Work Text:
Winn’s not sure if he wants this to end or never wants it to stop; all he knows is that he’s not sure how much longer he can honestly take. When Jimmy had suggested that he and his boyfriend wanted to have a foursome with Mon-El and him he had been ecstatic. Sure, he was nervous as fuck, but Jimmy was amazingly handsome, that deep voice and tall, muscular body enough to set anyone off. And of course he’d known that Mon-El would love getting to have someone else to fuck. It hadn’t even occurred to him who Jimmy’s boyfriend might be, his dick too preoccupied with the known participants.
It was only now as he kneeled on the bed, a vibrating, candy cane shaped prostate massager lodged deep inside him on nearly the highest setting, a silly reindeer jockstrap on and, something around his head that was mostly obscured by a blindfold that he started to wonder who their fourth participant was.
Surely it had to be someone wild, because as amazing as Jimmy and Mon-El were, he couldn’t imagine either of them thinking of something this freaky. Winn had never thought of himself as the kind of guy that would be into bondage, but then again when they’d put the leather harness on him, a little bit gag in his mouth, a chastity cage on his cock and even covered his hands with some weird mitts that left him unable to grab anything, he’d not minded. Mon-El and Jimmy would take care of him, he was sure of that.
Now he was getting worried though, because the sounds of Jimmy and his boyfriend making out had stopped, and he heard a door open, his head inclining to hear it better since he couldn’t see anything.
“Oh,” he heard Mon-El breathe, sounding shocked. “I didn’t know he was your boyfriend."
A low chuckle came from where Jimmy was, and Winn could practically picture the bashful smile the man would have. “Yeah, a lot of people say that, but I didn’t figure you’d be as surprised considering you and Winn.”
That only made him more curious who it could be, but he couldn’t ask, and his whimpers only got worse as he felt a strong hand gripping his ass tight before switching the massager to the highest setting. That finally got him to drop to all fours, whimpering and moaning as his prostate was assaulted by the intense vibrations, his caged cock leaking so bad he’d surely already stained the jockstrap they’d given him.
“I wasn’t sure when you said Winn would make a great sub for the night, but you were right Jimmy,” a new voice said, clear and crisp. Winn’s mind reeled as he placed it suddenly as Clark Kent, aka Kal-el, aka Superman. He was about to have a four way with two aliens and Jimmy Olsen.
As Winn tried to process all of this, he was being slowly spanked by Clark. Someone moved to take whatever was on his head off him, removing the blindfold and the bit gag. He was thankful for that because he needed to see them, needed to stretch and pop his jaw. And most of all because he needed to be able to get one of their cocks in his mouth as soon as possible. When he finally was able to blink his eyes open he noticed they’d put a full length mirror over one wall now, facing the bed and he could see himself.
Once the hood was pushed down he realized what had been done, they’d fixed it up to make him look like a reindeer, and with the jock, the harness and the mitts he was in a total puppy play outfit, albeit looking like a reindeer.
Directly behind him loomed Clark, large and imposing. His chest and arms flexed with every swat of Winn’s ass. That same little curl of hair hung down in his face, but the usual small town farm boy smile that rested on Clark’s face was lost instead to a devious smirk that had Winn’s ass clamping hard around the massager. Clark, like Mon-El, was wearing a bright green elf jockstrap that left little to the imagination. It made Winn whimper because just staring between Clark and Mon-El he knew that Superman was even more endowed than his boyfriend and the thought of that going inside him had another globule of pre-cum leaking from his locked cock.
Jimmy had a Santa themed thong on, along with a Santa hat, and his own ample cock was straining against the tiny fabric as he made out with Monel. The man stroked Mon-El until he was fully erect before turning his gaze towards Clark and Winn. “I think it’s time my little elves got our reindeer ready for his sleigh ride, don’t you?” Jimmy’s voice was darker than his ebony skin and it sent shivers down Winn’s spine.
