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Play Stupid Games, Win Stupid Prizes

Summary:

The demand was straightforward, though unexpected and peculiar. Nevertheless, it was a clear and easily understandable proposition. A contest was initiated, and victory was claimed by one participant, thereby fulfilling the terms of the original request.

Derek had emerged triumphant in the competition, his win undeniably fair and legitimate. Yet, Jordan was consumed by an irrational and excessive envy as he witnessed the events unfold before him. He was baffled by his own inexplicable acquiescence to such a situation.

Or the one where Jordan reluctantly agreed to let Derek have his way with Stiles, feeling a pang of jealousy after losing a bet with the Alpha werewolf.

Chapter 1: Jordan's Version

Chapter Text

The demand was straightforward, though unexpected and peculiar. Nevertheless, it was a clear and easily understandable proposition. A contest was initiated, and victory was claimed by one participant, thereby fulfilling the terms of the original request.

 

Derek had emerged triumphant in the competition, his win undeniably fair and legitimate. Yet, Jordan was consumed by an irrational and excessive envy as he witnessed the events unfold before him. He was baffled by his own inexplicable acquiescence to such a situation.

 

Derek was straight up saddling up Stiles' face, bouncing that fat ass of his on Jordan's boyfriend's face like it was the wildest rodeo in town. Stiles, being the trooper he is, was tonguing Derek's gaping, hairy, ass-pussy like it was the sweetest, most succulent pussy he'd ever tasted. You could see the spit flying as Stiles dove deep, lapping up every inch of Derek's most intimate hole. ass-worship as its finest.

 

"Fuck, Stiles!" Derek groaned, his voice thick with lust. The sensation of Stiles' talented tongue working his tight, furry hole had him on the brink of losing it. He could feel the heat pooling in his balls, threatening to erupt at any second. He gripped Stiles' head with the powerful muscles of his large and plump buttcheeks, guiding him deeper into his ass, needing that contact to be as intense as possible.

 

The deputy should have foreseen the negative consequences of the wager he had made. Considering the significant effort exerted to persuade Stiles to participate in the competition, his current enthusiasm was both unexpected and infuriating. Jordan was increasingly irritated by Stiles' apparent enjoyment of the situation. It became evident that the hellhound was uncomfortable with sharing his boyfriend, even temporarily.

 

"Fuck yeah, Stiles!" Derek howled, his moan echoing through the room. A thick, sticky bead of precum plopped onto Stiles' heaving chest, glistening in the dim light. Derek's hands were locked onto Stiles' pecs, keeping himself aloft as he rode the waves of pleasure crashing over him. His spine tingled and quivered, every nerve ending on fire as Stiles' talented, wet tongue worked its way around his pulsing, sensitive hole. Derek's insides were ignited, burning with the intense heat Stiles' ministrations had unleashed. His cock was aching, throbbing, and Derek knew he was on the verge of blowing his load.

 

Having enough of being just an spectator, Jordan was like, "Fuck it, I'm done just chillin', let's get this party started," and he dropped down on his knees in front of Stiles. He could see that Stiles' ten-inch cock was rock hard and ready to go. Jordan unzipped Stiles' fly and pulled down his pants and boxers, giving Stiles' aching cock some freedom. Jordan's mouth was watering, and he bit his bottom lip, trying to contain himself as he leaned in and dragged his tongue from the base of Stiles' cock up to the tip, taking his time, making it a real slow burn. Stiles shuttered, and Jordan knew he had his attention. Jordan put the tip in his mouth and started sucking on the head of his boyfriend’s cock, and he knew he had him right where he wanted him. He put his hands on Stiles' inner thighs and started rubbing circles with his thumbs, as he continued to suck on the head of his boyfriend’s cock.

 

"Fuck, J. Jordan..." 

 

"Yeah, that’s my name, baby, the only one that needs to leave your mouth" Jordan said in his mind, mentally giving himself a high-five for Stiles’s moans, "Damn, you sound so good, baby," and he took a deep drag on Stiles' cock, trying to show him what he was working with. But then Stiles went right back to what he was doing with Derek, and Jordan had to step up his game. He took as much of Stiles' cock as he could fit in his mouth and started bobbing his head up and down, hitting the back of his throat, and massaging Stiles' inner thighs. Jordan knew that Stiles could get off just from some thigh play, so he figured this would be the perfect way to get him to focus on him instead of Derek. But boy was he wrong, Stiles was like a machine, just kept on going.

 

"Oh, fuck, Stiles, that's it," Derek moaned, his voice breathy with pleasure. "You feel so damn good." 

 

Stiles' attention was still mostly focused on Derek, and Jordan was getting pissed. He decided to do something about it. The deputy stood up, kicked off his pants and boxers, and revealed his throbbing, hard cock. He was ready to go all in and make sure he got some of Stiles' attention.

 

"Fuck it, I'm taking matters into my own hands,"

 

Jordan grabbed the lube from the bedside table. He squeezed some onto his fingers and, without any hesitation, started fingering himself. He was so eager, he did it so fast he thought Derek and Stiles wouldn't even notice. But he knew he had to be ready for the next step. The deputy, with determination in his eyes, crawled back over to Stiles. He lined himself up with Stiles' massive cock, and without any warning, he slammed down, trying to impale himself on Stiles' thick meat. It was a tight, painful fit, but Jordan was determined. 

