A Challenge Ch. 02

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“So, who won that challenge?” Anton asked Dylan.

The challenge was simple. Anton, a very out gay man, had boasted of a recent conquest in which he made a nominally straight man shoot his load six times in one evening. The audience for Anton’s story was his straight friend, Dylan. The younger man scoffed at Anton’s claim, saying no straight man could be made to nut for a gay man once, much less six times. Anton took that as a challenge. He made a bet with Dylan that he could break his record and give Dylan seven orgasms in one night. Dylan thought it over, but he couldn’t resist a challenge that he figured would get him blown repeatedly. Besides, he didn’t really believe Anton, a gay man, could actually make him come. Dylan was soon disabused of that notion. Blowjobs were followed by handjobs and fucking, and within a few short hours, Dylan had indeed blown his load seven times.

He was in shock now.

“So, who won the challenge?” Anton asked again. He was naked and aroused.

“You did,” Dylan answered with a sigh of resignation.

“Damn right, I did.”

Dylan began to think about the terms of their wager and remembered his fatal mistake. If Dylan had won, he would have had Anton as a housekeeper for a week; if Anton won, Dylan was promised for a week of service which had remained unspecified. He hadn’t worried about the terms when he was sure he would win. He still couldn’t believe he had come seven times by the ministrations of a gay man. He had been sure that he was straight; he was not so sure of that now and he was troubled and tired. He had been blown, manipulated and fucked to mind-blowing orgasms far beyond any he’d ever experienced with women.

“You know what you need to do,” Anton said. Anton had just fucked Dylan’s brains out on the couch, but he himself had not come. His prick was at full-mast and at eye-level for Dylan, now sitting up on the edge of the couch.

His promise of service was not specific; only that he was at Anton’s command. How could he have been so stupid? That meant he was obliged to do anything the gay man asked him to do. What would that mean for Dylan?

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

Dylan knew there was no chance that an inexperienced cocksucker like himself would be able to get this confident gay man off enough times to break the standing record; that would entail giving Anton eight orgasms in one evening! As Dylan 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.

“Straight boy, eh?” Anton gloated with good humour. “We’ll see how that stands in seven days.”

Dylan’s protest was absorbed by the cock shoved back in his mouth. Anton laughed at his younger friend’s plight.

Anton had been having a great evening blowing and fucking this beautiful straight boy but he deliberately hadn’t allowed himself to come. Confident of victory all along, he saved himself for this.

As Dylan sucked Anton with hesitancy and clumsiness, Anton coached him to keep his teeth covered and put a gentle hand on Dylan’s head to guide his rhythm. He told the younger man to use his tongue to greater effect and to add suction to his nascent repertoire of cock-pleasing skills.

For his part, Dylan was stunned to find himself relaxing into the work. His jaw was already growing tired, but he found himself stimulated by his efforts. His cock remained straight as a ruler.

For all his self-control in preventing himself from coming earlier tonight, Anton was once again close to his orgasm. He wanted to savour this significant moment in the process of turning Dylan out. He wrapped his fingers in Dylan’s hair and began to control the speed of the younger man’s movements. For a time, the pace remained steady, but as Anton neared his climax, he held Dylan’s head stationary and began face-fucking his young friend. Dylan could not move his body, but his tongue never stopped massaging Anton’s cock.

Anton was lost in his pleasure. “Soon… soooon, Slave,” he moaned.

“Mmfff… Mmfff… Mmfff…” Dylan’s voice was muffled by the organ in his mouth.

“Yes… here it comes, my little cocksucking sissy faggot!”

Dylan couldn’t understand why being called those names made his dick spasm with strange delight. He was straight! Wasn’t he? Then all thought was forgotten as Anton groaned and ejaculated in Dylan’s mouth. The older man had been giving blowjobs and fucking Dylan all evening in his effort to win their bet, and in so doing he had effectively been edging himself for hours. When the flood came, it was full and copious. Anton groaned in his joy. He looked down at Dylan, and pushed him off his cock. The younger man’s eyes still bulged from the shock of receiving Anton’s wad. His mouth was full of semen. It trickled out over his chin.

“Relax, Dylan,” Anton said. “It’s your first time taking a load in your canlı bahis mouth. Savour it. Note the taste. Roll it over in your mouth and enjoy its texture. Open your mouth and show me your prize.”

