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It was objectively a little bonkers, this thing he had going with newly minted MD Dennis Whitaker. It had started with the kid working the night shift for a few days. He had some hours to make up, and they needed the most help at night at the moment. It ended with Jack taking him to a one-on-one breakfast which was not at all a date — except that it totally was.
By then, Jack was more than a little enamored of the guy, but that was neither here nor there because he had no fucking reason to think Dennis would be interested. He wasn't quite twice his age, but it was close enough to make him sure — so sure it hadn't even merited contemplation, it just was — that Dennis was similarly not thinking about him as a possibility. Even if he had been, Jack was aware he was a difficult guy to get to know. He masked everything with sarcasm and the kind of honesty that fools people into thinking you're revealing something of yourself when you're not.
Dennis, however, was not fooled. He was, instead, perceptive and totally disarming. He asked questions and he phrased them in a way that made you want to answer. By the end of the first night shift he worked, he'd already asked him about his military service, his late wife, and whether he had phantom pain in his leg. Normally, that sudden depth of engagement would have made him pretty fucking nervous, but Dennis appeared to have no motive other than understanding him better.
The next night, he asked Dennis some questions of his own, learning, among other things, that he was the youngest of four brothers, the first in his family to go to college but probably not the smartest (that would be brother #2), and that he was currently living with Trinity Santos.
On night three, they carried on a wide-ranging conversation that was dropped and picked up again over basically the whole shift, sharing opinions on food and music and sports and a million other things. It culminated in that breakfast, during which Dennis told him about some movie he was dying to see and Jack couldn't stop watching his mouth as he talked. He had the cutest smile when he was excited about something.
Later, Dennis admitted he spent most of the date that wasn't a date unable to focus on anything other than Jack licking syrup off his fingers — that he was chattering nervously, and to distract himself. Jack wasn't even trying to be seductive. If he'd had any clue that something was even possible, he probably would have been awkward and just as nervous. As it was, he smiled a lot and just really enjoyed the company.
After breakfast, Jack had driven him home, and they ended up sitting in his truck for a while, there at the curb, like they were trying to finish their conversation while in reality they were letting it further unfurl. But he still didn't know it was going anywhere until they finally decided to part ways. He impulsively reached out to pat Dennis's neck to say goodbye and apparently looked at him a little too fondly, in a very particular way — because Dennis's eyes went wide, like everything started to make sense. Everything, in that case, meant he hadn't realized Jack was into guys. Just as impulsively, Dennis leaned in and kissed his cheek, and it was Jack's turn to have a revelation: maybe Dennis could be into him.
That evening, before Jack went into work (Dennis had a blessed three days off), he got a couple of texts from a number he didn't recognize:
i’m sorry if i was weird this morning, i promise i can behave like a normal person
this is dennis whitaker by the way
They both knew exactly what he meant, of course, and why he needed to make the gesture. He was giving them both an out.
Jack looked at the message for a little too long, then he got in his head about how he should respond. The problem was he knew what he would do — if he wasn't a guy in his late forties communicating with a guy in his late twenties. In the end, he decided that the only reasonable course of action was to go with his gut, because he was, indeed, a middle aged man texting a Gen Z dude:
Not interested in "normal" really. But we're good, don’t worry.
He was pretty sure that could pass for friendly if Dennis wanted it to. While it was clear now that the guy was into him, he had no idea if he actually wanted to do anything about it.
He got some clarity on that a little later, when Dennis said:
what ARE you interested in?
Jack's could practically feel his blood pressure shoot up at that. He had been very much on the fence about pursuing something and had been willing to drop decisively onto the no side. Dennis would have to take the lead. And, fuck, he did. To find such boldness in a reserved guy, who also had capable hands and searching eyes and strong shoulders and a pretty perfect little ass…
And, yes, Jack was also lonely — not desperate (yet), just craving connection. It kind of surprised him. When he became a widower, he hadn't been able to imagine wanting to get close to anybody like that again. For the last few months, though, he'd felt possibility opening up inside him, suddenly. Still, he hadn't been at all convinced anything would come along to slip into his heart and pull him out of himself, to make him want to take that kind of emotional leap again.
Yet he did, didn't he? So Jack decided to be as bold as Whitaker:
What if I said you?
Once he hit send, his heart started beating so hard in his chest that it hurt a little. What the fuck was he doing? Apparently, Dennis felt roughly the same way:
really?