He nodded furiously, needing them to touch him, fuck him, anything to calm the growing frenzy inside him. Luckily they all seemed just as eager, with Mon-El moving behind him an unceremoniously yanking the prostate massager form him, causing Winn to yelp in shock.
“Come on baby… You’re doing so well,” Mon-El whispered to him, one hand gliding down his back, over the smooth leather of the harness and down to his ass, twin lubed fingers pressing inside him before they were replaced by the blunt head of the man’s cock.
Winn had been distracted by Mon-El pushing inside him, and only broken form it by being slapped across the face, what little of it was visible, by something long and soft. Opening his eyes he gulped, groaning as he saw it was Clark’s huge, mostly soft cock. His mouth watered, and thankfully Clark had pity on him and tipped his head back so he could feed his cock through the hood and into Winn’s eager mouth.
Clark tasted delicious, salty and warm and that unmistakable scent that only aliens it seemed carried. One he’d not been able to explain and was too scared to ask anyone else about. Swallowing as much as he could down he felt Clark stiffen in his mouth, tongue lapping at the underside of that thick length. Soon enough he was gagging around it, eyes watering as Clark pushed more and more until he’d breached Winn’s throat at the same time Mon-El had bottomed out in his ass.
It occurred to Winn he was currently filled in both holes with alien cock, and aside from the obvious weirdness of feeling like he was in some fetish porn, which his outfit certainly would have matched, he couldn’t have been happier.
His peripheral vision wasn’t the best in the hood, but he was able to make out the bob of Jimmy’s Santa hat as he took his place behind Clark, kneeling down. His hands stood out against Clark’s skin as they wrapped around the other’s thighs, and soon enough Clark was moaning even louder, cursing in a way he’d never expected to hear Superman curse.
There was a moment where Winn was too fucked out to understand what was happening, but after a moment he realized Jimmy was rimming Superman, Clark, and Clark loved it, his hips seeming to be rocking between Jimmy’s eager mouth and Winn’s.
After a while Winn was lost in his pleasure, as stifled as it may have been with his inability to cum, which he’d have likely done three times over without that pesky cage. Mon-El was riding him hard, one hand tugging on the harness to drag him back on his cock. For his part Clark was fucking his face so thoroughly Winn’s lips felt numb and his jaw was sore, but he couldn’t bear to ask anyone to stop, it all felt too good.
Finally Mon-El’s hips began to thrust more erratically and he knew what was coming. There came the familiar feeling of the Daxamite’s seed flooding his ass as he swallowed around Clark, whimpering. A keening noise left his throat, vibrating it around Clark, as Mon-El pulled out. He wasn’t empty long though as he felt a plug pushed into his abused hole to keep the man’s seed inside.
“This is amazing. Why don’t you guys do this every day?” Mon-El said, sounding just as eager and collected as if he hadn’t just spent 30 minutes fucking Winn to exhaustion. Winn wasn’t sure he’d survive having foursomes with aliens every day, but he’d gladly take that as his cause of death than some of his other options.
Winn felt Clark pull free of his mouth, that huge Kryptonian cock swinging in-between the man’s legs as he walked around behind him. Honestly Winn was a bit terrified of how that was going to feel inside him, but he was also excited enough his cock was straining in the cage that confined it.
“I’m gonna’ let them play with you for a bit baby,” Mon-El told him, cupping his face and kissing him hard, lips so plush against Winn’s puffy, cocksucking enlarged ones. Winn watched as Mon-El sat on the floor, his body sweaty and every line defined perfectly. He was still hard, and slowly he began to lube himself up and inserted the vibrating prostate massager that Winn had inside himself earlier into his own ass, moaning as he stared behind Winn.
That was the only reason Winn looked up, watching Jimmy and Clark making out behind him before he felt strong hands on his hips and a huge blunt head pressing at his already stretched entrance.