Dylan complied, letting his mouth gape wide open. The silvery spunk had mixed with the young man’s saliva and it hung in threads from the roof of his mouth. Dylan’s cock twitched as he realized how whorish he looked and Anton wondered if he couldn’t tease another load out of the lad.

But fuck that, the bet was won and it was time to reap the rewards of winning.

“Swallow my load,” Anton commanded. Dylan, with some sputtering and coughing, obeyed. He opened his mouth to show his new master that the deed was done. Anton nodded. “You’ve done good work here today. You should be proud, my slave.”

Dylan was confused. He did feel a spark of pride in making Anton come. He felt shame because he had been raised to hold homosexuality at length. His pride also withered when Anton labelled him his slave. Yet his belly was full of cum and his sexual appetite was profoundly satisfied.

“Get up,” Anton said, holding a hand out to help him up off his knees. “We’re not going to break any more records tonight. Let’s go get some sleep.”

Dylan hadn’t realized until just then how exhausted he was. Between them, they had been fucking and sucking for hours. Anton led Dylan to the bathroom. Dylan needed to piss and Anton insisted that he do so in front of him. “Slaves don’t get privacy,” Anton said. After a little bladder shyness, Dylan did his business. They stepped together into a hot shower. Anton ordered Dylan to wash himself thoroughly while he watched. When he finished slowly scrubbing himself from head to toe, Anton raised his arms and demanded his slave wash him down just as completely. They both had boners, but Anton was tired; he made no demands. After their shower, they collapsed naked in Anton’s bed and Anton led their chat.

“It’s Friday night; you belong to me until next Friday morning. Seven nights in my bed. Tomorrow, you’ll go to your place and bring back a few things to see you through your week as my slave.”

“Okay,” Dylan replied.

“I think you should start calling me Master.”

“Yes, Master.” That pleased Anton. Frankly, he’d been surprised that the younger man agreed to fulfil his obligations after losing the wager. After all, bets between two gents aren’t legally binding. If Dylan had decided to walk away after his eight orgasms, Anton would not have lifted a finger to stop him. To Anton’s surprise, it seemed Dylan didn’t even stop to think before capitulating. Getting Dylan to call him Master so easily was another pleasant surprise. So far, no task had been too demeaning for Dylan to complete. Anton would test these limits over the next few days. The less time it took for Dylan to adapt to his role as submissive slave, the better for Anton and his plans for Dylan’s future.

The two exhausted men fell asleep.


Anton woke up to answer the call of nature.

When he came back to bed, he scooped with his fingers a dollop of lube from a jar on his night table. He thrust those digits into Dylan’s crack. Dylan said nothing but spread his legs wide for the coming assault on his ass. Once Dylan was lubricated, Anton sunk into him slowly and, for the first time since they had begun their sexual escapades, with tenderness. Anton’s weight was on Dylan’s back as he began thrusting into his arse. He leaned close to Dylan’s neck, nuzzling it and nibbling at his earlobe, whispering dirty words and promises. Their rhythms were aligned; Dylan matched Anton thrust for thrust. Exertion and passion added urgency to their moans. As they grew closer to their climaxes, Anton whispered into Dylan’s ear.

“You cocksucking sissy bitch. You’re mine now.”

As Anton stiffened and shot his wad up Dylan’s arse, the younger man came into the bedsheets with a sound like a sob. Anton did not know if Dylan’s sob was one of joy or shame.


In the morning, Anton milked the benefits of having a slave. When he saw Dylan reaching for his pants, Anton told him slaves go unclad in his house. Dylan looked at him questioningly; after all, they were friends.

“Don’t forget, this week I’m your master, not your friend.”

Anton called for breakfast in bed and Dylan prepared it, bringing it to his master on a tray with a stand designed for use in bed. When he was finished eating, Anton had Dylan take the dishes away, wash them and place them back in the cupboards.

Once that was finished, Dylan rubbed Anton’s feet by command. He did so almost lovingly and Anton enjoyed it so much he had the younger man lick his feet and suck his toes. Anton’s feet were an erogenous zone for him and he was soon sporting a hard-on for his masseur. A few moments later, the cock was in Dylan’s mouth. He experimented with more technique this time and Anton noticed the improvement even over his last blowjob. Once again, Dylan’s mouth was flooded with his master’s semen.

SATURDAY AFTERNOON, 2 bahis siteleri P.M.

