I'm thinking of some crazy situation where trinity realises dennis's love for older men who are big and hairy (she knows about his crush on robby), and so as a gag gift she buys him a gay bear calendar, so he can look at a new older guy's body on his wall every month.
dennis goes bright red, but hangs it up and looks through it anyway. he won't say no to being provided some eye candy- and these guys are *very* hot, after all...
unbeknownst to them, robby had ended up, a few months back, doing some amateur modelling for one of his friends who did photography in the local queer scene. apparently the photos were going towards fun projects to raise money for the local clubs and centres, and he hadn't minded so much- no one would see his face anyway.
dennis's heart starts to pick up when he flips the calendar to october, and despite the fact the photos cut off at the neck and the guys faces aren't in view, there's something *very* familiar about the set of this guys posture and the shape of his belly... dennis was going to write it off as lucky coincidence that he'd been provided with shockingly robby-esque wank material, but then his eyes land on the guys arms. and see the tattoos.
oh. oh yeah. that's robby, attending physician of the ptmc emergency department, pictured half naked in high-res and hanging on his bedroom wall. dennis was fucking screwed.
Dennis in his fifties, blonde hair littered w grey. He still works in the ed but he also does classes from time to time, specifically about the differences present in rural medicine.
And jack and robby are college roommates and occasional fuck buddies who are foaming at the mouth every time Dr Whitaker guest lectures, getting excited every time they have a rotation at PTMC because that means they’re more likely to be able to sneak a glance at him at some point.
One day, they’re dicking around a bit leaving the lecture building, ready to get home, when robby stops dead in his tracks - jack is half on his back, arms around Robby’s neck. When he looks up, he sees what made him stop. Dr Whitaker is leaning against the wall of the building, cigarette hanging between his delicate fingers as he stares at them, smirking. They stay there staring for a bit, before Whitaker takes a final drag of his cigarette before stomping it out, leaving to his car with a wink and a lazy salute in the med students direction.
Jack and robby spend a week arguing about who that wink was for.
“Stay..” Daryl whined as he felt your hand leave his, and the mattress shift, clearly you had gotten up.
It didn’t matter if you had to piss, he turned to watch you like a sulking dog, droopy eyes and soft frown.
Maybe he’d follow you, for ‘protection’, because what if a walker magically spawned through the boarded up windows and barricaded doors and attacked you?
He loomed around the corner while you did your business, never saying a word, only a soft grunt while he followed you back down the hall, interlocking hands once you ended up back in the dingy bed y’all claimed for the night.
Thinking of that time im pretty sure i saw an OF creator at a craft market and thinking about making it huckleabbot. Hmmmmmm.
Now, Jack isn’t ashamed to admit he watches porn. He’s only human, and, sometimes, porn is the only way to get that release you need.
What he is (only slightly) ashamed to admit is he has a favourite creator, ghosttpup, Casper. It’s nothing abnormal, really, but he sometimes thinks he’d rather die than admit he has a thing for a wide-eyed and innocent-looking guy half his age fucking himself on huge dildos until he’s in tears. Totally normal.
What might not be normal is how fixated he is on the boy. How much money he has spent on him: personal videos, stream donations, gifts, he could go on. How much time he’s spent watching those videos, the mans face only slightly covered with a mask- a way to conceal his identity, but oh so fucking hot - but either plenty enough revealed that Jack can see Casper’s beautiful expressions as he screws his face up with pleasure.
He can easily imagine what it would be like to have him to himself, enjoys imagining, it’s his favourite pass time. He sometimes dreams about Casper, about how insatiable he would be, begging for more than just Jacks cock, begging to be fucked harder, faster, deeper. He dreams of biting his tattooed leg - a two headed calf tangled in barbed wire and ivy - a work of art he wants to taint and blemish.
It’s one of the few fantasies he lets himself relish in. His obsession stopped any shame he might have had months and months ago, but unfortunately it also brought up some self reflection.
Like, maybe becoming fixated on this porn streamer is an indicator that he might be ready to move on.
And wasn’t that a punch to the gut.
He kinda shut down for a few days after that thought first appeared. Missed several streams, which he is kinda mad about after the fact.
