A Challenge

All participants are over 18.

*****

"The most I've ever come in a single night is four times," Dylan said, doubting his friend's claim.

"I'm telling you I made him come six times in a three-hour period in one night." Anton said again. "I'd get him over here to tell you, but he says he's a straight boy like you, so he wouldn't appreciate me outing him with open discussion of our night together."

"So he was straight too?" Dylan laughed. "Now I'm really having a hard time believing you. Straight guys just can't get it up for gay guys, much less come for them six times. That's just the way it is."

"Maybe he wasn't as straight as he thought he was."

The two young men were on lunch break at work when the topic turned, as it often did, to sex. Dylan knew Anton was gay and Anton knew Dylan was straight... but Anton suspected that Dylan was more than just a little bi-curious. He was too interested in hearing about Anton's active sex life. And Anton liked nothing better than to turn out a straight boy. Today he thought he might have just the right lure to make a handsome catch.

Dylan laughed again. "It's easy to say that when you have a convenient excuse to hide the identity of your subject."

"Well, not that I have anything to prove," Anton said. "But if you doubt my word, I take that as a challenge to prove myself."

"So how are you going to prove it?"

"How would you suggest?"

"I'm not going to watch you blow a guy six times to prove it."

"No, as you are the challenging party, I'd have to prove it on you."

Dylan laughed with less certainty. "But I'm not gay."

"That's what the other guy said, remember? Besides you don't have to be gay to enjoy a blowjob. And to beat my record, I'm putting it on the line that I could make you come seven times."

"Just suppose I agreed to this, what happens if I win and you can't make me come seven times?"

"Then I'm at your service for say, a week. I'll cook your meals and do your laundry and clean your apartment."

Dylan laughed genuinely. "That would be awesome!"

"But if I win, you're at my service for a week."

"I'll think about it," said Dylan.

"No," Anton said. "It's a limited time offer. I can fill my nights with other activities than just proving myself to you. Accept now... or decline if you have something better to do than blowing your load seven times tonight."

"Tonight?"

"Tonight."

It was agreed and Dylan knew that he was going to win every way. Free blowjobs for the evening and then an unpaid housekeeper for a week. Life would be good. Bragging rights over Anton would be even better.

Anton acted like he was more concerned, and stuck to Dylan the rest of the day.

"I'm making sure you don't rub one out ahead of time to spoil the results tonight."

"So you are worried," Dylan laughed.

Anton let him think so.

They arrived at Dylan's apartment shortly after six.

By six-thirty, Anton was describing the perfect blow job and five minutes after that Dylan had a boner putting a tent in the front of his trousers.

It was Anton's turn to laugh. "A gay guy can't make a straight guy hard, huh?"

Dylan's confidence was a little shaken, but there was no reason to think his reaction to Anton's sexy talk would make him lose.

"Since you're ready, let's whip it out and get this show started."

Dylan shyly opened his fly and let his cock unfurl. Anton wasn't disappointed. He got down on his knees before his friend, took the tool in his mouth and began to lick and nuzzle at it before sucking it into his mouth and properly blowing him. Anton rocked back and forth on his knees and hind legs as he treated the beautiful organ to a feast for its senses.

Dylan felt a heat building in the end of his cock and then he emptied his balls into Anton's mouth. The gay man continued to lick and clean Dylan's cock.

When he was done, he leaned back and gargled the jism in his mouth before swallowing it. Looking down at that made Dylan hot all over again.

"I think we can agree that that was number one."

Before Dylan could go soft, Anton was back on his cock again, sucking vigorously and ramping up his friend's flagging arousal. A minute later, Dylan flexed his hips against the kneeling man's mouth and unloaded another great wad of semen into Anton's mouth.

"Two," said Anton. This time the gay man let his supposedly straight friend come down from his orgasm.

Dylan pulled up his pants and went out to his living room and sat on the couch, catching his breath. Anton was in his mind. He knew Dylan was a bit upset that he had been so powerfully aroused by the action of a gay man upon his person.

"It's okay, Dylan," Anton said. "It doesn't mean anything. It didn't mean anything those two times and it won't the next five times I make you come."

Anton sat down on the couch beside Dylan. "Let me show you what little difference it makes." Anton kissed Dylan passionately on the lips. Dylan resisted at first and then began to lean into the kiss, eventually opening his mouth to accept Anton's tongue and intertwining it with his own. Dylan was so distracted with the kiss that he hadn't noticed Anton unleashing his cock once more until the gay man was stroking it with his hand and fingers. It felt so good that Dylan couldn't break the kiss until he groaned in a third orgasm. This time he wore his own jizz all over himself.