 

"Fuck, J. Jordan!" Stiles shouted, his head thrown back, a combination of shock and pleasure painting his face. The heat of Jordan's tight, fat ass enveloped Stiles' cock in one swift motion, and he couldn't help but moan in delight.

 

Jordan had to pause and take a deep breath, gathering his strength before he began to move his hips up and down slowly. He was pleased to see that Stiles, in response, would pull his face away from Derek to moan or gasp. Jordan wanted more of Stiles' attention, so he started to pick up the pace. But he realized he'd have to get Derek out of the way if he wanted to fully claim Stiles' focus.

 

With a devious grin, Jordan reached out and grabbed the base of Derek's cock, pulling it out of Stiles' mouth. "Alright, Derek, it's my turn now," Jordan said, his voice filled with lust. He wanted every ounce of Stiles' attention, and he was ready to do whatever it took to get it.

 

"Fuck, Jordan!" Derek exclaimed, caught off guard by Jordan's icy touch. Jordan, not one to be deterred, leaned in and kissed Derek hard, silencing him in the process. Jordan was determined to have his way with his boyfriend, and he wasn't going to let anything get in his way.

 

Jordan and Derek locked lips, their tongues dueling passionately. As they kissed, the hellhound started to stroke the Alpha’s cock, his hand moving faster and pulling harder. He found that he was actually enjoying this new dynamic. It gave him a sense of satisfaction when Derek would turn his head away to moan Jordan's name or when he felt Derek's cock twitch in his grasp. Jordan had never seen Derek so submissive, and he was more than willing to take advantage of it.

 

He noticed Derek's muscles tensing and knew he was close to blowing his load. Jordan quickly seized the base of Derek's cock, stopping his climax in its tracks. "Not so fast, Derek," Jordan whispered huskily, smirking as he exerted his control over the Alpha werewolf’s cock.

 

"Please, J. Jordan... I need to come," Derek begged, his voice filled with desperation.

 

Jordan took a moment to study Derek's face, noticing his flushed cheeks, drooping eyelids, and the tears in his eyes. This was a far cry from the smug, sadistic expression Derek usually wore. Jordan felt a moment of pity for him, then decided it was time to let him go. He gave Derek's cock a few more strokes, and the Alpha werewolf erupted, shooting his load all over Stiles' chest and stomach. Spent and barely able to keep himself upright, Derek climbed off Stiles and collapsed onto the bed next to him.

 

Jordan smirked, satisfied with his control over the usually dominant Alpha. Now it was his turn to Stiles to focus on him, and he was eager to receive the attention of his boyfriend that he selfishly craved.

 

Now that Derek had been dealt with, Jordan leaned in to kiss Stiles deeply, their lips crashing together in a heated embrace. He pulled back, his forehead resting against Stiles' as he basked in the fact that he finally had his full attention. Jordan started riding Stiles' cock harder, feeling the pleasure of Stiles' moans with each thrust. He loved the sound of Stiles' pleasure, it was his favorite part about being with him. The louder Stiles moaned, the more turned on Jordan got, and he rode Stiles with renewed vigor, determined to make this the best experience for both of them.

 

Jordan felt Stiles' thrusts picking up, meeting his own with perfect synchronicity. The sensation of Stiles hitting his sweet spots sent chills down his spine, and he let out a low moan. This only seemed to spur Stiles on, as he aimed directly for Jordan's prostate. With each hit, Jordan's moans grew louder, his vision clouding as the pleasure intensified.

 

When Stiles stopped moving, Jordan took control again, using Stiles' cock to continue stimulating his prostate. It didn't take long before Jordan was driven to his climax, spurting his cum all over Stiles' stomach, joining Derek's load. He didn't stop there though, continuing to ride Stiles, determined to bring his boyfriend to his own climax inside him. Jordan's body trembled, his mind a haze of pleasure, completely absorbed in the moment.

 

Eventually, Jordan felt Stiles' thrusts picking up, meeting his own with perfect synchronicity. The sensation of Stiles hitting his sweet spots sent chills down his spine, and he let out a low moan. This only seemed to spur Stiles on, as he aimed directly for Jordan's prostate. With each hit, Jordan's moans grew louder, his vision clouding as the pleasure intensified.

 

When Stiles stopped moving, Jordan took control again, using Stiles' cock to continue stimulating his prostate. It didn't take long before Jordan was driven to his climax, spurting his cum all over Stiles' stomach, joining Derek's load. He didn't stop there though, continuing to ride Stiles, determined to bring his boyfriend to his own climax inside him. Jordan's body trembled, his mind a haze of pleasure, completely absorbed in the moment as he desperately wanted his boyfriend’s seed filling him.

 

"Wait, Jordan," Stiles said, trying to regain his composure as he spoke. "I'm not wearing a condom, it'll make a mess."

 

"Stiles," Jordan said, and that was enough for Stiles to know that Jordan wasn't concerned with the mess. Jordan continued to pound himself on Stiles' cock, with Stiles giving the occasional thrust to meet him. It didn't take long before Stiles' huge release spilled into Jordan's guts, causing the older man to let out a final breathy moan.

 

Jordan pulled himself off Stiles and laid down on the other side of him, resting his head on his boyfriend's shoulder. Derek crawled up and settled his head on Stiles' other shoulder. The three of them laid there in the hot, sticky mess, basking in the afterglow until Jordan spoke up, shocking both Derek and Stiles.

 

"We should definitely do this again," Jordan said, a mischievous glint in his eye.