“Fuck!” he cried out as Clark pressed inside, giving him just enough time to adjust between each new inch that splayed him open. His hips dropped lower to the bed, spreading him as wide as possible to take the man, or Superman. Mon-El’s eyes were traveling between his own face and the scene behind him and Winn tried to focus on that look of lust on his boyfriend’s face and not the splitting pressure of that huge cock in his ass.
Finally after what felt like forever Clark bottomed out and Winn was able to let out a breath he hadn’t realized he’d been holding. Of course, that was when Jimmy apparently pressed into Clark all in one go and caused Clark to buck deeper into Winn startling another cry out of him.
Mon-El had been the biggest man he’d ever taken, that thick eleven inches already felt like it had reshaped his ass around it. Now though, Clark truly felt inhuman as it speared him, longer and thicker than Mon-El, with so much pressure on his prostate just form it sitting there.
Clark had stilled, hands bruising on his hips, but not actually fucking him, just giving Winn’s body time to adjust, as the familiar sound of fucking filled the air. Jimmy was taking Clark from behind and Clark was moaning raggedly from it, his cock pressing into Winn a little at each thrust, but nothing like what Winn knew would come with a full buck of Clark’s hips.
“I… I’m ready, please,” Winn eventually whimpered, knowing his poor cock couldn’t wait much longer and he needed to cum. He only hoped that once they’d had their turns he’d be released and allowed to cum, he was so hard, or at least as hard as he could get with his dick squashed into the cage.
“It’s okay, we’ve got you,” Clark said, and he felt two pairs of hands on him, feeling up his ass and his flanks, stroking him and soothing him. He was finally starting to calm down right until he heard Clark say “hold on.”
Apparently that hadn’t been meant for him since he had no way to hold onto anything but soon he saw the bed falling away from him and he panicked for a moment, feeling weightless as he was effortlessly lifted into the air. It was only as he stared at the mirror that he realized Clark was floating, cock still buried deep in him, arms wrapped gently around him to support his weight.
“Fuck, what?” he said, staring down at Mon-El who seemed just as shocked about what was going on.
“Thought you’d get a kick out of this, Jimmy always liked it,” Clark teased him, and then he felt a thrust as lark’s cock pulled back and rammed into him. That was how Clark began to fuck him while floating three feet off the bed. “Finally got us a flying reindeer, huh?” Winn couldn’t believe Clark was making jokes right now, but it did look like he was flying with the outfit and the fact they were indeed in the air.
Jimmy was still inside of Clark too, one hand holding onto Winn’s harness for a bit of leverage, the other wrapped firmly around his boyfriend to get what pull he could to fuck into Clark as they settled in the air.
Clark was right, after a while the feeling of being fucked while weightless was different, even if his ass hurt form the stretch of Clark’s cock, it was a good burn and his body was struggling to deal with how much pleasure there was pumping through him. In the end they didn’t last in the air that long as Jimmy wanted to get down.
As they floated back down to the bed Clark kept fucking him, making Winn’s eyes roll back into his head. It took a while for him to regain focus, but when he did he noticed Jimmy and Mon-El were on the floor by the mirror, blowing each other. He wanted so bad to join them, even though he never wanted Clark to stop, even as the thrusts became more intense and it sometimes felt as if his ass was completely detached from the rest of his body, or maybe that all that was left of him was his ass. It was kind of hard to tell by now with how fucked out he was.
Time sort of got lost for a while as Winn enjoyed everything, and the next thing he knew he was resting against Clark’s strong chest, that huge Kryptonian member still lodged deep inside him. “Huh?” he asked, since he was pretty sure Mon-El was speaking to him but he hadn’t heard.
“I said, we’re going to try something new baby,” Mon-El whispered, cupping his face and kissing him.
“What?” he croaked, voice crackly from disuse, or maybe hoarse from all the whimpering and moaning earlier, he couldn’t tell any longer.
“We’re going to both fuck you, isn’t that crazy?” Mon-El informed him, as his eyes glanced down he saw that in fact Mon-El was slicking his own cock and had it dangerously close to where Clark was still inside him.
