Work Text:
Kiss my cheek and make amends
Dennis was a sweet kid. A lovely young man, for sure; a great colleague and an attentive resident doctor, even if a bit clumsy and honest to a fault. Sex-wise, he was still pretty green behind the ears but eager to make up for his lack of experience with great enthusiasm. When he was dedicated to a task — be it work or fucking — he was like a dog with a bone. His focus was echoing with Jack’s own ability to pour himself fully into what he aimed to achieve or to survive.
Dennis was also so impossibly needy. A trait that could have easily been overlooked or dealt with if Jack would stop crawling back to him (and his mouth, his fingers, his godforsaken sad eyes), but the guy was addictive. Or, more precisely, how much he wanted to please Jack was. Whatever Jack allowed him, Dennis took without question and still begged for more until he was put back in his place.
Jack had been a dominating kind of lover most of his life, out of habit and because of his partners’ expectations. He wasn’t forced into the position, and occasionally had the chance to switch; either submissive or bottom, he notably never was both at the same time before Whitaker… The opportunity (nor will to seek it) didn’t really present itself until now.
He had been curious, and privately envious, but had conceded years back that it was simply not in the cards for him. He was the caretaker, the one who protected and hoarded control; he had been molded for the role by his past and his circumstances. He had so much to prove and everything to lose, back then.
Maybe he was finally indulging this secret part of himself because he had the stability to afford being vulnerable without the fear of falling apart. He had spent decades building a strong foundation for his self; even if the house of his body and mind were to crumble, he could confidently rebuild it stronger. He had the blueprints for healing and moving on. He was a constantly ‘in progress’ fixer-upper — all his loved ones were. He had gained the tools along the way to help them and himself, and it was one of his biggest accomplishments.
Still remained the question of:
What the fuck was he doing letting himself be bossed around by a puny twenty-something former farm boy? He had tried rationalising it, even if he had already learnt earlier in life that desire doesn’t respond well to logic. Was he mirroring Robby’s midlife crisis? He hadn't been looking to date for almost a decade, first from grief after losing Arlo to cancer, then because he didn't really care enough to give his heart another go — he was afraid of surviving a second partner, if he were honest. He was still wearing their wedding band out of habit and comfort, as a memento for his late husband, their love and the person he had once been.
He wasn't even dating Dennis, they didn't engage in any real discussion about labels or a shared future; but it wasn't only sex, either… And his chances of surviving Dennis were slim. He couldn't picture him as old and jaded like Robby and himself were, because thankfully he'd be long gone by then. It was selfish, a bit messed up, but a relief nonetheless.
He was battling himself in regards to whatever Dennis was to him. He was torn because of their professional disposition, sure, but also because of their age difference and how little he actually cared about it. He had dated way older guys than himself in his own twenties. He didn’t consider that he’d date the other way around, one day — not dating, whatever the fuck this shit was.
Uh, he was getting on his own nerves. He didn’t want to turn himself into a martyr; either he chose this relationship and its consequences, or he moved the fuck on. He didn’t have the time nor patience to oscillate in his indecision. If not for himself, at least for Whitaker… The kid was clearly not torturing himself in regards to this thing they were doing, and it felt great. Fucking stellar, in fact! Getting nailed on the regular was doing wonders to Jack’s mood. It mellowed him into a contented little beast who forgot to be miserable about anything in his life — selfishly, he thought Robby’s absence was probably a reason too, because their morbid codependency was oftentime feeding into each other’s sadness.
Jack had the night off and so had taken a friend’s offer to go clubbing. He had pushed back his personal life to the background of his priorities, except for cheap beers in the park near the ER and depressed fuck fests at Robby’s. He missed the scene and his old faggy friends. They had history like he didn’t have with anybody else; it was similar to the trauma-bonding happening daily at the hospital, but decades longer. They sometimes didn’t see each other for months or years, but they never forgot. They went through fucking hells together; some were vets, some were survivors of the AIDS epidemic, some were both. They were standing memorials of History and the ones they had lost.