That text was chased quickly with another: i mean yes, but are you sure?
Are you? Jack replied.
It was a few minutes before Dennis answered. When he did, he said:
maybe we should go on a date and see?
He grinned to himself as he had a swooping feeling in his stomach. He could do this, right? He'd been doing it for days, of course — assuming it was just platonic, not expecting it to accomplish anything except amuse him and bring Dennis out of his shell a little.
Pretty sure we went on one this morning, he typed out.
Dennis responded with the smiling face emoji that was showing its teeth, then he said: ok but lets have one not in our scrubs smelling like the hospital
So the next night, which was his night off, they had a very casual date. They met at a restaurant in Dennis's neighborhood, one he had been wanting to try but couldn't get Trinity to go to for some reason. Dennis vetoed going to see a movie together — "not a great way to spend meaningful time with somebody" — so they ended up taking a walk, making loops around a local park. He wasn't sure how many because he was kind of distracted by the soft, warm tone of Dennis's voice and how when he reached for the man's hand, he immediately took it and threaded their fingers together.
Eventually, they settled on a bench, even though it was probably a little too cold to be outside without moving to keep warm. They leaned up against each other and kept talking until a nice silence set in. Jack couldn't remember the last time he was this nervous about just sitting next to somebody, or this excited. Dennis smelled good, like some kind of spicy herbal soap, and there was enough stubble on his jaw that it made Jack feel a little feral about kissing him.
As if he read his mind, Dennis said. "You look like maybe you wanna kiss me."
Jack's face lit into a smile. "Now you know my secret — I have no game whatsoever."
Dennis was also smiling, although a little more sheepishly: "Oh, me either. Like, what I should have said was: I want you to kiss me."
"Yeah?"
"Yes."
Jack pulled him in with a hand around his neck and kissed him softly on the mouth. Dennis's hand pressed against his chest, right over his sternum, as his mouth opened to him with a tease of the tongue against his bottom lip and then a soft sigh as he waited for Jack to reciprocate. So he did, despite the fact that they were sitting on a bench in a public park. Regardless of how genuinely chilly it was outside, he felt hot all over as Dennis's tongue licked against his and as his hand crept upward until it was settled warm over his collarbone. Everything about Dennis was warm, including those blue eyes when he finally pulled back from the kiss and looked at him.
"You know," Dennis said, "I didn't think you'd actually be interested in me. Beyond flirting, I mean."
"Because you're younger or because you're a guy?"
"Both."
"Well," Jack said, "I admit the age difference does give me a little pause. Clearly not enough to stop me, but…"
"Yeah." Dennis nodded seriously. "It's…not nothing. But not a deal breaker? Not for me.”
Jack nodded, then he said. "As to the other thing, I wasn't in the closet, but I guess it wasn't common—"
Dennis leaned in and kissed him to shut him up.
"I assumed,” Dennis said, “which I should know better than to do."
Jack reached out with his hand to touch Dennis's face, and Dennis flinched a little at the cold.
"Jesus," Dennis said. "We should probably get inside."
Jack just nodded, but neither of them moved. Jack would have happily stayed there, despite the cold, pressed close to him like this.
Dennis said, "So, do you have any rules about how many dates you have to go on before…you know…?" He raised his eyebrows.
"Before I'll put out?" Jack replied, grinning. Remarkably, he managed not to blush. "What? Because I'm old?"
Dennis gave him a dramatic, chastising eye roll.
“Because you're…of a different generation."
Jack snorted. He stood up finally, pulling Dennis with him.
"How many dates feels appropriate to you?" Jack asked.
"It's situational."
"I agree. Depends on the person, really. Just in case you were wondering, my generation is not prudish about sex. Even if it was, I'm not."
"Good to know," he replied with a sort of wicked grin.
He felt like he should be making a moral inventory of himself. Should he do this? And now? But he had to be honest with himself: he'd known the answer as soon as Dennis posed the question.
"Two dates seems reasonable to me," Jack said, "if you want to come back to my place. And that really is an if."
Dennis nodded and squeezed his hand, saying, "I do want."
Jack felt a flush creep up his neck and over his face as those words settled inside him: I do want.
The ride back to his townhouse was quiet, much like sitting on the bench had been — easy but charged, only now he was waiting to strip the guy out of his clothes instead of just kiss him. He honestly hadn't thought they'd end up here, not tonight, but it felt right.
