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Dennis and Robby were only about two months into their “relationship” when Robby invited Dennis to a medical conference—professionally, of course. He’d said something about it looking good on a CV. The whole career-advancement angle, with the obvious implication that Dennis would be going elsewhere with said career, it made Dennis feel a bit unsure of himself, of his fling with Robby.
Because, really, it wasn’t meant to be anything more than a fling, a standard they’d both agreed to. Dennis tried so valiantly to conceptualize it as a work relationship, just with different goals from when they were in the ER. Instead of Robby’s hand guiding him through a procedure, that same, calloused hand would pull Dennis’s towards his cock, showing Dennis how he liked to be touched.
It'd started like that, handjobs in bathroom stalls and fingering on the roof. Sometimes, there were weeks between their trysts; the ER wasn’t often an erotic environment. It didn’t migrate back to their homes—well, Robby’s home—until today. Robby suggested taking Dennis out to shop for formal-wear, as he had almost none. (Which ended up being a lucky break; Dennis was sure he’d put his foot in his mouth when he stammered, “But, uhm, I only have…I don’t have a tie. Or a suit jacket.”)
They’d already picked out a suit jacket at the menswear store, with Robby insisting on buying Dennis a pair of matching pants. Dennis didn’t have the heart to tell Robby that all men’s pants were too long on him after the fifth pair he tried on, and he assured Robby that he knew how to sew; he’d grown up on a farm, after all.
Now, they were back at Robby’s apartment, in front of Robby’s armoire, which stood opposite from his bed and was topped with a smart TV and a burnt-out candle. Inside, some ties were not-so-neatly folded, some were still in their packaging, and some were pre-knotted, set aside for when Robby was practically running out the door.
Dennis vaguely hoped that Robby would give him one he’d already worn, so that he could later bury his face into it for a whiff of cologne. (He’d already peeked in the bathroom’s medicine cabinet to see what he wore: Sauvage by Dior. Surprisingly modern. But buying a decanter wouldn’t quite be the same; he wanted the natural musk mixed in.)
Unfortunately, Robby pulled out one of the ties still on a plastic hook from the department store. It was a light, sea green, with little golden stars dotted along it in rows. If the two were in a romantic relationship, Dennis might think Robby had picked this one out for sentimental reasons, such as it matching Dennis’s eyes, but he tried to abort the thought. If he wanted to keep this thing with Robby, he couldn’t go all weepy asking about commitment. Nothing would scare his boss away faster.
“Brand-new,” Robby said with a smile. “How ‘bout that?” He seemed pleased with himself, pleased with his small collection of likely-gifted ties that he never wore. Dennis decided not to ruin his smug little expression.
“Thanks,” he said with his own smile. “It’s nice. I like, uh, the design.” He said it while gesturing vaguely to the stars.
“It’ll look good on you,” Robby said, self-satisfied, and Dennis’s mind ran with that compliment, the corners of his mouth tugging a bit further involuntarily. Dennis didn’t feel like he looked very good at that moment, with ill-fitting pants and the same dress shirt he wore to prom.
Then, Robby was giving him The Look. The crinkles around his eyes would soften—with Dennis swearing that his pupils dilated just the tiniest bit—but his eyebrows were pinched together. It was like he was laughing at a lame joke, or maybe a mean joke. Sometimes, this whole affair felt like a cruel joke.
Within moments, they were kissing ferociously, the department store tie dropped unceremoniously to the ground. When Robby’s hand gripped the back of Dennis’s dress shirt to pull their chests together, Dennis pulled back from the kiss to protest.
“You’re going to wrinkle my shirt,” he said, real worry in his voice. “My only shirt,” he reminded.
Robby chuckled, not a sexy, lecherous chuckle, but a candid, genuine one. “That’s what irons are for.”
Dennis didn’t own an iron.
It wasn’t until Dennis got home an hour later that he realized he didn’t know how to tie a tie either. As he practiced with YouTube tutorials, he considered playing ignorant for Robby, asking him for help just so that he could feel those deft hands near his chest.
…
The conference was in Richmond, and Robby, stubbornly and inconsistently frugal, had suggested that the two just take his car—which he’d been sure to brag was a Porsche Panamera. (When Dennis had no knowledge of the model, Robby had said, “Imagine the horsepower of a sports car, but you can still haul your groceries in it. It’ll have plenty of room for our bags.”) That was like Robby, to spend God-knows on a “practical” sports car but be too stingy for a plane ticket.