Jack was meeting them at Club Pittsburgh for the after hours on the second floor; the parties hosted by Heaven every third Saturday of the month were trans-centered, non exclusive but oftentimes following the club’s trans-for-men nights where the club’s gym was converted into a T4T lounge. Jack had been pissed at missing the previous week’s gathering for ‘Dungeon Night’ and was looking forward to relaxing in a way he only could in a place dedicated to his fellow kinky transsexuals and homosexuals. And he liked dressing up in his gear, but rarely had the occasion except for Pride (if he had the day off).
So tonight he was going for a full Leather Daddy’s look; from his leather cap to his well-polished (and well-loved) army boots, he knew he was good enough to eat. Even if he wasn’t looking to get into anybody’s pants (Whitaker’s fault), he would always welcome the wanting looks and words of appreciation. He wasn’t as well-built as he had been when in the military, but he was working out enough to still fill his leather vest and dark jeans in all the right places. His outfit was simple enough, completed with a denim shirt, his usual leather collar and a heavy chain connecting his belt to his crotch. As tradition, all of his leather items were past-along gifts from dead friends, from the eighties to the late nineties, as much a ritual as an honor from way back when leather was an expensive luxury.
Okay, maybe he was showing off. So what? Dennis wasn’t the only one who deserved to admire his physique. (And if he sent him a couple of pictures of himself in his full-length mirror, it didn’t mean much. Nor did Dennis’ heated replies. He wasn’t dressing up for him!) It got him a couple of wolf-whistles and a bit of cheek from Edward who had picked his leather uniform as well.
The music was loud and the open bar’s a welcome sight. Jack took everybody’s orders and played waiter for their table, always a tad more comfortable moving than sitting around. He had unused energy running under his skin and he was trying to drown it in liquor and dancing. He drained his glass of whisky and dragged Brice to the dancefloor — while Edward was left engrossed in Teddy’s retelling of his last mountain climbing excursion. The DJ was blasting a mix of Madonna and something electronic, Jack wasn’t an expert but as long as it got him moving, he was feeling terrific. Oh, he had really needed to let loose like that, really let go of responsibilities and anxieties and the smell of sickness —
He closed his eyes while pressing against his friend. He let the music take him far away, and his mind quietened. He was breathing freely, unbothered, out of body.
The night slipped by, time not a concern. The alcohol readily ran in his blood. He sweated through his shirt and ditched it after three in the morning. He met new people and saw old faces that had walked alongside him in his darkest moments. He laughed and giggled and snorted like he wasn’t Doctor Abbot but just Jack, one dude in a sea of hundreds of others. He longed for anonymity, being able to disappear in a crowd and shed his life like a second skin. He was tipsy and comfortable.
He grumbled when his group started parting ways — they weren’t used like him to staying up all night or going two days without sleep. He wished them a safe trip home and promised, like always, to plan to meet again sooner than later. He looked at their cab leaving from the club’s entrance.
It was cold out. He put back on his drenched shirt. He had forgone wearing a coat to avoid the hassle of carrying it all night. His home wasn’t so far that he could freeze his tits off. He looked up at the night sky, unable to catch any star because of the city’s busy streetlamps. He was starting to plan a camping trip in his mind, perhaps after Robby was back in the Pitt so he could take on some of his workload or maybe go out with him. Jack made mean s'mores and Michael knew it. He could be convinced. Jack could also invite —
“Dennis.” The name left his lips in a whisper when he saw him across the road, looking right back at him and waving him over.
The kid was a vision. He was wearing a see-through white tee (brand new, bought in a five-pack deal), a tight red leather chest harness (Trinity’s), a pair of worn-down jeans (that he had since he was sixteen), bordeaux platform boots (Trinity’s too), and a very alluring golden chain reaching his pecs (it was a second hand gift from his grandma).
When Jack reached him, he noticed his footwear made Dennis almost taller than him and that fact, even more than the clothing, was making him want to touch him with his entire soul. He could chuck it to his inebriated state or exhaustion. He could lie to himself. He could pretend he wasn’t craving what was offered to him.