He met with his therapist again, avoided the topic for at least 20 minutes out of sheer embarrassment of what he was going to confess. And it was embarrassing, but it did help, talking things through, actually hearing someone say that if he thought he was ready, it was okay to start dating. That he wasn’t moving on from his wife, just moving forward with his life.
He still felt like a pervert.
And let’s be honest, he is. His break from watching his streams barely lasted a week before he was desperate again, enough to push through his guilt. And God, hearing Casper whimper, saying how much he missed Jack these past few days as he grinds down deeper and deeper and God -
Yeah, Jack probably has a problem. But it’s fine. He knows nothing will come of it. Knows he’s just craving sex and intimacy all together. He can take steps to remedy that.
He tries going out. Tries a few times. Even ventures out onto dating apps. He always comes back to Casper.
But, he doesn’t close the door. Decides that actively seeking out people makes him feel like shit, that he would prefer one of those rom-com first meetings.
Which is something he kinda gets.
Dennis Whitaker caught his eye on that very first shift, but pittfest is a mess so he doesn’t interact with him much at all. He’s cute. Handsome. Blond hair cut far too short, plastered to his face with sweat, pointed chin and soft features. Jack can’t help but be endeared to him.
And that endearment grows over the next few weeks of brief interactions during shift changes. Knocking into each other and murmuring apologies in the hub, fingers brushing against each other when handing over charts. Hell, Jack starts praising the kid, giving him drinks and snacks just to see his face light up with a blush he’s grown far too fond of.
Its sweet. Its soft. He files dennis away under ‘maybe, someday’, and keeps Casper for the here and now, something to take the edge off in the interim.
Luck is on his side or something because Dennis joins street team and now they’re spending more time with each other. They spend several hours working side by side instead of the usual brief hand offs. Means it’s easier to reach out and touch, hands around his waist guiding him out of the way, arm around the shoulder, fingers brushing as they walk side by side.
Means it’s easier for Jack to ask him out for coffee. And then dinner. And then dinner again.
They had their first kiss right outside Dennis’s apartment after the fourth date, a nice breakfast thing. He had pressed Dennis up against the door frame, hands wandering up underneath his shirt to feel those farm muscles, delighting in the warmth of his skin. Dennis was bolder than he looked, one hand in Jacks curls, the other teasing at his waistband, pulling him closer and closer, trying to merge them together.
Jack likes to imagine they would have gone further if Santos didn’t open the door, giving them both a shit-eating grin as they pulled apart.
He went home and watched three of Caspers videos to take the edge off, thinking of Dennis’s tanned skin and strong arms, biting his lip trying to imagine it was Dennis’s teeth pulling the skin again.
He came far too hard, upset that the only witness was a screen, wishing he was cleaning cum off someone other than himself.
Their next date was at Jack’s apartment, under the guise of a movie night. They made it 10 minutes into a random Marvel movie before Dennis mounted him, climbing easily into his lap. Jack was quick to respond, hands around his waist, lips on his neck and chest as Dennis rolled his hips against him.
The makeout session on the couch didn’t last too much longer, both desperate for more. Jack hadn’t worn his prosthetic, moving around the apartment with his crutches, but if they were gonna get to the bedroom, they would have to pull apart, which, judging by Dennis's whine when Jack pulled away, wasn't likely to happen. Jack managed to mumble a "Wait, wait, we need to-", Dennis cutting off his murmurings with another kiss before sliding off his lap.
Jack adjusted his hips, expecting Dennis's wandering hands to go for his belt buckle, but was instead greeted with a firm grip on his ass, pulling him closer, so he was sat on the edge of the sofa, crotch to crotch. And then he was being lifted from the couch easily, with only a small grunt of effort. Jack wrapped his thighs around his waist, squeezing as tight as possible, arms following suit, near strangling Dennis with how tight he was gripping, terrified of falling. But Dennis didn't falter, grabbing his ass even tighter, pressing them against each other further, pulling a moan out of the both of them, the sound vibrating against their joined lips.
Getting out of the living room was no problem; it was getting to the bedroom that they seemed to struggle with, with Jack pulling on Dennis's head frequently to deepen the kiss further, sending the younger man stumbling into the walls - Jack was definitely going to have bruises on his back in the morning - pressing deeper against Jack as they licked into each other's mouths. He was harder than he ever thought would be possible, desperate for more. He pulled Dennis's hair again, pulling them apart just enough to mutter a breathless "bedroom", before allowing the man to dive back against him.
