Work Text:
Kyle’s been expecting this text message since he joined Don Callis.
He lowers his water and frowns at his phone. It’s a simple text, but that also means there’s not much to misunderstand about it. If your new boss sends you his hotel room number, a time to meet him, and a vague invitation for conversation after business hours, there’s not many other ways to interpret it.
He’s not bothered by it, exactly.
He slips his phone back into his bag and goes back to finish his workout. He chews his lip a little as he does, but again, he’s not exactly nervous or anything. Don’s never been anything but welcoming and kind to him – and in this business it’s not unheard of to reward mentorship with some “personal favors.”
He’d missed out on that so far, actually. Hooking up with Davis so early in his career had turned out to be a massive deterrent to scummy promoters and bookers everywhere. One look at Davis glowering over his shoulder was enough to send even the sleaziest men packing no matter how young and skinny and impressionable Kyle had looked at the time.
Davis isn’t here right now, though, and he can’t lean on him forever.
Besides, he thinks as he returns his weights to the rack, it’s not like Don is repulsive. Lots of people joke about him being a gross old man, but Kyle likes him. He’s funny and charming and he buys him nice things. When he really thinks it through, he wonders if he accidentally acquired a sugar daddy. He hadn’t really set out for one, but again, as he considers it, he’s not opposed. Trading a favor for a favor with his funny, nice boss doesn’t sound like a bad deal at all.
A little voice in his head that sounds like Davis scolds him about being naïve, but he brushes it off. He’s a big boy now, and if he wants to fuck his boss, then he’s going to fuck his boss.
That said, he needs to hurry a bit. He leaves the hotel gym and rides the elevator up to his floor so he can sling back his post workout calories and hop in the shower. As he scrubs down, he briefly considers getting a headstart and fingering himself, but he drops the idea before it can manifest.
He sort of assumes that’s the way this is supposed to go, but that doesn’t mean he’s thrilled about it. He’s bottomed before. Once or twice. Begrudgingly. He just doesn’t get the appeal, and he lucked out hooking up with Davis, who both gets him on a cellular level and is perfectly content to be a big useless bear and let Kyle plow his ass whenever he wants to. It’s been the perfect arrangement.
Maybe he can pass Don off on a blowie. He doesn’t mind doing that.
Hell, why is he even worrying about all this? Qué será, será and all that.
He checks the time and sends Don a text saying he’s on his way. They’re not booked in the same hotel – Don’s is the slightly nicer one a couple blocks away. Kyle spares a thought to wonder if that’s an arrangement with TK or if Don’s just particular enough to book his own hotels and not worry about the travel budget. Another useless thought. He flings that one off into the abyss and opts to just walk the couple of blocks down rather than waste time and money on an Uber. It’s a nice night, anyway.
He slips into the hotel and up an elevator, walking with confidence that does enough to cover how slightly out of place he looks in pink tracksuit pants and a band t-shirt in this upper scale hotel lobby. Confidence is key. He holds that thought in his head all the way up until he’s knocking on Don’s door.
Confidence.
He doesn’t even have to fake the wide smile on his face when the door opens, and Don greets him in the entryway. Don matches his smile with one of his own.
“You made it,” he says. He holds the door open wider and beckons him inside. “Come in, come in.”
Kyle slides past him, smile widening even further when Don inevitably takes liberties, trailing his hand over his shoulders and down to his lower back as he passes. Don may be a tricky old bastard, but he’s so transparent when it comes to his lads.
Don shuts the door and follows Kyle into his suite. It’s nice. Much more upscale than Kyle’s more regular-sized room, and TK didn’t cheap out on the hotel allotments, so saying Don’s room is nicer means it is significantly fancy. It has a spacious seating area detached from the bedroom and even a small kitchenette. It’s tastefully decorated, and the only sign of habitation he can see is an open bottle of wine and a couple of glasses on the coffee table, and a pair of Don’s shoes toed off neatly by the wall.
“Nice pajamas,” Kyle remarks as he decides to kick off his own sneakers and make himself at home.
Don chuckles, stepping past him. “Thank you. I hope you don’t mind I made myself comfortable.”
Kyle shrugs and takes a chair, bouncing a little on the cushion to test the softness. “I don’t care.”
Don doesn’t seem offended. They are nice pajamas. He thinks they’re probably real silk, one of those old fashioned styles with the bottom and matching buttoned up top all in a dark, shimmery burgundy. It doesn’t look too off from his suits. He’s even got cute little black slippers on, all dainty and proper. He can’t help but feel a little enamored with the old man.
“Wine?” Don asks, holding the bottle up.
“I’m not much for wine,” Kyle says, but he shrugs and adds, “I’ll try it, though.”