Dennis had waited until the night before to pack, staying up late his (Trinity’s) building’s laundry room. As a result, he’d slept in on accident and woken up to Robby calling him to say he was parked outside. After a sheepish and hurried explanation, Dennis fretted as he showered. They had to check in as early as possible, because the conference began that evening, and Robby had said that it took forever to get your event badge, and Robby’s panel was that evening, and—and—and—
Dennis had nearly panicked himself to the point of nausea by the time he exited his building and bent down to stuff his bags into Robby’s backseat. His hands were shaking as he settled into the passenger seat, putting a canvas bag at his feet. Though the suitcase he’d slid into the back was packed so loosely that he could hear his toothbrush rattling around as it rolled, the canvas bag was heavy with all the items it contained, squirreled away in his worry. It’d started with just lip balm and a book (in case Robby preferred to drive silently). Then, it progressed into a small notebook and a pen (in case Robby wanted to refine his talking points). Soon, he added a mini first aid kit, an umbrella, pain killers, tampons, and gum. Finally, at the top of the pile: protein bars and trail mix (in case Robby had a preference).
One thing he didn’t consider at all? Condoms.
Back in the present, Dennis was practically about to beg for forgiveness, feeling awful about setting them back, even if it was only by 20 minutes or so. But Robby made that familiar ah-ah sound, shushing him.
“I was a twenty-something once, long ago,” he said with a sly smile. He looked down at his watch instead of the car’s display. “I might’ve…overemphasized our time crunch. When I said we needed to get our badges by four o’clock, I guess I meant five.” He shrugged, still grinning. “Oh, well.”
Dennis let out a nervous little laugh, brain lagging a bit. Then, he realized, and a more genuine smile—a smirk—spread across his face.
“You tricked me?” he asked, an amused lilt in his voice.
“No, no, I just…encouraged you.” Though Robby was shaking his head, his bared canines said, “Exactly.”
“Well,” Dennis said, gaining a bit of confidence. “You should m-make it up to me. Since we have some extra time…” For good measure, he added a hesitant, “…If you want.”
Robby’s smile didn’t disappear immediately, but as he looked around them, it started to fade. Trinity and Dennis lived on a busy street; there were far too many innocent bystanders who would certainly call the cops. It’d been a silly idea.
“Not here,” Robby said with a shake of his head. Turning the keys in the ignition, he turned back to Dennis with an innocent, kid-at-the-candy-store smile, instead of the hungry one he wore just moments ago. “But I do know a place that does incredible waffles.”
…
The drive was uneventful, but nice.
It mostly consisted of Robby showing Dennis songs he liked, only getting halfway through most before piping up again with, “Oh, oh, have you ever heard…?” He was kind enough to offer the aux cord to Dennis at one point, but the intern was quick to say he just listened to whatever was on the radio. Truly though, he was afraid Robby would think less of him if the more worldly of the two deemed Dennis’s music taste poor. By that point, Robby must’ve thought he’d really grown up in a barn, because Dennis made it seem as if he’d never watched a movie either.
Once they crossed the border of Virginia, Robby stopped at the first gas station he saw to buy a bag of peach rings. Dennis didn’t like the texture when he tried them, but Robby was practically moaning while he tapped his knuckles against the steering wheel to the tune of dad rock. Occasionally, he would turn down Billy Joel to make a joke about one of the colleagues they’d be meeting that night or ask Dennis for his opinion on one of the pre-planned topics.
Robby’s panel that evening was on Workflow in Emergency Medicine, but Dennis wondered if he’d be better suited for Neurodivergency in Healthcare Providers—another panel Dennis had been interested in. He probably shouldn’t have been psychoanalyzing his boss, but Dennis was realizing recently that Robby was a bit scatterbrained outside of work, easily excitable. Maybe Dennis was seeing a glimpse of the real Robby, one not constrained and warped by the constant pressure of lives on the line. Maybe, but only in the privacy of his own mind, Dennis hoped that this was just how Robby acted with him specifically, or maybe, when he was in love. It was a dangerous thought.
They arrived at the hotel a few minutes before check-in, but Dennis was surprised by the lack of fellow conference-goers. He’d never been to a conference, granted, but that’s just what he expected from TV, a bunch of intellectuals milling around before check-in started.
“Where is everyone?” Dennis asked as they loaded their bags onto a luggage cart.
“Hm?” Robby questioned. “Oh, the conference is in a hotel a few blocks over. We’re staying somewhere nicer.” He smiled a bit at that.