When they made it into Jack's bedroom, leaving the hallway an absolute fucking state, Dennis lay them both on the bed, pressing Jack down, kissing his way down his still-clothed chest, wetting the fabric with his open mouth before finally getting to the hem and pulling it off. Dennis continued to move further down, pushing Jack down firmly when he tried to sit up, pulling down the pair of basketball shorts the other was wearing, releasing his red and dripping cock. The groan he let out at the contact quickly turned into a whiny gasp as Dennis licked the leaking tip, an evil smile on his face as he maintained eye contact, before he wrapped his lips around the aching dick and started moving.
And maybe it had been too long since Jack had had any sexual contact that wasn't his own hand, but the feeling of the intern's throat around him, swirling his tongue around his shaft and head, God, he didn't know if there could be anything better as he tangled one hand into the blond curls. The feeling increased when he felt wetness on his lower leg and a rocking pressure. He lifted his head slightly, and sure enough, Dennis had managed to straddle him and was rutting against him, desperate and soaking and oh so eager to please, as he looked up with those wide, watery blue eyes, drooling slightly around Jack's cock, moaning around him.
Jack tightened his grip in his hair, earning himself another delicious moan, and gently pulled Dennis up to him, bringing their lips together again for a moment and getting Dennis to straddle his chest. When they pulled apart, Jack rasped, "I'm gonna eat you out now." getting another eager kiss as Dennis moved off of him to remove his pants and underwear.
breaking off the kiss to remove his own shirt as well - Jack groaning a "you're gonna kill me" at the sight of two silver nipple piercings - Dennis returned to his position of straddling Jacks chest, but this time he was so close Jack could easily smell the slick dripping out of him. He began to help Dennis shift up to hover over his face, rubbing his thighs gently the whole, time when he noticed something. A very familiar tattoo. Something he had regularly fantasized about, and oh my god.
His eyes widened slightly in amazement, quickly shifting between the boy above him and the beautiful tattoo on his thigh, and God, this had to be a dream, right? There is no way he could be this lucky.
The angle was awkward, but he was able to manoeuvre his neck to press his lips against the tattoo, quickly moving to suck and bite at the inked skin. Dennis whined above him, either in impatience or pleasure from the attention to his sensitive thighs, but Jack only pulled away once he knew a mark would be left behind.
They would talk about it later, right now, he had a job to do. He pulled Dennis down slightly, and was engulfed by him.
Jack had always enjoyed eating pussy out like this, no matter what. being surrounded by legs, feeling the pressure of his partner on top of him. He always did his best work when his partner was sitting on his face. And Dennis would be no exception.
Being enveloped in the musky scent of his cunt, being able to taste how good he was feeling - how good Jack was making him feel - he could stay under Dennis forever. He began by just mouthing against the folds, using his tongue to tease at all the nerves, occasionally moving his head so his nose would nudge at Dennis's cock - he liked to start slowly, find his rhythm, learn what made Dennis whine and tighten his thighs around his head. When he got familiar and Dennis got comfortable with the steady pleasure he was providing, he moved his tongue into him.
The surprised gasp he received from the intrusion made him hum in contentment, the vibrations rewarding him with another moan as Dennis squeezed around his tongue - god, he was so tight, how long did he have to work himself open for his videos? Jack was somehow getting even harder with that thought, moaning into Dennis again as he swirled his tongue against his plush walls. He now imagined helping Dennis ease himself open before he went on camera and performed as Casper for all his viewers, watching him ride those monster dildos in person and getting to help him recover after - getting to watch him do this work, knowing that Jack was the only one he truly wanted.
He must have been moaning at these thoughts more than he realised, because Dennis was coming much sooner than he expected, come and squirt soaking his face and bedsheets. Jack tried to get as much of it in his mouth as possible, desperate for a taste as he gripped Dennis's hips tighter, helping ease him through the after shocks of the orgasm as he eased his movements.
After a few minutes, Dennis was tapping his arm, asking to be released, and then flopping down in bed next to him, breathless and smiling, "I'm gonna need you to do that again next time."
