Ball Boy Balling Challenge - Cover

Ball Boy Balling Challenge

by ChrisCross

Copyright© 2022 by ChrisCross

Erotica Sex Story: A dishy and arrogant twenty-six-year-old tennis pro, Leo Cinelli, is playing the second round of men’s singles at the U.S. Tennis Open. He has a reputation for taking fourteen-year-old boys, which is the legal age in Italy. He’s not in Italy, but what the hell. Two fourteen-year-old ball boys, Craig and Danny, make a bet on whether Danny can and will go under Cinelli.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/mt   Consensual   Reluctant   Gay   Fiction   Sports   Workplace   MaleDom   Rough   Anal Sex   Analingus   First   Safe Sex   Size   .

Craig stopped Danny in the ball boys’ locker room before they were to go out onto the Louis Armstrong Stadium for a U.S. Tennis Open second-round afternoon match between the twenty-six-year-old Italian, Leo Cinelli, heir to a bicycle manufacturing empire and a notorious bad boy, and the American Scott Denton. Both of the ball boys were fourteen and perfectly formed beautiful angels.

“You know what we discussed about Cinelli,” Craig said. “I bet you couldn’t.”

“I bet I can,” Danny retorted. “Piece of cake. He’s got a reputation for it.”

“Well, I’ve read it’s OK in Italy, but I bet he wouldn’t try it here.”

“If he does it at all, he’s hooked and will do it anywhere,” Danny said.

“So, what, you want to do the bet or not?”

“Sure. What’s the bet then?”

“If you can, you have to return this used, with him initialing the packet.” Craig surreptitiously pulled a Trojan Magnum condom packet out of his bag.

Danny laughed. “What do you have that for? And what makes you think Cinelli needs a Magnum?”

“His photos have been on the Internet. I know you’ve seen them. We’ve looked at them together. You tell me whether you think he needs a really big one or not. You’ve seen a hell of a lot more erections than I have.”

“OK, you’re right. But why again are you carrying that around? You haven’t done it. I’ve done it. You haven’t.”

“There always will be a first time,” Craig said. “That’s the bet. Take it or lose it.”

“What if I don’t get Cinelli to do me?”

“Then you have to let Taylor Wilson do you. You know he wants to.” Taylor Wilson was one of the U.S. Open venue managers. He had something to do with setting up the ball boy roster, and he’d made no bones about wanting to do fourteen-year-old Danny, who he knew had let some of the local tennis pros screw him.

“Yeah, but Wilson’s an old, fat, ogre.”

“That’s the bet. If you don’t really think you can get Cinelli—”


It really wasn’t that hard. Leo Cinelli was a bad boy in many ways and that was one of them. Fourteen-year-olds were fair game in Italy. Cinelli treated them as fair game everywhere, and there were rumors and Internet gossip about him taking boys young, none of which seemed to phase him a bit. He’d even told one gay Web site that doing boys was in the ancient Roman tradition. Fourteen was the legal age in Italy. That was “good to go” for him.

He was an arrogant son of a gun with every reason to be so. He was a gorgeous Italian—sleek and sensual, Mediterranean dark and sultry. Sex on a stick and independently wealthy. There wasn’t any stopping his fetish, at least in Italy. He had no trouble getting what he wanted. Any boy prone to go under a man would give it all up for Cinelli without a second thought. He had not only fame, fortune, and looks, but a big cock too.

During the match, which Cinelli won handily, Danny, through looks and flirting and letting Cinelli touch his hand longer than necessary when he provided the ball or the towel, and by floating gracefully around the court chasing balls with Cinelli ogling him and fantasizing about him, had no trouble making Cinelli want him. Danny, in turn, made it quite clear the Italian tennis pro could have him.

They met, not by accident, an hour after the match was over. As Cinelli was leaving the court, he had stopped where Danny was standing to pin down that he wanted the boy. Danny told him where he could find a usually deserted section of corridor under the stands that he could pretend was just a way he was trying to find to get out to where the courtesy cars were waiting to take players to their hotels if that was necessary.

It wasn’t necessary. They kissed and felt each other up in the corridor. Cinelli would have risked fucking the boy right there, up against the wall. But Danny needed an initialed condom packet and a used rubber, which would be hard to manage here, so he begged off, which made Cinelli want to spike him even more.

“Can I carry your bag out to the car taking you back to your hotel?” Danny asked, fluttering his long, thick eyelashes at the Italian.

“Sicuramente puoi—You certainly may,” Cinelli said.

Then, when they reached the area where the cars to the hotels were waiting, Cinelli said, “Entra. Voglio mostrarti il mio hotel—Get in. I want to show you my hotel room.”

They both knew what that meant, and a little chill went up Danny’s spine. It wasn’t just that this was so easy. It also was that he melted to a dominant man. The Italian was giving him orders. Danny got in the car.

The dominating mode continued when they entered the hotel room. “Striscia. Sdraiati sul letto. Allarga quelle gambe. Dammi il tuo buco—Strip. Lay down on the bed. Spread those legs, and give me your hole” the Italian demanded. At the same time, Cinelli was stripping off his own clothes. Danny gasped. Craig had been right. The man needed a Trojan Magnum. The boy whimpered and started to moan, but he stripped as Cinelli demand. It wasn’t that he hadn’t been fucked in the ass before. It was that he hadn’t been fucked by a shaft that thick and long before.

Before he was completely undressed, he pulled the condom packet out of his pocket that Craig had given him. “I’ll do it—whatever you want—if you use this and initial it afterward.”

Cinelli laughed. He didn’t ask the boy why, he just said, “You knew I’d need this size?” He took the condom packet from the boy and slit it open.

“Yes, I’ve seen the photos on the Internet,” Danny answered.

“And you’ve read the gossip too?”

“Yes.”

“So, you know I’ll need more than just that one.” He pulled two more Trojan Magnum packets out of the pocket of his shorts.

Danny gasped, his eye got as big as saucers, and he began to tremble, but when Cinelli repeated, “Lay on the bed, spread your legs, and show me your hole,” the boy did so. Cinelli walked over to him, naked, his body muscular, sleek, and magnificent, his erection enormous, and he fingered Danny’s hole. Danny flinched and groaned. Cinelli penetrated with a finger. The hole blossomed open. Danny whimpered, “Be good to me, Daddy.”

“I’m always good to my boys. You open right up. You’re not a virgin,” Cinelli said, sniffing his slight disappointment.

“No,” Danny answered.

“So, I don’t have to be gentle, at least.”

“No.” This “no” was a bit more forlorn.

 
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