Don smiles. He looks softer here without the heavy layers of bronzer and the tinted shades. He feels a little privileged to see him like this – like a secret side of Don just for the Family.
“Try it,” Don says, holding out the glass.
Kyle takes it and experimentally swirls his glass around like he’s seen in films. He’s got no idea what he’s doing, so he stops that pretty quickly and takes a sip. He thinks he’s got a good poker face, but there’s a sour, sucking dryness to the wine that makes his lips purse before he can stop it. He pulls the glass away and gives it a skeptical look.
Don laughs – a loud, proper laugh. Kyle shoots him a look, but he gets the idea Don’s not actually taking the piss. He takes the glass away and smiles at Kyle fondly as he sets it down.
“We’ll have to work on your palate,” he says. He takes a sip of his own wine and frowns. “I’m afraid I don’t have anything else here. I could order something up.”
“You don’t have to,” Kyle says, “We’re not here to drink, are we?”
Don lowers his glass and looks at him mildly. “Oh? And what are we here to do?”
He shrugs as if he couldn’t care less and says brashly, “We’re here to fuck.”
Don looks at him another moment before a smile cracks his face. He takes another sip of wine before setting it down.
“You are very direct,” he says. He steps closer and puts his hand on Kyle’s shoulder, standing over him and looking down. “I like that about you.”
“You want me to act coy?” Kyle peers up at him. He’s got no intention of pretending to be a shy little virgin – he just wants to see what Don will do with the idea.
Don rolls his eyes. “No, no, I don’t need an act. I asked you here because I wanted you, not a pretense.”
“And how do you want me?” Kyle leans back in his chair and adjusts his body minutely to draw attention down his long legs and over his shoulders. He licks his lips pointedly. He’s tired already of the playing around. He was promised sex.
Don smiles indulgently and slides his hand up to cup his face. “Ah, to be young. I remember being this impatient.”
Kyle’s not above pouting, so he does, sulking and crossing his arms now. Don just laughs and finally directs his chin up so he can kiss him gently and chastely on the lips.
“Fine, if you’re so eager… Strip. Let me see you.”
Don steps away and slowly lowers himself onto the other chair, shifting a little and looking uncomfortable for a moment before he settles down a little sideways and props his elbow on the armrest. It’s a little odd to get his gaze unfiltered by the sunglasses. It makes it him look sharper, more intense.
Kyle bends down and slips his socks off before he starts, because the last thing he wants is to interrupt a proper strip tease by having to decide if he’s going to take his socks off or not. He glances at Don as he wriggles his toes in the carpet, just to see if he’s maybe a feet guy, but he doesn’t seem interested. He just sits there patiently, not rushing him or commenting when he balls the socks up and tosses them towards his shoes.
Then he rises to his feet, enjoying the way he looms over Don when he’s seated. There’s not much to make a show out of – just his tracksuit bottom and his shirt and the nicest briefs he had on short notice, but he takes his time teasing the shirt off and inching his pants down. He toys with the waistband of his briefs for a moment before Don raises a hand to stop him.
“Wait. Let me look at you.”
Kyle raises an eyebrow, but hey, he’s game for it. He strikes a pose for him, flexing to show off his physique.
“Perfect,” Don says.
Kyle’s not surprised when Don stands and comes over to run his hands over his muscles. He holds the pose, watching Don as Don seems to take his time inspecting every inch of him like he’s a work of art being appraised.
“Another pose,” Don orders.
Obediently, he shifts into a different shape. Don runs his hands over him again slowly, lovingly, as if he’s in awe.
“Magnificent.”
They repeat a few more times. It’s not sexy, but it’s… sensual. In a way Kyle wasn’t expecting. He’d never thought to do something like this, but the way Don fawns over his body is a huge ego boost. He finds he doesn’t mind the odd request at all. In fact, the more attention Don pours onto him, the more he wants to go further, to do more.
“Don,” he says, just a slight whine to his tone.
Don looks up at him and meets his eyes. His own crinkle around the edges with a sympathetic smile.
“Still impatient?”
Kyle nods. He opens his mouth to say something, but he pauses, surprised, when Don’s hands are replaced with his mouth. He kisses his flexing bicep and smooths a soothing hand over the crest of his hip.
“Let me enjoy you a bit longer,” Don says. It’s a request, but Kyle takes it as an order, nodding mutely.
He shifts back into the first flexing pose and holds it as Don indulges. The touches are feather-light, just the tease of his lips as he kisses different muscle groups, the wispy brush of his fingertips across his skin. Kyle’s eyes flutter shut, mesmerized by the tiniest sensations. He’s never been worshipped like this. That’s the only word he can think of to describe it, every inch of his body falling under Don’s scrutiny and – as far as he understands – his approval.
