The Interview

Erotic short. A workplace roleplay with age difference and some hearty degradation.

Photo by Max Vakhtbovych via Pexels.

Rated E, 4k, cis M/trans M. Younger boss/older prospective employee, pre-negotiated roleplay, degradation and humiliation, daddy kink, nipple play, PIV, riding, sex in the office, casual sex, bareback. The older man is fat, but none of the degrading language is about his body or his size except for commenting on the size of his chest — the degradation primarily is about his age and assumed loneliness.

Words used for the trans man’s body are tits and chest, one comparison to a cow’s udder; cock, cunt, hole.


It’s as yet early in the evening, not yet seven o’clock. Alec shivers to himself as he stood in the lift — it isn’t even that the air is extraordinarily cold inside, merely that there’s a hot flush on his skin under his clothes, a creeping blush he can feel on the back of his neck, across his chest. He wonders if it shows obviously in his cheeks.

A part of him can’t quite believe he’s doing this, can’t even believe he had the conversation, let alone that he’s here. He’s thrumming all over with anticipation, his mouth dry as he steps out from the lift.

The reception area for these offices is finely appointed and really quite lovely, which somehow makes his skin feel tighter, makes the whole situation more precarious, feel like it’s higher stakes.

“Hi, can I help?” chimes the receptionist. He’s pretty, a twinky thing with an undercut and dyed blue curls and matching nail polish — does he know? Just looking at Alec, does he know what he’s here for? Has he seen other men just like him and known on sight with them too? Even more titillating, has he seen men like Alec again and again and never known, not even wondered?

“I’m here to see Micheál,” Alec hears himself say, feels his mouth move without needing his actual permission. He doesn’t even stammer, which is something of a surprise.

“Mr Heneghan?” asks the twink, and doesn’t even wait for Alec to confirm, just taps something on the phone and says clearly into his headset, “Hi, Mr Heneghan, I’ve someone here for you… Interviewing for the Claremont position?”

He looks to Alec, who nods even though cold sweat gathers on the back of his neck. He’s so wet and so hard he feels like he can’t fucking breathe, half of his consciousness concentrated on the sensations between his legs, and no one’s even touched him yet.

“Yep. Okiedoke, I’ll send him through.” The twink smiles at Alec, sweet and pretty, and says in his bell-like voice, “Down the long hall, and his door is there on your left.”

Alec’s feet move as if he’s on autopilot. Down the hall, on the left, okay. He does past meeting rooms that are still in use, groups of business people talking seriously over papers and figures, people in suits and shirts.

Who among them would even believe he was here for an interview at his age, pushing 50, not even dressed up in a suit because the only suit he owns is a linen one for wearing on holiday, even if this is one of his nicer pairs of trousers, even if he’s wearing a nice shirt, a pleasant, plum-coloured cardigan.

A man giving a serious-looking presentation involving a lot of graphs looks through the half-frosted glass and his eyes land on Alec, and Alec immediately averts his eyes downward, certain he can see through Alec’s clothes and know.

He breathes out a gusting sigh of relief upon reaching Micheál’s office and finding it’s a proper, enclosed room with four walls, and none of them are made of glass, even frosted glass, like many of the meeting rooms and office he’s been past this morning. He knocks, so softly he can barely even hear it himself, and curses under his breath. He knocks again, harder this time.

“Come in,” calls Micheál crisply. He’s got a good voice, strong and with a sweet sharpness to it — he’s from Waterford, originally, Alec thinks; his accent isn’t strong.

Alec shivers again as he turns the handle, steps inside, barely allows himself a glimpse of Micheál behind his desk before he turns away to close the door again. “Should I lock it?” he asks, staring at the lock over the handle.

“Mmm,” agrees Micheál airily, as if he couldn’t care less. Alec turns the lock, exhales shakily as he feels the bolt slide across. He was thinking something in him might relax, but it doesn’t, how could it? This is a real office, a real workplace, this is Micheál’s real workplace, there’s real people out there, and Alec clenches around nothing and feels so empty he can barely stand it. “Did you find the place alright?”

Oh, fuck.

Oh, fuck, they’re just going right into it, just right —

Alec swallows and says, to the wall more than the room at large, “Yes, yes. I, erm, ah. I found it alright.”

“Parking okay?”