Why spoil the mood? He wanted his great night to end perfectly.
“Come here often, pretty boy?” Jack asked him, not even trying to be suave about it. Dennis’ surprised chuckle was the reward he was hoping for.
“Did you have a good night, sir?” Jack slid his hands over Dennis’ ribs, feeling the goosebumps rising over his bare arms.
“Look like we’re both under-dressed for the weather, uh? Whatever could we do to warm ourselves up?”
“Oh,” Dennis whimpered, flustered, almost against Jack’s mouth. “I’d love a tour of your place. Looked pretty toasty from the selfies you sent me.”
Jack was agreeing before he understood the request. For once Dennis wasn’t trying to jump his bones in public, so he would cash on the idea. He had no reason to not invite him in; he had finally chosen to put to rest the illusion of keeping a safe distance between them. Whatever this grew into, he would ride or die. He was ready to feel alive.
“Were you stalking me?”
“I was with Trin most of the evening, I swear! I was literally walking home!” His attendee — colleague? Lover? — quickly sputtered. “She posted pics on insta, I can show you —”
“It's fine if you were, kid. I think you'd like the club I was at, anyway. I'll bring you along one night, if you'd like.”
“I — I’d really love to, Jack.”
“Good. It's a date then.” He looked at Dennis from the corner of his eyes, his gaze sticking to his face like a glutton. Each new look offered him another detail to catalogue; a brush of glitter on his eyelids, a wave of curls tickling his neck, a litany of small zit scars on his cheeks, a bit of lip gloss dragging down his chin. Did he kiss someone tonight?
They weren't exclusive. Jack had no right to be vexed. Jealousy was an ugly feeling to feed. He trusted Dennis to at least come back to him, in the end. He was who he really wanted, right?
“Did you have a good time?” He didn't want to investigate the subject furthermore — he truly was just making conversation. Trying to learn more about Dennis. Did he only go for older guys?
“Yeah, it was pretty fun to spend a night with the girls outside of work or anywhere nearby. Like, don't get me wrong, I love my job,” Dennis’ eyes flicked to Jack as he blushed, “but we needed the escape. Gotta act our age, you know?”
“There's no age to party!”
“Oh, you get what I meant!” He shoved playfully at Jack’s arm who took it as a chance to slot his hand in his. It was a simple act, but the openness of it left him raw. Affected more than a closet make-out session. They were doing everything backwards, uh.
“Yeah, yeah…”
“Were you out by yourself or…?” Dennis was trying to act nonchalant about his answer but he wasn't as trained a liar as Jack was. He was also digging for intel. Goddamn it, was he cute when he wasn't horny. (Even then he was, who was he fooling?)
“I met up with three old friends,” Jack offered, taking pity on his nervous boy. “They don't work at the hospital, they're from even before you were conceived.”
“That's hot.”
“No it's not, you perverted little rat!”
“Just friends?” Dennis inquired furthermore, always greedy, “or friends like we are?”
“I don't know… Who smudged your lipstick, sweetheart?”
“Ugh, it's not what you think! Look, you can't tell anybody, and I really mean not one soul or Trin will hunt my ass for sport. She's a real lightweight and she gets all lovey-dovey when she's drunk… And she always ends up kissing me, and Vic and Mel, and whoever will let her. She’s actually so sweet when she lets herself be, I promise you it's completely platonic!”
“Don't sweat it, Dennis, I was teasing.” Jack held their linked hands to his mouth to kiss it better. Dennis’ responding smile was blinding. “My friends are platonic friends as well. Eddie, Teddy and Brice… They're a part of me I always carry around. I'm sure you'd like them, they're nothing like the doctors we hang around.”
They share a private laugh, both left lighter at the admission. They had both left space for the other. They hadn't verbally committed to each other, but their desires had met in the middle still. It felt soothing. Like more pieces of themselves were slotting into places.