"Let's get you out of these dirty clothes." Dylan was a silent witness to his own undressing. He seemed to be lost in disbelief that he had already come three times in half-an-hour with hours remaining for Anton to make him come just four more times.

Now he was nude in front of a fully dressed gay man.

"I want you to think about what will happen next," Anton said.

"I... I don't know..." Dylan said, unable to process his feelings.

"I have you at a disadvantage, being fully dressed. Do you want to see me naked?"

"Yes," Dylan croaked.

Anton undressed very slowly, folding every discarded garment neatly. When he stood fully nude before his friend, he asked him a question.

"What should two attractive naked men do?"

Dylan mumbled something. His erection voted silently.

"I need to hear you ask for it, Dylan."

"Fuck," Dylan stammered.

"Say it in a sentence."

"We need to fuck."

"Ask for it."

"Will you please fuck me?"

"Of course, I will. How can I resist?"

Anton produced a tube of lube out of the pocket of his coat. He instructed Dylan to lean over the back of the couch while he lubed up his asshole. Then he applied more lube to his penis and without preparation or warning, he penetrated Dylan's anus and began fucking him.

"Uuuugghhh," Dylan groaned. The shock of pain passed quickly and already Anton could feel an unaccustomed heat in his rectum, a building sensation of pleasure. When Anton felt Dylan meeting his thrusts he decided the time was right to reposition his erstwhile friend, for whatever he was now to Anton, he was not a mere friend.

Anton extracted his cock from Dylan's arse in a sudden flex of his hips. He was delighted to hear Dylan whimper in disappointment.

"Don't worry," Anton told him. "He's going back in there. You're really going to like this."

Anton manoeuvred Dylan onto his back on the cushions of the couch and mounted him. Now they were fucking face to face.

"This probably won't work," Anton said.

"What won't work?" Dylan asked between breaths.

"Since you're straight, I likely can't fuck you to a hands-free orgasm," Anton explained. "Only gay men can come like that while someone fucks their ass."

Dylan's cock twitched, but it did not surrender.

"You're not some fairy who just needs to be fucked hard enough to nut, are you?"

Dylan moaned loudly as Anton increased the pace of his thrusts.

"You're not some faggot, are you?"

"Nooooo," Dylan groaned in total surrender as his cock spit up a small amount of cum onto his belly. There couldn't be much left in there after the four previous orgasms.

"That's five," Anton counted. "Are you sure you're straight? Sure you haven't maybe done this before?"

"No," Dylan was utterly mortified at getting off from being fucked by a man, from having even begged him to take him, and from being called a fairy faggot.

Anton withdrew from Dylan's ass and looked down at his challenger's cum-covered cock. It only seemed like good manners to clean it up. As he began lapping up the jizz off Dylan's cock, he was delighted to see the cock stayed stiff and high. Anton had blown Dylan earlier but he hadn't used all his best tricks on him. Now he brought his patented suction lock and talented tongue to bear, concentrating his efforts on the glans of Dylan's penis.

It took him only five minutes to come.

Anton gave Dylan no coming-down time from his sixth orgasm. Instead, scenting victory, Anton prepared his final assault on the young man's senses using his secret weapon. He lubed his own ass-hole, planted his legs on either side of Dylan's hips and smoothly mounted himself on Dylan's prick before it lost its stiffness. Dylan was fucking Anton before he knew what was happening.

Anton and Dylan both groaned with pleasure. Dylan was normally a top, but sometimes he liked a dick up his ass, and it was a small price to pay to fulfil the terms of the challenge. He rocked up and down on Dylan for several minutes, feeling his challenger hardening against the tightness of his rectum. Sensing the moment of truth was not far away, Anton leaned down onto Dylan and as he continued fucking him at the hips, he penetrated his mouth with a deep kiss. Dylan responded helplessly, letting his own tongue be dominated by the muscle invading his mouth.

With a sigh, Dylan came for the seventh time.

Anton broke the sensual kiss heartlessly and called it number seven. He dismounted immediately and stood above the exhausted Dylan.

"Who won that challenge?" Anton asked.

Dylan sighed again. "You did," he said with resignation.

"Damn right, I did."

Dylan cast his mind back over the terms of their agreement and remembered his fatal mistake. If Dylan had won, he had a housekeeper for a week; if Anton won, Dylan was his for a week of unspecified service.

"You know what you need to do," Anton said.

His prick was at full-mast and at eye-level as Dylan sat up on the edge of the couch. As he began to suck Anton's cock, he realized to his astonishment and not a little horror that his dick was hard again. He looked up from his work and saw Anton grinning down at him in triumph.

"Let's see if you can break my record. Don't worry if it doesn't happen tonight. We have all week."