“I took the bus,” says Alec almost breathlessly as he turns around, and he looks at Micheál at his desk, feels his heart flutter at the subtle shift in his expression, the furrow between his brows, the tightness that slightly pinches his lips.

“I see,” he says, not looking up from his paperwork. He’s good at this, is already so good at this Alec could scream, and he feels a bit weak at the knees as he stumbles forward.

He’s even more handsome in person than he is in his photos — he’s wearing a suit now, of course, instead of a t-shirt or something, because he’s at work, but it’s not just that, it’s how his hair’s swept back — light brown and blond, wheat-coloured — and his neatly groomed beard and his square glasses. The ones in the photo, the round pair, must have been old: these ones suit him better, lend him a sterner, more mature air.

How old is he again? 29?

Alec’s heart won’t stop pounding in his chest.

“You can take a seat,” says Micheál, then glances at his phone — not surreptitiously, but obviously, really making a show of having to check — “Alec.”

Alec pulls out the chair and sinks into it, trying to swallow the tremor that runs through him.

“Thank you,” says Micheál mildly, looking him up and down in a condescending way that makes Alec’s cock throb, “for your application.”

“Thanks,” whispers Alec.

Something changes in Micheál’s expression, a kind of softening or a show of something melting away. “Time out for a second,” he says in a warmer, kinder voice. “Alec, are you okay? Do you still want to play this out?”

“Yeah, yes, yeah, sorry,” Alec blurts out, “sorry, I’m just — nervous, I definitely, yes, I do want to, I’ve just not done this sort of thing in quite some time. I really — I really don’t want to ruin it.”

“Oh, babes,” says Micheál sweetly, the nickname so unexpected — though not unwelcome — that he feels himself blink. “What’s to ruin? It’s just a bit of roleplay, all we’re doing is playing pretend with each other. Would you like to take a rain check, do this another time?”

“No, no, I’d love to go ahead with it, if it’s alright,” says Alec, squirming, and just this feels obscene, feels ridiculous, asking a young man twenty years his junior for permission, all but begging him.

Micheál smirks. “All hot and bothered already, huh?”

Alec exhales, ignoring the burn in his cheeks. “Isn’t that the point?”

“Oh, God, yeah, it’s absolutely the point. I’ve been thinking about getting my cock in you all day.”

Fuck,” Alec whimpers, cock jumping against his trousers, and he wishes he’d worn jeans or just a tighter pair, wishes that when he clenched his muscles and his cock jumped it had something to rub against, to grind against.

“I just meant,” amends Micheál, “if you want, I can pack all this up and we can just go back to mine.”

Alec shakes his head, and Micheál smiles at him. “Traffic lights still okay?” he asks.

“Yeah,” says Alec. “Yes.”

“Okay,” says Micheál. “Just relax, okay? Just say a colour if you need me to stop.” Alec watches as he takes a little breath in, seems to reconstitute himself, draw himself up, before he says, more seriously again, “Okay…” Condescension drips from his voice. “So this would obviously be a junior role in the department, primarily secretarial duties.”

“Right, yes,” says Alec, with a tiny bit more confidence.

Micheál looks at him with astounding coolness as he asks, “And have you worked in similar roles before?”

“Absolutely, yes,” says Alec. “For years, you know, I ran the payroll and inventory for a bookshop, those books, you know. I’m comfortable with all the office software, more than proficient with it.”

“Mmm,” says Micheál, sounding unconvinced as he looks down at Alec’s imaginary CV. “And are you sure about the pace of the role?”

Fuck, but Alec is so aroused he feels like he might swallow his tongue.

“I beg your pardon?” he asks, managing to inject some indignation into his voice even though it quavers with arousal.

“This is a serious business, Alec,” says Micheál snidely, putting a pointed emphasis on Alec’s first name. “It’s a bit busier than a little old bookshop.”

“The shop wasn’t especially little.”

“How long since you worked there?”

Alec waits a moment — he knows the answer, has rehearsed the answer in his head, but the hesitation is important, is a big part of the role.

“Two years,” he says finally — his voice is quieter this time.

“And in the meantime?” presses Micheál, and Alec looks at him, feels pinned by the younger man’s eyes, which are a dark, flinty green.

“I took early retirement.”

“… Retirement?” repeats Micheál, so scathingly, with a sort of swallowed laugh, that Alec almost moans, his whole body feeling electrified.