Once they were in his living room, having cast off their jackets, Dennis drew him close and brought his cold hands to his chest, covering them with his own. They stood there playfully kissing for a few minutes as Jack warmed up, something that under other circumstances might've been sweet and only mildly arousing. Tonight, he came up hard pretty much as soon as Dennis nibbled a little at his neck, even before he started sucking at a spot until it stung a little. He could feel that Dennis was hard, too — their bodies were resting together — but they were holding off on just going for it. It didn't feel hesitant, but he wondered, given Dennis's age and kind of sheltered background…
"You've done this before, right?" Jack said.
Dennis chuckled, low and amused. "Depends on what this is, I guess."
Jack shook his head at himself for maybe being a mildly condescending jerk, but Dennis just smiled at him.
"Are you worrying about me now, Jack?" he said, eyes warming with fondness and maybe a little mischief.
"Don't take offense. It's what I do. Generally because I'm projecting, according to my therapist."
"What are you worried about?" Dennis asked.
Jack smiled, but then he had to look into himself a little, which wasn't fun.
"Been a long time," he found himself saying. It was mortifying, in a way, but it also felt good to get it off his chest. "I don't just mean sex."
Dennis held his face in his hands and kissed him, long and slow. When he finally pulled back, he said:
"You wanna know where I am, experience-wise?"
"If you want me to know."
"It's relevant," he said, his expression turning saucy as he added, "I hope, anyway."
"Mmm hmm," Jack said, planting a feather-light kiss on his mouth.
"I've never had actual penetrative sex, but I've done pretty much everything else. Not trying to avoid it, by the way. I just haven't been comfortable enough to want to go there, you know?"
Jack nodded. "I do know. Do you think you're a top or bottom?"
Dennis grimaced. "I…"
"We don't have to talk about it if you don't—"
"No," he said. "It's fine. I guess the answer is I don't know how I'm supposed to know until I do it."
"But you know what appeals to you," Jack said.
"Yeah."
"Look, I'll happily top, if that's what you want."
"But you…don't, usually?"
"Not usually." He huffed out a helpless laugh at himself, then he turned to him with a self-deprecating smile: "But saying that feels absurd because I'm pretty sure the year started with a 19 the last time I did this."
Dennis raised his eyebrows and tried not to laugh, then he said, "Don't ask me the year I was born, by the way."
Jack groaned, then he felt his face get hot, but Dennis didn't look like he wanted to run.
"It sounds like it'll benefit us both to go slow," Jack said.
Dennis frowned a little forlornly at that.
Jack corrected himself: "I mean, with, you know, sex."
Jack pulled him closer, finally bringing their hips flush so they could grind a little. It sent actual sparks of pleasure up his spine to hear Dennis gasp against his neck.
Jack said, "Lots of other things we can do. I didn't bring you back here just to suck face like teenagers, although that's a hell of a lot of fun. But, to be clear, if that's all you—"
Dennis kissed him hard, quickly leading with tongue as his hand went to Jack's belt buckle. Jack did his best not to giggle at Dennis's eager energy, mainly because he felt a little desperate himself. As Dennis worked at getting his belt off and his fly open, his mouth eventually migrated to Jack's neck. Jack just stood there clutching his hips, trying not to lose his mind with every brush of Dennis's fingers near his cock.
Jack's hands pressed up under Dennis's shirt, and after a few seconds of palming so much soft, warm skin, he impatiently tugged the garment off over his head. Dennis’s other hand found his nipples, which he rubbed experimentally with his thumbs as Jack’s mouth came down, teeth first, against Dennis's throat.
"Shit," Dennis hissed. "Jesus."
It distracted Dennis's hands, but only momentarily. As Jack laved his tongue over Dennis's neck and slipped his hands down the back of the man's pants, Dennis got his hand around Jack's cock, through his underwear.
Jack groaned pretty loudly, which he thought might earn him a chuckle. Instead, it made Dennis rub his still-clothed hard-on against his hip and shiver a little. Jack tried not to buck too much into Dennis's hand. He let his mouth trail wet and teasing up toward Dennis's ear, and he said:
"You smell so good. I need to know how you taste, too."
Dennis shivered again. "Okay. I— Yes. Please."