Once Dylan had Anton’s cock cleaned up, the two men got dressed and drove to Dylan’s place. Dylan felt his worlds colliding as Anton joined him in order to meet Dylan’s roommates. He begged him not to come up to his apartment, but Anton insisted. For a slave, there was nothing to say to that. Once inside the residence, Dylan’s roommates, Chuck and Said, introduced themselves to Anton.

Anton was thirty, just five or six years older than these lads. He had come out of the closet many years ago and was very comfortable with his identity. He was not quite a stereotype, but he definitely looked and sounded gay. He had chosen to wear a rainbow t-shirt today, and Dylan wondered if that was deliberate. Dylan stood by as his roommates and his master made small talk. Dylan saw the looks on their faces and knew they were curious about the link between their roommate and this obviously gay stranger.

Chuck asked Anton and Dylan what they were up to today. Anton told him that Dylan was coming over to his place to do a few jobs around the house for the week, so they were just here to pick up a few things for the visit. This sounded fishy to Chuck and Said, but they didn’t press the matter. The three roomies were casual friends, not close friends.

When Dylan went off to his room to pack some things, Anton followed him in. Dylan was bending down to take clothes out of his bottom dresser drawer; his ass was suggestively available to his master. Anton reached forward, circling Dylan’s waste with his arms while pressing his cock into his ass provocatively.

“I could take you right now,” Anton said.

The thrill of it, to take Dylan’s ass in his own room where his nearby and inquisitive Neanderthal roommates would hear it happening. Anton sprung an instant boner at the thought of outing his ‘straight’ slave.

Dylan had a surprise hard-on too, but he begged him not to make him do it there. “People must never know.”

Anton weighed his arousal with his decency. It wasn’t his place to out someone else on a bet, but opportunities for thrills like this didn’t come every day. In the end his decency prevailed and Anton guarded his slave’s secret.

After Anton and Dylan left, the immature roommates made fun of the pair. They weren’t sure what was going on, but the Dylan they knew wouldn’t shack up with a gay man to do his chores. Dylan was alarmed that they had cause to suspect, but his mind was kept occupied at his new home.

As soon as Anton and Dylan arrived back at his place, Anton ordered Dylan to strip naked. The younger man obeyed and placed his folded clothes in a dresser drawer Anton cleared out for him.

“You won’t be needing clothes now until Monday morning.”


Anton enjoyed having a slave. Dylan prepared his supper and it was delicious; it was fortunate that the young man was a good cook. Anton watched some television after his meal, using Dylan as a footstool for over an hour. When the show was over, Anton sent Dylan to do his laundry. When all of the clothes were folded to Anton’s strict standards, Anton took Dylan to bed where he availed himself of both Dylan’s mouth and his ass. Dylan’s orifices were becoming used to being stuffed with Anton’s cock. Before their relations for the evening ended, both Anton and Dylan had come multiple times.

The difference tonight was that Anton cuddled his slave. He kissed him on the forehead and held him until he was asleep.


Morning wood needed taking care of. With all of the heavy training he was experiencing, Dylan was becoming a very proficient cocksucker. Anton was enjoying the blowjob very much, but he had a sexy idea to make it hotter.

“Slave, go to the nightstand and take out my dildo. Lube it and your ass up. I want you to rock back and forth with that ten-inch rubber dick up your arse as you suck my cock.”

Dylan obeyed instructions and was soon bouncing up and down on the artificial cock. Anton was curious to see how an ostensibly straight young man would weather this challenge. Dylan’s reactions hardly seemed straight at all. His riding and cocksucking pace synchronized and grew faster by the second. Before long, he was losing control. His moans and groans were only partially muffled by the organ in his mouth. Then, with an outburst worthy of erotic fame, Dylan came, his bouncing, shivering cock spraying his cum onto his chest and his legs, not to mention the bedding and the carpet. When he was in control of himself again, Dylan continued bobbing on the dildo until Anton finally blew a load in his mouth again.

Dylan looked down at himself, still erect and splattered with his own cum. He had swallowed Anton’s load again. He wondered if he would ever recover from this humiliating experience, but he also wondered if there was a danger he could grow to love it.