His cock strains against his briefs, ignored, and he spares the thought to drop the pose and touch it, to get some kind of relief for the building arousal that’s now aching for something more. He’s beginning to not even care if Don does want to fuck him. He’s game for anything now. Anything more than the tease.
He opens his eyes, opening his mouth, too, to complain, but Don’s one step ahead of him. His complaint is punched out in a surprised groan as Don’s light touch disappears and suddenly there’s a warm, firm hand wrapped over his dick through the cloth.
“You’ve been so patient,” Don praises.
Kyle hums in agreement and nods. He’d agree to anything. He’s got his hand around his dick – he’d agree the moon was made of cheese if he’d get more dick touching right now please and thank you.
Don chuckles lightly like he can read his mind. He squeezes and lets go, only to slide his hand under the waistband of his briefs to stroke his cock directly. Kyle drops his body builder pose in surprise, hands coming to clamp around Don’s shoulders instead.
“You don’t disappoint anywhere, do you?” Don says mildly.
He strokes his cock again, seeming to be admiring the heft and length of it. Kyle can’t find it in himself to care if he’s being appraised. He just bucks his hips slightly into the contact, chasing more touch, more pressure, anything. Don tuts and lets go, earning a whine of disappointment from Kyle.
“Patience. I know it’s hard for such a stud like you.” He leans forward and for the first time offers a real kiss.
Kyle leans forward eagerly. Almost too eagerly – he nearly crashes their noses together before Don gently corrects him. He tries to deepen the kiss, desperately licking at the seam of Don’s mouth, but the older man seems determined to tease him by being insanely slow and lazy and unhurried. Kyle whines again, but Don takes his time brushing their lips together before finally he opens his mouth and allows Kyle to kiss him properly.
That’s over too soon, too. Don pulls away and gently pushes Kyle’s chest to get him to back away. He goes willingly, though his eyes stay fixed on Don’s mouth. He licks his lips.
“Alright, alright. You’ve been patient enough. Come on.”
Don turns and starts walking to the bedroom adjacent. Kyle doesn’t need to be told twice – he takes the initiative to pull his underwear off, cock bobbing flushed and eager between his legs. Don doesn’t even look at him. He just walks into the next room and calmly takes a towel off the hook to lie on the bed.
It’s such an old man thing to do. Kyle is stumped for a moment trying to remember if he and Davis ever bothered to put a towel down or if they just bitched to each other about sleeping in a wet spot.
Don doesn’t even acknowledge his momentary confusion. He just calmly undoes the buttons of his silk pajama top and takes off his pants, folding them both neatly and setting them aside on the dresser. His little slippers get kicked off by the bed, and then his plain – but probably expensive – underwear joins them on the floor. Kyle’s mildly offended to see he’s not even half-hard.
Don catches his gaze and gives him a wry smile. “Just wait until you’re older.”
Kyle is not in the mood to wait for anything. He approaches the bed, stopping when Don holds a hand up and points to the bedside table.
“Lube and condoms are in there. I bought a multi-pack. Please choose the right size.”
Kyle opens his mouth, closes it, and then walks over to the bedside table. He opens the drawer and stares inside for a moment before he asks, feeling kind of stupid, “Why do I need a condom?”
Don gives him a strange look. “Because I was going to have you fuck me.”
Oh.
Don raises an eyebrow. “Would you prefer something else?”
Kyle blinks and holds his hands up on reflex. “No, no, this is good. Fucking is good.”
Don laughs. “Good. If you were expecting the other way around, I’m afraid there’s a little pill I would have had to take, and you seem impatient enough already.”
Kyle nods absently, still hesitating. “I just assumed…”
“No, no, I’m quite content to let you do all the work,” Don says, winking. “That’s why I have you young studs around, isn’t it?”
Kyle’s pretty sure he’s fucking with him. He decides to just go with it. “I thought you had us around to win belts,” he says, turning his attention back to the box of condoms to sift through it to find what he thinks is his size.
“I do. This is just a perk.”
Kyle snorts. When he looks up, Don’s not even looking at him. He seems distracted, feeling behind himself with a look of mild concentration. After a moment, he relaxes, and his hand appears again holding –
“You were wearing a plug?”
Don sets it on a hand towel and neatly folds the towel over it before setting it aside. He turns his attention back to Kyle. He doesn’t seem bothered at all. He just smirks.
“You’re the one who’s impatient,” he says. He slides back up on the bed and makes himself comfortable, seeming content to watch Kyle roll the condom on himself. He adds, “This isn’t my first rodeo with impatient young studs.”
Kyle’s brain unwillingly flatlines for a moment trying to decide who he’s talking about. Ospreay? Takeshita? Sammy Guevara? Hell, he could be talking about Kenny Omega. He decides right then and there to not worry about it. He’s got more important things to think about – like the fact that he’s about to fuck his boss.