Jack slipped one hand down between them and grasped him through his pants. Dennis whimpered. His cock wasn't thick, but it was on the long side. He couldn't help but immediately shove his hand down past Dennis's waistband, into his boxer briefs, and run his fingers over it, just to get a feel for the shape.
"Dammit," Dennis murmured, "my plan was to literally blow your mind."
"We can do that," Jack said. "You like giving head?"
"More than just about anything," he replied, and now he was working his hand down into Jack's underwear so he could stroke the leaking head of his cock.
Jack said, "I'm a little out of practice, but I remember really liking it, too."
"Maybe we should go to the bedroom," Dennis said. "I really wanna get you naked."
"Yeah?"
Dennis nodded and gave him a hot, heavy look.
Once they got there, he managed to get to work on Dennis's clothes first, stripping him completely before he let Dennis tackle his. Dennis’s eyes went dark with lust as he pulled his shirt off, and his hands roamed Jack's torso, occasionally stopping to squeeze. Jack felt another rush of hot arousal flood his body. How long had it been since someone so openly desired him? Too long, probably.
Before Dennis could get him out of his pants, Jack motioned for him to wait, leaning over to flip the releases on his prosthetic and let it fall. Dennis got on his knees to pull down his jeans and underwear, pausing to get Jack to sit before he took them off. Before Jack could make a move, Dennis took his cock in his mouth, hands spread wide over the inside of his thighs like two hot anchor points as his even hotter mouth closed over the head, tongue circling the crown.
“Fuck,” Jack murmured. "Alright, I'm gonna let you do that for a minute, but only a minute."
Dennis looked up at him from where his soft lips were stretched around his dick and nodded in a way that somehow managed to be sarcastic: sure you are.
Dennis truly did seem to like sucking cock. He couldn't take him very deep, but he was doing fantastic things with his tongue, sometimes stopping to lick him from base to tip. Jack had to use every ounce of willpower at his disposal to push him back and off so he could follow through on his own plan.
When he got Dennis to climb onto the bed and prop himself up against the headboard, he stopped and looked his fill at the guy’s body, thicker in places than one might guess seeing him in scrubs, especially his torso, strong but soft. Dennis took his own cock in his hand and started stroking, which made Jack's mouth go a little dry — right before he started salivating. He reached out and swiped his thumb over the flushed head, picking up a little pre-cum and then sucking that thumb into his mouth.
"You are fucking gorgeous," he said, which made Dennis close his eyes, clearly unaccustomed to compliments, which was a shame. Jack added, "Honestly. I can't take my eyes off you."
Dennis's eyes popped open again, and he was smiling over a reluctant grimace.
Jack gave him an amused grin, saying, "You think I'm lying?"
"No. I just—"
Jack leaned over him and took over stroking his cock. He said in his ear:
"Trust me when I say I can't wait for when you open me up and fuck me."
Dennis shuddered. "Jack."
"But there's no pressure. Alright, baby?”
Dennis grinned and raised an eyebrow at him.
"That okay?" Jack asked.
Dennis nodded. He looked and felt a little desperate now.
"Can you…?"
Jack grinned. "Ready for my mouth, huh?"
"Please. It— It probably won't take long. I don't know if I've ever been quite this turned on before."
"Oh yeah?"
Without further teasing, Jack dropped down and wrapped his hands around the man's hips, right over the hip bone, and took him in his mouth.
He'd forgotten how much doing this could make his jaw ache, but it was a small price to pay. This was exactly where he wanted to be, doing precisely this: licking and mouthing over him, hearing all the little noises he made, feeling the weight of him on his tongue, and watching his eyes go wide and dark with raw need. Then finally he felt Dennis's whole body tremble as he came.
By the time Dennis finished spending down his throat, his own dick was so hard it ached a little. Fortunately, Dennis immediately pushed him onto his back and bent over to take him down. Just like before, his mouth was as a hot as the rest of him, and he quickly built up speed, clearly meaning to get him off, not to tease. He held Jack's hips down with his forearm across his midsection, and the other hand held the root of his cock so he could bob his head up and down without worrying about getting choked.
"Shit, Dennis," Jack muttered. "I'm close. Fuck."
Dennis looked up at him with those liquid blue eyes.
Jack said, "I'm gonna come." Another couple of pulls of that beautiful wet mouth down over his cock, and he moaned, "Fuck, I'm coming," and spilled over his tongue, feeling him swallow it all down.