The alcohol was making a stupid poet out of him. Jack distracted himself from his thoughts by looking for his keys, as they neared his home.
As soon as the door closed, Dennis was on Jack with no room between their bodies. Their chests exchanged the same breaths, the chill of the night already forgotten. The lights weren’t on, adding to the intimate tension.
“You look so fucking good,” Dennis exhaled, “Are you a leather daddy? Should I call you daddy?”
Jack shivered but shook his head. “Jack’s alright, kid.”
“‘Sir’ is still on the table?” Jack nodded. “What about ‘mommy’?” Jack couldn’t control the jolt of surprised arousal the single word shot into his pants.
“Let’s revisit this one later, okay? Let’s keep it simple tonight..”
“I studied more about kinks,” Dennis continued talking right against Jack’s skin, peppering his bristled cheeks with little pecks. “I think I’m what’s called a ‘Pleasure Dom’. That’s the closest term I found to what I want to be for you.” His reverence towards Jack was pure euphoria, turning him into putty in his softer hands. His calluses were tender against Jack’s, a contrast of what years did to hard-working bodies. “It’s all about control of your pleasure, I think? Like, I don’t even care which position you want me in. I’ll do anything to make you cum.”
His dedication to Jack’s pleasure was almost absurd. But he was right on the money, as it was a pretty popular dynamic role in the dominant scene. Jack had played into it from time to time himself. Mind you, not on the receiving end of it until now. Until Dennis Whitaker. A young man who barely knew shit about sex and BDSM etiquette and rules, driven mostly by what felt right to him and his partner. It was both a curse and a blessing; he didn’t know the basics of power plays like safewords, aftercare or sub-drops. But he saw it all with fresh eyes and was free of pre-conceived or dated ideas in regards to what made a good dom. He didn’t care about how well he fitted the category, nor didn’t judge Jack in his lack of practice in submission. It was exhilarating. Dennis was incredible.
Even though Jack was supposedly the teacher out of the two of them, Dennis’ unpredictability kept making him learn shit about himself with each new encounter. It was humbling and also very fucking hot.
“Please take me to bed,” Jack pleaded, finally kissing him fully on the mouth. His tongue didn’t wait to find its twin and make it all very messy very quickly. It pushed his languid interest into an impatient hunger. “I need to take off my leg before I keel over.”
Dennis picked him up like a sloshed bulky fifty-year-old guy didn’t weigh much more than a bag of groceries. Jack turned a brilliant red, mind blanking, even more turned on. “Jesus Christ,” he whispered, amazed and ashamed by his own reaction, “you’re going to kill me, kid.”
“I won’t drop you, sir.”
“‘Not what I meant —” Jack didn’t finish his sentence, suddenly bashful, instead pointing to the direction of his bedroom. Despite the darkness, Dennis navigated the space pretty well, which was funny in itself since the boy was the ER’s favourite klutz. Horny intoxication was boosting his confidence to new heights, it seemed, and Jack was all too happy to be the lucky benefactor of this new facet of him.
He tried to switch the lights on when they passed the bedroom's threshold but Dennis pushed him down against the bed before he could reach it. He instead turned on the bedside’s lamp, the atmosphere keeping a glimpse of that romantic darkness’ intimacy. Its diffused glow blurred the corners of the shadows falling on Dennis’. It made him look more delicate, misty, about to disappear like a daydream. Jack hurriedly clung to his neck, certain he was slipping away, and Dennis must have sensed his distress as he paused and hovered above him.
“Can I help you take off your prosthetic leg?” His voice soothed like a balm to his frizzled nerves. Jack nodded, unsure he could vocalize what he felt in this moment. Something was shifting in him, or maybe Dennis was different? It all felt more real than usual. More vital, life-altering. He was trusting him enough to let him see him in his entirety, without restraint. This was Jack, the everything and nothing of him. Would he be enough for Dennis? Could they really make it work?