Jack turned to his side, sitting up to lean over Dennis and peck at his lips, the kid eagerly returning, wanting to taste himself, "Oh, next time? You don't want to go again?"
His voice was teasing, but the tone changed into something far more desperate and pathetic as Dennis dragged his hand down and gave one firm stroke of his cock. "I think it would be rude of me to neglect such a pretty cock, right, Jack?"
He could only let out another whine as Dennis began to straddle him again, leaning down to kiss him deeply again, whispering, "Besides, I would hate to disappoint my biggest fan."
Samira & magpie!Samira + Mel & hamster!Mel ! 🐦💖🐹 for oakleft (on twitter) who asked for some art of them <3 I hope you like them!
(I think I'll draw the whole series of the da pitt characters and their animal selves, they're just so cuteee)
Based on his st1cker sheet I drew for my sh0p! I'll try to draw them all this week 🫡
Jack’s composure finally snapped. He had Dennis exactly where he’d wanted him for all this time. Jack standing between his legs, hands under his shirt, tongue in his mouth.
It was heaven.
What he didn’t notice was someone else in the restaurant. Not until the office door opened and he jumped like he just got burned.
Robby. Shit.
“Robby- fuck man I-“ he didn’t even know how to explain this. Getting caught fondling their sous chef in the office after hours. He was so fucked.
Robby was staring. He didn’t say anything. But his eyes darkened. He took a step closer. “Keep touching him.”
“What?” Jack was blinking, confused, looking at Robby despite Dennis trying to pull him closer.
“Fuck he’d been working you up too, hasn’t he?” Robby took a few more steps closer, eyes on Dennis. “Late nights, accidental touches…” he looked Dennis up and down.
Jack cursed. Son of a bitch. Dennis had them exactly where he wanted him. “This is exactly what you want, isn’t it? Have both of us fuck you open on this desk.”
Dennis shuddered and Jack gripped his thighs.
“Fucking hell…” Jack exhale, pressing his forehead to Dennis’s shoulder. He was so hard it was insane. “Fine. Ok. You get to just watch.” He shot a look at Robby.
Robby frowned and opened his mouth to protest. Jack raised an eyebrow and he closed his mouth again. An unspoken tension between them snapping.
daddy doms robby and jack picking up nervous and panicking newbie puppy dennis in the bdsm club, and letting him snuggle into them on one of the couches until he calms down... they ask if he's okay with them keeping him safe for a little while, and he agrees, settled by their deep voices and easy control. they just cuddle him and pet his little fabric puppy ears, and tell him that he's such a good boy for them...
he ends up drifting into subspace between their warm, comforting bodies, and they just hold him gently as he eventually falls asleep on them- a worn out pup whos found a safe spot to nap. while it's not *exactly* how dennis thought his first bdsm club experience would go, he does end up finding himself a doting pair of daddies who officially collar him as their pup just a couple of weeks later.
robby's on an online meeting from home with the department heads and management etc, to discuss the performance of the new med students and interns- and hes spending his time praising dennis for his promise and skill in his work, recommending him for everything he can and lobbying for him to stay at ptmc....
all while, unseen to management, dennis whitaker the golden boy intern is curled up naked under the desk, snoozing in a puppy bed at robby's feet. robby talks about dennis's alert nature and fast reactions while the pup snuffles in his sleep and shifts, showing off the heavy black collar buckled on his neck.
he talks about dennis's independence and initiative, while thinking of the leash and harness he's going to fasten the puppy into as soon as the call ends. talks about dennis's good contributions to discussions while thinking of the muzzle he'll use to control the puppy's barks and yips.
he talks about how dennis has all the makings of a great leader, while thinking about the way he holds his boy down and fucks him stupid every night, leash in hand and the puppy relying on him for everything. management nod agreeably, and seem convinced dr whitaker should stay.
dr whitaker in question had just woken up, and was nuzzling his face against the leg of his attending, puppy eyes dumb and wide and blue. he wondered what the computer voices were talking about, since words didn't mean much to a silly little pup. it didn't matter though, his owner would take control and denny could relax. his brain fuzzed back out to static and he snuggled back into his bed- daddy would take care of him.
