She was answered by a cool squirt of lube into her anus. "No, you can't do that to me! I've never done that. It'll hurt!" she begged—but she was as helpless to prevent her own anal violation as Ryan had been.

His erection was already liberally lubed with her juices, but he added extra from the bottle, then positioned the head of his cock against her frantically wriggling ass. He took his time, gently rubbing the tip of his penis on her anus, getting her used to the erotic feeling. Then he started to push.

"Push back against me, it'll go easier for you."

She must have complied. He held his cock in his hand to control the speed, and felt her helpless muscles give way. With slow, continued pressure, his cock head was making progress, invading her virgin ass. In a moment, he slipped inside of the muscular ring.

"Ohhh!" she groaned, but didn't complain, so he kept up the slow, steady progress, sinking deeper inside of her, until he was buried to his balls in her gorgeous ass.

The friction was incredible! Her ass was tight, and with the plentiful lube, slick and warm. He pulled out and pushed back into her, and she grunted with each thrust. Then he reached around her belly and down to her swollen clit, massaging it with two fingers while he butt fucked her. She whimpered, and begged him,

"Oh! Do it harder!" thrusting her ass back against him now with each new invasion. She came even before he did, and her internal spasms around his trapped cock triggered his own powerful orgasm.