“Thank you, sir.” Jack huffed, enamoured by his boy’s commitment to thanking him for the bare minimum. Which wasn't exactly true, as his leg was a scarred part of him he acknowledged, lived with, but didn't overtly share. He was allowing Dennis a final, complete access to himself. He was so far gone for that precious mutt.
Of course Dennis’ devoutness bled into the motion of removing his synthetic limb. He took his time to learn its mechanism, placing it against the wall lodged to a chair to make sure it wouldn't fall to the floor. He massaged the muscles of his right thigh, relieving the cramps his hours-long dancing had settled there. His undisguised care for Jack’s whole well-being, even outside of sexual pleasure, was a hard pill to swallow — it had been easier to protect his heart when it was only about physical reprieve. The boy had wormed his way in one loving touch at a time, like a waterfall eroding the sharp edges of a cliff edge.
Jack was overwhelmed. He needed something to ground himself back in his own skin, against Dennis’ feverish own, he needed them as close as possible.
“I want you in my mouth,” he found himself urging, “I need you on my tongue.”
Dennis whined, his assured air morphing into a wrecked expression. “Yes, sir, of course, let me just —”
He got rid of his old pair of pants, boots and socks; Jack was delighted to see the harness and paper-thin tee still on. He crawled towards Dennis’ boxers, absolutely out of style in comparison to his glamourous fit. Jack chuckled at the garment, finding at least two holes at the elastic band.
“I didn't know I’d get to see you tonight,” he admitted sheepishly, “or I would have worn something else. This is like my old periods pair, it's fucking gross.”
“I don't give a shit about it, honey. I'm more into what's inside —” Jack mouthed at his dick, hard and poking through. He adored how big his Dennis was. He licked at it until he properly could suck him off, his hands spreading on the velvet of his hairy thighs. His dark blonde hair was barely visible in the low light, a fine dusting of silky fur.
Dennis’ moans were sinful and glorious. Jack drowned in his sounds, encouraged to push aside the fabric and suck him harder, his fingers testing the waters of his wetting cunt. His body was so reactive to his touch, the product of youth and testosterone increased libido. Jack couldn't slick up half as much as Dennis could, unless he decided to take him apart and bend his body’s limits to his will.
A hand took off his cap to card through his curls, petting him gently, only to guide him away from his well deserved treat.
“What —”
“I don't want to cum yet,” Dennis cut him off. “That mouth is too skillful, sir, I was halfway through wetting the sheets.”
“And that's a bad thing, why?”
“Sir, respectfully, I have a job to do. You are the one who will cum tonight. Until we are both satisfied.”
Jack flushed, dazed by the cocky assurance he found in his lover’s tone. He stared at him for a beat or two, admiring him. Dennis didn't hide away from his intense gaze. He craved it, in fact, enslaved by his attention, akin to a flower opening up its petals to the morning sunlight.
“Okay, my turn!”
Dennis peeled off every article of clothing Jack was wearing except for his leather collar — prudently setting down his packer on the bedside table. He was naked, not self-conscious. Uh, that was a new feeling… He was basically basking in Dennis’ ravenous scrutiny.
Jack laid down in what he hoped was a seductive pose, eyes half lidded and imploring. “Come on, baby boy, I'm all yours.”
Those were the magic words. Dennis all but pounced on him, burying his nose in his left armpit and slipping the tips of two fingers at his entrance. The intrusion was a bit of a startle but not unpleasant, as it seemed Dennis had the forethought to lube them somehow — was it spit? His own pussy’s wetness? His boy was a dirty pup, scenting and marking him all over as if he wouldn't notice. It was a feral display of possessiveness, a promise directly inputted into his flesh. Fuck, he was fast approaching his first orgasm — the dual sensation of drool all over his pit and the two fingers stretching him so well, putting precise pressure on his g-spot, was the perfect recipe for a rapid climax.
Jack came in a litany of whimpers, drawn out by Dennis’ slowing pace on his cunt’s inner walls.
“One down, two to go.”
“Uh?” Was all Jack’s blissed-out mind could muster up.
“You will cum three times tonight, sir, I promise you.”