“Oh, you didn’t have to—” Dennis began.
But Robby cut him off. “There was no reason to pay for two rooms when we could get a suite here for the same price.”
A suite? Oo-la-la, fancy.
“Is that alright?” Robby asked, suddenly losing his confidence a bit.
Dennis just smiled and nodded approvingly. He was very much alright with sharing a bed with Robby, had fantasized about it for months, honestly.
The room was nice, with embroidered towels and a little wet bar included. Dennis was surprised to watch Robby actually unpack his bags and put everything into the provided drawers. When Dennis was between homes, he’d never unpacked his bags at those motels. That was just a good way to infest them with bed bugs.
“I’m going to grab a shower,” Robby said. “Didn’t get a chance this morning.” So, it wasn’t just twenty-somethings who ran late.
An hour later, both of them were ready, dressed to the nines in all ways except black ties. Robby was wearing a skinny tie with a pink floral design, and Dennis thought he looked just incredible, dashing, etc. He let him know so by pulling his boss by the tie into a kiss, feeling Robby’s smile against his lips.
Robby liked when Dennis was assertive, and Dennis had learned that weeks ago, when he’d similarly pulled Robby close by the stethoscope and commanded he fuck Dennis in the family restroom as soon as the shift was over. Sue him; he was angry that day, from baggage he’d brought in from outside. Family drama, a (very small) argument with Trinity, and a lack of breakfast had clenched his jaw for the entire day, made his eye twitch. He’d needed some sort of relief. If he’d stuffed a condom into his pocket that morning, Robby didn’t need to know.
Dennis never considered himself a power bottom—nor as perverted as he recently found himself—but Robby just brought out something in him. They would start out vanilla, or sometimes with the expected power dynamics of boss/intern, but as soon as Dennis said something the slightest bit dominant, Robby was ferocious to please.
“Not now,” Robby said, pulling back. There was still that pleased smile on his face, though. “We’ll actually be late.”
The moments between then and Robby’s panel were a blur. They drove to the hotel the conference was actually being held in, they got their badges, and they had a few drinks. Maybe more than a few. The two certainly weren’t belligerently drunk, but Robby couldn’t seem to keep his lips off the edge of a glass, sucking anxiously. Dennis found his thoughts drifting towards ones in which those lips were wrapped around his tcock, his fingers too. Once, Dennis had put two fingers in Robby’s mouth as makeshift lube for a handjob, and Robby had nipped him a bit, flirtily. (They’d quickly discovered that Dennis wetting his fingers in his own pants was far more effective for quickie handjobs, but Dennis missed the feeling of his phalanges swabbing Robby’s cheek.)
It was all part of the spell Robby put over him. In any moment of mental silence, the blurry time between tasks, Dennis was thinking about fucking Robby. In the shower, in bed, anywhere when he was home alone, he absentmindedly rubbed thinking about fucking Robby. So, you’d better believe, when he was in front of Robby, he was thinking about fucking Robby.
Dennis himself was a bad lightweight, and that night was a perfect example. Two glasses of old-fashioned, and he nearly stumbled into his boss. That’d just earned him that earnest chuckle and The Look. Dennis didn’t know how he had the self-control not to kiss him in front of this crowd of faceless colleagues.
So, when Robby stepped out onto the stage, Dennis drunkenly, unashamedly cheered while those around him politely clapped. It didn’t seem as if Robby could see or hear him; it was a large auditorium, after all. Still, he knew Dennis was there, supporting him. After a sharp look from someone nearby, Dennis did feel a bit of his patented self-efficacy, but his focus was soon drawn back to how Robby’s tie was a bit lopsided with how he was sitting.
Robby, admittedly, wasn’t the best panelist or public speaker Dennis had ever seen. He was eloquent and likeable, but he domineered the conversation, had an opinion on everything. Dennis could see those flaws clearly, and he liked them, found them charming—which was scary. One day, Robby would see it on his face, how much he cared. And then, this would be over.
Then, Robby was speaking up again, and Dennis was shaken out of his thoughts.
“And, y’know, especially in Emergency Medicine, your team makes or breaks you,” Robby said, mouth so close to the microphone that you could hear his mustache hairs scratch it. “I don’t just mean in the ‘weakest link’ way. I mean that the right team can inspire you.” He scratched the back of his neck. “I, uh, work at a teaching hospital, and this might sound cheesy but…those students teach me things all the time. There’s this one, and he’s, well—” He looked from the host of the panel to the audience, not catching Dennis’s eyes but obviously thinking of him. But in that moment of silence, another panelist had already spoken up to agree with Robby.