“Yes.”

“I’m sorry,” says Micheál insincerely, clearing his throat. “It didn’t even occur to me that you might be an OAP.” He says the word like it tastes bad in his mouth, and Alec feels lightheaded. “Are you sure you’re up to it?”

“I’m not an OAP — I took early retirement. This is the second time you’ve asked if I’m up to the role,” says Alec, and he’s breathing a little heavily out of arousal, but he hopes it reads more as frustration. “I think I’m more than able to manage two days a week answering phones and filling out email templates.”

“Are you sure?” asks Micheál, pouting out his lips and clucking his tongue in faux-concern before he says, “Do you even know how to email?”

“How old precisely do you think I am!?”

Old.”

“You insolent little — ”

“Insolent?” repeats Micheál, and he actually laughs, and God, it’s cheeky, unspeakably insulting, and it makes Alec’s whole body throb. “See? You are old.”

“You seem like you’re angling for something, young man, and I really don’t — ”

“Angling for what, exactly? For you to put me over your knee? The way you are, I bet you’d rather I put you over mine.”

Alec’s gasp is quite genuine, no matter that they scripted this beforehand.

“Oh my God,” says Micheál, and his nasty little laugh is going to be imprinted on Alec’s psyche forever, indelibly connected to his next erection. “Are you serious?”

“Listen, you — ”

“No, no, you listen,” crows Micheál, all cruel energy now, and Alec’s breath hitches as he stands — he’s a tall man but slim, has a delicacy to him. “Is that why you want a secretarial job, because you’ll get off on it? I thought you were just sad and lonely because you’re retired and on your own at home all day.”

Alec swallows as Micheál comes closer, stands over him, looms.

His voice is softer, more deliberate, has a cutting edge to it that makes the hair on the back of Alec’s neck stand on end. “Do you really want this job, Alec?”

“Yes,” whispers Alec. He’s so wet he feels like it must be soaking through his trousers, and he can feel his heartbeat in his cunt.

“Huh,” says Micheál softly, his eyes sparkling. “Take your top off, then.”

Alec’s eyes are almost watering as he looks up at Micheál’s face, at the mischief shining in his eyes, the hunger there, the desire, not just for Alec to bare more of his body, to fuck him, but to humiliate him, to degrade him.

“Excuse me?”

“You heard me.”

Alec stares up at him, feels his lip quiver, and fuck, but he doesn’t want to just strip, he wants to get to the fucking now, wants Micheál’s cock buried in his throat or his cunt, just craves it, feels like he’ll fucking burst for wanting it now. His hands tremble and he fumbles on the buttons of his cardigan, he’s so desperate, and Micheál says, “You can’t even take your clothes off and you want a fucking job?”

Alec shudders, struggling through the buttons on his shirt, and Micheál whistles softly once he gets it open. “Huh.”

“Wait,” Alec says, but Micheál’s hands are on his chest, cupping his tits from underneath, squeezing. Alec’s been so desperate to be touched all fucking evening, and Micheál’s hands are warm and his tits throb. “Wait,” he moans again, but Micheál is grasping his nipples between his thumb and forefinger on each side and tugging. It throbs and it aches and it makes his cock jump, and he can’t help it, can’t help the way he rocks down in the seat, desperate for any sort of friction.

“God, you’re fucking pathetic,” Micheál says, rolling his nipples between his fingers as Alec tries not to whine too loudly, one of his own hands between his legs for him to rock against. “Are you seriously this desperate?”

“Fuck, fuck,” moans Alec, and he can’t help it now, how he’s grinding his cock against the heel of his own hand through his trousers before Micheál squeezes hard and sends a powerful thrill between his legs.

“These are fucking huge,” he says, and Alec shudders. “They’re like a cow’s udders, I’m surprised I can’t fucking milk them.”

“Please,” whimpers Alec, and Micheál looks down at him, grinning as he keeps tugging and squeezing, pulling down like he really is trying to milk him; it’s so fucking humiliating he can’t bear it, can’t stand it, is making his hips jump and his whole body judder.

“Please?” Micheál repeats softly, and then he’s moving and Alec shivers and tries to grasp at himself, but Micheál grabs his wrists and shoves his hands to his sides, pinning them by the wrists as he sucks one of Alec’s nipples directly into his mouth.