“What? Why…?”
“Because that's what you need and what I want to give you.”
Holy fucking shit, Dennis wore dominance excellently. His conviction was bold enough to convince Jack too. He hadn't cum that much in — decades? Ever? But if his lover believed it was feasible, barely a challenge at that, then so be it.
“Show me what you're made of, Whitaker.” Dennis’ answering grin was all teeth. Jack was ready to be ravaged. His boy wouldn't disappoint him; this wasn't an option.
“Do you have any strap-on or dildo I could use? I didn't really plan accordingly.”
“Here.” Jack bent down to reach under his bed, where he kept a box filled with what they needed. He opened it on the bed between his legs, revealing a bottle of lube, condoms, a leather harness and its three sized silicone dick options. The toys weren't realistic, all black and smooth, more utilitarian than fancy. He preferred simple and efficient design as a baseline to please his partners. Then, if the relationship continued, they would move on to more fun shapes and sizes. He started thinking about what kind of dick Dennis enjoyed — did he own any toy? Were they colorful, vibrating, veined or fantasist?
“Please choose which one I will use.” Dennis brought him back into the present. Maybe he was growing needy as well, since even after a gratifying orgasm he was already thinking about new ways to get fucked stupid. It felt naughty to willingly revel in this much pleasure…
“I'm surprised you're not choosing for me, kid.”
“I don't want to take the choice away from you, Jack. Whatever you choose, I will make it work.” It was strangely satisfying to be given a say by his dom. Dennis put his well-being before anything else, not looking for complete submission but trusted abandon. Fucking hell, this was heaven.
“The smaller one, then… Less prep’ and less chance that I'll feel sore when you keep fucking me into multiple orgasms.”
Dennis thanked him with a sloppy kiss, offering Jack his own taste on his tongue. It was salty and bitter, diluted by the amount of saliva his pet could produce. He took note in a nook of his brain to bring up ‘pet play’ suggestions to Dennis on a later day.
“You're so handsome, Jack, I can't believe I get to have you like that, I dream about you under me so often and yet it's never enough — I wish I could fuck you forever —”
“Do it already, baby, come on, I'm right here —”
Dennis hurriedly put on the strap-on with Jack’s guidance. He was delectable standing up with the dildo erect on top of his dick, his expressive eyes locked on Jack as if to judge his approval of the fit.
“You're so fucking sexy, sweetheart. You sure you weren't made for me?”
“I really think I was, sir. Can't imagine being anywhere else, ever.” Dang boy always had the exact words to shake Jack’s world upside down. He made grabby hands to usher him back on the bed, chest to chest.
Dennis generously lubed them both. He started rubbing against Jack’s stomach, then lower against his engorged clit. Jack was losing patience.
“Come on in, come on —”
Dennis slipped back home. They moaned in unison at the relief, the rightness of it. He started fucking him with shallow thrusts, barely moving out of his cunt, but his aim was true and deep.
He buried his face in Jack’s chest, lapping at his nipples with his usual excessive drooling. The sounds of his hole and of the wet licking were lewd. Dirty. He wondered if Dennis would taste him from head to toe if he allowed him.
“You don't have scars —” Dennis babbled with his right nipple between his teeth.
“I have plenty, kid.”
“‘Meant on your chest.”
“Oh, yeah. Didn't get top surgery. Turned out if I work out just enough, the fat of my tits turn into great pecs.”
“You're damn right about that.” Dennis chuckled, redoubling his efforts to drench him in his spit. “I'm saving up for top surgery, but maybe I should do the same —”
“You should still check in with a qualified surgeon, just for health reasons. I'll make you a list of top dogs in the FTM game.”
“You're too good to me, thank you Jack, thank you —”
His thrusting started picking up in intensity, knocking against the back of his cunt with a solid tempo. Cervix orgasms were probably Jack’s favourite, because of how vividly they spread through his whole body. He sometimes felt it right into his ovaries with aftershocks cramping. They were meant to ruin him for anybody else. He was at Dennis’ command.