Maybe Dennis should’ve known long before this point, but it was nice to know Robby respected him—maybe even as an equal? No, that was a stupid thought. Still, a few drinks obviously had a candid effect on Robby, and Dennis was soon salivating at the idea of reaping that reward. He’d never seen Robby the slightest bit intoxicated before now, just hungover.
After the panel, Dennis put his hand on Robby’s arm and gave him a pleading look, and moments later, they were the first ones out of the door, speed-walking and giggling back to the car. Leaning against the trunk, Dennis pulled Robby in for another kiss and blindly groped for the door handle.
Pulling them into the backseat, Dennis was grinning big, a bit dizzy from the alcohol still in his system but elated; he was a cheerful drunk. Robby seemed to be a horny drunk, with his blush disappearing below his beard and the way he was clawing at his belt buckle. Dennis was glad he didn’t seem to get whiskey dick, but if he had, the two had…techniques for when Robby’s dick wasn’t entirely in the game.
The curse of the bottom was that they had much more clothes to get out of. Somehow, even with Robby leaning over him in the confined space of the backseat, Dennis was able to get his pants and boxers to his knees. He tried to shimmy out further, but suddenly, Robby’s hands were below those knees, pushing his thighs towards his chest. Dennis wasn’t quite flexible enough—especially with those tight formal pants leg-cuffing him—to get his knees to his shoulders, but Robby still smirked when Dennis let out a little yelp.
Robby ate pussy like a man starved, and the first time, it’d almost been too much for Dennis. That first time, on the roof, he hadn’t exactly been able to tell when one orgasm ended and the other began, rocking against Robby’s face for what must’ve felt like hours to the fifty-something with concrete against his knees. Dennis felt powerful like that, seeing Robby worshiping him.
In the backseat, with an open palm to the back of Robby’s head, he practically shoved that talented mouth against his cunt, nails catching dandruff with how his fingers curled. Robby went to work right away, suckling on Dennis’s tdick with his middle finger entering with one smooth stroke. Dennis unashamedly groaned. This parking garage was the perfect combination of public and private; he could moan all he wanted while still feeling the risk.
He swore he wasn’t this way before he started fucking Robby. He had, like, normal desires, boring kinks meant to be kept in the bedroom. There was just something forbidden and oh-so wrong about being with Robby—even beyond the expected wrongness of fucking your much-older boss—and Dennis found himself leaning into it all too often.
For example, “You—ah, you like that, you—” a hiss through his teeth, “—you d-dirty old man?”
Robby made a sound of confirmation, something between a groan and a verbal yes. Dennis clawed at his scalp in response to the vibration.
The sound of the word “perv” escaped through Dennis’s clenched teeth. It only seemed to encourage Robby, inciting him to swirl his tongue around Dennis’s foreskin.
“F-fucking your—Christ—y-your med student?” Dennis let out a snarky little laugh. “HR—fuck—field day with—fuck, fuck.”
When he was alone, Dennis could feel his orgasm coming from a mile away, had to work himself extra hard to over the edge, fantasies on overdrive. But when Robby was working away on him, it was Robby who had a sense of when Dennis was close, fingers repeatedly curling against his gspot before Dennis had even noticed a second finger.
This one particularly surprised him though, especially with its intensity. He sunk his fingers into the meat of his hand to keep from screaming.
Before he’d completely come back to Earth, he felt Robby sit up, hands desperately groping at Dennis’s pants to get them all the way off. The poor old man first had to struggle with Dennis’s loafers, but it gave the intern enough time to recover his senses. Once Dennis had opened his eyes, he laughed good-naturedly at Robby’s struggle, which earned him a bemused chuckle in return.
“Little brat…” Robby muttered. Dennis doubted he knew what “brat” meant in a BDSM context, which surprisingly made the comment hotter.
Dennis, in his afterglow, let his cover slip a bit.
A pleased sigh. “Just for you,” he said.
But instead of some sort of rejection, it just earned him The Look. Then, Robby was patting his pockets.
“Fuck,” he hissed.
“I-is something wrong?” Dennis asked, a little spear of anxiety in his chest.
“I don’t have a condom…” Robby said, almost sheepish. He sighed disappointedly, seeming to give up.
Dennis gulped; then, he said, “That’s what P-Plan B is for.” His voice had gotten quieter and squeaker with every syllable, but he got the point across, as well as their little inside joke.