Dennis kissed his way up his chest, finally taking his mouth in a bruising kiss. Jack thrust his tongue in to chase the taste of himself, and he moaned to feel the man's body settle on top of his, so warm and substantial.
With a rough voice, Dennis said, "That didn't feel like you were out of practice."
Jack gave him a sly grin and said, "You sure you're not just easy, bro?"
Dennis cackled out a laugh. "Definitely easy for you. Do you have any idea how hot you are?"
Jack gripped him by that very squeezable ass and said, "Even if I'm wrinkly in places and going gray?"
Dennis gave him a very dramatic dubious face. Yes, he was fishing — because he was suddenly feeling a little anxiety about, well, a lot of things, but especially his age.
"Not seeing a ton of wrinkles except on your face,” Dennis said, “and those are very attractive. As for the gray, your hair makes you look so effing sexy, in case nobody's told you that before. And, if I can be a little unhinged for a second, the silver pubes mixed in there are really doing something for me."
It was Jack's turn to laugh out loud. "Thank fuck for that."
"Seriously," Dennis said, settling now at his side, throwing a leg over his hip and laying his head on his shoulder. "I won't even say that I don't care that you're older. I like that you're older. Not in a weird way, just… Yeah, you're...very much what I want."
"Ditto," Jack found himself saying.
But as it got quiet and he sank into the moment, Dennis suddenly felt kind of tense, which made Jack take a deep breath and let it out slowly.
"What?" Dennis asked.
"Do you actually want…a relationship? I'm not trying to push you into anything."
"I know." Dennis found one of Jack's hands and threaded their fingers together, saying, "And, yeah, I do."
"But, I mean, you want to get tied up with me?"
"Why wouldn't I?" Dennis replied, like it was obvious. Then he added, "If anything, I thought you might have some hesitation."
"Oh?"
Dennis looked down at his other hand — at the ring — and Jack nodded.
"Yeah," Jack said. "Sorry."
"Don't tell me you're sorry unless it means you're not ready."
It didn't, did it? He'd had his hands all over Dennis, and he hadn't thought about it, mainly because it was just another part of him now.
"It's just habit," he said. "Comfort, maybe." This was nothing he'd ever bothered to articulate to other people, not even his therapist, so he ended up talking around it a little. "It was a good relationship, and I liked being married. That's why I haven't taken it off, because I liked who I was. Who I still am, I guess. But she's been gone for a while, and I don't have any hesitation on that account. It's…weird moving on, but it's time." Dennis's eyes were wide and serious, so he added, "Not because of you, if you're freaking out a little. This happening, with us, is because I was ready, you know?"
He felt Dennis take a breath and let it out, then he must've decided he needed to say something, because he squeezed his hand and said, "Okay. Good."
Jack then added, "The real thing it should tell you — maybe even warn you about — is that I'm a boring monogamy kind of guy."
"A feature, not a bug."
"Yeah?"
"The fact that you didn't try to say, If you want me to take it off, I will… I know what kind of man you are. I like him."
Dennis finally climbed off him, settling at his side, head on his shoulder.
“Not to put any pressure on anything,” Dennis murmured. “I’m just excited to see where this could go."
"Me, too," Jack said, pressing a kiss to the top of his head. "Will you stay tonight?"
"Kinda have to. You drove me here."
Jack made a displeased noise, and Dennis snorted.
"Yes, I wanna stay,” Dennis said. “But you don't sleep at night."
Jack turned Dennis’s face up to look at him.
"Who said we were gonna sleep?" he said with a friendly leer.
Dennis gave him a careful smile. "So that's…on the table?"
"My recovery time is longer than it used to be, but my stamina is maybe better, because I'm in better shape, and because it's marginally more difficult for me to orgasm. Notice I said marginally."
"Well," Dennis replied, "my recovery time has always been not-so-great, so we're a good match."
In a lot of ways, Jack thought. Somehow.
They did, indeed, settle in for a little while. Dennis, with the perpetual sleep deficit of a resident, dozed. Jack just lay there, stroking his fingers up and down his back — that is, until those fingers woke the man again, making him shift and sigh before he was quite conscious.
Then Dennis was warm and naked in his arms, kissing his neck lazily, humming out his contentment — right up until he wasn’t content anymore, until he was crawling on top of him again, hard and insistent and grinning.