Stroking over Daryl’s face like you would a dog, pushing his oily hair out of his eyes, thumbing over the wrinkles along his eyes and forehead. He visibly relaxes, sighing and leaning into it.
If he had a tail, it would likely be wagging between his legs, halfway melted into the couch and you by now.
Praise kink - rewarding Dennis with a sticker chart
Finding out Dennis had a praise kink wasnt a surprise for the the older men, he lit up when they complimented him at work, he always wanted to please others, and was always looking at them for a response when he said something for their approval. Being called a good boy and telling him he was taking it so well whilst Jack thrusted behind him and Robby in his mouth, lit the younger man's body on fire. He wore his heart on his sleeve.
In the sweaty aftermath, covered in drool, sweat, and cum, Dennis rested his head on Robby's chest with Jack spooning him from behind. Both men giving him compliments and petting him like a dog as he came down from his high.
"Such a good boy, should get a sticker on your reward chart."
Jack muttered into Dennis's neck jokingly, the two older men laughed but the other man flushed in embarrassment, hoping that they didnt notice his dick twitching in excitement. They did though. They chose not to say anything.
The next day they had off, Jack was returning from his shift, later than normal as Dennis was on his knees with Robby on the sofa and in his mouth. The younger man continued as he heard the door open, only stopping after Jack spoke into his ear.
"Finish him off and I'll give you a sticker on your chart, do it in under two minutes and I'll let you pick the sticker."
Robby's hand was on the back of his head holding him in place when he went to pull off to look at his returning boyfriend. Instead he carried on with his task and listened to the usual sounds of Jack moving his crutch to the armchair and unfasten his prosthetic, the new sound was plastic rustling though.
When Dennis finally swallowed and pulled of his partner, he was quick to look at Jack who was smiling at him.
"Under two minutes, dinosaur or bone sticker?"
Sure enough, he was showing Dennis a children's reward chart and a sticker sheet that he must have bought on his way home.
"Dinosaur..."
Then it became routine.
"If you can make it another fice minutes before cumming, I'll give you a sticker"
"15 spanks and you'll get a sticker, make it to 20 and I'll give you two"
"Warm my cock for 30 minutes while I read this and you can have a sticker, but no moving."
Dennis was pretty good at getting rewards and he was so excited to find out what his prize was when he filled the chart.
thinking about huckleabbot sugar baby dennis au where at the tail end of COVID, jack wanted some guaranteed safe fun. it seemed easier to ask for vaccine cards, masking, regular testing, and limited social interaction within an arrangement.
dennis was at the tail end of his undergraduate, taking a bunch of pre-requisites for medical school still. he was broke, overwhelmed, and desperate for some in person guidance.
it was a match made in heaven. or hell. or wherever they belonged. it’s was mutually beneficial at the least.
so dennis would come over after they both tested negative, they would get take out, jack would tutor dennis, and it would always somehow devolve into fucking.
dennis was on jack’s lap with his old ass laptop on his thighs. his professor’s video lecture on the vascular system was incredibly vague. or maybe dennis just couldn’t internalize anything tonight. it could be that.
or it could be that he was sitting in jack’s fucking lap, and dennis could never think straight when jack was touching him. he couldn’t believe he got paid for this.
jack noticed how lost dennis was. he started to help dennis fill out the stupid quiz he had to do after the lecture was wrapped up.
it was asking him to match the major arteries to their locations on the body. jack skimmed the rough pads of his fingers up dennis’s neck, a ghost of a touch that made them both shiver. “this here is the carotid,” jack whispered. dennis dragged the answer shakily to it’s place. jack palmed the inside of dennis’s thigh. “and this is...”
dennis tried to fill in the blank jack had left for him, but he couldn’t fucking think. “i-um-it’s-shit!” dennis gasped when jack moved up just a little higher, squeezing him lightly through his shorts.
jack’s voice had a teasing lilt, “come on, you know this. be a good boy.”
dennis breathed deep, steadying himself, “the-the femoral.”
“there’s my good boy!” jack praised. dennis submitted his quiz, facing lighting up when he got a 100%. jack huskily laughed. “my straight A student.”
dennis dropped his laptop on the floor in his haste to turn around and straddle jack. it was fine. jack would get him a new one.
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