He expected Robby to say no, to be responsible. He also sort of expected Robby to laugh. But Robby did neither. Instead, his jaw dropped open the tiniest bit and his nostrils flared, as if oxygen had been punched out of his lungs.
The first time Robby had penetrated Dennis, he’d seemed nervous to hurt his med student, even rejecting the offer in previous encounters. That first time though, he’d brought a lubed condom—which he was sure to mention—and his thrusts were shallow and languid.
In the back of Robby’s Panamera outside of a conference hall, the thrusts were neither shallow nor languid. No, it felt like Robby was in his lungs, forcing moans out. When Dennis couldn’t initially form a verbal response, he demonstrated his enjoyment of this roughness by wrapping his legs around Robby’s waist. He realized belatedly that they’d never fucked in missionary before.
Finally, Dennis had the composure to speak, groaning, “Old—” another hiss through his teeth, “—pervert. O-of course you want to—” a moan at a particularly loud slap of skin, “—c-come inside.”
Robby’s body was blanketing Dennis’s, so he could feel the rumble in the older man’s chest as he groaned against his neck.
“W-what, do you want to g-get me—shit—p-pregnant or something?”
Dennis worried for a moment that the question was too far, certainly not expecting Robby to moan out, “Yes, please, baby, please.” It sounded so raw, so clogged with emotion, but that only drove Dennis wilder, hitting Robby’s back with his heel.
“Tell m-me,” Dennis commanded, losing a few points on the landing.
Robby wasn’t terribly eloquent when his dick was in the self-admitted tightest hole he’d ever had, but surely he knew by now that Dennis was crazy for dirty talk.
Wet lips at his ear whispering, “Make you mine,” and then, “Fuckin’ keep you forever.”
Dennis let out a high-pitched whine, feeling himself pulse around Robby. He wasn’t quite yet coming again, but his partner seemed to still enjoy it.
Though Robby’s face was still hidden in his neck and unable to see it, Dennis tried to suppress a smile as he said, “That’s right,” a shaky breath, “My good boy.” Little Robby also got a kick out of that, a twitch that signaled Big Robby was getting close.
“Ask me,” Dennis muttered. “B-beg.”
To Dennis’s surprise, Robby sat up a bit, on his elbows and leaning over Dennis.
Robby met Dennis’s eyes to say, “Please, baby.” His lips were wet, and there were beads of sweat dotting his temples. The tips of his ears were so red in the dim glow of the automatic lights that they looked transparent, like putting a finger over a flashlight.
“W-what do you—” a hiss, “—do you want, boy?” Dennis asked, trying to imitate the tone of how one might talk to a dog but failing to keep lechery from leaking out in the form of sharp breaths and curses.
The face Robby made could only be described as pouting. His bottom lip even stuck out of a bit. But to Dennis’s delight, he was opening his mouth.
“Let—let me come inside,” Robby said with furrowed brows and a truly pleading voice. After a moment of hesitation, he continued, “Please, just wanna put my love in you—shit—get you pregnant, please, baby.”
Then, Robby did something that made the world drop out from under Dennis, made him come harder than he ever had in his life. With desperate, jerky movements, Robby’s fingers ran across Dennis’s features as if trying to memorize braille. Those shaking digits would push a sweaty strand of hair out of Dennis’s face, then run along his browbone, then his cheekbone, and finally, two fingers landed on the cupid’s bow of Dennis’s lips.
Robby was studying his face, reverently, as if he wanted to be able to recreate it in a sculpture. Or, maybe, as if he was actually wondering what a combination of those features with his own would look like.
Dennis’s eyes rolled back and his eyelids fluttered as he unconsciously tightened his leglock around Robby. He gasped as if coming up from a near-drowning but made no other noise. Though the older man had never explicitly gotten his permission from Dennis, feeling Robby’s “love” flooding every nook and cranny only extended his own orgasm.
When Dennis came back down for a second time, Robby was still pussy-drunk, smacking wet kisses on his face and neck while Dennis continued to twitch around his softening cock.
When Dennis was alone with his hand and a toy, these fantasies triggered so much guilt. He could barely enjoy the afterglow before the self-disgust made him sick. It wasn’t right to be so attracted to risk, so self-destructive as to fantasize about letting your boss hit unprotected.
But the shame didn’t come. Panic didn’t either. When their disconnection made a squelching sound, Dennis laughed, and Robby laughed at Dennis’s laugh.