“Next time, you'll wear the chest harness,” Dennis told him before reconnecting their mouths, noses bumping in his haste to completion, “it will hug it so beautifully, and I'll suck on your tits for hours, maybe you'll leak milk if I suck hard enough —” The notion was insane but the fantasy devastatingly appealing.
Jack came a second time with the picture of him nursing Dennis on a lazy Sunday, with no worry but how good his baby boy made him.
He was trembling with the force of his climax. Dennis was shushing him and stroking his skin, grounding him. He was a quick learner, wasn't he? Attentive to his body’s tells to prevent any sub-crashing. Jack felt like he was floating. Static buzzed in his system as he was pampered by his sweet boy.
When he started coming back to himself, he noticed how smelly he had gotten, rank and sweaty all over, heart beating a devilish rhythm under his ribs. Dennis was glistening with sudor, his biceps bulging from the effort. How did he continue looking so good? Jack was mesmerized. Still a bit high from cumming, or maybe still a bit drunk. He was still working on catching his breath but didn’t dare forget his pup’s promise.
“Give me a minute, okay? I know you’re still on a mission.” He kissed the top of Dennis’ messy mop, finding him sweaty there as well. Who needs working out when you get fucked like that?
“Hmm, you’re so good for me, sir… I can wait more, whatever you need. Was I alright? Did I do anything that felt uncomfortable?”
“Nope. Relax, you’ve been a good boy so far. I know how to use my big words when something is off, okay? You’re perfect, pup.” Dennis keened at the praise, burying his face in the crook of his neck, pressing against him like he was trying to crawl inside him completely.
“Can I continue? Just one more, Jack.”
“Yeah, yeah, I heard you… Do what you gotta do, pet.” Ah, he heard another whimper at the nickname. He needed to start a list of all the sweet things his boy liked to be called. “Use me like you want to, baby.”
Dennis needn't have to be told twice. He grabbed the unused pillow by Jack’s head and positioned him under his ass, then flipped Jack around so it rested against his stomach. His t-dick was slightly rubbing against the fabric, which was about to get interesting since Dennis had been neglecting the nub so far.
He wedged his head in between his crossed arms, looking over his shoulder to appreciate the sight no longer facing him; his lover was adding more lube to his strap-on dildo, then warmed some more between his palms to add to Jack’s already glossy wet mess of a pussy. His consideration was useless yet so tender, as if the action was more an act of worship than necessary.
“Sir, I'm going to fuck you until you cum one last time. I know this time may take a big longer to accomplish, so I will edge you occasionally to help you reach that final climax. Is it good with you?”
“You're doing all the work, pet. I'm peachy where I am.”
“Do you trust me?”
Fuck, the single question threw Jack for a loop. It wasn't supposed to be an existential request. Just a green light. A simple check-in. Jack trusted Dennis, yeah, but that also left him in a very exposed position. More than having his butt in the air, in fact. Because by allowing Dennis in, truly inviting him in the halls of his haunted being, he was defenseless against heartbreak. It was a leap of faith, of sorts. He felt tears rise up his eyes, but tried as best he could to push it all down. He was overwhelmed in the best way. He felt… Loved.
“...yeah, baby boy. I trust you.”
Dennis’ lips were on his shoulders as he murmured a prayer of ‘thank you’s and ‘you’re too good’s against his freckled back. Jack was being taken care of. He was granting Dennis full control over him, to wreck and remake him in a safe scene. This felt like a revelation. Fucking pure bliss.
Dennis started fucking into him in a slow cadence, languid and measured. It would have lulled Jack to sleep if not for the pressure it applied on his clit, sending quiet shocks of pleasure here and there. It was a tortuous pace — it was a true lovers’ embrace.
His definition of edging seemed to be stopping mid-fuck, crawl down Jack’s body and eat him out, pussy and asshole. And as soon as Jack was starting to grind into his face, Dennis would go back to fuck into him, only slightly harder. The back and forth was maddening — and an objectively good plan — but it was grating on Jack’s composure.