The sensation is overwhelming and Alec has to concentrate not to howl out loud at it, at the heat and wetness of Micheál’s mouth and the powerful way he sucks, the way he puts on pressure with his teeth and makes Alec writhe in his place. “God, fuck,” grunts Micheál as he draws back, and that makes Alec want to fucking wail, how enthusiastic he is, the way his eyes rove down Alec’s body.

“You fucking love this,” says Micheál in a low, breathless growl.

“I’m only doing this because I, because I have to,” Alec says, and it rings false in his own ears, so false it sounds hollow, and Micheál’s laugh is low and dirty as he takes one of his hands off Alec’s wrist and shoves between his legs.

Alec yelps at the sudden strong hand cupping him, squeezing — his thumb shoves against Alec’s cock until it clumsily finds it, and then Micheál drags down the head of it through the fabric of his trousers and underwear with a blunt fingernail. The sensation is so abruptly direct that his hips buck, and where Micheál’s fingers are pressing against his open cunt, he knows there’s wetness soaking through.

“You fucking liar,” whispers Micheál as if all his Christmasses have come early. “You fucking whore, you fucking want this, fucking — Take your clothes off.”

“N — No,” whimpers Alec, and then Micheál’s hands are on his trousers, undoing them as Alec’s hands hover over his; his mouth is sucking at Alec’s other nipple, digging in with his teeth and laving over the tip of it with his tongue, making Alec’s head spin. “Fuck, fuck, fuck, please — ”

“Get up,” growls Micheál, and Alec clumsily obeys, stands up and lets Micheál drag his trousers and his underwear down to his knees, makes Alec kick them off at the same time he toes off his loafers, and Micheál lets out a low, greedy sound under his breath as he stares between his legs.

Alec’s cock is hard and straining up and away from his cunt, which is soaked with slick and there’s more on his thighs, and Micheál reaches out with his thumb and forefinger and just squeezes, doesn’t even tug or pull but just squeezes. Blackness bursts behind Alec’s eyes as he closes them shut tightly, his hips bucking uncontrollably into Micheál’s hand — the pressure is fucking sublime, so pleasurable it’s on the verge of agony, and there are harsh, desperate noises eking out of his throat.

“Fuck, fuck,” growls Micheál, and when he pulls his fingers away from Alec’s cock Alec can’t help but let out a noise of loss, but he strains up and into it when Micheál’s fingers dip into his open cunt. He’s so open and so hungry for it he feels fucking raw, and the barest teasing of Micheál’s fingers is an unspeakable tease.

Micheál draws his fingers back, and Alec stares up at him, desperate, as he puts out his tongue and tastes his fingers, sucks Alec’s slick from where it’s shining on their tips.

“You want this job,” he says lowly, eyes flitting to Alec’s face, “you’re going to sit on my cock, and I’m fucking you raw.”

“N,” starts Alec, breathless, and he doesn’t have to put on much of an act to get the reluctance into his voice, the plain fucking desperation. He saw Micheál’s cock in the photos, knows it’s thick, aches to be filled like he’s never ached for anything. “No…”

“Wanna stay unemployed, huh?” asks Micheál softly, smirking and raising his eyebrows as he goes back to his seat, unbuckling his belt, his trousers. His cock bounces up when they’re shoved down, coming up thick and pink at its perfect head. “Wanna stay at home all day, fucking your lonely cunt with your fingers instead of someone’s cock?”

“That’s not why I wanted this job,” Alec manages to say, even as he’s on his feet again, his knees shaky and tremulous underneath him. “I wanted — I wanted to just be a bit busier — ”

“Busier on your knees maybe,” says Micheál. “Isn’t it pathetic for an old man like you to be this much of a slut? Fuck, look how wet you are.”

“Fuck off,” hisses Alec, and before Micheál can reply, Alec is straddling him, feels his breath hitch in his throat at the way that Micheál stiffens underneath him, under the weight of his thighs. Alec is hurried about grasping at Micheál’s cock and lining it up, and then he sinks himself down onto him and moans, gasps against Micheál’s hair at the feeling of finally being split open, having Micheál seated inside him.

“Yeah, yeah, fuck,” groans Micheál, and he takes two handfuls of Alec’s arse, squeezes and grabs at him as roughly as he had Alec’s tits, nudges him to lift himself up and then sink himself down again and fuck, fuck, but the friction is glorious, the drag inside him. “That’s it, that’s it. Fucking — More. Faster.”