Anton didn’t let Dylan have much time to think about it. He had a honey-do list for his short-term live-in lover. Dylan’s first job was to clean his own cum stains bahis şirketleri out of the carpet. Then he was required to wash the soiled bedding. While the sheets were in the wash, Dylan was given a bucket and a cloth and sent off to clean all the windows. He objected that he could not do so in the nude, but Anton reassured him that nobody would see him in daylight glare.


Dylan was exhausted. He had just finished putting a second coat of paint on the walls of the spare bedroom Anton used for an office. While the first coat had dried, he made the bed with the linens he had washed and he vacuumed the entire apartment. Before long, it was time to make the master’s supper.

Anton looked over his naked and paint-splattered slave. The younger man was sweaty and dirty. He would make a delicious meal himself. Anton grabbed Dylan by the cock and led him to the bedroom. He sat him on the edge of the bed and began to lick and suck his cock. Dylan’s cock rose to the stimulation. It was more than just a blowjob Anton had in mind; he wanted to mindfuck Dylan. Anton talked to his slave in between oral ministrations, but if his mouth wasn’t on him every second, then his hand was.

“No woman can suck cock like this,” Anton said as he licked around the head of Dylan’s cock. “It takes a man to truly please a man’s cock.”

“Yes, Master,” Dylan said.

“I have taught you the secrets of man-on-man pleasure. What woman ever made you come seven times in one night?”

“No one, Master. Only you.”

“Only a man understands another man’s need.”

“Yes, Master.”

“Say it back.”

“Uh, only a man can really please a man. Only a man understands his needs.”

“And what about you? Has anyone ever sucked you off or fucked you better than I do?”

Dylan hesitated.


“No one has ever fucked or sucked me better than you do, Master.” For Dylan the answer was true, but it was also treason against his heterosexuality.

“Do you remember just two days ago when you told me no straight man could possibly be aroused or brought to orgasm by another man?”

“Yes, Master.”

“I’ve lost track of how many times you have nutted since Friday night, all thanks to the efforts of another man. That must make you very gay.”



“I’m straight, Master.”

“Are you? I wonder… it seems to me that any straight man would have welshed on our bet if he was to be the slave of a gay man for a week. Yet here you are. That could just mean you’re good as your word, but you certainly could have bailed even earlier, when I stopped blowing you Friday night and started fucking your ass. Wouldn’t any straight man have backed off of our deal there and then?”

Dylan groaned, not only because he was defeated in logic, but also because he was close to coming one more time in the hands or mouth of his new master.

“You’re going to come in my mouth and it’s going to make you that much more gay.” Anton’s mouth was full-time on Dylan’s cock again.

Dylan emitted a whiny reply. “Noooo…”

But Dylan never was in control. Anton bobbed his head expertly over Dylan’s penis while massaging his balls with his fingers. With a deft and sudden move, he thrust a finger into Dylan’s butt crack. With him sitting back on the bed, the area was not very accessible, but the knock at his back door was just enough to bring Dylan over the edge.

“Nooooo…” he moaned, falling back on the bed as Anton tore the pleasure centres of his brain out through his cock. He spilled a mighty load in his Master’s mouth. It took him a long time to come down from the mind-blowing orgasm.


Dylan continued to submit to Anton’s every demand. The first day of the work week began with Dylan curing Anton’s morning wood in the now-customary oral manner. When Dylan had swallowed all of his cum and licked him clean, the two men took a shower together. When they were dry, they dressed for work and had breakfast.

It was convenient that Anton and Dylan worked in the same office. Anton decided to Dylan’s relief that they would not pursue their master/slave relationship during business hours. Anton couldn’t have cared less about people knowing he was gay, but he appeared respectful of his slave’s right to return to his private life when their arrangement was complete. For this, Dylan was grateful.

In this more normal environment, Dylan had time to stop and think about what he was involved in. Anton’s words from the evening before echoed in his mind. Was it possible that he really always had been gay? Or was Anton somehow converting him— Dylan stopped himself. It was well known that conversion therapy, which worked the opposite way anyway, was fully discredited scientifically.

Yet why would a straight man like himself find himself a million miles away and staring at Anton sitting at his desk? Why did he have no interest in flirting with Marie, the beautiful co-worker from Accounting with whom he normally maintained a mildly HR-unfriendly banter? He had a lot on his mind; that had to be it. With this foolish bet and the consequences, he had been undersleeping and letting Anton set the narrative of each day. When this week was over, honour would be satisfied and Dylan would keep his gay friend at arm’s length.

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