“N-no. No, I can’t. Mon-El, I can’t take that much,” he said, panic tinging his voice. Mon-El just caressed his cheek, letting his cock rest against where Winn and Clark were joined.
“You can. We’ve got this. You’re already taking Clark, you just have to let me in a bit, okay?”
“I… I…” Winn was terrified, both of what that would do to his ass, but also that he didn’t think he could actually deny how much he wanted to have both of them inside of him right now.
“If it starts to hurt, you can always tell them to stop. You don’t have to do this,” came Jimmy’s vice from the side, and he was touching Winn too, they all were. Hands smoothing over his skin, his muscles, playing with his balls and his locked cock, his nipples. It was so much and Winn was sure he’d never have an experience like this again, or this opportunity.
“Do it. Fuck me,” he said to Mon-El with passion and determination, which was greeted with a winning smile and a deep kiss from his boyfriend.
Mon-El’s hands rested on his hips, the fat head of his slicked dick pressing insistently at his entrance. He felt the man pushing in, but he couldn’t take it, there was just too much despite how much he wanted it. His body couldn’t relax. At least not until the three men began to work him over in tandem.
Clark’s adroit hands came from behind, teasing his nipples and making him groan, and then Mon-El’s lips latched onto his neck, sucking hickeys there that he knew would be visible for days. Finally Jimmy caught his mouth, licking into it, claiming him and taking away any last thoughts of doubt. A few moments later he heard a triumphant sound from Mon-El right as he felt his ass stretched even wider. It was in.
He was so full, he had no idea how his body was accommodating for both of their thick cocks, but it was doing it and it was driving him mad. His breath was hitching, ass spasming around the invasion that left him breathless and so horny he felt like he was going insane.
When they were finally both seated he was fuller than he’d ever been and he wasn’t sure how he’d ever be satisfied with anything less than this again, knowing his body could take this, wanted this. He kept shuddering as the pressure against that spot inside him was so strong now, and then they started to move and he screamed.
As one slid out, the other fucked into him, setting a languid, torturous pace. Jimmy stood above him now, cock pressed past his lips and into his slack jaw, fucking his face vigorously. Winn couldn’t do anything but lay there and be used by the other men, loving every second of it.
Things kept ratcheting up in intensity, building to a crescendo, feeling it in the thrum of his veins, the pulse of the cocks inside him in so many ways and then, then he finally came even with the cage on his cock, the pressure simply too great to hold it as his cock spurted shot after shot of cum out.
His jock was entirely soaked with his own ejaculate now, but he had no time to worry about that because the three men seemed to take his spontaneous orgasm as their cue to dive in one last wanton set of thrusts before all coming within seconds of each other, flooding his body form both ends with endless supplies of cum.
After that he sort of blacked out, unaware of anything but the immense pleasure he’d felt at the orgasm, even if it had been stifled somewhat by the cage. When he finally came too, he was lying in bed, naked and cleaned, mostly, with the other all around him.
“You did so good for us Winn,” Jimmy spoke first, smiling at him, Clark’s arm wrapped around him from behind.
“I’m amazed you were able to take us both,” Clark said, peering at him over Jimmy’s shoulder.
“I knew you could do it baby,” Mon-El whispered from behind him, kissing at his neck, his own arms wrapped protectively around Winn.
“I don’t… I don’t think I’ll ever be able to top that in my life,” Winn laughed nervously, staring between the men and just unsure how to deal with all the intense emotions that were running through his mind.
“Just rest, we’ve got you. We can talk more tomorrow,” Mon-El said, kissing him again, and then in turn he was kissed by Jimmy and Clark as well.
Nodding he lay his head down, drifting off quickly to sleep, even if he knew he’d be sore tomorrow, he couldn’t regret anything that had happened. It was the best orgasm of his life, and he was hoping that one day soon it’d happen again.