“I ca — ”

“You fucking can,” says Micheál, delivering a sharp slap to Alec’s arse that’s hard, a bright hot sting, and Alec gasps but jerks up and then drops down again, thrusts himself down in his place as fast as he can. His knees feel strange in the position and he can hear the chair creaking at their combined weights but fuck, fuck, Micheál’s cock is wonderful inside him, wet and thick and so perfect he could cry. “That’s it, that’s it, you fucking — pathetic old man, you like that? You like my cock inside you, like a younger guy to ride?”

“Shut up,” whimpers Alec, and Micheál responds by grabbing his cock with fingers he’s licked wet, squeezing and pulling on it. Alec yelps, his hips stuttering without his permission, and God, but he could come right now, could come just from this already. “Shut up — ”

“You want the job?” asks Micheál breathlessly, pulling and squeezing at Alec’s cock and fuck, fuck, but he can feel the tension in him, feel himself winding tighter and tighter and tighter, feels like he’s about to explode.

“Ye — es — ”

“Say please.”

Please — ”

“Call me — ” Micheál laughs, squeezes so hard on the shaft of his cock that Alec yelps, hips stuttering, and the pleasure keels sharply on the side of pain, severe and raw in a way he wants to never stop and at the same time can’t quite handle. “Call me Daddy.”

What?”

“You fucking heard me,” says Micheál, slapping his arse again, and he does it hard, and the pain is wonderful, makes him jump. “Call me Daddy. You want the job? Call me Daddy. Say please.”

“I’m not, I’m not doing that,” moans Alec, and it’s hard to think, hard to string the thoughts together while he’s rocking down on Micheál’s cock, while he can feel him.

“You want it or not?”

Fuck,” Alec whines, and he says it even though it’s so humiliating he feels like he’s blushing all over, it’s so fucking degrading, says, “Please, please, Daddy, I need — I need the job, please — ”

“How’s that feel, huh? When I’m young enough to be your actual son, calling me Daddy?”

“Fuck, fuck — ”

“It fucking gets you off, doesn’t it?” asks Micheál, his laugh dirty and short and Alec can feel his belly shift, feel his cock buried in him as he laughs, feel its sharp, short jerks as he grinds up to meet Alec’s thrusts. “You fucking want it, you love this. I can feel your cock jumping, you gonna come? You gonna come calling me Daddy, your new young boss?”

“Daddy,” Alec whimpers, and he is, can feel the sudden tension unravelling and can’t bear it, his head spinning, his whole body shaking with the waves of pleasure that radiate outward and rock him to his fucking core. “Daddy, Daddy, Daddy, please, please — “

“Christ,” hisses Micheál, and Alec collapses forward as the aftershocks wrack his body, breathing heavily. There’s sweat shining all over his skin, and he’s sure he’s red all over — Micheál’s hand comes up to his lower back, rubbing over the skin in a slow circle. Alec thinks about how Micheál’s cock is buried in him, how when he gets to his feet, Micheál’s come is going to be dripping out of him, frothing down his thighs, mixed with his own slick.

“Alright?” asks Alec.

“Yeah,” mumbles Micheál, reaching up and sweeping his hair back from his face — he’s flushed too, and sweating as well. “Are you really retired?”

“Semi-retired, I went part time last year,” says Alec softly. “My nephews and niece run the shop now, more than me.”

“You don’t seem old enough to be retired,” says Micheál. “You’ve got great skin.”

“Oh, what a lovely thing to say,” says Alec, laughing, surprised. The flush on his cheeks feels a bit different in the face of a compliment rather than sexual degradation. “You charming young thing.”

Micheál chuckles, and he buries his face against Alec’s chest, rubbing his face slowly back and forth so that Alec can feel the bristles of his beard against the skin, and he swallows, touching the back of his neck, cupping it and the back of Micheál’s hair.

“Mmm,” hums Micheál. “I love your chest, God. Can I play with these some more? Can you go again?”

Alec, feeling dazed, says, “Erm — Yes. Yes, I think so.”

“Good, good,” says Micheál. “Gimme a second to get back into character.”

“Fuck,” says Alec under his breath, but nods his head and concentrates on doing the same.


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