“Come on Dennis, I'm really close, just touch me —”
“What do you need, sir?” He panted right into his ear. Fuck, Jack was a goner, or almost, just a hair-trigger away from attaining that third climax.
“Just — jerk me off, pound into me, I don't know just use me, harder, make me feel you right in my throat —”
His pleas were the fuel Dennis’ fire was hunkering for. He bit into the meat of Jack’s shoulder and rubbed him off in rhythm with his thrusts. Jack tried to count to ten but came on the sixth mark.
“Fuuuuck —” He groaned into the mattress. Dennis played his body like a damn maestro. His cunt pulsated around his silicone dick, overstimulated yet still cumming in long spasms. Fuck, he would feel him for days. Eh, he could attribute the limping to his prosthetic. Or his old age. He could use the excuse to lean more into Dennis and just drape himself all over him whenever he wanted.
Jack settled back to his senses when Dennis left his cunt empty. He heard the familiar sounds of taking off the strap-on, and his getting up to go rinse it into the bathroom’s sink. Good boy… His perfect little thing. Bloody hell was he a lucky fucker.
Dennis settled back over him with a damp towel, taking seriously his role of conscientious dom. Jack hadn't moved an inch, more than satiated; fulfilled. Owned and delivered.
Something was itching at his brain, though. The thought kept slipping out, probably evading him through the fog of a good night of clubbing and fucking. He started humming to himself, Dennis’ responding to him in kind. Until —
“Wait. Dennis, wait!”
“What? What is it, Jack? Are you sore? Uncomfortable?”
“Did you even cum?” He almost shouted in the dead of night. He was growing hysterical at the realization.
A stretched out silence hung in the charged air.
“...I didn't, sir.” Dennis finally confessed.
“Oh for fuck’s sake —” Jack tried to turn around to give him an earful about reciprocity, how this was an exchange of pleasure and not just for his own selfish gain — but Dennis cut him off before he could get to it:
“I would really like to fuck your ass, Jack. I stretched it out enough to fit just right in. Could that be alright?”
Jack let out an annoyed chuckle. Of course Dennis already had an idea in mind. Probably was planning on it since they fell into bed. It helped ease Jack’s temper. He knew Dennis’ pleasure was directly linked to how much he was enjoying himself, but he didn't want to leave him wanting either. He was looking for a partnership here.
“Hell yeah you can, pet. Good choice. But don't you ever try to get out of my bed without cumming again, you hear me?”
“Loud and clear, sir.” Was Dennis’ amused reply.
As much as Jack had been annoyed that Dennis had pushed aside his own completion, he soon found out Dennis had probably been edging himself all along for how quickly he came once inside him. He didn't even last a minute before he was whimpering and spraying slick all over his thighs. Lord, was that unfairly hot… How desperate he had been to please that he forgot himself. They shared control over each other harmoniously.
“Jack, you always feel so right around me, holy shit —”
“All yours, baby, only for you.”
That earned him a lazy kiss. Delicious.
Dennis was finally free to get back to his previous task of cleaning Jack up, which was probably pointless since they were both gross and viscous all over. The sheets were ruined. They'd need a shower and a new set of bedding… But the sun was about to stick its nose at the horizon and it was a workless Sunday. They would deal with all of this later.
He flipped back on his back with a groan and accepted Dennis’ offered glass of water, as he was nursing his own. Jack was losing himself in reminiscing about all the ways and fashions Dennis had pleased him, fighting his own body to not get hard a painful forth time.
“Is it okay if I stay over?” A cautious voice broke through his thoughts.
“Dennis, you are not leaving this bed until Monday at least. Don't make me restrain you to the bedpost.” He found himself busy with an armful of cuddly Whitaker in retaliation.
“Don't threaten me with a good time, Jack.”
He let out a genuine guffaw at the ridiculous retort. His Dennis’ perverted inclinations seemed to know no bounds. How fortunate for a dirty old dog like himself.