Which, you know, fuck it.
He’s going to fuck his boss.
He grabs the lube and crawls up into bed with Don, who does seem content to let Kyle do the rest of the work. Fine by him. He’s used to Davis being lazy. He squirts some lube onto his hand and waits for it to warm up.
“Do you need much more prep?” he asks.
“I think I’ll be fine,” Don says indulgently.
If he says so. Kyle still takes his time – he turns off the part of his brain still reeling a little from the “this is my boss” thing and manhandles him a little bit to his liking before he experimentally prods at Don’s ass. He does seem pretty loosened up, but the last thing he wants is to hurt the old man, so Kyle takes some time adding more lube and fingering him a little more. Don doesn’t stop him. He just watches him like watching Kyle is what he’s getting out of it.
Satisfied, Kyle pulls his fingers away and coats his cock in a little more lube. It should be awkward, going missionary position with his much older boss, but Don’s got this way of making him feel at ease. He doesn’t rush him or chatter too much. In fact, he seems a bit preoccupied looking at Kyle’s biceps bulging near his head where he braces himself.
“Okay?” he asks.
Don smiles. “Yes, you’re good.”
Kyle nods. If he says he’s good, then he’s good. He positions himself and presses inside.
Fucking is fucking. He likes fucking. Fucking Don Callis is no exception. It’s the same wonderful tight heat around him, the same feeling that he’d probably chase all the time if he wasn’t busy doing his actual job.
“Good, good,” Don echoes again absently.
Kyle opens his eyes – he’d screwed them shut at some point – and checks in. Don seems fine, seems like he’s enjoying himself. Because he can and because he wants to, he leans down and kisses him.
Don kisses him back indulgently for a long moment before he pulls away to hiss out, “Fuck me.”
Kyle can be an obedient boy.
He starts slow, but when Don doesn’t complain, he speeds up, catching himself up in his own pleasure until he’s slamming into the old man without a thought. He seems fine, though, happy to hold on for the ride, so Kyle indulges himself. Maybe that’s the old man’s thing.
He’s still not hard when Kyle spares him a glance, but if he’s not going to bring it up, Kyle won’t. He curls around Don’s body and stops worrying about anything – about performing a certain way, about looking or sounding right. He just ruts into him mindlessly, groaning and sweating and panting. Don’s hands roam over him, grasping at his muscles. He keeps up a steady stream of praise and endearments that flow in Kyle’s head without sticking, but the approval fires him up regardless.
Too soon, he feels himself reaching his peak. He slows down, stuttering out, “Don – “
Don’s legs tighten around him, and he hushes him. “It’s okay, shh. Go ahead and come.”
Kyle groans. It’s only a minute more, perhaps, before his rhythm stutters and pleasure crashes over him, momentarily knocking him senseless.
He comes back to himself a second later, panting, with Don’s legs still wrapped around him. His hand is stroking through his hair as he continues to praise him.
Kyle’s abruptly not sure what to say.
Don makes the choice for him. He urges him up and off of him and sits up. He seems satisfied even if he never quite got hard and certainly didn’t come. Kyle must have been right – maybe watching Kyle come apart had been the point. He closes his eyes and accepts the kiss Don places on his lips.
“You’re magnificent,” Don murmurs against his mouth.
Kyle accepts the praise, nodding against Don’s head. He lets him sit up now and dispose of the condom. This is probably the point he’d expect to be kicked out, but when he comes back from the bathroom, Don is calmly redressing himself in his silk pajamas. He gives Kyle a beaming smile.
“You’re more than welcome to stay here tonight,” he says, gesturing to the bed. When Kyle hesitates, Don adds, “I was thinking tomorrow I could treat you to breakfast and then go shopping. There’s time before Dynamite. Unless you had some other plans?”
Kyle shakes his head and, testing the waters, says, “I don’t have the money for a shopping trip.”
Don waves him off before he’s finished the statement. “Don’t worry about it. It’s my treat. Only the best for my Protostar.”
Oh, damn. He really did get a sugar daddy.
“That sounds nice,” he says.
Don beams. Kyle walks naked to the other room to slip his briefs back on. He doesn’t bother with anything else, and Don seems pleased when he comes back with most of his body still exposed. When Kyle joins him on the bed, he doesn’t resist running his hands over him again, apparently never satisfied with how much attention he’s given him already.
“We’ll outfit you like a king,” Don promises him.
Kyle nods and gives him a kiss. As far as inappropriate relationships with bosses go, he might have just hit the jackpot. Don seems happy. Kyle’s happy. It’s a win-win.
And if he gets bought a bunch of gifts on top of getting to fuck his boss, well, he can’t say his job doesn’t have perks.